The 100 Best East Coast Hip-Hop Songs of All Time

Early-Nineties trio Naughty by Nature’s sound leaned toward what their leader Treach called “street-type shit.” But “O.P.P.” was pop-type shit at its finest.Treach used acronyms for genitalia and coded quips to help the group’s breakout smash slip past FCC regulations and land on mainstream radio. Producer Kay Gee freaked a choice snippet of the Jackson 5’s “ABC,” touching a nerve for nostalgic samples that Bad Boy’s Hitmen team and the Trackmasters would stay on top of to dominate the mid-Nineties.The rugged-but-smooth results took “O.P.P.” to the top of Billboard’s rap charts, giving the world a mysterious, fun catchphrase that’s still with us today. —J.F.

Back in the early days of hip-hop’s golden age, rap groups still often outnumbered and regularly outshone the efforts of individual spitters. This dynamic Bronx crew made a strong entry in the era’s canonical singles with their 12-inch debut. Though it shares DNA with the park jams and MC battles that preceded it, rappers Kool Keith and Ced Gee took their verses here to a whole new level, bringing intricate flows and idiosyncratic wordplay complemented by DJ Moe Luv’s scratches. Credited as the first to sample R&B-jazz drummer Bernard Purdie’s part of Melvin Bliss’ “Synthetic Substitution,” the pioneering track would soon lead countless other artists to follow suit. —G.S.

The lean, no-frills, grime-coated “Who Got da Props?” from Brooklyn trio Black Moon was the powerful warning shot that anticipated the next decade in New York rap. It was the first volley from the doggedly grimy Boot Camp Click, whose true-school-centered Duck Down label would provide an early experiment for the sound and ethos of underground hip-hop, and hit the streets well before the albums by Wu-Tang Clan, Nas, Notorious B.I.G., and Mobb Deep that would be credited with “bringing New York back.” “With ‘Props’ the thing was that there was no bass line in the song. The beat was all about vibes, and there were two drum loops,” producer Evil Dee told author Brian Coleman. Dee treated one drum loop as the “mids and highs” and the other as the bass. “I really wanted it to be loud on radio.” —C.W.

So many hip-hop personas took inspiration from the world of superheroes and one of the most fascinating of comic-book tropes has always been the crossover event. Big Daddy Kane, Kool G Rap, Craig G and Masta Ace—members of iconic producer Marley Marl’s loosely-knit Juice Crew—blended competing verses into a single rap extravaganza that set the template for posse cuts to come. Fans have long lamented the exclusion of Juice Crew all-stars MC Shan and Roxanne Shanté. But what this fantastic four served up (using the classic piano trill of Otis Redding’s “Hard to Handle”) stands the test of time as a drop-the-mic endgame all its own. —M.M.L.

Wale’s career has often seemed torn between repping his Washington, D.C., hometown, experimenting with different styles of post-millennial pop, and aiming for radio ubiquity with conventional rap-and-R&B jams. It’s a sensibility borne by the title of his major-label debut, Attention Deficit. But at least the album yielded “Pretty Girls,” a single where he successfully blends his disparate artistic impulses. Produced by Best Kept Secret, it brims with go-go flavor, a hook from Weensey of the Backyard Band, and a guest verse from Atlanta rapper and unofficial 2009 MVP Gucci Mane. The track is inspired by the Moments’ Seventies soul chestnut “Girls,” and gives Wale a chance to float and glide on “cloud nine” as he praises a woman’s charms. Hate on him all you want, but Wale put D.C. hip-hop on the map, with the likes of GoldLink, Shy Glizzy, and others following in his footsteps. —M.R.

“Made You Look” is great writing about great writing: ”You a slave to a page in my rhyme book,” Nas raps, going way outside the margin with lines like “Mobsters don’t box, my pump shot obliges/Every invitation to fight you punk chazzers.” On Illmatic, Nas had already perfected the New Rap Language, making syllables dance in delicious patterns. Here, he brilliantly dumbs it down to something closer to 12 internal rhymes, as opposed to 60. The way he tempers his artistry into something so breezily complicated can bring to mind the Miles Davis of Kind of Blue in its effortlessly complex restraint. —W.D.

Crewmates in the GS9 collective, Rowdy Rebel and Bobby Shmurda are the elder statesmen of New York drill, laying the city’s aggressive cornerstones when the genre was still primarily a Chicago phenomenon. Following the viral success of Shmurda’s “Hot Nigga” in 2014, “Computers” became a beloved street hit, the pair detailing a revenge fantasy where they confront some adversaries that are hiding behind their keyboards. “I didn’t really put an effort into [the song], but it was truthful,” Rowdy told Power 105.1. “It was something I went through in life. I feel like when you be natural with your music, it always come quickly; when you try to do the most, that’s when you fuck up.” —S.I.

The third single off Fugees’ seven-times-platinum sensation The Score came with plenty of hurdles to overcome. The song itself is a response to how The Source treated their 1994 debut, Blunted on Reality.  Lauryn Hill wasn’t a part of Fugees anymore when she laid down the reference track, even breaking down crying while doing the hook (she thankfully returned to the group). The trio, who said they were unacquainted with copyright laws at the time, were also nearly sued for sampling Enya’s “Boadicea” before reaching an agreement with the New Age pop icon. “What’s dope about ‘Ready or Not’ to me is that it’s not one of those anthems that gets in your face with the hype, where everybody is getting hype busting beer bottles over their heads,” said the group’s Pras, who told Vulture that it’s his favorite Fugees song. “It’s a silent killer, like a gas leak. You want to smell it, but it’s killing you.” —A.L.L.

Nine minutes of almost comically infectious mic-passing joy, “That’s the Joint” is old-school rap at its most buoyant and optimistic, the sound of kids from the Bronx “with golden voices and hearts of steel,” rising up to get funky and make money, and have their voices heard in the world. As the Sugar Hill house band lays down an elastic groove, every member of the Funky 4 +1 gets on the mic, rhyming and singing together in a routine that also came with choreographed dance moves onstage. Everybody shines,but the history-making star turn comes from Sha-Rock, making her iconic presence known as the first woman to appear on a rap record. —J.D.

At the turn of the century, the Wu-Tang was splintering: Method Man toward superstardom, the RZA deeper into film, most of the rest heading down the paths established by the Clan. But Ghostface had other plans. Always the crew’s most word-drunk, he went supernova on Supreme Clientele, an Apollo kid now rapping like the words came to him in psychoactive sparks. “Nutmeg” kicks open the door with regal fanfare before Ghost dubs himself the vivid laser-eye guy and proceeds to slice the barely there beat to ribbons. The bars remain unmatched in sensory detail: He feasts upon giraffe ribs and “hickory cinnamon-scented glaze,” proclaiming, “Perfect find truth within self/Let’s smoke.” If Ghost insists. —C.P. 

Queens mafioso Kool G Rap set a new standard for street-life ferocity with his 1989 classic “Road to the Riches.” It was the closest thing yet to Scarface on wax. “Road to the Riches” is the foundation of his fearsome legend — as Nas summed it up, “G Rap wrote the Bible.” He spins a complex rise-and-fall gangster story, over a Marley Marl production with a paranoid Billy Joel piano loop. Kool G Rap recalls, “I shot up stores and I kicked down doors/Collected scars from little neighborhood wars.” “That was drawn a little bit from my life experience, and a little bit from made-up shit,” he told Complex in 2014. “That’s what hip-hop is to me.” —R.S.

“Crush, kill, destroy, stress!” goes the chorus on Organized Konfusion’s most famous track. Produced by Buckwild, the first single from the Queens duo’s second album, Stress: The Extinction Agenda, arrived when it seemed like all of New York rap was locked in urban combat, whether detailing lives spent in near-poverty or the illegal tactics people of color use to survive. Prince Po and Pharoahe Monch explore how these ills affect their mental health. “Pain, stress, my brain!” cries out Po. Meanwhile, Pharoahe Monche shoots a taxi driver who refuses to transport the duo even though it’s raining outside, then criticizes wack MCs, R&B, and lame music that gets played out on the radio. While Pharoahe later admitted that Organized Konfusion “sold wood in the hood,” “Stress” remains an indelible portrait of Black male angst. —M.R.

The hair-trigger precision of Roc Marciano’s rhymes on this standout from his 2010 album, Marcberg, is so jarring you almost feel stranded on some desolate NYC block during a sudden shootout. Roc Marci’s bars are as dense as a Pollack painting. While his aughts contemporaries kept it (entrancingly) basic, Roc came on like a highbrow hoodlum, posting up on dicey corners and spitting abstract couplets. “Wrist glow pink gold fat like the Disco 3,” he boasts, citing the Eighties trio comprised of Buffy, Prince Markie Dee, and Kool Rock-Ski; Roc’s watch is (apparently) like the Fat Boys (under their original moniker!). All left-of-center goons should kiss the ring. —W.D.

D.C.’s Nonchalant dropped gems all over this 1996 hit, which took drug dealers to task while sounding sympathetic instead of judgy. Her syrupy lilt — a hallmark of peeps who pronounce their sister state as “Murh-a-lund” — somehow strengthens her scathing commentary: It’s like she unknowingly slipped candy in her proverbial medicine. Venting on this bass-heavy cut, she wearily notes, “I see all my brothers underground/Pushing up daisies, man, it amazes me/That you can’t see where you gonna be.” While peers poured Cristal, Nonchalant attacked the system like Jimmy McNulty. The video may as well have opened with a quote. —W.D.

Jeru the Damaja took the streets by storm in 1993, flexing intellect, unorthodox flows, and a cool, determined presence that couldn’t go ignored. On the landmark “Come Clean,” Jeru roasted fake-gangsta rappers over DJ Premier’s ingenious flip of Shelly Manne’s 1973 song, “Infinity,” winning both the mixtape circuit and New York City radio. The song secured a record deal for the MC’s searing debut, The Sun Rises in the East, the following year, and it was a breakout moment for Primo, stepping out from his role in Gang Starr to become one of the most sought-after and revered hip-hop producers of all time. —J.F.

In the Eighties NYC Golden Age, there was no dispute about rap’s battle queen: Roxanne Shanté. She grabbed her mic and passed it on to every female MC who grew up dreaming of being her, like Lil Kim and Foxy Brown. “She was dope,” Foxy told Rolling Stone in 1997. “And excuse my language, but she didn’t give a fuck. In the Eighties, she was rockin’ full-length minks.” The Queensbridge warrior blew up at 14 with “Roxanne’s Revenge,” dissing UTFO in a hit freestyle. But she kept serving her unique lyrical beatdowns, from “Bite This” to “Queen of Rox” to “Brothers Ain’t Shit.” “Have a Nice Day” slammed BDP in the Queens-versus-Bronx turf battle. There were two legendary old-school rap beefs — the “Roxanne” Wars and the Bridge Wars — but Shanté was the only commando who conquered in both of them. —R.S.

Formed by Bronx artists Lord Finesse, Diamond D, and Showbiz & AG, D.I.T.C. expanded into a collective of MCs and producers better known for their unimpeachable hip-hop bona fides than mainstream success. The independent hip-hop movement of the late 1990s prompted them to create a brand that resonated among heads worldwide. Their first 12-inch together, “Day One,” is a mission statement, a Diamond-produced mixtape banger, and a lyrical showcase for Lord Finesse, A.G., the late Harlem rapper Big L, Bronx rapper Fat Joe, Brooklyn rapper O.C. Big L comes off particularly nice on his verse: “The price of my ice is sky high/I’m a fly guy/That’s every thug’s dream, I really love cream/It’s in my bloodstream.” D.I.T.C. became a model for industrious supergroups like Slaughterhouse, and every rap collective more committed to beats and rhymes than pop gimmicks. —M.R.

New Jersey native Reggie Noble proudly reps for the Hit Squad collective throughout Whut? Thee Album, his Def Jam debut. Most of its tracks were produced by mentor Erick Sermon (of EPMD fame), as was the case for this rugged single that showcased Redman’s aggressive yet engaging delivery. Though he blended just enough realism into the mix, his outlandish lyrics immediately set him apart from the competition — gobbling concrete to make entire avenues, for example. To complete its funkadelic beat, Sermon reached for a Cypress Hill record, sampled an isolated B Real line for the hook, and the rest is hip-hop history. —G.S. 

Long Island’s EPMD were the Golden Era’s funkiest duo, mixing hard-rocking samples and molasses flows for New York rap’s greatest four-album run. The first single off their second LP, “So Wat Cha Sayin’” takes shots at anyone who doubted the duo — still in their teens and already able to brag about Gold records and Billboard spots. “So Wat Cha Sayin’” got its monstrous drums from dance group Soul II Soul, who hadn’t even released them yet. “I happened to be going on tour, and we were overseas in London. The DJ plays this beat, and it’s ‘Fairplay,’ by Soul II Soul,” Erick Sermon told Complex. “And I’m like, ‘What the fuck is that?!’ And he gives me the dub plate. I still got it, it’s warped now.” —C.W. 

Following the tragic death of his brother Subroc and the industry interference in their rap group KMD, Daniel Dumile could have easily quit. Instead, he reemerged as the masked mad villain MF DOOM, unveiling a complicated catalog of lore while concurrently stepping up his rhyme game and his production skills. After a few 12” singles for influential radio host Bobbito’s Fondle ‘Em imprint, he dropped 1999’s Operation: Doomsday full-length with a vengeance. Boasting of his prolific lyricism, this album highlight delivers a diverse barrage of densely-packed dope bars from somewhere between science fiction and street dreams, with a buttery flow unmistakably his own. —G.S.

By the early 2000s, Roc-A-Fella Records boasted three of the finest street lyricists around. Freeway, Beanie Sigel, and Jay-Z effectively previewed their trio configuration with the memorable posse cut “1-900-Hustler,” but it took the North Philadelphia battle rapper’s 2002 single to truly deliver on their collective promise. Built around Just Blaze’s cleverly sampled hook, “What We Do” features all three executing some of the sharpest coke raps the world has ever heard. Freeway dominates the track with a veritable death wish, leaving listeners shook with his near-nihilistic portrayal of dope-game circumstances. In second position, Jigga feeds off that energy with ski-mask menace, leaving the absolutely ruthless Beans to bring the painful consequences. —S.G.

“The Clan would be ready to do the shows and when shit would jump off they were fightin’ n****s with their fists,” remembers Brooklyn Zu member Buddha Monk in The Dirty Version, his book about Ol’ Dirty Bastard, “but the Zu would be the ones who would show up and people would say, ‘Oh, here come the flying chairs. Here come the pool sticks. Here come the broken windows.’” ODB launched his solo career with this sparks-spitting tirade that name-checks his six-man crew. In the song, produced by ODB and True Master, its drunken piano stabs came from the same Ensoniq sampler than produced many Wu-Tang hits. Although ODB frequently borrowed rhymes from his cousins RZA and GZA, the RZA insists the loopy, delirious “Zoo” is pure Dirty. —C.W.

“Top Billin’” is one of the most quotable, flippable raps in history despite of — or because of — a plethora of unlikely, sui generis elements: the nasal delivery of rapper Milk Dee, a low-fi basement production recorded via foot-pedal sampler and a four-track, and a stuttering beat that repeats every three bars instead of four. After making mincemeat out of the drum break from Honeydrippers’ “Impeach the President,” Milk Dee spit a rap containing line after line that have become bedrock for samplers, scratchers, and songwriters: “What more can I say?”, “I get money,” “got it good,” “stop scheming and looking hard,” and on and on. “They said I sounded like a girl and [MC Lyte] sounded like a boy.… So when we first serviced ‘Top Billin’ to DJs, they were like, ‘What is this?’” Milk Dee told Fat Lace magazine. “We serviced Red Alert with ‘Top Billin” probably 50 times. When he’d see us coming he’d start running. And one day, Marley Marl just started playing it, and when he started playing it, it took off.” —C.W.

Backwoodz Studios founder billy woods and his Armand Hammer bandmate Elucid are leading the current charge in New York underground art-rap — fiercely independent, semi-anonymous, reference-heavy, deeply experimental, personal, political, and existential. “Mangosteen” showcases the best of both rappers in under two minutes. Elucid effortlessly delivers left-field boasts (“You talk out your neck/I curse from my core”), while Woods opts for a sardonically evocative look at his NYC home turf (“Unannounced visitors may well find the lead flyin’/My sleep app is negroes arguin’ and wailin’ sirens”). —A.L.L.

“Sometimes I Rhyme Slow” was a departure for Greg Nice and Smooth B, a Bronx duo who kept the spirit of old-school party-rocking alive with club jams like “Dope on a Rope,” “Funky for You,” and “Hip-Hop Junkies.” By contrast, “Sometimes I Rhyme Slow” centers on an interpolation of Tracy Chapman’s “Fast Car,” with James Propp re-creating Chapman’s famous guitar melody. Nice opens with a characteristically bombastic verse, only for Smooth B to take Nice’s “too much of anything makes you an addict” line into a sharp detour about dealing with a girlfriend hooked on drugs. Thanks to its memorable video, the downbeat “Sometimes I Rhyme Slow” became an MTV smash, and the biggest chart hit of Nice & Smooth’s long, underrated career. —M.R.

There’s a growling, far-gone energy driving “Hit Different,” where these two Bronx originals hold court over a brooding down-tempo groove. Known for his melodic hooks and slick barbs, A Boogie helped bring NYC back to prominence with fun, infectious songs bursting with unstoppable brio. Tapping into drill, he lets his Boogie Down chum B-Lovee set things off with a brutal verse, barking, “I’m-a shoot ’til my last, I ain’t you/If he duck, knock the hoodie right off of his goose.” Then A slides in, cooing, “Everything be different/You know that shit hit different.” Even violent threats feel like idiosyncratic charms. —W.D.

Featuring a synth interpolation of the Inspector Gadget theme song and a less-than-pitch-perfect Slick Rick warbling the Beatles’ “Michelle,” this song dominated handball courts, block parties, and embryonic rap radio the whole summer and fall of its release. With a rap single omnipresence practically unseen since “Rapper’s Delight,” its production (assisted by Teddy Riley, on the verge of creating New Jack Swing) put this song about backstage concert dramas over the top. Centrally placed synthesizer stabs, R&B-like beat machine programming, and Doug E. Fresh’s singular beatbox phrasings — as well as the presence of Slick Rick, one of rap’s most fascinating voices — made “The Show” one of one. —M.M.L.

Cash Cobain and Chow Lee’s gorgeous, lusty “Vacant” sounds like twentysomething NYC going HAM in these streets. Its mellow chords and brisk percussion — a titillating mix of New Jersey club and smooth sample drill — feel like how the packed lounges and Stories-sanctioned bistros look when it’s warm out, and there’s nothing to do but act out bad decisions. The pungent J. Holiday sample in “Vacant” embodies a first-day-of-summer allure — perfect for those balmy late-night trysts. And when Chow Lee wonders, “How you a queen and a thot at the same time? Is that crazy or not?” it’s precisely the kind of odd question that pops into your head when you’re young, dumb, and driven by your hormones on a vivid first date. —W.D.

Brooklyn rapper-producer El-P and DJ Mr. Len had already released a little-heard 12-inch, 1993‘s “Juvenile Techniques,” when they began collaborating with graffiti writer Big Juss on an informal — and then formal — basis. The trio completed some demos that caught the attention of famed college-radio program The Stretch & Bobbito Show, including their breakout single, “8 Steps to Perfection.” “Rugged like Rwanda,” begins Juss as he and El-P exchange verses over El’s plodding, Sasquatch-like beat. By flipping dense rhymes with super-scientifical zeal, Company Flow became the center of New York’s burgeoning independent, anti-commercial movement. El-P remained an underground hero for years after Company Flow officially split in 2001 before finally gaining mainstream stardom with Run the Jewels, his group with Atlanta rapper Killer Mike. —M.R.

Reality rap starts here. Philadelphia rapper Schoolly D delivers a nonchalant flow over the hollow echo chamber, Megasaurus thump of a Roland TR-909 drum machine — a slice of life from his local Park Side Killas posse full of sex, violence, drugs, guns, B-words, and N-words galore. After a weed-filled recording session, the MC awakened at 5 a.m. and recalls, “I was like, ‘What the fuck is this?’ And the engineer saying, ‘All you kept saying was more reverb. More reverb. More reverb. More reverb.” Schoolly certainly got what he asked for. The end result inspired Ice-T out in L.A. to abandon electro-funk and record “6 in the Mornin’ ” in 1986, launching gangster rap in full force. —M.M.L.

Maryland-by-way-of-Brooklyn spitter Rico Nasty sounds like a young-old soul. And this rock-oriented 2018 bop embodied the heady allure of mid-Eighties Def Jam, even as it went viral on YouTube. But there’s nothing “reduced” here: Nasty squawks like someone stole her pink wig. “Thank God I ain’t have to smack a bitch today!” goes the hook over guitars that screech like someone ripped off a dozen manhole covers. Messily, she moans, “She hatin’ ’cause I’m up, you can tell on her face!” Here, Nasty fights for her right to be petty. —W.D.

Jettisoning the jocularity and playful skits of previous albums, Stakes Is High set course for a slightly more serious De La Soul of straight rhyme-spitters — with Dilla-produced horn snatches from jazz pianist’s Ahmad Jamal’s “Swahililand.” In a hip-hop milieu of Scarface acolytes, marijuana advocates, and an overall “greed is good” mentality, rappers Pos and Dave struck back loud and clear (“I’m sick of talkin’ about blunts/Sick of Versace glasses …”). For so-called backpack rap fans, De La Soul were unquestionably the good guys — alongside MCs like Common, Mos Def, and A Tribe Called Quest, all of whom make appearances in this song’s video. —M.M.L.

The tragically sylvan assault of 22Gz’s iconic “Suburban” feels like Southern Gothic for Brooklynites. Its ragged chorus — “It’s a man down when we lurkin’/Pull up in all black, we purgin’” — is haunting, elegiac, and perverse. And there’s a tingly yearning (for bloodlust, respect, notoriety) at its core. 22’s blatant threats, accentuated by stoic synths, made this grisly drill loosie the inaugural salvo for New York’s most popular (and violent) subgenre. “Where’s the responsibility?” asked critics. And for good reason: Kids 22’s age should be spinning bottles, not blocks. Still, no one was this clever or charismatic. No surprise: “Suburban” went global. —W.D.

Younger hip-hop fans may not know that for a few months in 1985 and 1986, MC Shan was arguably the hottest rapper in NYC, the tip of the spear for the legendary Juice Crew, and a Queensbridge MC whose unique flow exerted a major influence on what became known as “rap’s new generation.” “The Bridge” was initially released as the B side to “Beat Biter,” where Shan accused fellow Queens rapper LL Cool J of copying “Marley Marl Scratch” to make “Rock the Bells.” Despite that controversy, “The Bridge,” with Marl’s oscillating noise effects (which inspired Public Enemy) and Shan’s reminiscence of early hip-hop in Queens, had the most lasting impact. “You love to hear the story, again and again/Of how it all got started, way back when,” raps Shan. “They used to do it out in the park.” Shan and Marl’s masterpiece kicked off the yearslong “Bridge Wars” with several rival acts, including a legendary battle with Boogie Down Productions. Meanwhile, Shan sustained his career into the early Nineties, from writing and producing Canadian reggae act Snow’s 1993 chart-topper “Informer” to making a cameo in the 1991 Steve Martin vehicleL.A. Story. —M.R.

East Flatbush rapper Fivio Foreign navigates the empty space of “Big Drip” with sparse lyricism but heavy character, one of the most viral moments in the second wave of New York drill. His biggest hit has a barely-there beat, but Fivio navigates it with a deep catalog of chaotic — and occasionally onomatopoetic — ad-libs that gave the bombastic and belligerent track its unique sound. “The way the ad-libs came out, I think the person who mixed it made my ad-libs higher than what it’s supposed to be. So I don’t think the song was mixed right,” Foreign told Hot 97. “He must have heard something so he kept it like that. I was like, ‘Fuck it.’” —S.I.

There’s a bittersweet quality behind this Bronx duo’s biggest hit. The only way the band Steely Dan would permit their song “Black Cow” to be sampled here would be for Lord Tariq, Peter Gunz, and the producer KNS to give up all publishing rights. Such gut-wrenching and wallet-shrinking consequences notwithstanding, “Déjà Vu” remains an anthem that celebrates hip-hop’s uptown and outer-borough heritage with no shortage of hometown pride. Befitting the themes of its time, the track mixes references to luxury and gunplay with righteous nods to New York neighborhoods as well as locales beyond the city limits like Mount Vernon and Yonkers. —G.S.

Lil Uzi Vert grew up in Philadelphia, and when they dive in on a beat, they can slash as hard as Meek Mill. But on “XO Tour Llif3,” they sound raised by the internet: keyed into global trends, high on Atlanta hi-hats, and Soundcloud angst, transforming heartache into a viral earworm. Really, it’s about that hook. Uzi had always been an uncommonly tuneful MC but something about producer TM88’s spry beat — and a recent relationship-ending argument with their beau — unlocked the rapper’s inner Hayley Williams. As ever with Uzi, heartache and paper-chasing are closely related, giving the song’s fatalism a triumphant edge. —C.P.

Harlem’s Kurtis Blow was hip-hop’s dominant star in the years between “Rapper’s Delight” and Run-D.M.C., helping invent the idea of a solo MC rocking the mic with clever wordplay and pop-star charisma. His signature hit is a master class in light hard-luck realism delivered over a funky, no-frills backing track. The breaks in “The Breaks” come fast and furious. The poor sucker in the song loses his girl, his job, gets audited by the IRS, runs afoul of the Mafia, and becomes the victim of corporate malfeasance when Ma Bell sends him “a whoppin’ bill/With 18 phone calls to Brazil.” And that’s all in the first verse! “The Breaks” went to Number 87 on the Billboard Hot 100, and it became the first rap record to go gold. “I went from about 300 to 400 people to about 5,000 or 6,000 people at the show,” Blow later recalled. “It was crazy.” —J.D.

If Westside Gunn is a progenitor of so-called “museum rap” — the Twitter designation for arty street fare — then “Hall” is the piece in his collection that demands you to know about cutting-edge couture and prison day-room etiquette. Over charged strings and a pleading soul yelp, the Buffalo, New York rapper spits, “Camo Valentino off the runway, on the corner serving work like a baker.” Call it high culture for cutthroats. Gritty, emotive, and abstract, “Hall” is Westside Gunn at his best. —W.D.

The raggamuffin vibes of Mos Def and Talib Kweli’s joyful “Definition” are so Brooklyn, like neutered consonants and boosted Nets gear. Def and Kweli were earthy and easygoing, a sharp contrast to the sliver-toned garb and presidential Rolexes of mainstream fixtures like Puff Daddy.These two pals come off like the best match since diagonally sliced PB&J on whole wheat. Floating on Hi-Tek’s worldly dub, Def asserts, “Me and Kweli close like Bethlehem and Nazareth.” And when Kweli adds, “People follow me, and other cats, they hear me flow/And assume I’m the real one with the lyrics like I’m Cyrano,” it’s evident that Black Star is the definition of dope. —W.D.

The reigning queen of Bronx drill captured her crown with this song made in her bedroom in about an hour. With a self-assured and unattainable swagger, Ice Spice created a sensation with colloquialisms that came out via razor-sharp elocution but oozed with nonchalance: “Bitch, I’m a baddie I get what I want, like/You thought I was feelin you?” “I was challenging myself to make the quickest song I could make, and I was just like, ‘I’m not going to think too much,’” Ice Spice told SiriusXM. “I think I was a little wine drunk.” —A.L.L.

By the time A Tribe Called Quest debuted, rappers had already written memorable odes to Roxanne, Yvette, Veronica, and Jenifa, oh Jenny. But playing with musical space under the intentional influence of Miles Davis — in between an unforgettable sitar hook sampled from Rotary Connection’s “Memory Band” — Q-Tip set a template for future neo-soul and emo rap, recording the smoothest come-on hip-hop had ever heard. The Fugees’ Roberta Flack cover “Killing Me Softly” borrowed from it musically to reach Number One; Mos Def’s similarly proportioned “Ms. Fat Booty” borrowed from it thematically. But for centering the feminine wiles of a Black woman in a way more respectful fashion than hip-hop’s usual freaky tales, nothing beats Bonita, Bonita, Bonita. —M.M.L.

The frantic bop of French Montana’s “Shot Caller” felt like a new vibe (or wave, if you will) for New York. It was loose and fun at a time when so much of New York rap felt cloistered and conservative. The bounce is hypnotic and in pocket (appropriate for down-South strip joints and hicks who frequent strip malls). But those loud trumpets — from the 1979 curio “A Theme for L.A.’s Team” — were ubiquitous in New York, like so many just-off-the-hanger Jeremy Lin jerseys. Not since 50 Cent had a diehard East Coast rapper sounded so melodic. Montana doesn’t so much rap as cascade over the woofer-bursting track — his verses are practically Rodgers and Hammerstein hooks. “Shot Caller” reminded us of the Boogie Down Bronx at its best. —W.D.

A story told in two acts, “Dreams and Nightmares” reads like an uninterrupted diary entry charting Meek Mill’s trials and tribulations in his journey to success: violence, poverty, incarceration. Despite — or because of — its lack of a hook, it has become a triumphant underdog anthem embraced by Meek’s Philadelphia hometown, embodying the grit and ambition that personifies the city’s identity. The song starts with a sublime piano melody and ultimately swells into a sweeping, maximalist battle cry from the trenches. “I start off real calm and just talkin’ to ’em, really, over a beat,” Mill explained to Songkick. “And the second part, when it get to the ‘nightmare’ part, I just start screaming, going bananas, to the top of my lungs. Stating facts and getting real arrogant and real disrespectful, just showing the both sides. I could be a dream or I could be a nightmare.” —S.I.

The towering double-disc mixtape Diplomatic Immunity was a coronation for Harlem’s Dipset crew, the moment when Cam’ron’s delirious wordplay, Juelz Santana’s elemental flow, and the Heatmakerz’s soulful, pitched-up beats coalesced into a creative wellspring. Full of jingoistic imagery and still-raw references to 9/11, the 2003 tape serves as a coming-out party in particular for Santana, who wrote the immortal “Dipset Anthem” in a few hours while the rest of the crew was at a club. Egged on by reggae horns sliced into instigating stabs, Santana flips weight on the verses and plays his own hype man on the hook, that simple “Ay!” ad-lib getting more insistent every time he chirps it. —C.P.

Foxy Brown enraptured the hip-hop world in the mid-’90s: The Brooklyn native could be aggressive, sultry, provocative, or contemplative at will, leveraging raunchy lyrics with the precision of a scalpel. The commanding beauty immediately appealed to young girls and the fashion world and, on her biggest hit, “I’ll Be,” she overshadows a Jay-Z feature with pure lyricism and charisma — a Lola Falana, dripped in Gabbana. Producer Tone of Trackmasters said they wanted Brown to be “the hard, uptempo bitch,” but she ended up being so much more. “I do things to keep people talking. To bring issues that the average female MC ain’t raising. To talk about things average females talk about,” she told Vibe. “[Women have] been fighting for respect; we’ve been fighting for equality since back in the Bessie Smith days. Millie Jackson, all that.” —S.I.

A self-described “Young OG,” Fabolous is a Brooklyn icon known for making lavish club hits as easily as he deploys mixtape-annihilating freestyles. On this 2013 slap, Fabolous was like a human AI conjurer, cooking up meme after hilarious meme. He references shallow bottle waitresses, fake-deep IG captions, and gold diggers willing to “commit sins for Chipotle,” kicking lines that still feel as current as a trending topic. But there’s nothing generic or artificial here: Every bar feels sui generis. Suavely, he spits, “Every rapper in a cypher, every player in a huddle/You really wanna fuck, but you say you want to cuddle.” Fab’s foresight and wit make “Cuffin’ Season” bang all year round. —W.D.

“It Takes Two” made absolute dance-floor magic utilizing and popularizing what the Spin Alternative Record Guide called “the best definition of a break”: drums and two errant shouts from Lyn Collins’ “Think (About It),” a loop that would ultimately dominate Chicago house, U.K. drum-and-bass, and Baltimore club. “A lot of people said, ‘Oh, too much “woo, yeah,” you need to take it out at some point,’” Rob Base told Rolling Stone about its famous loop. “I had to fight and say, ‘Nah, we got to keep that in the whole record. That’s got to stay in there.’ And people didn’t understand where I was coming from.” —C.W.

Long before dominating hip-hop media with Drink Champs, this podcasting power player built his credibility as an MC. A product of Queens’ LeFrak City and the Green Haven Correctional Facility, Noreaga fully transitioned from spitting urban war-zone bars in a duo with Capone to a solo career with the semi-eponymous N.O.R.E. album. Dropping amid the so-called Shiny Suit Era, this single exemplified the period’s lyrically luxe excesses and forward-thinking production. Over a frenetic, rubbery beat by then up-and-comers The Neptunes and backed by seasoned R&B singer Tammy Lucas, he lives up to the song’s titular grandeur, jet-setting while on the run with braggadocio for days. —G.S.

London-born, Bronx-raised rapper Slick Rick named his fourth album The Art of Storytelling because of his enviable reputation for spooling out incredibly crystal-clear narratives, like this classic from The Great Adventures of Slick Rick. Framed as a bedtime story (complete with kids’ voices assuring they’re all tucked in), Rick weaves a winding morality tale of a 17-year-old on the run from police for various gun-toting activities until he finally gets his comeuppance. Montell Jordan’s everlasting “This Is How We Do It” has kept Rick’s backing track alive for nearly 30 years. But it’s hard to find more well-known, instantly quotable lyrics from hip-hop’s golden age than these. —M.M.L.