New York City is a center for many things in the world: fashion, art, media, finance, subway rats fighting park pigeons in battles for ultimate supremacy, etc. But New York didn’t birth any of those things. New York—and the Bronx specifically—is the birthplace of hip-hop. Which means New York City and hip-hop are forever intertwined. Rap listeners around the world who’ve never been to the Big Apple still know places like Nas’ Queensbridge projects, the slums of Wu-Tang’s Shaolin, and KRS-One’s South Bronx.

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So it should come as no surprise that all five of its boroughs have produced many of rap’s greatest talents. Slick Rick, KRS-One, and Big Pun all hail from the Bronx. Big Daddy Kane, the Notorious B.I.G., and Jay Z are all from Brooklyn. Nas, LL Cool J, and 50 Cent rep Queens. Staten Island’s main contributions come from one camp but remain significant with Method Man, Ghostface Killah, and Raekwon. Even Manhattan has its own Harlem World fresh with stars like Kool Moe Dee, Diddy, and Cam’ron. The fact that artists who even attempt to carry NYC’s flag these days are inevitably crushed by its sheer weight is a testament to the city’s contribution to the foundation of hip-hop.

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All of that is reason why picking the 100 Best New York City Rap Songs is no easy task. There’s so much to choose from that so much still gets left out. For this list, we gave special preference to songs that repped for the city itself. We also imposed the limitation of no more than two songs per artist to reflect a greater diversity. And we only included artists who hail from within the city’s borders—so sorry but no Long Island like De La Soul or Public Enemy and no Yonkers like DMX and the LOX. So make sure there’s money in your Metro Card because this is a trip through New York and its five boroughs.

Listen to the playlist on Apple Music and Spotify.

Producer:Ty Beats
Album:Live.Love.A$AP
Label: RCA

While “​Purple Swag”​ put Rocky on the map, it was “Peso” that turned him into a star. Once that video dropped in 2011 with the A$AP Mob showing out in the streets of Harlem the crew never looked back. NYC was yearning for relevancy in the mainstream during this period and were conflicted with Rockys sound. Either way the song breathed some life back into the NYC rap scene. “Sure, he’s from here, but he sounds like he’s from Houston,” they said, not fully understanding the influence the Internet played in forming a young artist’s musical taste. The web is the new underground, and Rocky is as underground as they come in that sense. Eastside Stevie’s Tumblr page literally made his career. It seemed fitting that one of the first regionally ambiguous rappers to pop was from rap’s birthplace. —Angel Diaz

99. Foxy Brown f/ Jay Z “I’ll Be” (1997)

Producer: Trackmasters
Album:Ill Na Na
Label: Def Jam

I’m a vapid and jiggy “rap-n-b” heretic for preferring Foxy’s “I’ll Be” to Jay Z's “Ain’t No.” So be it. Foxy’s single is the slickest shit I’ve ever heard in my life, and god bless Hov for rocking those fuchsia-tinted Duane Reade-ing glasses in the music video. The uptempo glide of “I’ll Be” feels rather like soaring in a black sedan through an interstate tunnel post-midnight. For those of you keeping track at home, “I’ll Be” is the first of two major Rene & Angela samples that Jay Z hopped on in March 1997, the second being “I Love the Dough” from Life After Death by the late Notorious B.I.G. It’s funny recalling Shawn Carter before he became a sentient tax haven, when Jay Z was just a hot rapper with several top-notch features. As for Foxy: Here’s the biggest hit of her career, a feminist mafioso jig that peaked at No. 7 on the Hot 100. On “I’ll Be,” her sneer was its very sharpest. —Justin Charity

Producer: DJ Premier
Album:Livin’ Proof
Label: Payday/FFRR/PolyGram

DJ Premier really gave Group Home some of the best beats he ever made in his life. Lil Dap and Melachi the Nutcracker weren’t the best rappers and still managed to give us a classic album. That says a lot about Premo’s producing abilities. He was untouchable during the mid-’90s. Livin’ Proof was and still is a masterpiece. “Tha Realness” sounds like it could be the score to an epic Samurai battle. The humming sound in the background always grabs my soul and makes me want to roam the NYC streets during scary hours. This beat is like an after school street fight. It could’ve made The Warriors soundtrack. —Angel Diaz

Producer: Georges Sulmers
Album:N/A
Label: Raw Shack​

If you were tasked with explaining the appeal of mid-to-late 1990s underground New York rap to an alien in 2115 or, say, a millennial next week, you could do worse (a lot worse) than simply cueing up J-Live’s “Braggin’ Writes.” In another era—one where artists ran their own labels or were able to efficiently release music sans executive meddling—J-Live might’ve been a star or at least pretty damn wealthy. Instead, the story of his early career is a classic tale of Defcon 7-levels of stupidity in the music industry: an album finished, with support and contributions from the heaviest hitters in the game (Premier, Pete Rock, and Prince Paul supplied production), which, due to misguided notions of “creative control” and “commercial appeal,” begun in 1995 and completed in 1998 is not released until 2001. As it is, J-Live’s crafted a prolific underground career (seven albums released since his debut), and he’ll always have “Braggin’ Writes,” a prime example of why a certain vintage of hip-hop will always hold an inordinate sway over the culture: a funky, funky soul sample, with actual cuts provided by Primo, overlaid with raps so literate they could populate the syllabus of a “Rhetoric in Poetry” class (during his purgatory in major label fuckery, J-Live worked as an English teacher in various Brooklyn public schools). Metaphor, internal rhymes, and enjambment like a motherfucker make for a set of raps that seem to burst at the seams—the bars can’t contain the couplets, and the verses struggle to accommodate the bars. It’s rapping for rapping’s sake, but with production that’s clearly dedicated to the art of moving butts (or at least making heads nod). Remember a time when “backpack rap” wasn’t a pejorative. —Jack Erwin

Producer: Bluez Brothas, Ase One​
Album:SlaughtaHouse
Label: Delicious Vinyl ​

Masta Ace’s “Jeep Ass Niguh” is a rap rarity, a dope song that was turned into another dope song, “Born to Roll,” simply by flipping the beat and adding more bass. A lot more bass. Which is fine and all, especially for the woofers in your Jeep, but honestly the original was fine the way it was. It starts with police sirens as the subject of the song gets pulled over, and after a verbal gymnastic intro—“Braniac dumb-dumbs, bust the scientifical/Approach to the course and the force is centrifugal”—and some verification of lyrical prowess, it bangs for three uptempo verses about the joys of car-stereo battling and the mellow-harshing of getting pulled over for it. Clearly this takes place in the summer as evidenced from “rolling down my windows, yeah, I have a air conditioner/But I got the sound I want the whole world to listen ta,” although Ace’s Cypress Hill-style flow would be equally at home in Cali systems. —Russ Bengtson

Producer:Heatmakerz
Album:Come Home With Me
Label: Roc-A-Fella/Def Jam

As the title track of Cam’ron’s third studio album (and Roc-A-Fella Records debut), “Come Home With Me” marked a watershed moment in the Harlem rapper’s career. Following up his poorly received sophomore album, S.D.E., Cam’ron was looking for a reboot. He did so in part by retooling his collaborative group Dipset. Although Dipset had existed in some form for several years, and both Juelz Santana and Jim Jones (along with fourth member Freekey Zekey) had appeared on records with Cam’ron before, it wasn’t until “Come Home With Me” that all three men would appear together on a track. It was clear from the outset that the collaboration just worked, as each rapper dropped a fire verse. It’s hard to say who comes away the best, but with lines like Cam’ron’s “’Cause I ain’t never scared ma/Unless you miss your period,” Juelz Santana’s “Kids don’t trick or treat/They get tricked for treating,” and Jim Jones’ “7 keys to the home/11 trees to the dome/13 I ran the streets with the chrome” there’s certainly a wealth of options. Ultimately, “Come Home With Me” marks the commercially successful beginning of the Dipset era, and New York hip-hop would never be the same. —Chris Mench

Producer: Showbiz
Album:Return of the Boom Bap
Label: Jive

These days the world is finally catching up with what rappers have been saying for years about police harassment and abuse. KRS-One’s “Sound of da Police”—much like similar records by Large Professor and N.W.A—has aged exceedingly well, which is to say that America has made essentially no progress over the course of the past two decades. Or two centuries, a link KRS makes explicit in his “overseer”/“officer” section. Part of what makes “Sound of da Police” so vibrant is its visceral aggression, the absolute fury of its slumping assault. It begins with piercing vocal sirens, a breakbeat that sounds titanic in memory even if it feels straightforward at close range. The beat’s primary strength is in that tightly coiled groove and heavy bass tone, a sound that—relative to many productions of the same era—has a timeless quality, an identity as unique as a thumbprint on a police blotter. (French Montana and Fat Joe went back to the well with “We Run NY” in 2010, and it sounded as modern as ever.) But it’s KRS’ driving performance that gives the record its cathartic, explosive energy. With Kris’ patois adding a furious, serrated edge, “there can never really be justice on stolen land” remains as tragically true today as it was when the song was crafted. —David Drake

Producer:Kanye West
Album:Quality
Label: Rawkus

“We sell crack to our own out the back of our homes/We smell the musk of the dust in the crack of the dawn,” begins Talib Kweli on “Get By.” The song proved to be the Brooklyn native’s solo breakout moment in hip-hop as the third (and most successful) single from his album Quality in 2003. It’s impossible to talk about “Get By” without first mentioning the blazing hot sample of Nina Simone’s “Sinnerman” by a post-Blueprint, pre-“Through the Wire” Kanye West. Kweli took this stellar beat and ran with it, lacing the catchy production with serious reflections on the condition of minority communities in New York with lines like “The blacks and Latins in prison/Numbers have risen/They’re victims; lacking the vision/And shit all they got is rapping to listen to.” Although the movement started many years earlier, “Get By” would come to embody the conscious rap wave that swelled during that era of hip-hop. —Chris Mench

Producer:Jahlil Beats
Album: Shmurda She Wrote EP
Label:Epic

“Hot Nigga” is a case study of how the particular elements of a record can, in perfect concert, become a four-dimensional craze. So here we have a sparse and incredible beat from Jahlil, a rhythm that rapper Bobby Shmurda elevated with a peculiar little dance that is, essentially, the calisthenic representation of the kid’s limber cockiness and inconclusive flow. As a single that first caught traction on the strength of a famous Vine clip, “Hot Nigga” is New York’s first truly, massively viral DIY rap single; or at least the first since A$AP Rocky’s “Purple Swag” in 2011. The discrete details behind the record, including certain co-conspirators named throughout, amount to a truly sad story: At present, Epic Records has effectively forsaken Bobby Shmurda and declined to put up $2 million for his bail. —Justin Charity

Producer: Chris Forte
Album: Put It in Your Mouth EP
Label: Stress/Zoo/BMG

Plies, Juvenile, Kevin Gates—these horndogs, plus a few dozen others, are essentially derived from Akinyele, “a particularly lewd character with a solid discography, a distinctive rap style, and an amusing, over-the-top-albeit frequently offensive-lyrical approach,” according to our own retrospective on the Queens rapper. Akinyele is, himself, channeling Eazy-E, Biz Markie, and Kool G Rap on his biggest, definitive hit, “Put It in Your Mouth,” a hook so scatologically catchy that I used to chant it as a funny little hymn in after-school detention. —Justin Charity

Producer:Teddy Riley, Ty Fyffe, Aqil Davidson, Markell Riley, David Wynn
Album: Hard or Smooth
Label:MCA

“Rump Shaker” is the sunniest rap song produced by a New York rap group ever. New York hip-hop is typically claustrophobic and dense—a reflection of a city where it takes two hours to go two blocks in traffic and a thin layer of grime is permanently caked on the streets in even the nice neighborhoods. “Rump Shaker” is so atypically warm and luminous that when this song showed up in this list, I temporarily forgot that Uptown-based Wreckx-n-Effect were a product of the group’s producer Teddy Riley—as big a Harlem music legend as there ever was. “Rump Shaker” is so effortlessly DayGlo that they shot the iconic video at the damn beach, spawning probably thousands of rap videos with a formula of beautiful women in bikinis shaking their backsides at the camera. The song itself is obviously classic. You got that killer saxophone loop and the nonsensical chorus that everybody happily sings along to. “Rump Shaker” might not sound like classic New York, but you can’t deny that it’s one of the brightest tracks that’s ever come out of Gotham. —B.J. Steiner

Producer:Chubb Rock, Howie Tee
Album:The One
Label: Select
“Chubb has been dope since he came out the shaft of his pop’s wood.” That’s pretty much all you need to know about Chuck Rock. Oh, and that his producer was dope, too. Though “Treat ‘Em Right” may have been the biggest single of his career, a song that effortlessly blended the current hip-hop stylings with the then-burgeoning New Jack Swing sound, it was the second single from this Rock’s third album that showcased what the Jamaica-born, New York-raised, Brown University-educated MC could really do. He wasn’t trying to future-proof his music. He and his cousin, producer Howie Tee, produced a song that, though not as dancefloor-ready as the first single, provided an easy-going platform for Rock to layout how ill he and his kin were. “But yo cousin Howie Tee and me /Our love is all about making a dope LP/ That will crush and sell and bum rush/ Don't hush, how we gonna do it, How?” Just the two of them. —Damien Scott

Producer: L.E.S.
Album:Doe or Die
Label:EMI

If we’re talking full catalogs, Nas and AZ are more evenly matched than their lifetime revenue trends might suggest. The rap critic Marty McCready has written the definitive AZ apologia; here I’ll simply add that much of AZ’s catalog has aged way, way better than most of the projects that Nas has dropped since 1996. AZ’s aesthetic is the more cohesive of the two, and his legacy is more coherent. While a song like “Street Dreams” is filled with immersive and fantastical bravado in the first-person, “Sugar Hill” is a bit less desperate, a bit more personable, and perfectly dreamy. The most successful single from AZ’s debut album, Do or Die, “Sugar Hill” dropped in 1995, g-funk’s last wind, hence the traces of DJ Quik, Warren G, and 2Pac that you’ve likely detected in this beat from L.E.S. —Justin Charity

Producer: EZ Elpee
Album: Child of the Ghetto
Label: Bad Boy

I think of “Special Delivery” as Bad Boy’s stab at making a Rakim record. The goofy, bloopy simplicity of the beat, plus Puffy’s prolonged and coked-up introduction, plus the FedEx spoof that is the “Special Delivery” music video—all these quirks belie the care, precision, and peculiar brilliance of G-Dep’s verses. “The rap vampire/Retire in the morn; warm like a campfire/Matter of fact, I’m blazin’, raisin’ the roof up/And slide off with your rooster.” These fluid bursts of surrealism and straight nonsense make for a song that’s amorphous and expirmental on the whole, but a radio jam nonetheless. Somewhere between “No Omega” and Thugger’s “Halftime,” G-Dep smoothed the lane for weirdo rappers in Billboard’s rap charts. —Justin Charity

Producer: Ron Browz
Album: The Big Picture​
Label: Rawkus

“I talk with slang, and I’ma never stop speaking it.” In a more just world, “Ebonics” would have made Big L into a star, propelling him into the rarefied air later occupied by fellow Diggin’ in the Crates crew member Fat Joe. On Feb. 5, 1999, he was in the process of being signed to Roc-A-Fella. A week later, L was killed, victim of a drive-by in his beloved Harlem. He was 24 years old. Big L’s name doesn’t come up in mainstream conversations of rap tragedy—those seemingly reserved for Biggie and Pac—which is a tragedy in and of itself. Because L was every bit as nimble a wordsmith as Big, almost as charismatic as Pac. He was the Scottie Pippen of rap, well-versed (pun fully intended) in every technique, a punchline master, a freestyle king, and a storyteller nonpareil. “Ebonics” stands as a wordplay masterpiece, as L explains late-’90s slang terms over an insistent Ron Browz beat: “A burglary is a jook, a wolf’s a crook/Mobb Deep already explained the meanin’ of shook.” A Nas sample completed it, a Harlem rapper from a Bronx crew giving a nod to Queensbridge. Some of the slang sounds hilariously outdated now—“hit me on the hip means page me”—but Big L never will. Rest in peace. —Russ Bengtson

85. Heltah Skeltah f/ O.G.C. “Leflaur Leflah Eshkoshka” (1996)

Producer:Buckshot, Baby Paul​
Album:Nocturnal ​​
Label: Priority

New York rappers—especially those who would deign to describe themselves as purists—have earned a reputation for being far too serious about their craft for their own good. Watch 15 seconds of the video for HeltahSkeltah’s“LeflaurLeflahEshkoshka” and you’ll discover how much joy can be found in the simple art of rapping, though. The song, a fun, vibrant posse cut between competing Boot Camp Clik groups HeltahSkeltah and O.G.C., is what happens when five hungry, like-minded rappers trade goofy in-jokes, finish each others’ bars, and try to top one another. It’s never serious business with these guys, but you can tell how much fun these guys are having when you treat your craft seriously. —B.J. Steiner

84. East Flatbush Project f/ DeS “Tried by 12” (1996)

Producer:Spencer Bellamy
Album: N/A
Label: Uproar

How to explain America’s fascination with pop culture depictions of violence? Violent movies, violent video games, violent rap songs—from “Stagger Lee” to Bonnie and Clyde to Grand Theft Auto, what’s the appeal of stories about young people dying too early? As callous as it may sound, in the case of “Tried by 12” maybe it starts with the beat? The plinky minor chord loop that underpins the song sounds scary and mysterious but also, undeniably fascinating. Fifteen years after the original was first released, Spencer Bellamy’s eerie, RZA-influenced production was adopted by DJ Premier in 2011 for the Shady 2.0 Cypher, and with good reason—the instrumental is a near perfect background for erudite, complex raps. But there is an underlying truth to the lyrics of the original “Tried by 12” that bluntly describes both the violence that continues to permeate America and the role of rap music as a mirror to reflect our own worst instincts: “Beef starts with the shove and ends with the shovel.” In a country defined by the capitalist imperative of ends justifying means and bigger banks taking little banks, why wouldn’t you want to be the bastard who blasts and doesn’t get blasted? —Jack Erwin

Producer: Blahzay Blahzay
Album:Blah Blah Blah
Label: Fader/Mercury

Brooklyn duo Blahzay Blahzay can officially be tucked into New York’s one-hit-wonder column. But their sole hit was official. Released in the fall of 1995, “Danger” had all the makings of a dope track. DJ P.F. Cuttin’ and rapper Outloud came out the gate swinging and repping on the East Coast/East New York anthem that features aptly used samples from Ol’ Dirty Bastard and Jeru the Damaja. It’s gritty. It’s in-your-face. It’s definitely Timb boot and Starter jacket state of mind music. It’s New York in the mid-1990s. The video featured cameos from Guru, Jeru, Fat Joe, Tony Touch, DJ Premier and others. The song peaked at No. 4 on Billboard’s Hot Rap Songs Chart, which sadly coincided with the peak of BB’s career. But at a time when New York was pushing to get the stranglehold from its Left Coast counterparts, this was definitely a song that let heads know, the East was in the house. —C. Vernon Coleman II

Producer: Prince Paul ​
Album:The Cactus Album ​
Label: Def Jam

“The Gas Face” doesn’t just educate the youth on PW Botha and feature a young Combat Jack in the music video. Today, the record may seem a little strange, a little disjointed: Over an Aretha Franklin intro loop, Pete Nice opens with an abstractly devised verse. (This was the pre-pop hip-hop era, and the group were proudly not that—see the Hammer disses that close out the record.) It operates as a Beastie Boys subliminal; the trio had recently left 3rd Bass’ label Def Jam for Capitol Records. Then MC Serch enters dropping some post-Public Enemy anti-racist wisdom before shifting into a verse from Zev Love X, now known as MF Doom. Zev Love X was the one who coined the term “the Gas Face,” according to Serch and Pete Nice, who told Billboard about it (http://www.billboard.com/3rd-Bass-on-Pop-Goes-the-Weasel-Beastie-Boys-MC-Hammer-Russell-Simmons-Check-the-Technique-Volume-2-Book) in 2014: “When a girl would diss us, Doom started saying, ‘She just gave me the gas face.’ Which meant that we just spent our gas money to get to the mall, only to get dissed. The gas face was when girls would suck their teeth and just walk away.” I find it helps to envision the Gas Face (the action, not the song) as a prehistoric “What are thoooose.” —David Drake

Producer: Ski ​
Album:Uptown Saturday Night​ ​
Label: Profile

Hip-hop was built on slang, street talk, and speaking in codes that could either alienate listeners or pull them into a world they wanted to know more about. And in the mid-’90s, New York rappers began to dramatically escalate the lengths to which they’d go to create new phrases and popularize obscure jargon, whether it was Smootha da Hustler’s “Broken Language,” Mobb Deep’s “dun language,” or the Wu-Tang Clan’s kung fu movie references. But the Bronx duo of Geechi Suede and Sonny Cheeba gave the rap world some of the most delightfully inscrutable bars of all time on their breakout 1997 hit, “Luchini A.K.A. This Is It.” Ski Beatz, a North Carolina producer fresh off of playing a major role in Jay Z’s Reasonable Doubt, solidified his rep in New York by giving Camp Lo the funky, propulsive beat that made lines like “Anatomy for seduction be this ebony junction” jump out of speakers. —Al Shipley

Producer: RZA
Album:Liquid Swords​​ ​
Label: Geffen/MCA

Let’s really take it back to 1995 for a minute. The Wu-Tang Clan was gaining steam as a crew who could spit venomous bars on any beat sent their way. Members Ol’ Dirty Bastard, Method Man, and Raekwon were already getting love from their solo projects. That leaves GZA (a.k.a. the Genius) with his heralded classic Liquid Swords. Any of you who were Wu fans knew about their reputation as lyrical showmen with an affinity for kung fu flicks. The entire mood of Liquid Swords was created by dialogue from the 1980 film Shogun Assassin and established its dark and gritty tone. The opening verse of the album can be best described as GZA in his truest form piling so many layers of braggdocious rhymes, metaphor, and similes that it required multiple listens. Supported by a hook from the song’s beatmaker, RZA, it tells a tale of an MC’s mission and what they must to do spark influence, which is exactly what “Liquid Swords” did to New York hip-hop in the 1990s. —Eric Diep

Producer: Howie Tee
Album:Youngest in Charge​​​ ​
Label: Profile

We live in an era of mind-bogglingly rich rappers who can boast of owning practically anything and it’s at least plausible. But in 1988, hip-hop was far from a billion-dollar industry, and a Flatbush kid named Edward Archer upped the ante for how much a rapper could at least dream of earning. The first two verses of “I Got It Made,” released just before Special Ed’s 16th birthday, are full of justifiable boasts of the young MC’s rapping skills. But in the third verse he starts with an ambitious claim, “Make a million dollars every record that I cut,” and keeps escalating the stakes until he owns a private island in the Caribbean. The debut album that followed, Youngest in Charge, put Special Ed in the company of LL Cool J as one of the rare high school-age rappers who could hang with the adults. And Special Ed continued cashing checks with cameos in the movie Juice, and on The Cosby Show, playing a rapper named JT Freeze. He probably hasn’t gotten that island yet, though. —Al Shipley

Producer:Scott Storch
Album:True Story ​
Label:Universal

Fat Joe was ahead of the curve in the hit-single-doubles-as-a-new-dance department when he delivered “Lean Back,” a summer smash in 2004 that gave even the laziest dude in the club a chance to call his poor posture a move. Scott Storch came through with the Midas Touch® on the production side, though according to Joe, he helped out too. “I made the beat. Whenever I work with Scott Storch, I make the beats with him,” he told us in 2011. In any case, “Lean Back” had “it,” from the earworm backdrop to Joe’s effortless BX demeanor and an über-simplistic yet effective hook to match. While the record was billed as Terror Squad—Fat Joe’s now-defunct crew—the only other featured act was Remy Ma, who was formally introduced here as a viable threat with the pen. Joe held his own too, paying homage to Biggie and sending a cheeky jab at Jay Z over the infamous 2003 Rucker Park basketball game that never happened. “That’s the only beat I ever had for two months that I was scared to rap to because it was so incredible,” Joe said of “Lean Back.” We’re guessing that fear turned to dollar signs when the single went No. 1 for three consecutive weeks and cemented “Lean Back” as a club staple. —Edwin Ortiz

Producer: Buckwild
Album:Life Story ​
Label: Bad Boy/Arista

In 1999, Bad Boy was floundering on two fronts: R&B, with Faith Evans, 112, and Total having entered a simultaneous downtime; and hip-hop, with Ma$e and the LOX having pretty much run their respective courses. Puffy’s debut solo album, Forever, flopped; it’s largely remembered for Chris Rock’s having clowned the album at the 1999 VMAs. Before Carl Thomas dropped Emotional, before G-Dep and Loon flung their many crossover sequels and remixes at the wall, Black Rob would release his debut single, “Whoa!,” Bad Boy’s very first hit of this century. Black Rob’s debut album went platinum on the strength of this one lead single, which, beyond New York, was a continental banger that married Rob’s grizzled, mafioso affect to a beat that any region could love. ”Whoa!” is the most impressive incorporation of strings into a hit rap single, with a certain Save the Last Dance quality that perhaps explains the universal ’00s appeal of a rap record that’s otherwise grimy as auto garage denim. —Justin Charity

Producer: Q-Tip
Album:Crooklyn, Vol. 1​ ​
Label: MCA

The “Crooklyn Dodgers” series of rap songs that emerged in the mid-1990s was truly magical. Created to promote a pair of Spike Lee joints, the Crooklyn Dodgers managed to become one of rap’s earliest supergroups despite a rotating cast of Brooklyn-bred MCs and a fleeting discography of two whole songs—three if you really count the rehashed ’07 version of the squad. You can make a case for the 1995 sequel, “Return of the Crooklyn Dodgers,” being the superior track if you want, but the original “Crooklyn” is where the group’s magic is codified. On the track, Special Ed, Masta Ace, and Buckshot trade supernaturally lyrical verses expounding on life in the borough that seems to naturally crescendo into Ace’s unforgettable “Feels so good to be a Crooklyn Dodger” line in the final verse. Of course, the straw that stirs the drink is producer Q-Tip’s darkly jazzy beat that lurks stealthily beneath the surface. A classic posse cut that serves as the definitive homage to Planet Brooklyn. —B.J. Steiner

Producer:Das EFX
Album:Dead Serious
Label:East West/Atlantic

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OK, so Skoob is from Brooklyn and Krazy Drayzy is from Teaneck, N.J. That counts as a New York song, right? We think so. The duo set the game ablaze with their unique rhyming style that was an off-shoot of Kool G. Rap’s signature machine-gun flow. Over a James Brown loop and a Malcom McLaren sample, Skoob and Drayzy flip nursery rhymes and make pop culture references like an evangelist speaking in tongues. Lines like “So Peter Piper, I’m hyper than Pinocchio’s nose/I’m the supercalifragilistic tic-tac pro” blew my young mind. The bedtime stories my parents read to me and the Disney movies I watched came in handy for me when this song dropped. They also look like twins, which mindfucked me. The video was a great juxtaposition of the song’s lyrics with its underground setting. It was all very bizarre. —Angel Diaz

Producer: The Neptunes
Album:N.O.R.E.
Label: Tommy Boy

Although they’d paid dues with Teddy Riley, and got a foot in the door to the New York rap establishment with a single off Ma$e’s Harlem World, “Superthug” was the song that minted the Neptunes as a production team to be reckoned with. It didn’t sound like anything Capone-N-Noreaga had rapped over on War Report, but then it did not sound much like anything that had come before, which contributed to the track’s broad appeal. And N.O.R.E. seemed to recognize from the jump that the Virginia Beach duo’s sound transcended regional taste, and could make a New York rap hero a national star: “Yo, hit Louisiana, then Atlanta, Indiana/Forget a city slicker, got country grammar/Ayo, we goin’ places where my SoundScan ain’t tough.” Just as N.O.R.E. predicted, the oddball banger crossed him over, creating an enduring partnership with the Neptunes that generated several more hits for him and gave Pharrell and Chad a calling card that put them in the studio with New York stars from Jay Z to ODB. —Al Shipley

Producer: Detail
Album:Young Money: Rise of an Empire
Label: Young Money/Cash Money/Universal Motown

It comes up all the time, and how can it not? The dichotomy of Nicki Minaj’s music gets wild frustrating, b. No shade to the pop life, but it’s hard not to yearn for Mixtape Nicki, the famed moniker used for those times when she says fuck a Z100 and goes Queens mean mug on the track and any rapper unlucky enough to share the track with her. We just don’t see enough of her, plain and simple. She’ll casually out-rap her boyfriend on their blatant radio bid then follow that up opening the VMAs singing “Bad Blood” with Taylor Swift. Where the bars, Nick? Where’s the breathless flow that made Taylor go on the radio reciting every word all those years back? That’s why we cling to the fleeting moments when she does indeed bless us with a brief return. “Lookin Ass Nigga” is like a series of semi-auto machine gun bursts, with effortlessly deft wordplay and #IsItYou lampooning of lame male fuckboy behavior. She owns her sexuality then clowns your thirst. And most of all, she reminds that she can be as good a lyricist as your favorite hot rapper when she wants to be. Be warned—you never know when and where she’ll bring the chopper out next. —Frazier Tharpe

Producer: Bobby Robinson
Album:N/A
Label: BMI

Often heralded as the father of gangsta rap, Harlem’s Spoonie Gee also had a softer side. Originally on the b-side of a single he had with the Treacherous Three called “The New Rap Language,” “Love Rap” plays like a time capsule of hip-hop’s infancy. It had your quintessential breakbeat and signature cadence of the era. What made the track stand out, though, was Spoonie’s futuristic lyricism. He raps about going broke if he helped make a baby, gossip, and a girl he’s crushing over, subject matter that likely came from him growing up around the R&B scene because his uncle was a producer. Prior to this record, rap was all about either rocking a party or boasting. Spoonie flipped it and made a love song, bringing the genre closer to popular culture. —Angel Diaz

71. The Beatnuts f/ Big Pun “Off the Books” (1997)

Producer: The Beatnuts
Album: Stone Crazy
Label: Relativity
Featuring four rappers in less than four minutes of runtime, “Off the Books” stands as the Beatnuts’ magnum opus. First there is the backing track, pieced together from a Lafayette Afro Rock Band breakbeat and a bouncy two-note hit from a composer who primarily wrote music for Disney films. Then, in an appearance that came nearly a full year before his own major-label debut, 25-year-old Big Pun comes in and destroys it: “Hey yo it’s all love, but love's got a thin line/And Pun’s got a big nine, respect crime but not when it reflect mine.” He’s followed by fellow Terror Squader to-be Cuban Link before the ’Nuts even get on, JuJu followed by Psycho Les. And gracious hosts though they be for allowing the guests to blow first, the Super Supreme Team from Queens more than hold their own—just check JuJu’s first four bars: “Whattup Duke-o, you know, politickin papi chuco/I’m out here, watching for Jake, getting this loot though/Shoot bro, I got a waterproof suit yo/Swervin like a A.K.A. in Beirut yo.” Damn near the whole thing rhymes with itself. The only thing to do when you get to the end of the track is play it again. —Russ Bengtson

Producer: Rick Rubin​
Album:Licensed to Ill
Label: Def Jam/Columbia

There are a lot of cringe-worthy moments on the Beastie Boys’ debut LP, 1986’s Licensed to Ill, most of which are lyrical in nature, and most of which were cringed at by the Beasties themselves first. In ensuing years and on ensuing albums, they did whatever they could to distance themselves from it, both stylistically and geographically, winging to Cali to record the follow-up, 1989’s Paul’s Boutique. But Licensed to Ill should be remembered for more than just Budweiser-fueled misogyny and a series of outlandish videos. Take “No Sleep Till Brooklyn,” which can be seen as the next evolutionary step from songs like Run-DMC’s “King of Rock,” pairing boasts (“While you’re at the job working nine to five the Beastie Boys at the Garden—cold kickin’ it live”) with guitar riffs. But not just any guitar riffs. Producer Rick Rubin called on guitarist Kerry King of Slayer, who were recording their own masterpiece, Reign in Blood, in the same studio. King provided the driving metal in a half-hour session, the Beasties did their three-way thing over the top, and a classic was born. —Russ Bengtson

69. Capone-N-Noreaga “T.O.N.Y. (Top of New York)” (1997)

Producer: Nashiem Myrick and Carlos “6 July” Broady for the Hitmen
Album:The War Report
Label: Penalty/Tommy Boy/Warner Bros.

The Shiny Suit Era was profitable for some but mostly annoying to many. Street raps over gritty beats took a backseat in favor of flashy lyrics and smoother sounds. Rap was becoming popular culture. So when CNN dropped War Report it was dubbed as a direct answer to what Puffy was pumping out over at Bad Boy. But what was interesting about that dynamic was that Bad Boy’s in-house production team, the Hitmen, had multiple credits including this track. “T.O.N.Y.” was Queensbridge’s claim to NYC’s vacant rap throne. Biggie had passed and Jigga fumbled his opportunity to replace him as the Big Apple’s king by trying to go pop on In My Lifetime, Vol. 1. QB also was the first to respond to Death Row’s “New York, New York” diss track. From ’97 to about 2003, Queens and Brooklyn battled for the crown. “T.O.N.Y.” was the first shot over the bow. —Angel Diaz

68. Fat Joe f/ Nas, Big Pun, Jadakiss, and Raekwon “John Blaze” (1998)

Producer: Ski​
Album:Don Cartagena
Label: Terror Squad/Mystic/Big Beat/Atlantic

Talk about New York giants. As a young Purerto Rican rap fan, I ate this joint up. Fat Joe’s *Don Cartagena* is a classic in my eyes. Nas set this shit off with the line about stabbing students and preachers with a No. 2 pencil. And Pun’s verse? Dawg, I still get hype when the beat switches up for him. He was definitely coming for the crown during this period. “As soon as I chitter-chatter, you shitter-shatter.” Come on, man, his verse was ridiculous. Then you have Jada going the fuck off and Rae going in with the Snoopy Iceberg in the video. “John Blaze” is easily one of the best posse cuts of all time. And by the sound of the beat you wouldn’t have guessed Ski Beatz produced it since he’s known for a more jazzy sound. We got five of the hardest rappers on one track, and for that we are forever grateful. —Angel Diaz

Producer: Just Blaze
Album:Real Talk
Label: Atlantic

Whenever you read or hear anyone slagging contemporary “turn-up” music, think of “Breathe.” Not because it’s the first or the definitive anthem of this sort, but because it’s such an elegant flex and demonstration of just how engrossing even the simplest song can be; the whole song is just Fabolous juggling various imagery of people gasping, panting, guzzling, etc., hence the title. “Breathe” is a definitive example of how big, anthemic rap singles pervaded the ’00s, when call-and-response to a pitched-up sample could yield huge, indelible hooks. At the record’s core, we have Just Blaze’s greatest beat—essentially a souped-up, perfected second-take on Cam and Hov’s “Welcome to New York City”—a hard-rock naval onslaught rivaled only by T.I.’s “What Up, What’s Haapnin’” in raw wattage. —Justin Charity

66. Mobb Deep f/ Lil’ Kim “Quiet Storm (Remix)” (1999)

Producer: Havoc, Jonathan Williams
Album:Murda Muzik
Label: Loud

Mobb Deep makes the scariest club bangers in hip-hop history. Prodigy and Havoc’s music always has an ominous flair that gives a night on the town the rippling tension of danger. “Quiet Storm (Remix)” sounds like the last moment of portent before a nightclub is raided by the Feds. The bass line—a clever rip from Grandmaster Flash and the Furious Five’s “White Lines”—sounds like the circling helicopter thumping just loud enough through the ceiling to signal impending doom. Everybody snaps hard on this track especially guest rapper Lil’ Kim who delivers a viciously alluring performance that might just be the best verse of her career—a spiritual predecessor to Nicki’s scene-stealing show on Kanye’s “Monster” a decade later. “Quiet Storm (Remix)” is a darkly sexy track that remains a staple for discerning party monsters 16 years later. —B.J. Steiner

65. N.O.R.E. f/ Big Pun, Cam’ron, the Lox, and Nature “Banned From TV” (1998)

Producer: Swizz Beatz
Album:N.O.R.E.
Label: Tommy Boy

Noreaga’s “Superthug” might have been a more memorable song since it helped usher in the Neptunes era of commercial dominance, but “Banned From TV” is the type of posse cut for hip-hop heads who love street rap. With Swizz Beatz behind the boards, all six rappers go for the gusto on their verses, but it’s Nature—the least acclaimed rapper of the bunch—who steals the show. Though his verse is dated now with references to the Latrell Sprewell choking incident, Abner Louima (though he mistakenly refers to him as Abdul), and Live ’98, at the time the verse still blew us away like it was part of the plan. Besides replacing Cormega in the Firm, Nature’s other career highlight is arguably this verse. In the ’90s, even C-list rappers like Nature could blackout on a verse, making him a part of an embarrassment of riches for the NYC scene. —Insanul Ahmed

Producer: Chyskillz, Jam Master Jay
Album:Bacdafucup
Label: Def Jam

Onyx debuted in 1991 with a single, “Ah, And We Do It Like This,” that reflected the jazzy sound of New York hip-hop at the time. But by the time they launched their platinum album, Bacdafucup, in 1993, they were at the forefront of a move toward raw, aggressive anthems like “Slam,” with Fredro Starr declaring, “Now everybody wanna sound grimy” a year before the Wu-Tang Clan blew up. “Slam”’s gang shout chorus, animated verses, and moshpit-ready attitude made Onyx prime candidates for the most prominent rap/metal crossover after Public Enemy and Anthrax. So they teamed up with Biohazard for a remix of “Slam” that followed the original into MTV rotation, and the two groups reunited for the title track to the soundtrack to the 1993 film Judgment Night that helped make rap/rock collaborations commonplace. Onyx continued with a string of minor hits over the next few years, and released an album as recently as 2014, but nothing made the same impact as “Slam”’s unlikely climb to No. 4 on the Hot 100. —Al Shipley

Producer: Pharaohe Monch
Album:Internal Affairs
Label: Rawkus/Priority

In the Great BBQ Debate of 2015, Talib Kweli raised one astute counterpoint: Pharoahe Monch is, for instance, An Intelligent Rapper, yet “Simon Says” is one of the greatest and grimiest party rap records of all time. I can’t name another single on which the principal MC is as forthright and immediately effective as Pharoahe Monch is in his launching “Simon Says” with such a blunt-force invocation: “Get the FUCK up!” A couple years ago DJ and radio host Cipha Sounds, formerly of Hot 97, ranked “Simon Says” among the biggest rap bangers in the history of the Tunnel. “It was Rawkus’ first real club banger,” he told us. “It was an underground record that became a street record,” as crunchy and self-aware as it is vulgar and shameless. “Queens is in the back, sipping ’nac, y’all, what’s up? Girrrrrllllllsss, rub on your titties.” Well, all right then. —Justin Charity

Producer: Bobby Robinson ​
Album:N/A
Label: Enjoy

Like many younger heads I first heard “Rockin It” in a film—some heard it in Wildstyle, but for me it was the context of 1983’s Style Wars, a soundtrack to an early ’80s hip-hop culture that seemed as distant as a Russian Revolution. The enhanced Kraftwerk sample (1978’s “The Man Machine”) was a massive, dancefloor-driven structure made for the generous frequencies of 12” vinyl, rather than the flattened garble of the cassette tapes. The first group signed to a major label (Kurtis Blow was the first MC), the Fearless Four—confusingly, a six-piece group made up of Mighty Mike C, Krazy Eddie, Great Peso, Devastating Tito, Master OC, and DLB—were handy at lifting samples and remaking them in their image (“It’s Magic” sampled Cat Stevens’ “Was Dog a Doughnut”). The song opened with a reference to the 1982 film Poltergeist (“They’re here….”), yet the song’s production has aged better than many records from that decade; Jay Z even remade it for the oft-maligned “Sunshine” in 1997, which sounds better than you remember. —David Drake

Producer:Larry Smith ​
Album:Escape
Label:Jive/Arista

Along with Run-DMC, Whodini ran mid-’80s New York, thanks in large part to visionary producer Larry Smith, who passed away last year at the age of 62. Smith, who produced the entirety of the group’s second album, Escape, had an ear for timeless compositions: “Five Minutes of Funk,” which opens this album, practically upstages the rappers themselves, its searing synthesizers conjuring mid-’80s New York in all its complex, dirty, progressive grandeur. But it was on “The Freaks Come Out at Night” the group really fleshed out a vision of the Big Apple as a space experimentation. “The Freaks Come Out at Night” is a classic contradiction: In warning listeners away from the dangers of the nightlife, they create an aura of romance, the forbidden seduction of an unknowable identity. “So if you want to live a nice quiet life,” rapper Ecstasy concludes, “do yourself a favor, don’t come out at night.” A warning that doubles as an invitation, “Freaks Come Out at Night” captures the nightlife’s enigmatic promise. —David Drake

Producer: DJ Premier, Guru​
Album:Hard to Earn
Label: Chrysalis/EMI

The record still has that bounce to it, don’t it? “DWYCK” is a classic summer jam and would get any party jumpin’. While everybody killed their respective verses, Greg Nice was the star of the show. He set the table nicely, and Premier did him and the record justice by adding the echo after certain bars. This was also one of those rare cuts where Guru switched up his signature monotone flow. He and Greg Nice set it off with crazy energy and quotables like “You could say I’m sort of the boss so get lost” and “I say Muhammad Ali, you say Cassius Clay/I say butter, you say Parkay” that I still rap randomly. Finally, Nice’s partner Smooth comes through with the laid-back flow to balance things out. With all that being said, though, Premier’s production is still what makes this song one of the group’s best. Remember to always do what you can, kid. —Angel Diaz

59. Afrika Bambaataa and the Jazzy Five “Planet Rock” (1982)

Producer:Arthur Baker, John Robie
Album:Planet Rock: The Album
Label:Tommy Boy

Afrikaa Bambaataa and the Jazzy Five released “Planet Rock” in 1982, and the song went on to become one of hip-hop’s first major hits. Perhaps no song captures the dance-focused shift of the New York club scene in the early 1980s better than “Planet Rock.” Borrowing heavily from the works of electronic bands from Germany (Kraftwerk) and Japan (Yellow Magic Orchestra), Afrikaa Bambaataa had a flash of electro-tinged brilliance, and his song would go on to infest the dancefloors of clubs all around New York (and beyond). It spawned an entire sub-genre of “electro-boogie” music and became a blueprint for many dance and rap records that followed it. Even today, traces of its sound can be heard in everything from the expansive EDM scene to electronic-tinged hip-hop artists like Future. Beyond its influence, the funky melody and synchronized rapping of the Jazzy Five is just fun to listen to. “Planet Rock” represents both hip-hop and electronic music on the precipice between underground genres and worldwide phenomenons. —Chris Mench

Producer: Marley Marl
Album:Long Live the Kane
Label: Cold Chillin’

“Ain’t No Half Steppin’” is one of hip-hop’s great soundclashes, with samples that mix sweet and sour into a satisfying new flavor: peppy harmonies from Heatwave’s hit of the same name, a funky piano loop from the Emotions’ “Blind Alley,” and an eerie, unsettling drone from ESG, the Bronx-born No Wave pioneers who became unlikely staples of ’80s rap. With Marley Marl having woven those disparate samples into a tense banger (that Kane oddly calls a “nice mellow beat”), the biggest hit from the aptly titled debut album, Long Live the Kane, cemented the Juice Crew standout’s lasting legacy. In the iconic video for the track, Big Daddy Kane dresses as a boxer and punches a speedbag in time to his smooth triplet flow on the song’s second verse, a moment that demonstrates how Kane combined skillful rapping and a suave, charismatic screen presence like few have before or since. —Al Shipley

Producer:Da Beatminerz
Album:N/A
Label:Nervous

“Who Got Da Props” was an unlikely Billboard record when it dropped—impossible to imagine just a few years later. Black Moon were never true hitmakers, of course. Buckshot Shorty, the 5 Ft Assassin, and DJ Evil Dee created records that proudly flaunted pop’s rules, a harcore group whose underground sound was one of controlled ferocity, shadow, and gritty ambiance. Which is why the remix to “I Got Cha Opin” is such a powerful record in that context: With an elegant sample from Barry White’s “Playing Your Game Baby,” the song gave a group whose sound prowled back alleys a regal frame, draped their hoodies, tims, and razorblade raps in silk scarves. A sound that was about sinewy, muscular rap verses and scrappy assertion of power became, for a moment, power realized, an accomplished stability—even a ray of sunshine, albeit one that drew attention to all the dust motes and smog in the atmosphere. On the record, Buckshot raps about the ”pressure to come up with another fat single,” as if he weren’t sure this would do it. It did, and the record reached No. 15 on Hot Rap Singles and marked their return to the Billboard Hot 100. —David Drake

56. Busta Rhymes “Put Your Hands Where My Eyes Could See” (1997)

Producer:Shamello, Buddah, Epitome
Album: When Disaster Strikes..
Label:Flipmode/Elektra

Hip-hop is so miraculous that a team of obscure producers from Long Island could promote an L.A. soft rock album cut into furious excellence as the backbone of one of New York’s gulliest-ever rap beats. (Seriously, the origin story of this song reads like a Final Fantasy VII sidequest in the slums of Midgar.) 1997, “dawn of the shiny suit era,” was an amazingly diverse year, in fact, with Biggie, Wu-Tang, Capone-N-Noreaga, Camp Lo, and Rawkus all having released career-defining projects in those 12 hallowed months. Of the several tremendous rap singles that the year yielded, “Put Your Hands” is the weirdest (with or without the music video) and most visionary of the bunch, with its amazingly playful rhyme scheme matched against a beat that’s nearly too cool for all the dancing that it’s inspired. There was a time, mind you, when rappers shouted Biggie in songs because they’d known Christopher Wallace personally. —Justin Charity

55. Jadakiss f/ Styles P “We Gonna Make It” (2001)

Producer: The Alchemist
Album: Kiss tha Game Goodbye
Label: Ruff Ryders/Interscope

It doesn’t get any more New York than Jadakiss. In 2001, the Ruff Ryders signee released his debut album, Kiss tha Game Goodbye, going head-to-head with Jay Z’s The Blueprint and Fabolous’ Ghetto Fabolous. ’Kiss was lucky enough to strike gold when Alchemist blessed him with a beat worthy of a DJ Premier co-sign. The Yonkers native grabbed his partner-in-rhyme Styles P for “We Gonna Make It,” an inspirational record that symbolizes the power of the underdog. There are really only a few rappers who can spit knowledge about the drug game and somehow make you feel ready to take on the world. ’Kiss and Styles went back and forth finishing each other’s rhymes, which became a staple of theirs anytime you saw them on a song. Eve appeared on the remix—killed it—and made the song one of the top Ruff Ryders’ anthems ever. But more importantly, “We Gonna Make It” gave ’Kiss the proper shine as a lyricist and jump started his career. —Eric Diep

54. Ghostface Killah f/ Mary J. Blige “All I Got Is You”

Producer: RZA
Album:Ironman
Label: Razor Sharp/Epic

Though this list isn’t limited to songs about New York City, a good number of them do well in describing what it is like for a certain segment of people to live and die in the five boroughs that comprise it. Very few do that better than the first single from Ghostface Killah’s debut solo album. Backed by a beautiful Jackson 5 sample looped by RZA, Ghost focuses his uncanny wit and emotional delivery to vividly detail what it was like growing up on Staten Island with a mother who struggled to provide things like toilet paper and winter coats, two brothers with muscular dystrophy, and a cousin named John John who always peed the bed. It’s a soulful confessional from a burgeoning rap star, helped along greatly by fellow rising New Yorker Mary J. Blige, that manages to not be overly sappy or cross over into triteness. Listening to the song nearly 20 years after its release, it’s not hard to understand why a guy who had to “go to Tech’s house with a note statin’ ‘Gloria, can I borrow some food, I’m dead broke’” wound up copping a bracelet with a large golden eagle on it. If you went through what he went through, you would, too. —Damien Scott

53. Kool G Rap and DJ Polo “Ill Street Blues” (1992)

Producer: Trackmasters
Album: Live and Let Die
Label:Cold Chillin’/Warner Bros.

Kool G. Rap transcended everything—eras, coasts, you name it. He was one of the first real gangsta rappers, whose complex storytelling flows made even Marley Marl’s production sound dated. For their third album, Live and Let Die, G Rap and Polo jetted to Los Angeles, where they linked up with producer Sir Jinx for a decidedly West Coast sounding record featuring G Rap’s decidedly East Coast mafioso flow. “Ill Street Blues” wasn’t a Jinx track, though—the jaunty jazz-inflected track was done by Brooklyn’s Trackmasters, who flipped a Joe Williams piano loop. “Ill Street Blues” certainly stands as the most upbeat cut to ever feature someone being thrown from a window, and helped establish G. Rap further as one of the godfathers of gangsta, along with Ice Cube and Scarface—both of whom appeared on Live and Let Die. “Ill Street Blues” opened a lot like Rakim’s “Paid in Full,” with G. Rap musing, “I’m right in front of my front steps thinking of a plan/Looking like Raggedy Ann, no dough in hand, kicking a can/Thinking of a plot to pull some bank in,” only he goes on to get his via crimes, not rhymes. A 9-to-5 for Kool G. Rap? Never that. —Russ Bengtson

Producer:Ayatollah
Album:Black on Both Sides
Label:Rawkus

New York is the definition of a big city. But as anyone who’s actually lived in a big city can tell you, it’s really just a small town (and boy, is it a small world). So Mos Def running into the same woman twice at two different parties on “Ms. Fat Booty” doesn’t come across as a convenience of songwriting as much as something that often happens to people running in the same social circles. Their initial meeting—a Meet Booty, if you will—has Sharice patting down Mos’ advances with ice water. But soon enough they’re dating before things take an unexpected turn with one of the best plot twists of any storytelling rap song. The song served as the first single to Mos’ solo debut, Black on Both Sides, and despite the label of “conscious rap” Mos is often billed with, the song is proof that even the most enlightened of us have been swayed by a cute smile and a big butt. —Insanul Ahmed

51. Lost Boyz “Jeeps, Lex Coups, Bimaz, and Benz” (1995)

Producer: Easy Mo Bee
Album: Legal Drug Money
Label: Uptown/Universal

Legal Drug Money, the debut album by the Jamaica, Queens, quartet Lost Boyz, was one of the great rap radio records of the mid-’90s that never crossed over or went platinum, despite spinning off five Hot 100 hits. And the most enduring of those singles was “Jeeps, Lex Coups, Bimaz, and Benz,” a funky, anthemic club track produced by Easy Mo Bee. Mr. Cheeks claimed that the group was “puttin’ Queens on the map,” which is strange considering how many of the borough’s MCs were prominent at the time, but like everything Cheeks says, it rolled off his tongue with an infectious flow. The group struggled to keep the singles coming on their next two albums and disbanded after the murder of Freaky Tah. But Mr. Cheeks went solo and made more club hits, and even helped deliver the “Jeeps, Lex Coups, Bimaz, and Benz” hook once again on Lil’ Kim’s 2003 single “The Jump Off.” —Al Shipley

50. Main Source f/ Nas, Akinyele, and Joe Fatal “Live at the Barbeque” (1991)

Producer: Main Source
Album: Breaking Atoms
Label: Wild Pitch/EMI

For hip-hop newbies and basics alike, “Live at the Barbeque” is usually introduced as the blistering on-wax debut of a wild, teenage Nasir Jones, shooting slugs from his brain and casually threatening some sucker named Jesus Christ. While it is an easily iconic debut, “Live at the Barbeque” is so much more than one great Nas verse. For one, this timeless posse cut is the standout track on Breaking Atoms, the classic debut of Queens’ own, criminally underappreciated rap group Main Source. “Live at the Barbeque” has a frenetic energy that won’t be denied. Lead producer/MC Large Professor provides a chaotic soundscape built on Bob James and blaxploitation soundtrack samples for the four rappers—Large Pro, Akinyele, Joe Fatal, and of course, Nas—to drop some serious science on. What’s impressive most of all is how great every rapper on this track sounds—even the largely forgotten Joe Fatal cooks on this track—delivering an old school party jam that still crackles two decades later. —B.J. Steiner

Producer:True Master, Ol’ Dirty Bastard
Album:Return to the 36 Chambers: The Dirty Version
Label:Elektra

The average price of a home in the neighborhood around the Ol’ Dirty Bastard mural in Bed-Stuy is now $1.2 million; four blocks up Franklin Avenue they’re going to blow up the chicken, man (i.e. tear down Popeye’s) to make way for a 119-unit apartment building with a motherfucking on-site gym. Everything dies baby, that’s a fact, and the Brooklyn of ODB’s “Brooklyn Zoo” is no more. But Ason—one-man army, keeper of planets in orbit, and creator of rhymes as good as Tastykakes—has never been nor ever will be tooken out. This self-produced first single from Ol’ Dirty Bastard, an unhinged series of semi-sequiturs set to a syncopated lurch, took the already abstruse Wu-Tang mythology and somehow made it even more confusing. Dirty applied a strike-through to his own rap (“Introducing—yo, fuck that nigga’s name”), dropped deliciously punny disses (“act like a pig trying to hog shit”), and even managed to stump Ed Lover with his outer borough arcania. Buildings come and go, and people, too, but the ODB is for eternity. —Jack Erwin

Producer: Rick Rubin
Album:N/A
Label:Def Jam

This is the song that built Def Jam. After nearly a decade of DJing and breaking in the Bronx, T La Rock was tipped off by his brother, Special K of the Treacherous Three, to meet with a producer named Rick Rubin who was attending NYU. The two met and decided to cut a few records, the first of which was “It’s Yours.” Aside from the then-next-level rapping that Rock brought to the record (Russell Simmons told the New York Times that Rock “created a special poetry.”), Rubin’s use of the Roland 808 helped change the landscape. “It’s Yours” introduced bass that if played loud enough could make your teeth rattle. With lines like “Common talk deserves to walk, the situation’s changed/Everything said from now on has to be prearranged,” it’s clear T La Rock knew he was changing the game. —Damien Scott

Dj Mitsu The Beats Extra Feeding Rare Cats

Producer: Trackmasters
Album:It Was Written
Label:Columbia

It Was Written was wild underrated when it came out. I honestly feel like it aged better than Illmatic, but that’s a different conversation for another day. The Trackmasters set out to make a cinematic masterpiece, and they did. And what better way to start off the album than with “The Message”? The strings set the tone as Nas rushes in and spits: “Fake thug, no love/You get the slug CB4 Gusto/Your luck low, I didn’t know ’til I was drunk though/You freak niggas played out, get fucked and ate out.” His lines on this track are as vivid as a rapper ever spit. The second verse when he talks about being in the Jeep when he seen homie frontin’ about how he ran the island still paints the most perfect picture. That verse should be hung up in the MoMA. —Angel Diaz

Producer:Knobody
Album:Capital Punishment
Label:Loud/RCA

Make no mistake: Hip-hop is black music. But it’s important to remember that there were plenty of Hispanic people who participated in the block parties in the Bronx the late ’70s where hip-hop was invented. Puerto Ricans in particular have accounted for a significant population in New York City ever since “The Great Migration” of the 1950s, making them yet another immigrant group in NYC’s rich mosaic of ethnicities. But while Latinos have always had a hand in hip-hop, they were rarely at the forefront until the late, great Big Pun became the first Latin rapper to go platinum with his 1998 debut album, Capital Punishment. The album was powered by the success of the single “Still Not a Player” where an overweight Pun casts himself as a suave lady’s man ready to “regulate every shade of the ass.” As the song fades out, the chant of “Boricua, morena” is a reminder that like Pun’s legacy, Latinos’ contribution to hip-hop should never be forgotten. —Insanul Ahmed

Producer:Russell Simmons, Larry Smith
Album:Run-DMC
Label:Profile

There are a few rap songs that provide watershed moments. “It’s Like That” and its accompanying b-side “Sucker MCs” was just that back in 1983. With Larry Smith’s stark and sparse instrumentals Run and D.M.C. were able to showcase their lyrical ability without any superfluousness getting in the way. While “It’s Like That” went on to be the commercial smash, “Sucker MCs” was the track that served as the group’s mission statement. It told the story of how the two rappers wound up recording music and what they planned to do with their new platform. For Run, it was to “rock on the mic and make girls wanna dance” while avoiding getting his rhymes bitten by sucker MCs rocking Calvin Klein. For D.M.C., the plan was to “rock a party with the hip-hop” and let doubters know that he’ll never stop. Not a bad way to make an entrance —Damien Scott

Producer:Stevie J
Album:Hard Core
Label:Atlantic/Queen Bee

Queen Bee came through on her debut album talking the same shit that made her a household name on tracks with Biggie and Junior M.A.F.I.A.: casually dismissing lame dudes and asserting herself as a Boss Bitch. Where other tracks like this are aggressive, Kimmy’s proto-Ain’t Nobody Got Time for That anthem is all laid back. She can barely register a fuck to give, and if you’ve got a problem with it, talk to Puffy. —Frazier Tharpe

Producer:Cliff Hall
Album:N/A
Label:Profile

“A party ain’t a party without ‘Triggerman,’ not in New Orleans,” Mannie Fresh once said. “Triggerman” is of course another name for “Drag Rap.” Yes, that’s the Dragnet theme you hear—the song’s melody was a take-off from the TV show—but the record was never nearly as popular in New York as it was in New Orleans. In fact, New York’s flop essentially spawned an entire genre, becoming the primary backbone of the region’s bounce style. Memphis also picked up on the record, a fact the Showboys didn’t even realize until later, when they discovered they’d become superstars halfway across the country. To this day, the record’s trademark “Alright” vocal sample can be heard wafting up the Mississippi. —David Drake

Producer:RZA
Album:Tical
Label:Def Jam

After the Wu-Tang Clan shook up the industry with their 1993 debut album, Enter the Wu-Tang: (36 Chambers), Method Man was hailed as the group’s breakout star. Like his East Coast contemporaries Nas and Biggie and his West Coast counterpart Snoop Dogg, Meth helped standardize the perfectly in-pocket flow that shunned the “old school flows” that even Clan members like the GZA continued to champion. So of course his solo album, Tical, was highly anticipated after the success of 36 Chambers. The album’s lead single “Bring the Pain” picks up right where “METHOD Man” left off, right down to the refrain of the torture skit at the end. Sonically, it’s yet another murky, dusty groove courtesy of the RZA that sounds about as dirty as the studios Meth recorded Tical in. But at the center is still Meth rapping with elasticity; his delivery was swift as a kung fu kick, but his rhymes were as sharp as a Shaolin sword. Is it real, son, is it really real? Indeed it is. —Insanul Ahmed

Producer:Zukhan-Bey
Album:Hustler’s P.O.M.E. (Product of My Environment)
Label: Koch/Diplomat

What a moment in time. After two solid albums and dutifully playing his position within Dipset, the Capo stepped fully to the forefront and achieved the perfect synthesis of a crossover hit that rang off with hometown pride. This was the coolest song of 2006. Quite possibly the best song of 2006. I’d just turned 16 when this dropped, and it was the song to hear at any and every function the following fall. It was simply perfect, but you almost knew he would never do it again, even as the freaking New York Giants hit the ballin’ dance on the sidelines. But in a year when the game was flooded with heaters from other regions, one goon rose to help put his city back on top, however fleetingly. —Frazier Tharpe

Producer:Marley Marl
Album:Roxanne’s Revenge
Label:N/A

Before MC Lyte, Foxy Brown, or Nicki Minaj, there was one woman who set New York’s male-dominated hip-hop community on fire and became queen of the scene. And the teenager born Lolita Shante Gooden accomplished that by any means necessary, adopting a stage name so that she could deliver an “official” response record from the subject of UTFO’s hit “Roxanne, Roxanne.” What could’ve been an amusing novelty remix became a career-launching sensation, mainly because Roxanne Shante rapped more capably and furiously than most women or men at the time, including UTFO. A jaw-dropping one-take recording in Marley Marl’s Queensbridge apartment inducted Roxanne Shante into the Juice Crew and led to her becoming a trailblazer for women in hip-hop. Years later, Shante would record two albums for a Warner Bros. subsidiary. And years later, she became embroiled in a controversy for unsubstantiated claims that a clause in her Warner Bros. contract wound up paying for her college education. —Al Shipley

39. Puff Daddy f/ the Notorious B.I.G. and Busta Rhymes “Victory” (1998)

Producer: Sean Combs, Steven “Stevie J” Jordan, the Hitmen
Album: No Way Out
Label: Bad Boy/Arista

Despite the passing of the Notorious BIG, in 1997 Bad Boy Records had plenty of victories to celebrate. With the massive sales of Biggie’s Life After Death, Ma$e’s Harlem World, Puff Daddy’s No Way Out, the label hit an unprecedented commercial peak and brought hip-hop (and shiny suits!) to the forefront of pop culture. Puffy took his cues from pop culture himself, sampling Bill Conti’s “Going the Distance” from Rocky giving “Victory” its cinematic feel. That feel served the song well for its completely overblown video, which plays homage to The Running Man, spans almost eight minutes, and reportedly cost $2.7 million dollars. Critics were quick to point out Puffy’s flawed rapping, but his opening verse is the perfect setup to hear Big spit the last verses he’d ever record. Puffy might have been a flawed rapper, but he was a ringmaster like no other. —Insanul Ahmed

Producer:Marley Marl
Album: Mama Said Knock You Out
Label:Def Jam

“Don’t call it a comeback! I’ve been here for years!” Rarely has a song started out with an opening line so purely ferocious in purpose—LL Cool J was pissed that fans felt his career was waning and needed everybody to know how deeply wrong they were. By 1990, LL Cool J had become increasingly disdained by purist hip-hop fans as a pop sellout—a hackneyed relic of the 1980s who tossed his hardcore bona fides aside to sure up crossover appeal with romantic pap like “I Need Love.” LL (and his titular grandmother) thought differently. You can hear the raw frustration, the unchecked contempt for all doubters, critics, and haters in every word of “Mama Said Knock You Out.” It’s a diss track that’s aimed at the fans that’s fundamental bitterness is the primary appeal—a soundtrack to give the middle finger to your dismissive boss or your backstabbing friends when life’s got you down. —B.J. Steiner

37. Lord Tariq and Peter Gunz “Déjà Vu (Uptown Baby)” (1998)

Producer: KNS
Album: Make It Reign
Label: Columbia

The short-lived ’90s rap duo that was Lord Tariq and Peter Gunz released one less-than-notable album and one undeniable anthem. KNS was behind the production of “Déjà Vu (Uptown Baby),” which generously and unlawfully cribbed Steely Dan’s “Black Cow”—so much that a six-figure settlement over the song went in the favor of the ’70s jazz rock band. It was this funky and familiar backdrop that helped propel “Déjà Vu” into the mainstream, with Peter and Tariq reppin’ the Bronx to the fullest. Lyrically, the song had its shortcomings, but the duo made up for it with swagger on 100, which translated nicely when the song dropped at clubs and house parties. Hell, you could throw this on today and the reaction would be just as fresh as it was in ’98. From a commercial standpoint, “Déjà Vu” became a top 10 hit and went platinum, earning Lord Tariq and Peter Gunz one-hit wonder status. We’ll call that another W for Uptown, baby. —Edwin Ortiz

36. Rob Base and DJ E-Z Rock “It Takes Two” (1988)

Producer: Rob Base, William Hamilton
Album: It Takes Two
Label: Profile

Building their first Profile Records single on samples from the James Brown-produced Lynn Collins single “Think (About It),” Rob Base and DJ E-Z Rock fit well into the feeding frenzy of James Brown samples already in progress in New York by 1988. But by using not just a drum break from the song but Collins’ voice for the hook of “It Takes Two,” the Harlem duo wound up with a trendsetting summer smash that hit the R&B and dance charts and popularized a new template for sampled sung hooks on rap songs. Spin magazine named “It Takes Two” the single of the year for 1988 and then named it the greatest single of all time in 1989. And while Rob Base scored a few other hits, with and without DJ E-Z Rock, who passed away in 2014, “It Takes Two” looms so large over their legacy that they’re mistakenly remembered by many as a one-hit wonder. —Al Shipley

35. Raekwon f/ Method Man, Ghostface Killah, and Cappadonna “Ice Cream” (1995)

Producer: RZA
Album: Only Built 4 Cuban Linx..
Label: Loud

What’s more New York than ice cream trucks..and street-level sexual harassment? Raekwon and company’s ode to the honey dips of the Big Apple might have a dubious claim to being an actual tribute to women—comparing various female skin tones to dessert is, quite literally, objectification, but this is rap so we’ll keep it moving—but it’s emblematic of the Wu-Tang Clan at the absolute height of their powers. A minor key plucked guitar loop draped over a kick-drum heavy beat is a quintessential RZA keep-it-simple production; Rae, Ghost, and Cappadonna trading dense verses that are by turns cryptic (“Lazy eyeball, small feet, six shoe”) and goofy (“I love you like I love my dick size”) pretty much sums up the lyrical appeal of the Wu in the ’90s. And then that Method Man hook: vaguely menacing, literally sweet, and delivered with a panache so swagged the fuck out that simply calling it “swag” seems cornier than ethanol. The Wu-Tang Clan reached their commercial peak with their second group album, and they took more creative chances on other projects, but this song—the third single on the best solo album the group would produce, delivered near the end of a year-long streak that saw the outfit release a very good/great/classic album roughly every four months—represents a moment when Shaolin’s Finest could damn near literally do no wrong. —Jack Erwin

Producer: Marley Marl
Album: Down by Law
Label: Cold Chillin’/Warner Bros.

New Yorkers are some prideful MFs. Very few songs exude more borough love than MC Shan’s 1986 magnum opus “The Bridge.” Built on a classic Marley Marl boom-bap instrumental that utilizes a seminal sample from the Honey Drippers’ “Impeach the President,” the ode was one of hip-hop’s earliest anthems with Shan paying homage to the largest public housing development in North America (Queensbridge Houses). With that being said, he unintentionally jumped off one of the most memorable beefs in rap history known as the Bridge Wars with KRS-One and the Boogie Down Productions crew over the locations of the origins of hip-hop, which lasted years. Shan’s career never panned out, but for his project psalm he will forever be looked up to as a QB VC from those who came up after him, like Nas, Mobb Deep, Cormega, and others. Win, lose, or draw, that’s water under the bridge now. —C. Vernon Coleman II

33. Craig Mack f/ the Notorious B.I.G., Rampage, LL Cool J, and Busta Rhymes “Flava in Ya Ear (Remix)” (1994)

Producer: Easy Mo Bee
Album: Project Funk da World
Label: Bad Boy

Sean “Puff Daddy” Combs and Bad Boy Records didn’t “invent the remix,” as they would later famously claim. But they did set the standard for what an all-star remix to a rap hit sounded like and even what it looked like, with the “Flava in Ya Ear” remix and its iconic video. When the remix was recorded, Craig Mack and the Notorious B.I.G. were the two rising stars of Bad Boy’s rookie year releasing their debut albums the same month, and you might only guess their differing trajectories in the near future by the quality of Biggie’s verse. Busta Rhymes was already a posse cut powerhouse off the strength of his “Scenario” verse, but he was still in the process of developing the flow that would launch his “Woo Hah”-powered solo career a couple years later, bringing his buddy Rampage along on the track. And LL Cool J was the living legend who sounded shockingly at home alongside all these up-and-comers. —Al Shipley

Producer: Marlon Williams
Album: Goin’ Off
Label: Cold Chillin’

Biz Markie’s underground hit “Nobody Beats the Biz” is a marriage of everything that’s great about New York hip-hop. From Marley Marl’s classic sample of Steve Miller Band’s “Fly Like an Eagle” to Biz’s comedic but complex lyricism, “Nobody Beats the Biz” is one of the city’s early classics. The track was released in 1988, on Biz Markie’s debut album, Goin’ Off, and referenced the commercial jingle of popular electronics store the Wiz. Although he fits in many party-rap lines (“I’m guaranteed to rock/I make the ladies scream and shout/I’m bound to wreck your body and say turn the party out”), Biz also manages to work in some political commentary, noting that “Reagan is the prez, but I voted for Shirley Chisom.” The song would go on to be sampled by everyone from A Tribe Called Quest to Pete Rock to Large Professor, proving “Nobody Beats the Biz” remains a staple of the genre. —Chris Mench

Producer: RZA
Album: Only Built 4 Cuban Linx..
Label: Loud

Only Built 4 Cuban Linx.. is a record that draws attention to boundaries: You understand it, but you don’t, until you do, but even then you don’t. You’re an outsider, but study it long enough and you’ll understand its shape and flow, the logic of how different their Staten Island is from your own world. It worked in its own rhythm, with its own patterns, its own slang, and its own sound. This was a record that pushed and pulled at the very texture of hip-hop, music that created new sensations and new ripples in the American musical continuum. Shit sounded cool as fuck, first: “You rollin’ like Trump, you get your meat lumped” went one piece of timeless dialogue, or “Chef’ll shine like marble, rhyme remarkable.” The way the words fit together was like carefully imbricated puzzle pieces, overlapping and operating at a level of pure sonic feel that seemed to mold the very slang around this different frequency. Meanwhile you had a drum break that felt like being slapped in the head with a sack of quarters and a chorus delivered with the seams showing as if to flaunt the handiwork. Like a 27-inch Zenith, believe it. —David Drake

30. Jay Z f/ the Notorious B.I.G. “Brooklyn’s Finest” (1996)

Producer: Clark Kent
Album: Reasonable Doubt
Label: Roc-A-Fella/Priority

Today a collaboration of this magnitude—even the magnitude it was in 1996 when Biggie was the hottest out and Jay Z was just a promising upstart—would have a high chance of being anticlimactic. So in retrospect, even given that Jay and Big are two of the nicest ever, it’s kind of amazing that their pre-mortem unions actually meet expectations and then some. It was disappointing to learn they didn’t actually record this together, because it’s one of the best back-and-forth rap tracks of all time. Jay’s casually sharper here than he normally is—“Like short sleeves, I bear arms”—while Biggie coasts comfortably in the pocket. This shit sounds like a Made Men celebration, the jovial mafia dinner scene from “Can’t Knock the Hustle” on wax; they’re rapping like two bosses celebrating after just hitting a lick. And the interplay, omg: “Have the paramedics breathing soft on ya..‘What’s ya name?’” “Who shot ya?” Good God, the Commission album would’ve been amazing. —Frazier Tharpe

Producer: Ez Elpee, Jacob York
Album: Conspiracy
Label: Undeas/Big Beat

“Get Money” was the third (and last) single off of Junior M.A.F.I.A.’s album Conspiracy, and the song embodied the culture of Bad Boy and its no-fucks-given attitude. In 1995, the original had verses from Biggie and Kim playing their roles perfectly. Biggie was the heart-eyed gangster who would make his main squeeze “milk box material” if she crossed him. Kim’s lyrics were peak Queen Bee with lines like, “Grab on your dick as this bitch gets deep/Deeper than the pussy of a bitch 6 feet.” Just like other Bad Boy hits, it received the “this is the remix” treatment with “Gettin’ Money (The Get Money Remix),” but you can’t top this one. The unparalleled dynamic of Biggie and Kimmy was enough for Junior M.A.F.I.A. to earn a platinum plaque for their biggest single. Their art still influences today’s hip-hop class, where you won’t be surprised to hear new Biggie and Kim comparisons from a selected few. —Eric Diep

Producer: Dr. Dre, Mike Elizondo
Album: Get Rich or Die Tryin’
Label: Shady/Aftermath/Interscope

Before we say anything about “In da Club,” let’s look at the music video. 50 is in the Shady/Aftermath artist development lab with Dr. Dre and Eminem who are taking notes on their latest protégé. Fif excels in all the tests they throw at him. He’s physically adept. He can record a hot 16. He even passes the heat check of “In da Club” in the actual club. This was the first single off Get Rich or Die Tryin’ and it became the perfect crossover song. The catchy intro turned into a pop culture mainstay (“Go shorty, it’s your birthday/We gon’ party like it’s your birthday”), and more examples of his boastful wordplay (“I’m fully focused, man, my money on my mind/Got a mill out the deal and I’m still on the grind”), as well as a succinct chorus cemented him as a certifiable hit maker. Dre’s minimal production comprised of hand claps and synths helped drive “In da Club” to the top of the charts and international radio. Get Rich or Die Tryin’ really put the rap game in a choke hold (his first-week sales are still something to marvel at) and placed 50 among the greatest New York rappers of all time. He has “In da Club” to thank for that. —Eric Diep

Producer: DJ Premier
Album: The Sun Rises in the East
Label: Full Frequency Range

In the early 1990s, the proverbial rap scales were tipping in the West Coast’s favor. But as the middle of the decade approached, NYC was starting to rise like the phoenix with the help of Afrocentricity and Eastern philosophy-kicking MCs like the Wu-Tang Clan, Brand Nubian, Guru, Leaders of the New School, and others. One of the dopest jams to come from an artist of this unclassified rap subgenre was Jeru the Damaja’s “Come Clean” off his 1994 debut LP, The Sun Rises in the East. There are certain tracks that catch you as soon as they come on, before a word is even uttered or a bar is put down. This is one of them. Containing one of the most memorable loops of the decade, sampled from Shelly Manne’s 1972 instrumental track “Infinity,” JTD’s debut single bumps like acne thanks to a undeniable head-nodding instrumental from crate-digger and scratch extraordinaire DJ Premier. The Crooklyn MC’s unapologetic flow and belittling of wack rappers is effortless. Beats, bars, and a few jewels dropped. A clean sweep. —C. Vernon Coleman II

Producer: Ced Gee, DJ Scott La Rock, KRS-One
Album: Criminal Minded
Label: B-Boy

Before “Fuck Wit Dre Day” or “Back to Back,” Boogie Down Productions started one of hip-hop’s most unlikely traditions with arguably the first diss record that you could party to. BDP claimed they took umbrage at Marley Marl and MC Shan’s “The Bridge” misrepresenting Queens as the birthplace of hip-hop, while others argue that KRS-One and Scott La Rock had a previous score to settle with members of the Juice Crew. But no matter what the motivation, “South Bronx” lit the match for one of hip-hop’s most righteous feuds, defending the honor of the borough where hip-hop was born and spinning off multiple classic songs in response. And the way Ced Gee slices and dices and pitchshifts the horns from “Get Up Offa That Thing” over slamming drums and guitar from “Get Up, Get Into It, Get Involved” make “South Bronx” one of the most explosive and distinct sample chops of the James Brown loop era. —Al Shipley

Producer: Prince Rakeem
Album: Enter the Wu-Tang (36 Chambers)
Label: Loud

“Protect Ya Neck” was more than just Wu-Tang Clan’s debut single, it was in effect a five-minute demo tape for a whole crew of rappers, each trying their hardest to get put on, backed by RZA’s relentless kung fu sample-laden track. The plan, set up by the RZA, was an audacious one: get the whole Clan signed to one label, then get each individual rapper signed as an individual, all on DIFFERENT labels. For the RZA and the GZA, the Genius, each who’d already been signed and dropped, this was more than just a game. This was survival. So while “Protect Ya Neck” served as a seven-pronged attack on the industry (it couldn’t have escaped the martial arts obsessed RZA that the seven verses by seven rappers mirrored Kurosawa’s Seven Samurai), it was also a battle WITHIN the Clan to establish some sense of hierarchy. Inspectah Deck sets things off with a blazing verse: “I smoke on the mic like Smokin’ Joe Frazier/The hell-raiser, raising hell with the flavor/Terrorize the jam like troops in Pakistan/Swinging through your town like your neighborhood Spider-Man.” That is quickly followed in succession by the whole Clan: Raekwon, Method Man, U-God (with a transitional four-bar interlude), Ol’ Dirty Bastard, Ghostface Killah, the RZA, and the GZA, each showing off their unique style (forgive me). Perhaps strategically—no doubt strategically—the best is saved for last, as the GZA uses his own experience with Cold Chillin’ to raze the industry—“Who’s your A&R/A mountain climber who plays an electric guitar?”—and try and ready the world for what’s to come: “I’m the dirtiest thing in sight/Matter of fact, bring out the girls and let’s have a mudfight.” You best protect ya neck. —Russ Bengtson

Producer: Sean Combs, Nashiem Myrick
Album: Ready to Die
Label: Bad Boy/Arista

In early 1995, Christopher Wallace was riding high on the success of his Ready to Die album released a few months earlier, with “Big Poppa” crossing over and giving the Brooklyn MC his first top 10 hit. But the b-side of the single’s 12”, a newly released track more vicious than anything Biggie had put on record to date, became a surprise flashpoint of controversy. Biggie initially recorded “Who Shot Ya” for Mary J. Blige’s 1994 album, My Life, although the violent lyrics didn’t fit the project, which ultimately included an interlude of Keith Murray spitting over the same beat. But by the time the song surfaced on the “Big Poppa” single, its lyrics seemed to allude to a November 1994 incident in which 2Pac was shot in a New York studio, fueling hip-hop’s most tragic feud. Removed from that context, however, “Who Shot Ya” remains a masterful work of lyricism, the most essential Biggie song that didn’t appear on either of his albums. —Al Shipley

23. Black Sheep “The Choice Is Yours (Revisited)” (1991)

Producer: Black Sheep
Album: A Wolf in Sheep’s Clothing
Label: Mercury/PolyGram

Dres, Black Sheep’s frontman, is one of the most underrated rappers ever. Although he never quite blew like some would’ve hoped, he and his partner, Mista Lawnge, have a platinum single to their credit. Shit, “this or that” was one of the first memes, and the beginning of the third verse is played at parties till this day. Everyone from the neighborhood hustler to your grandmother sings along to “Engine, engine, number nine/On the New York transit line/If my train goes off the track/Pick it up! Pick it up! Pick it up!” when the DJ puts it on. —Angel Diaz

22. Doug E. Fresh and The Get Fresh Crew “The Show”

Producer: Dennis Bell, Ollie Cotton
Album: N/A
Label: Reality

What more is there left to say about “The Show”? It’s one of those songs cemented in the bedrock of rap music. The single that propelled the “Human Beatbox” and one of the greatest rappers of all time who was then a young Brit who called himself MC Ricky D (he would later change his name to Slick Rock) to stardom is one simply fundamental to the fabric of modern hip-hop. Just look at this list of artists who have borrowed a piece of the track: The Notorious B.I.G., Eminem, Kanye West, Lauryn Hill, the Beasite Boys, Missy Elliott, Redman, De La Soul, Mary J. Blige, and many, many more looked to the seminal song for inspiration. Whether it’s Doug E.’s percussion or Rick’s raps or ad-libs, the song has proved to be not only one of the best but also one of the most important and essential rap songs ever created. Fun fact: Haim Saban, the creator of Power Rangers, helped create the Inspector Gadget theme song that this song samples. Power Rangers is great and all, but it’s safe to say this may be the most significant piece of art with which he’s ever been involved. —Damien Scott

Producer: Slick Rick
Album: The Great Adventures of Slick Rick
Label: Def Jam/Columbia

Listen to enough hip-hop and you’ll hear influence in the shape of a river, of tributaries and inlets, the ever-expanding topography of an evolving art. But in the 1980s, some artists just seemed to burst from the earth like a wellspring, and Slick Rick was one of those. (Well, arguably—Spoonie Gee might qualify as a lone antecedent.) His style was fully formed on arrival, and it’s epitomized by his virtuosic performance on “Mona Lisa.” Though known for his skills as a storyteller, he brought a winking self-awareness to familiar narratives, bemused at the juxtaposition between contemporary urban life and the formal frameworks of the tall tales he told: “Ladies and gentlemen..and low-lifes,” he begins. Despite the tone, “Mona Lisa” is not pure irony; there’s a human heart to it, and unlike the moral parables of “Children’s Story” or “The Moment I Feared,” it’s comedic melancholy, ultimately open-ended, finishing with an interpolation of Dionne Warwick’s “Walk on By.” “Mona Lisa” is a flirtation, a snapshot scene as ambiguous as Rick’s explanation of what the “C” in MC Ricky D stands for: “courageous or careless.” —David Drake

Producer: DJ Premier
Album: Hard to Earn
Label: Chrysalis/EMI

If any group captured New York rap’s mid-’90s ethos it was Gang Starr. They existed on no margin except that of popular music as a whole: They were hip-hop’s center at a time when that center was defiantly apart from the cultural mainstream. They were street smart, groundbreaking, conscious, and effortlessly cool. They were a Venn diagram of what a rap fan could possibly want from New York by the decade’s midpoint—everything except stars. For Guru, chasing mass appeal was the quickest way to play yourself, and when a record like ”Mass Appeal” was playing, such was the song’s power that pop felt diminished by the comparison. Premier’s beat took a noise-first approach that bleeped like subway cars and rattled like chain link fences, while Guru’s slippery monotone provided a graphite center. Repetition, noise, the only melody a loop that played not just through the chorus but through every second of the record made the song an insistent hit in a real world if not the real one. —David Drake

Producer: JB Moore, Robert Ford Jr.
Album: Kurtis Blow
Label: Mercury

No matter how you slice it, Kurtis Blow’s “The Breaks” stands as one of the most important records in hip-hop history. Commercially, it became rap’s first gold-selling single in 1980, a huge feat for a genre still in its infant stages. More than that, it encapsulated the essence of a musical style that was all about hyping up the crowd at a communal block party. In that respect, Kurtis was a mastermind on the mic. His energy was contagious; his rhymes infused with truth. Whether he raps something comical (“And the IRS says they want to chat/And you can’t explain why you claimed your cat”) or even discouraging (“And he told you the story of his life/But he forgot the part about his wife”), you can relate to what he’s saying. The kicker is the upbeat and funky backdrop from J.B. Moore and Robert Ford Jr., which disguises Kurtis’ sobering rhymes about misfortunes in life. The song is still a favorite in the b-boying community to this day thanks to the breakbeat production. All of this is why “The Breaks” easily positioned Kurtis Blow as one of the best rappers alive at the time. Break it up, break it up, break it up! —Edwin Ortiz

Producer: Just Blaze
Album: Diplomatic Immunity
Label: Roc-A-Fella/Diplomat/Def Jam

Can the congregation rise? Peace be unto you, brothers and sisters. I would like to let the clergy know that we will be nominating Just Blaze for sainthood because this beat is a miracle. It has saved lives. I seen it with mine own eyes. Brothers, can you please pass the collection plate around? Remember, we don’t trip about whether or not you can give. We’re just trying to keep the lights on. Thank you. Back to the Gospel of Cam’ron Disc 2:Track 1:Verse 2. “Look at my life/First movie ever murked out Mekhi Phife” the god said unto thee, Amen. OK, seriously that line should be engraved on his tombstone. Also, let us not forget the Jim Jones rant. One Eyed Willy is truly one of the best when it comes to talking shit over a track. This entire song is just tew much, chile. Play this at a party, especially in the five boroughs, and watch the rap hands fly. “Fuck it, bucket by Osh Kosh B’gosh/Golly, I’m gully, look at his galoshes/Gucci, gold, platinum plaque collages” doesn’t make sense because it’s a metaphor for life, and life makes no sense at all. What I’m trying to say is Cam’ron might be Yahweh in the flesh. —Angel Diaz

Producer: Daddy O, Audio Two
Album: What More Can I Say?
Label: First Priority Music

Brooklyn brothers Kirk “Milk Dee” Robinson and Nat “Gizmo” Robinson were chillin’ in 1987, and there wasn’t much more they had to say. But the way they said it, with Milk Dee’s high, nasal voice cutting through the air over Gizmo’s slamming breakbeat, was all that “Top Billin’” needed to attain immortality. That beat, which chops up the often-sampled “Impeach the President” drums with a unique new stutter, became an iconic groove in its own right, later serving as the basis for Mary J. Blige’s “Real Love.” And Milk Dee’s freewheeling quotables were sampled and interpolated in hits by everyone from Jay Z to 50 Cent, cementing “Top Billin’” as an essential piece of New York rap’s DNA. Later Audio Two singles failed to chart, and the duo was dropped from Atlantic Records. But Milk Dee got a taste of the spotlight again in 2004 when he mentored Eamon and co-wrote his hit “Fuck It (I Don’t Want You Back).” In 2007, Milk Dee even remixed 50 Cent’s “I Get Money” to personally thank some of the artists whose “Top Billin’” samples have continued lining his pockets over the years. —Al Shipley

Producer: Rick Rubin
Album: Licensed to Ill
Label: Def Jam/Columbia

Amongst the many classic songs off the Beastie Boys’ debut album, Licensed to Ill, “Paul Revere” is perhaps the most enduring. Underscored by an innovative backward 808 drum machine beat by legendary producer Rick Rubin, the group delved into a fictionalized story of how they met, including fanciful tales of robbery, stick ups, and a hunt for women. The song is reportedly inspired by their wait to record with fellow New York hip-hop group Run-DMC. Run (Joseph Simmons) came running down the street yelling, and when he reached them, he launched into a long-winded story. Eventually, the Beastie Boys and Run-DMC would collaborate on the song’s lyrics, producing a hilarious and unique track that would go on to help define the Beasties’ early work. Nobody else was making music that sounded like this in 1986, and its popularity would propel not only the group but the genre as a whole to a new level of commercial and critical success. —Chris Mench

Producer: DR Period
Album: Warriorz
Label: Loud/Relativity

Billy Danze and Lil’ Fame have seen New York rap go from boom bap to shiny suits, from gold ropes to platinum bezels, and all the while managed to stay the course. After recording their debut album, the Brownsville duo linked up with DJ Premier, who produced the lion’s share of their next albums. The Mash Out Posse made reliably good hardcore rap that played well to a small but dedicated legion of fans. It wasn’t until 2000’s Warriorz album that the pair breached the mainstream thanks in large part to “Ante Up.” Produced by DR Period, who hadn’t worked with Billy or Fame since he produced their entire first album, “Ante Up” is all kinetic energy. The beat sounds like a broken power cable fell into a puddle on the street. It’s nearly impossible to hear it and not get amped, mainly because it combines genuine aggression accrued from long periods of struggle, the hypeness of a straight-up party record, and the encouragement to wildout with your crew. It’s exactly the kind of hit record two guys from a section of Brooklyn that has a median income of $15,000 and 18 public housing projects could make. They didn’t run to the Neptunes or get a Lil Mo hook. Instead, they stayed the course and continued to define the sound of Brownsville. —Damien Scott

Producer: Hurby Azor
Album: Hot, Cool, and Vicious
Label: Next Plateau

The Queens from Queens were buzzing during the mid-1980s, but they reached the next level of stardom with their ubiquitous 1986 song “Push It.” At a time when rap music was still considered by many to be a fad (and a male-dominated fad at that), Salt-N-Pepa flipped the script by taking their independently released single to No 19 on the Billboard Hot 100. The song became the first major radio hit by a female hip-hop artist, breaking down barriers for other women struggling to be recognized in the industry and scoring the duo a major label deal in the process. It also pushed back against feminist skepticism of hip-hop at the time, which viewed it as an exploitative genre where women were treated as objects and not given a voice of their own. From its sexually charged lyrics to the duo’s racy outfits, “Push It” strived to show that women in hip-hop could own their sexuality and still be successful in their own right. Subsequent New York hip-hop icons like Lil’ Kim and Nicki Minaj would follow this formula to great success. —Chris Mench

13. A Tribe Called Quest f/ Leaders of the New School “Scenario” (1992)

Producer: A Tribe Called Quest
Album: The Low End Theory
Label: Jive

The Native Tongues collective may have been on the mellow end of the spectrum of New York rap’s golden era, but they birthed perhaps the rowdiest posse cut of all time. Ending A Tribe Called Quest’s jazzy 1991 album, The Low End Theory, with an atypical bang, “Scenario” erupted with ominous organs, bruising breakbeats, an irresistible gang shout chorus, and a flurry of verses by Tribe and Native Tongues expansion team Leaders of the New School. Leaders rapper Busta Rhymes practically burst out of the speakers, comparing himself to a cannon, Horatio Hornblower, Peter Tosh, and of course, a dungeon dragon, with an infectious energy that few MCs up until that point had ever demonstrated on record. The heat around Busta created by “Scenario” would help split up the Leaders of the New School within a couple years, setting the stage for a hugely successful solo career that probably seemed inevitable from the moment he laid that verse. Don’t let the narrative overshadow the greatness of the entire song, however: Q-Tip, Phife, and Charlie Brown all got busy on “Scenario.” —Al Shipley

Producer: Rick Rubin, Russell Simmons
Album: Raising Hell
Label: Profile

Rap music is fun! (OK, not always. Sometimes it’s serious, as it should be—shit can get really heavy in this life. But let’s not be serious ALL the time, yeah? Because then you’ve got guys playing Lupe Fiasco deep cuts at BBQs and harshing the general mellow of the turn up, and who really wants that? But I pretty seriously digress.) And this is one of the funnest rap songs of all time (yes, I know “funnest” isn’t a word, you herb). Start with the acapella intro: Two friends—literally completing each other’s sentences—boasting, mostly about their other friend. Then add the beat: a carnivalesque organ (as befitting a sample of a song called “Take Me to the Mardi Gras”) whirls in off of a signature Jam Master Jay scratch and deposits that tinkling percussion loop, both funky and demented. Children’s rhymes remixed to celebrate the guy playing great records at a party—goddamn that DJ made my day, indeed. R.I.P. JMJ. —Jack Erwin

Dj Mitsu The Beats Extra Feeding Rare Dragon

Producer: Rick Rubin, LL Cool J
Album: Radio
Label: Def Jam

Let’s be clear: LL Cool J is legend. While “Rock the Bells” might not be his first hit—that credit goes to 1985’s “I Can’t Live Without My Radio”—the go-go and rock-infused “Bells,” produced by hip-hop stalwart Rick Rubin, is the Queens native’s coming out party. Off Mr. Smith’s 1985 debut album, Radio, the song is classic from the very first hard-hitting line: “LL Cool J is hard as hell/Battle anybody I don’t care who tell.” The bar still rings off as one of the most iconic lines in rap’s history. From there L follows up with ferocious bars that seem like body blow after body blow to his unnamed competition. It was innovative. It was brash. It proved that beyond being a Kangol and rope chain rocking guy with an affliction for beats and radios, he was a force to be reckoned with. Cool J helped usher in the golden age of hip-hop, and this is the song he did it with. —C. Vernon Coleman II

Producer: Rob 'Reef' Tewlow
Album: Get Rich or Die Tryin'
Label: Shady/Aftermath/Interscope

“They say I walk around like I got an S on my chest/Nah, that’s a semi-auto, and a vest on my chest.” This is superhero rap. Or super villain rap, either or. Either way, very few rap albums have delivered a better opening line. The first proper song off Get Rich or Die Tryin’ certainly wasn’t radio-single material, but it cemented 50 Cent as the larger-than-life, streetwise rapper everyone believed him to be. “What Up Gangsta?” established the urgency that would run all throughout the diamond-selling album and completely subsumed listeners into a world full of street legends, stick-up kids, pimps, and rap legends that would unfold over the course of 19 tracks. While it doesn’t have the same mainstream popularity as “In Da Club” or “21 Questions,” “What Up Gangsta” found the G-Unit general keeping it strictly New York with nasty rhymes and a hardcore instrumental. —Eric Diep

09. Boogie Down Productions “The Bridge Is Over” (1987)

Producer: Ced Gee, DJ Scott La Rock, KRS-One, Partner Lee Smith
Album: Criminal Minded
Label: B-Boy

The follow-up to Boogie Down Productions’ “South Bronx” and the climax of the infamous Bridge Wars is BDP’s “The Bridge Is Over”—one of rap’s all-time great diss songs. Its skeletal production values may make it feel almost elementary to listeners these days, but the melodies KRS-One delivers chanting “Di-di di-da, di di-di, dida di-day, aiy!” remain some of the catchiest rap lines ever. There are other memorable flashes of Jamaican patois sprinkled in like “gwan!” and “biddy-bye-bye!” Aside from beef being a vehicle to jumpstart their careers, BDP’s original issue with MC Shan and the Juice Crew was Shan’s supposed claim that hip-hop started in Queens, not BDP’s the Bronx. But as anyone from KRS-One to Kingston-born DJ Kool Herc could tell you, hip-hop (and the Bronx) owe a certain debt to Jamaican music and culture for the origins of the genre. So even if Queens keeps on faking it and the Bronx keeps creating it, there’s no denying Jamaica helped originate it. —Insanul Ahmed

08. Jay Z “Hard Knock Life (Ghetto Anthem)” (1998)

Producer: The 45 King
Album: Vol. 2.. Hard Knock Life
Label: Roc-A-Fella/Def Jam

1998 was a transformative year that saw Jay Z make the transition from a moderately successful rapper, one among many, to the singular superstar he’d remain in perpetuity. The Streets Is Watching film and soundtrack solidified his core following, “Money Ain’t a Thing” with Jermaine Dupri set Hot 97 on fire, and “Can I Get a…” attached a club banger to a blockbuster movie. But it was “Hard Knock Life (Ghetto Anthem),” with its shrewd contrast between an adorable pop culture touchstone from Annie and Jay’s much darker, more adult definition of a hard knock life that put him over the top. “Hard Knock Life” presented America with the Jay Z that they’d know for the next couple decades: a tough, clever Brooklynite who doesn’t mince words about the reality he comes from but always finds a package to wrap it in for universal consumption. Jay Z told interviewers that he got the idea for the sample from watching Annie himself, although the truth was that he heard Mark “The 45 King” James spinning the track on Puff Daddy’s No Way Out tour and jumped to buy the beat. —Al Shipley

07. Puff Daddy f/ the LOX, Lil’ Kim, and the Notorious B.I.G. “It’s All About the Benjamins” (1997)

Producer: D-Dot
Album: No Way Out
Label: Bad Boy

“Now, what y’all want to do? You want to be ballers, shot callers, brawlers?” Back in 1997, Bad Boy had rap on lock. Everything released by Puffy's label (with the exception of Craig Mack's debut) was a crazy success. And despite losing its biggest star, Bad Boy kept the party going with No Way Out. Propped up by 'Can't Nobody Hold Me Down' and the Biggie homage 'I'll Be Missing You,' Puff's debut album was on track to be as big a success as Life After Death. The album's third single, 'It's All About the Benjamins' sealed the deal. Backed by head-nodding production from Deric “D-Dot” Angelettie of the Hitmen, 'Benjamins' was decidedly less shiny than previous Bad Boy singles, but just as grand in ambition. And while everyone had standout verses, you have to give it up for the OG Queen Bee Lil’ Kim who spit a verse so ill it felt right at home coming before one of Biggie's last star turns. —Eric Diep

Producer: RZA
Album: Enter the Wu-Tang (36 Chambers)
Label: Loud

In the cultural memory the Wu-Tang Clan are identified with the cliches of their identity: the kung fu samples, the slang, the lyrical acrobatics, the way they’ve redecorated the footwear of college students for the past two decades. It can be tough to remember that their initial success was as much about New York’s return to the streets, as the West Coast flanked the city with a new generation of hardcore stars. “C.R.E.A.M.” wasn’t the group’s first single, but it was the first one I heard, and one that feels the most indelible today. Raekwon wasn’t spitting in back-to-back similes nor was he spitting street slang so deep it makes Young Thug seem intelligible. “C.R.E.A.M.” was raw emotion, a narrative of a kid caught up in his environment, one where the combination of cracks and weed made his eyes bleed; where Inspectah Deck dodges stick-up kids, corrupt cops, crack rocks, and stray shots. Nothing was labored, every line was iconic, each detail suggesting a world beyond, where the only drive beyond survival was ambition: “Ready to give up so I seek the old Earth/Who explained working hard may help you maintain/To learn to overcome the heartaches and pain.” —David Drake

Producer: Eric B. & Rakim
Album: Paid in Full
Label: 4th & B’way

Rakim is Jesus, and Paid in Full is the gospel. At the time no one rapped like Rakim Allah. His vocabulary was extensive, which made it easy for him to rhyme without using curse words. It’s truly a marvel. Eric B.’s sample flips and layered beats helped the genre evolve to where it is now. The album’s title cut had a whole bunch of shit going on: an intro, Rakim reminiscing about being a stick up kid, an interlude, and finally an ending with Eric B. making his claim as the president of mix masters. Record deals save lives. For many, either rapping, balling, or trapping is the only way out of fucked up situations. “Paid in Full” really is a story of perseverance and glory. The prototypical rags to riches story. One day you’re rocking Lees with holes in them, the next you’re dipped in custom Dapper Dan. Let the rhythm hit you. —Angel Diaz

Producer: Havoc
Album: The Infamous
Label: Loud/RCA/BMG

“We wrote that in the crib high on drugs,” Havoc told Complex in 2011. “Probably weed, probably was some dust in there, mad 40s, getting twisted.” It follows that such a strange and awful brew would yield this beat in particular, with its horrific screech, its screwed piano, and a somber toll that rings clean through the record’s vinyl crackle. A horrorcore ambience to soundtrack Prodigy’s morbid celebration of Queensbridge, which he pretty much warns against ever visiting. Passion of the Weiss recently declared The Infamous the hardest rap album of all time, and really the contest was just a formality so far as that No. 1 spot was concerned. In all his braggadocio and madness, Prodigy issues one of the most vivid and visceral threats ever: “Rock you in your face, stab your brain wit your nose bone.”
The genre’s most sublime beat is, to this day, an enigma. Is the sample “​Thackeray Meets Faculty,” or is it Herbie Hancock? Will Havoc ever answer the question definitively? (No.) It’s an essential ’​90s gangsta rap record that nonetheless presages much of contemporary trap. “Shook Ones” isn’t just timeless, it’s essential to understanding why contemporary hip-hop now sounds how it does. —Justin Charity

03. Grandmaster Flash and the Furious Five “The Message” (1982)

Producer: Ed Fletcher, Clifton “Jiggs” Chase, Sylvia Robinson
Album: The Message
Label: Sugar Hill

“The Message” is indisputably one of the most important songs in the history of hip-hop. In an era when most popular hip-hop records were party/dance-oriented, “The Message” became one of the first rap songs to become a hit while addressing social issues, including poverty, crime, and gang violence in the South Bronx. “It’s like a jungle/Sometimes it makes me wonder how I keep from going under,” rang out the famous chorus. The socioeconomic and racial issues raised by Grandmaster Flash and the Furious 5 became popular themes in the rap world going forward. Soon, many of the biggest hip-hop records were talking more about race and politics and less about partying. Eventually, this would pave the way for the conscious rap movement and would birth wildly popular New York hip-hop acts like Run-DMC and Public Enemy. The song itself would also be remixed, sampled, and imitated by a whole host of big names in hip-hop. All of this came from one group deciding to tackle new and controversial topics through rap music. —Chris Mench

Producer: Poke of Trackmasters, Pete Rock
Album: Ready to Die
Label: Bad Boy/Arista

For all intents and purposes, “Juicy” is one of the greatest rap songs of all time. It’s not just because it smoothed out his edges and ushered the Notorious B.I.G. into pop stardom, which helped paved the road to GOAT status; it’s not just because of its excellent flip of Mtume’s “Juicy Fruit”; and it’s not just because nearly every other line is something plenty of rap fans can instantly quote. No, what makes “Juicy” so great, so essential, is that it’s the quintessential aspirational rap song. The song tells the story of how Biggie was seen as a criminal by his neighbors and a failure by his teachers but he was inspired by the rap stars of the ’​80s. He was all of the worst things you could be—not just a drug dealer but a self-described fat, black, and ugly one at that. But none of that mattered when he picked up a mic. On the song, he’s genuinely happy to achieve success, to be up in The Source, to put five carats in his baby girl’s ear. He’s happy to go from negative to positive. And all of it is possible thanks to the transformative power of hip-hop music. —Insanul Ahmed

Producer: DJ Premier
Album: Illmatic
Label: Columbia

By the time Illmatic released in April of 1994, 20-year-old Nas was already something of a known quantity in New York City hip-hop circles. His blazing opening verse on Main Source’s “Live at the Barbeque” had dropped in 1991, the same year he recorded his “Nasty Nas” demo, and “Halftime” followed in 1992 as part of the Zebrahead soundtrack—a movie that also introduced the world to an actor named Michael Rapaport. The first track on Illmatic—following the introduction of “The Genesis”—was “N.Y. State of Mind,” which while never released as a single still stands as pure of a distillation of Illmatic as there is. There’s the metronome-steady DJ Premier beat, built from a pair of jazz loops, and Nas’ lyricism, which emerges fully formed right after a false start: “Rappers I monkey flip ’em with the funky rhythm I be kickin’/Musician/Inflictin’ composition/Of pain I’m like Scarface sniffin’ cocaine/Holdin’ an M16, see with the pen I’m extreme.” Unlike the Wu-Tang Clan, who dropped their own debut—the grimy yet cartoonish Enter the Wu-Tang (36 Chambers)—six months earlier, Nas presented a crystal-clear vision of the New York he grew up in, wielding words like the guns he rhymed about. He came off like a hood poet laureate, doing more in 40 bars than most rappers did in careers. “I never sleep because sleep is the cousin of death.” You could almost believe it. —Russ Bengtson