50 Best New York Rappers of All Time, Ranked

Birthplace: Casablanca, Morocco

Biggest Hit: "Unforgettable" (feat. Swae Lee)

Essential Deep Cut: “Sanctuary"

Before French Montana was making global hits with the likes of Doja Cat and Swae Lee, he was dropping gritty lo-fi gangsta music about slinging cocaine released exclusively via hood DVDs. The second half of his career is what made him rich, but the first part is why he belongs on this list. French was never an exceptional rapper, but he made up for it with charisma; a real entrepreneurial minded spirit; this really great drunken flow that shines on soulful, street rap; an elite ear for production; and an A&R-like level of taste for scooping underrated talent. He started riding with Max B after the Harlem rapper had his fallout with Jim Jones and helped put NY staples like Chinx—who got his start with Stack Bundles—and Harry Fraud on the map. —Dimas Sanfiorenzo

Birthplace: The Bronx

Biggest Hit: "Drowning" (feat. Kodak Black)

Essential Deep Cut: “Skeezers”

There is an entire generation of New York City music fans raised on A Boogie Wit Da Hoodie, which is why the Highbridge-native can perform at Madison Square Garden as the headliner, guest, or halftime show for a Knicks playoff game, and the crowd will know every word to his hits.

Boogie's legacy is marked by the run he went on in the late 2010s. His first three albums are all certified platinum, and his sophomore record, Hoodie SZN, debuted at No. 1. The charts don’t tell the whole story, though. Some of Boogie’s most ubiquitous New York hits like “Jungle,” “Timeless,” and “My Shit” didn’t chart the highest, but they’re songs that get played in the city to this day. His brand of melodic rap was pivotal in an era when the city was rediscovering its sound. —Jordan Rose

Birthplace: Baltimore, MD

Biggest Hit: "On Fire"

Essential Deep Cut: “South Side Story”

There was a time when a really well-executed punchline—one that either made you smile like you ate something sweet, or scrunch up like it was something sour—was what a rapper aspired to. Even with every rapper chasing that same high, none were as good at it as Lloyd Banks in his prime, who somehow merged a deadpan delivery with some of the most hilarious bars you could think of. He had quotables for days, from "This shit will get uglier than a Master P sneaker" to "Banks is cooler than the other side of the pillow."

And yet that gift never translated the way it should have. He never really produced the classic album fans wanted from him, nor did he have a world-conquering hit. In fact, as the years went on, he stopped chasing mainstream success and went for a more understated, underground approach, his voice dropping to something closer to gravel. Punchlines weren't the end-all-be-all anymore—he grew more interested in the architecture of a verse, stacking rhyme schemes on top of each other.

In other words, he grew up. — Dimas Sanfiorenzo

Birthplace: Long Island, NY

Biggest Hit: "Just a Friend"

Essential Deep Cut: “Pickin’ Boogers”

Biz Markie and my grandmother passed away on the same day, July 16, 2021. Growing up, my cousin and I would watch music videos in her living room for hours. One of the videos we watched the most was “Just a Friend.” We’d be in that living room singing our little hearts out just like Biz did. His undeniable charm and humorous approach reminded hip-hop fans that music could be fun too. His influence on the game is major. Snoop remade his song “Vapors” and his music has been sampled a ton, too—most notably by Mary J. Blige on “I Love You.” He was a dancer, a beatboxer, a singer, a rapper. Biz was hip-hop. —Angel Diaz

Birthplace: Queens

Biggest Hit: "Good Times"

Essential Deep Cut: "I'm Black" (feat. Marsha Ambrosius)

Think of The Lox as a Peter Luger porterhouse fresh out of the broiler. Sheek is the bone. Jadakiss is the sizzle. David Styles is the steak. The youngest member of the crew established himself early on as their preternaturally wizened soul, able to trade kidnapping threats in his patented back and forth with Jada or acknowledge Allah in the midst of the Lox’s grimiest anthems.

If you want to understand Styles’ greatness, it culminates with his debut, 2002’s A Gangster & A Gentleman, which is still the best solo Lox album. On it, Styles displays the mature and fully developed vision of himself as an artist, as the album title suggests, equal parts vicious and grounded, hyper literate in both book and street smarts. —Abe Beame

Birthplace: The Bronx

Biggest Hit: "We Fly High"

Essential Deep Cut: "Only One Way Up" (feat. Cam'ron and Juelz Santana)

Don’t underestimate Jim Jones’ ability to stay relevant. Everyone knows his biggest solo hit, “We Fly High (Ballin'),” but he’s strung together countless defining moments in addition to that commercial peak.

He’s been an integral part of New York’s rap scene for over 20 years, inspiring many of the city’s young artists along the way and influencing massive stars from other areas (like Drake). Jones has a knack for injecting his natural New York grit into street anthems that have commercial appeal without sacrificing any authenticity. —Eric Skelton

Birthplace: New Rochelle, NY

Biggest Hit: “360 Degrees (What Goes Around)”

Essential Deep Cut: “Lickshot”

Grand Puba was one of the most influential New York rappers of his era. He first emerged as an artist in the ’80s, but didn't make a mark until 1990 as part of Brand Nubian. On One for All, Puba turned Five-Percent Nation teachings into catchy earworms, helping spark a rise of mainstream conscious rap.

As a solo artist, Puba leaned less into rhetoric and more into the playful charm of a street-smart New Yorker—exemplified on his two seminal rap/R&B collabs with Mary J. Blige (1992's "What's the 411?" and "Check It Out"). And let's not forget Puba's trendsetting fashion, name-dropping brands that became hip-hop staples: "Girbauds hangin’ baggy, Hilfiger on the top," he rapped on "360 (What Goes Around).” —Donnie Kwak

Birthplace: Brooklyn

Biggest Hit: "Make Me Better" (feat. Ne-Yo)

Essential Deep Cut: Gangsta Don't Play (feat. Junior Reid)

Before Fab, there was a clear delineation between “mixtape rappers” and “mainstream rappers.” Mixtape rappers were well-respected, battle-tested rappers who traded in the currency of bars but couldn’t translate their talent to mainstream songwriting. In came Fab, a Frankenstein-like monster created by mixtape king DJ Clue to destroy freestyles with witty and hilarious punchlines.

He shocked the world by packing his debut, Ghetto Fabolous, with addictive early 2000s hits that still highlighted all the elements of his style that made him great. It led to a remarkably consistent, ongoing career that changed the way we thought about the facility of the mixtape and the mixtape rapper. —Abe Beame

Birthplace: The Bronx,

Biggest Hit: "Me Myself and I"

Essential Deep Cut: "I Am I Be" (feat. Maceo Parker, Fred Wesley and Pee Wee Ellis)

Kelvin Mercer. Plug One. Pos. Picture him in round glasses and a flattop in 1989. In an early interview, he sounds almost annoyed explaining how, during the recording of his group De La Soul’s debut 3 Feet High and Rising, experimentation was the order of the day. “If you spilled milk on the turntable and it sounded dope, it just stayed,” he says, always good for an absurd, memorable image.

The crew met in the suburbs of Long Island and quickly became standard-bearers for the unorthodox, the playful, the strange yet inviting. Across their early albums, and in particular on the underrated masterpiece Buhloone Mindstate, Pos distinguished himself as one of the most intelligent and inventive MCs to ever do this. “Now people, stop taking my styling for a joke / I don't sassafras, I put the foot up the ass,” he raps on “Ego Trippin.’” And that’s just something casual. On “I Am I Be,” he gives his life’s story in the context of work and the predatory ills of the record biz. It’s beautiful, melancholy, honest, and everything else you might want out of art. —Ross Scarano

Birthplace: The Bronx

Biggest Hit: “The Message” (as part of Grandmaster Flash and the Furious Five)

Essential Deep Cut: “Step Off” (feat. Cowboy & Scorpio)

If you can claim to have redefined an artform, you’re a legend. Grandmaster Flash and the Furious Five’s “The Message” refashioned what a rap song could be about. While previous songs had been defined by playful braggadocio and call-and-response interactions, “The Message” was decidedly grim—a collage of broken glass, exasperation, and despair. Melle Mel didn’t write most of the lyrics—Duke Bootee reportedly wrote all but one of the verses on the song—but he was the primary vessel for the anthem, one that gave voice to a marginalized group and the perils of living “close to the edge.” Among rappers who blew up in the late ‘80s, idolizing Melle Mel was a given. —Peter A. Berry

Birthplace: Manhattan

Biggest Hit: "Fuckin' Problems" (feat. Drake, 2 Chainz, and Kendrick Lamar)

Essential Deep Cut: “Fine Whine” (feat. Joe Fox, Future and M.I.A.)

ASAP Rocky’s blend of fashion-forward style, charismatic delivery, and pretty-boy aesthetic set him apart as a standout talent from day one. Rocky's debut mixtape, Live. Love. ASAP, garnered attention with hits like "Peso" and "Purple Swag," showcasing his smooth yet hard-hitting rhymes. But what truly solidified ASAP Rocky's artistry is his relentless pursuit of evolution and experimentation. His debut studio album, Long. Live. ASAP, featuring hits like "Fuckin' Problems" and "Wild for the Night," demonstrated his versatility and crossover appeal. The Harlem rapper effortlessly brings Southern rap influences into his world, infusing outside sounds like Houston’s chopped and screwed choruses into his New York perspective. As he rapped on "Purple Swag," "I'm Texas trill, Texas trill, but in NY we spit it slow." —Jessica McKinney

Birthplace: Manhattan

Biggest Hit: "Wild Wild West"

Essential Deep Cut: "Bad Mutha"

Kool Moe Dee’s name is synonymous with three things: his 1987 classic album How Ya Like Me Now, his iconic sunglasses, and his legendary feud with LL Cool J. But those accomplishments undersell the Harlem rapper’s longevity and impact. Starting in the late '70s with the Treacherous Three, he pioneered double-time rap. As memorable as his LL feud was, his battle with Busy Bee Starski in 1981 was one of the earliest documented rap battles. While Busy Bee focused on crowd pleasing, Moe Dee emerged victorious by dissing his opponent—making it more akin to the Ultimate Rap League of today. A tape of the battle was passed around in early rap circles, making it one of the first viral hip-hop moments. —Insanul Ahmed

Birthplace: Queens

Biggest Hit: "Nothin'"

Essential Deep Cut: "I Love My Life" (feat. Carl Thomas)

Noreaga is one of the most unique rappers in hip-hop’s history. We first heard the rapper on “L.A., L.A.”—the East Coast’s response to the Dogg Pound’s “New York, New York” (the song where Snoop came through and crushed the buildings).

Soon after, Noreaga held down the majority of songs on his group Capone-N-Noreaga’s debut album, The War Report, while his partner completed a skid bid. Capone’s physical absence didn’t matter, though, as C-N-N became underground darlings, delivering a classic New York street album. Although not widely recognized for his lyrical prowess, N.O.R.E. captured hearts and minds with his personality and penchant for hitmaking. The Neptunes will tell you themselves that the Queens rapper helped put them on the map. —Angel Diaz

Birthplace: Queens

Biggest Hit: "Cold Rock a Party" (Bad Boy Remix) (Feat. Missy Elliott)”

Essential Deep Cut: “I Am Woman”

Tiny in stature, MC Lyte broke out with weighty bars. Her 1988 debut Lyte as a Rock showcased her rugged and feminist-leaning rhymes. At just 17 years old, Lyte’s lines were incisive, declaring herself as a force to be reckoned with on the album’s titular track, “MC Lyte Likes Swingin’,” “10% Dis”, and “Paper Thin.”

In the ‘90s, Lyte continued to leave a mark. Unless women rappers were already in a group together, it was rare to see separate acts join forces, but the “I Wanna Be Down (Remix)” proved that three ladies could rock the mic without competing. Lyte’s women-empowerment influence has echoed in the unabashed confidence and humor of female rap heirs Lil’ Kim, Eve, Ms. Lauryn Hill, and Missy Elliott. —Jaelani Turner-Williams

Birthplace: Queens

Biggest Hit: "Always on Time" (feat. Ashanti)

Essential Deep Cut: "Race Against Time"

Ja Rule made a lane for his tough-guy posturing, melodic flows, and crossover hits.

The Queens rapper followed a blueprint that artists like LL Cool J created for how New York acts would navigate the delicate line of making love songs while still maintaining street credibility. Some of his biggest records are collaborations with women vocalists like Jennifer Lopez and Ashanti, the latter of which is pivotal in some of his biggest songs “Mesmerize.” Between “I’m Real,” “Always on Time,” and “Put It On Me,” Ja has three No. 1 hit records and tracks that span barbeques and clubs across several decades. —Jordan Rose

Birthplace: The Bronx

Biggest Hit: "Give the Drummer Some"

Essential Deep Cut: “Watch Me Now,” as part of Ultramagnetic MCs

Before eccentric artists like the late MF DOOM took hip-hop by storm, there was Kool Keith.

The wordsmith founded local rap enclave the Ultramagnetic MCs in 1984 and after a long hiatus, Keith set out on his own. He adopted alter egos like Dr. Octagon, Dr. Dooom, and Black Elvis, drawing inspiration from sci-fi movies and comic books to create his mind-boggling, image-heavy rhymes. Keith’s lyricism pushed the boundaries of strangeness, surpassing his heroes De La Soul and oddball parodist Blowfly on the rapper’s 1996 breakthrough Dr. Octagonecologyst. His unusual and morbid bars referenced pornography (“Girl Let Me Touch You”) and homicide (“Earth People”) over synthetic production, making Keith a real pioneer who has never truly been imitated. —Jaelani Turner-Williams

Birthplace: Brooklyn

Biggest Hit: "Got Your Money" (feat. Kelis)

Essential Deep Cut: "Raw Hide" (feat. Method Man and Raekwon)

Ol’ Dirty Bastard’s Return to the 36 Chambers: The Dirty Version is a masterpiece in the way it distills the rapper’s unpredictable flows and idiosyncratic perspective into a one air-tight 17-song serving.

Only Ol’ Dirty Bastard would think to turn his EBT card into an album cover, creating an instant classic image that has been replicated and turned into rugs for college dorm rooms across the country. —Jordan Rose

Birthplace: Brooklyn

Biggest Hit: "I'll Be" (feat. Jay-Z)

Essential Deep Cut: "(Holy Matrimony) Letter to the Firm"

Foxy burst onto the scene in 1996, first she played Bonnie to Jay-Z’s Clyde on “Ain’t No.”

Then she assisted R&B singer Case on the banger “Touch Me, Tease Me,” which—like “Ain’t No”—was featured on the Nutty Professor soundtrack. By the end of the year, she signed to Def Jam and released her solo debut, Ill Na Na, which went platinum within a month.

She then became the first lady of the Firm—the supergroup featuring Nas, AZ, and Nature, with production spearheaded by Dr. Dre. Thirty years later, Fox Boogie stands not only as one of the most influential women rappers to ever live, but she's a style icon as well, with her signature thin eyebrows, dark lipstick, and high-end fashion pieces being a favorite of internet hip-hop archivists. —Angel Diaz

Birthplace: Brooklyn

Biggest Hit: "Liquid Swords"

Essential Deep Cut: "Investigative Reports" (feat. Ghostface Killah, Raekwon, and U-God)

While many ’90s New York rappers were flashy and iced out, and others were didactic and preachy, GZA was neither. A student of Rakim, he was smooth on the mic, rarely raising his voice. His words carried weight, mixing street knowledge with philosophical insight.

He had an uncommon lexicon: “Rhyming while impaired, dart hit your garment/Pierced your internal, streamlined compartments,” he rapped on Wu’s “Reunited.” He may not be as adored as Rae, Ghost, or Method Man, but is just as respected on the mic, and GZA’s Liquid Swords can easily be argued as the best Wu solo album. —Insanul Ahmed

Birthplace: The Bronx

Biggest Hit: "What's Luv?" (feat. Ja Rule and Ashanti)

Essential Deep Cut: "Definition of a Don" (feat. Remy Ma)

There are few rappers on this list that have been able to notch a hit in nearly every decade they’ve been active; Fat Joe holds that distinction. The Bronx rapper has a generational barbecue classic with “What’s Luv,” a street staple with “Lean Back,” an undeniable hit with “Make It Rain, and a radio constant with “All The Way Up.” Joe laced his songs with his Bronx personality, making them uniquely his but also malleable to fit with other massive acts in the city, which ultimately helped them endure for so long. —Jordan Rose

Birthplace: Queens

Biggest Hit: "Fast Life" (feat. Nas)

Essential Deep Cut: "A Thugs Love Story (Chapter I, II, III)"

A product of the Juice Crew, Kool G Rap quickly forged a reputation as one of hip-hop’s most ferocious rhymers, injecting plenty of color into street narratives while being one of the first MCs to master the art of multi-syllabic rhyming. Produced by the late collaborator DJ Polo, the critically acclaimed Wanted: Dead or Alive helped introduce mafioso rap into the hip-hop continuum years before artists like Raekwon, Nas, or the Notorious B.I.G. would consider doing so—arguably making him the godfather of mafioso rap. —Peter A. Berry

Birthplace: Manhattan

Biggest Hit: “Flamboyant”

Essential Deep Cut: “Casualties of a Dice Game”

Nas once told Funkmaster Flex that Big L "scared me to death." And why wouldn't he? Big L's elite storytelling and dense verses were enough to rattle even his most accomplished peers. Who could forget the time he pulled off one of the all-time great radio freestyles on The Stretch Armstrong and Bobbito Show alongside Jay-Z.

Big L wasn't always understood by the music industry, getting dropped from Columbia in 1996 after a reported dispute over artistic differences with the company, before ultimately releasing his music independently. Jay-Z later revealed that Roc-a-Fella was about to sign him right before he was killed when “Ebonics (Criminal Slang)” was bubbling—a reminder of just how much was lost. —Eric Skelton

Birthplace: Jacksonville, Florida

Biggest Hit: "Feel So Good" (feat. Kelly Price)

Essential Deep Cut: "Same Niggas"

Mason Betha first emerged as teenage rapper Murda Mase in the early ’90s, joining forces with fellow Harlemites Cam'ron and Big L as part of a short-lived group called Children of the Corn.

But after a shiny-suit Bad Boy makeover, Mase went pop and adopted a more radio-friendly demeanor. His smiley persona, paired with a slow-motion rap style, became iconic through a bevy of Bad Boy hits. It also made him somewhat of a villain in the peak backpack-rap days of the late ’90s. But the "Mase flow" persevered. His delivery—deliberate, nonchalant, and perfectly in the pocket of the beat—almost feels like a lost art now, akin to a midrange jumpshot. —Donnie Kwak

Birthplace: Brooklyn

Biggest Hit: "For the Night" (feat. Lil Baby and DaBaby)

Essential Deep Cut: "PTSD"

Pop Smoke took inspiration from the existing drill sound that originated in Chicago and made its way to New York by way of London producers, infusing it with his own gritty DNA to help create the New York drill subgenre that we have today. His 2019 mixtape Meet The Woo set the city on fire, featuring hit tracks like “Welcome to the Party” and “Dior” that solidified Pop’s recognizable voice and emphatic flow—both of which would go on to inspire other up-and-coming drill rappers from the city. His posthumous debut Shoot For the Stars, Aim For the Moon proved that the young rapper was only just getting started, as the project debuted at No. 1 on the Billboard Hot 200 charts and showcased Pop’s versatility with radio-driven songs like “Mood Swings,” “The Woo,” and “What You Know Bout Love.” —Jordan Rose

Birthplace: Brooklyn

Biggest Hit: "Incarcerated Scarfaces"

Essential Deep Cut: "Glaciers of Ice" (feat. Ghostface Killah and Masta Killa)

Along with his partner-in-rhyme Ghostface Killah, Raekwon ushered in a style of rap on The Purple Tape that has been oft replicated, but never duplicated. During the mid-’90s, Rae, Ghost, and the Clan popularized movie samples and mafia references in rap music, along with encrypted wordplay (see: “Criminology”) that still makes your head spin after all these years. His solo debut, Only Built 4 Cuban Linx…, remains the bar as far as rookie campaigns go. The decision to make the cassette purple—mimicking the marketing of drug spots—was a home run, as the color is still referenced 31 years later. —Angel Diaz

Birthplace: Manhattan

Biggest Hit: "Bodak Yellow"

Essential Deep Cut: "Magnet"

Cardi B is anything but a regular degular, shmegular girl. The Manhattan-born, Bronx-raised rapper represented a new era of hip-hop in the late 2010s, when internet sensations could and would transform into celebrated rappers and cultural icons.

But Cardi did it better than any of her counterparts. While her early singles like "Foreva" and "On Fleek" showed promise, it was the release of the chart-topping club anthem "Bodak Yellow" in 2016 that catapulted her to new heights. With her no-nonsense attitude and relatable lyrics, Cardi B won over hearts far beyond her roots. Beyond her undeniable talent, Cardi has begun to serve as a mentor figure in the industry, supporting and embracing standout up-and-coming artists like GloRilla and Latto, demonstrating her keen eye for identifying and embracing the new generation of talent. —Jessica McKinney

Birthplace: Manhattan

Biggest Hit: "Vivrant Thing"

Essential Deep Cut: "Things U Do"

A Tribe Called Quest undeniably pioneered alternative hip-hop, and Q-Tip was the architect. At a time when hip-hop seemed sequestered into P-Funk and James Brown samples, gangsta rap and raging political consciousness, Q-Tip fused eclectic jazz sounds with an even-keeled, introspective cool.

As a part of Tribe, he addressed first-world issues like capitalism, sexual politics, and mundanities like lusting over a baddie, threading them all with warmth and nuance. Together, Tribe dropped multiple classic albums that helped define an era, and as the crew’s producer. In the years since the clique’s debut, Q-Tip and Tribe have become known as forefathers of backpack rap, opening the doors for folks like Yasiin Bey, Talib Kweli, Kanye West, and countless others. —Peter A. Berry

Birthplace: Queens

Biggest Hit: "Walk This Way" (with Aerosmith)

Essential Deep Cut: "Queens Day" (feat. Nas and Prodigy)

As a part of Run-DMC, Joseph “Run” Simmons kicked off hip-hop’s golden age with fellow MC Darryl “D.M.C.” McDaniels and DJ Jason “Jam Master Jay” Mizell. The trio thrived because D.M.C. was a sharp and reverberant rapper, but it was Run’s energetic and abrasive delivery that shone most, particularly on memorable tracks like “It’s Tricky,” “Christmas in Hollis,” and “Sucker MCs.” Influenced by ‘60s and ‘70s musical acts like the Rolling Stones, Rick James, and Parliament-Funkadelic, Run-DMC transformed hip-hop’s formerly disco-oriented style into pure b-boy flair: Kangol hats, embossed leather jackets, and shell toe Adidas were often the group’s uniform. The Def Jam signees even dedicated Raising Hell standout “My Adidas” to their sneaker of choice; they are hip-hop’s OG style icons. —Jaelani Turner-Williams

Birthplace: Long Island

Biggest Hit: "Give It Up"

Essential Deep Cut: "Burn Hollywood Burn" (feat. Ice Cube and Big Daddy Kane)

Incorporating themes of Black nationalism into his music, Chuck D, alongside Flavor Flav and Professor Griff, made noise as Public Enemy, a radical rap group that changed hip-hop forever.

His thick, authoritative baritone felt genetically engineered for leadership, and Public Enemy albums were amongst the first in hip-hop to play out like soundtracks for revolution. Flipping classic American cinema, Public Enemy’s iconic 1988 single “Rebel Without a Pause” is a salute to Black revolutionaries and a middle finger to the status quo.

A teenage Tupac Shakur would sample Chuck’s first verse for a rebel anthem of his own, “Panther Power,” which was also one of his earliest recordings. Chuck D made a career out of challenging the establishment, emboldening future stars to do the same. —Peter A. Berry

Birthplace: Hempstead, NY

Biggest Hit: "I'll Be There for You/You're All I Need to Get By" (Feat. Mary J. Blige)

Essential Deep Cut: "Meth vs. Chef" (feat. Raekwon)

Meth is one of the few generational rappers who has maintained relevance––as a personality if not for his bars––for decades.

If you could go back and chart the winner of the entirely silly and made-up and all important title of “King of New York,” Clifford Smith Jr. was the definitive belt holder in 1993. On the page, the Staten Island rapper would spit in remixed nursery rhymes that were both fractured and R-rated, stealing the cadences of “Patty Cake '' and quoting Dr. Seuss.

But Meth was the first to stand out amongst Wu's nine-man army, garnering attention for his wildly energetic stage presence and magnetic movie star quality. That’s why Biggie tapped him as the lone rapper to feature on Ready to Die in ’94. —Abe Beame

Birthplace: London

Biggest Hit: "Children's Story"

Essential Deep Cut: “Lick the Balls”

When hip-hop was still testing its limits, Slick Rick delivered The Great Adventures of Slick Rick in 1988 and put on a clinic in rap storytelling that is still studied today.

There’s a reason why Kanye West called himself “the new Slick Rick” on “Knock You Down,” or why Nas said “Slick Rick is like Jesus, G Rap wrote the bible” on his “Let Nas Down” remix. Even before that, tracks like “La Di Da Di” and “The Show” made indelible marks on rap, with the former being a staple via sampling, whether you know its title or not. Couple those artistic high water marks with his unique look and you get one of the most recognizable figures, and styles, in hip-hop. —Jordan Rose

Birthplace: Brooklyn

Biggest Hit: "Very Special" (feat. DJ Spinderella)

Essential Deep Cut: “Warm It Up, Kane”

There are arguably no rappers more important than Rakim and Kane in terms of ushering in the modern era of New York rap. On his first two albums, Long Live The Kane in ’88 and It’s a Big Daddy Thing in ’89, the Brooklyn rapper presented the next evolutionary link of the New York MC, taking the reins from the clipped and shouty rappers of the mid ’80s like Run-DMC, The Beastie Boys, and early LL.

The elements he’s known for—the witty setup and punchline, and casually spoken, rapid-fire delivery of brags and boasts about greatness while luxuriating in the pleasure of wordplay—would later be adopted by fellow Brooklynites Biggie and Jay-Z, as well as several subsequent generations of New York mixtape rappers like Jadakiss, Fabolous, Cam’ron, and more. —Abe Beame

Birthplace: Brooklyn

Biggest Hit: "Ms. Fat Booty"

Essential Deep Cut: "Hip Hop"

Mos Def, who now goes by Yasiin Bey, has a legacy defined by his bars. His debut solo studio album, Black on Both Sides, is a classic, with its inventive wordplay, provocative subject matter, and general intelligence.“Ms. Fat Booty” is a cheeky hit, “Do It Now” showcases his versatility while rapping alongside Busta Rhymes, and “Mathematics” is one of the more impressive displays of lyricism. “For ch-ching, cats get the ‘Cha-pow!’—you dead now/Killing fields need blood to graze the cash cow/It's a numbers game, but shit don't add up somehow,” is a masterclass in both alliteration and double entendre that highlights the corrupt and cyclical nature of a capitalist state. —Jordan Rose

Birthplace: Manhattan

Biggest Hit: "Hey Ma" (feat. Juelz Santana)

Essential Deep Cut: "Sports, Drugs & Entertainment"

Cam was once in line to take New York Rap’s crown.

After rapping with the likes of Big L early in his career, the Harlem native watched his stock rise quickly after releasing his debut album, Confessions of Fire, in 1998. However, between his debut and sophomore albums, his career stalled. He and Mase had a falling out, and he felt his deal with Sony/Epic was going nowhere, so Cam signed with his childhood friend Dame Dash over at Roc-a-fella and that’s when his run really began.

Killa waged a mixtape campaign and street movement that’s still talked about today. He hopped on a bunch of Blueprint beats and went crazy, not only helping Roc in their ongoing feud with Nas and Queens, but also solidifying the Dips as a viable crew for years to come. —Angel Diaz

Birthplace: Yonkers

Biggest Hit: "Why" (feat. Anthony Hamilton)

Essential Deep Cut: "Feel Me"

Jadakiss’ dexterous skill set is breathtaking in such an obvious way that even a casual fan would notice.

Debuting toward the beginning of the shiny suit era, Jada emerged as a humanoid flurry of incisive punchlines, macabre ghetto aphorisms, and tidy rhyme schemes. He’s rapped with The Notorious B.I.G.,had hit singles with Mariah Carey, and capably battled 50 Cent at the peak of his powers. As a member of the Lox, he’s got the honor of appearing on a song that’s so classic that it’s a veritable cliché.

In a microcosm of his career, 24 years after he first surfaced in the mainstream, his commanding performance in the Lox’s one-sided Dipset Verzuz battle schooled a new generation on the virtue of simply being a great MC. —Peter A. Berry

Birthplace: The Bronx

Biggest Hit: "Still Not a Player" (feat. Joe)

Essential Deep Cut: "You Ain't a Killer"

Big Pun’s larger-than-life persona made him one of the most beloved rappers to ever hail from the Bronx. His rapid-fire, tongue-twisting flow and masterful wordplay could baffle your brain, yet he was also one of the funniest rappers ever. He loved a word salad one-liner (“Dead in the middle of Little Italy”) but there was plenty else on the menu. One minute he would shoot up the block; the next he would be rapping about, “Packing the mac in the back of the Ac.”

He never forgot his heritage; incorporating Spanish into his rhymes, sampling Danny Rivera’s “En Un Rincon Del Alma” on “It’s So Hard,” and making Puerto Rican anthems like “100%.” As he proudly declared on “You Came Up,” “Latins going platinum was destined to come.” —Insanul Ahmed

Birthplace: London

Biggest Hit: "Rapp Snitch Knishes" (feat. Mr. Fantastik)

Essential Deep Cut: "Fancy Clown" (feat. Viktor Vaughn)

The biographical myth of MF DOOM is just as complicated, compelling, and enduring as his artistic legacy. While DOOM was born in London, his origin story begins in Long Island, where the rapper grew up alongside his brother DJ Subroc and started KMD. DOOM went by Zev Love X at the time, and KMD would release one album before Subroc died tragically in a car accident in 1993. Zev Love X disappeared for several years after that, and returned in the mid ’90s as the Metal Faced man, MF DOOM. With his blend of dense and imaginative lyricism, flips of quiet storm classics, and comic book inspirations, Operation: Doomsday become a cult classic.

DOOM would drop a number of masterful records throughout the 2000s and thanks in part to his work with Adult Swim his legend would transcend generations, with Madvillainy vinyl gracing the walls of NYU college dorm rooms and barbershops to this day. His metal mask is one of the most recognizable hip-hop artifacts ever. —Jordan Rose

Birthplace: Staten Island

Biggest Hit: "Back Like That" (feat. Ne-Yo)

Essential Deep Cut: "Mighty Healthy"

When Wu emerged from the slums of Shaolin with 36 Chambers, Ghost’s sword wasn’t as razor sharp as seasoned members like GZA, nor did he have the natural charisma of Method Man. His true identity as one of rap’s most gifted storytellers gradually emerged on Raekwon’s Only Built 4 Cuban Linx…, Ghost’s debut, Ironman, and Wu-Tang Forever. He narrated crime escapades on “Verbal Intercourse” yet could still deliver heartbreaking stories on tracks like “All That I Got Is You” and “Impossible.”

Ghost separated himself from his Wu brethren in the 2000s. The Staten Island rapper found success after signing to Def Jam and releasing albums like The Pretty Toney Album and Fishscale. But his all-time classic is still 2000’s Supreme Clientele, where he maintained his passionate delivery and comic splash panel–styled raps while adding a layer of abstraction. —Insanul Ahmed

Birthplace: Brooklyn

Biggest Hit: "Magic Stick" (feat. 50 Cent)

Essential Deep Cut: "Queen Bitch"

Lil’ Kim’s influence on fashion is undeniable, but we can’t ignore her prowess as a rapper. She stormed the industry with 1996’s Hard Core, using explicit imagery (who can forget the album poster of Kim crouched down with her legs propped open?) and songs that were equally as explicit. Kim, the only woman in Junior M.A.F.I.A., a rap group formed under the tutelage of the late Biggie Smalls, debuted during a time when being sexually provocative wasn’t the norm for women rappers. Most erred on the side of tomboy, and if they did lean into being sexy, none of them embraced it in the same way Kim did.

The Brooklyn rapper was so much more than her sexy image. She was a star with stage presence who delivered her lyrics in such a commanding and captivating way. Take her first single, “No Time”; she introduces herself with a strong “huhhh” and then proceeds to bend each bar and syllable to her will: “Nothin' make a woman feel better than berettas and Amarettas, butter leathers and mad cheddars/Chillin' in a Benz with my amigos, tryin' to stick a nigga for his pesos.”

After Biggie, a key collaborator for Kim, was murdered in 1997, her career could have easily come to a halt. But she went on to deliver many more of her own classic songs and memorable features. —Aria Hughes

Birthplace: Hempstead, NY

Biggest Hit: "Shook Ones (Part II)"

Essential Deep Cut: "Q.U. – Hectic"

Although he was born in Long Island, Prodigy is best associated with Queensbridge due to the late rapper’s work as one-half of the influential duo Mobb Deep. In the ‘90s, Mobb Deep released classics like The Infamous and Hell on Earth and timeless hits like “Quiet Storm,” “Get Away,” and “Shook Ones, Pt. II.” On the latter, Prodigy uttered the greatest threat ever made on wax: “Rock you in your face/tab your brain with your nose bone.” He vividly portrayed street life's harsh realities and explored themes of spirituality, metaphysics, and darkness. For all his lyrical prowess, his delivery made him unique. He was conversational on the mic, giving his menacing rhymes the calmness of an unyielding horror villain.

P’s Mobb Deep work is enough to make this list, but his solo career is why he belongs so high. Not only did he make bangers like “Keep It Thoro,” but in 2007, after a lackluster bid to cash out with G-Unit, P went independent and released Return of the Mac, a masterpiece in which he paired up with the Alchemist. The formula of a veteran rapper making a one-artist/one-producer album continues to this day, with artists like Freddie Gibbs, Roc Marciano, and Larry June all seeking out ALC’s beats to make a statement. Just another testament to why you should never question P’s trendsetting. —Insanul Ahmed

Birthplace: Brooklyn

Biggest Hit: "MC's Act Like They Don't Know"

Essential Deep Cut: "Outta Here"

In the late ’80s, KRS-One was known as "The Teacha," which may imply that going back through those records is akin to eating your vegetables. But he stands the test of time because, while he's one of the greatest conscious rappers ever, he was absolutely fresh. He became one of the first MCs to show you could spit critical race theory in the midst of a song dope enough to pass the car test. When MC Shan rewrote the parentage of rap in 1985 with “The Bridge,” KRS took on an army by himself and won it back for the Bronx, creating the modern concept of the rap battle in the process. Beyond that, the Jamaican Bronxite made the inextricable link between rap and the genre’s Caribbean heritage tangible by spitting in patois. —Abe Beame

Birthplace: Brooklyn

Biggest Hit: "I Know What You Want" (with Mariah Carey and the Flipmode Squad)

Essential Deep Cut: "Show Me What You Got"

After getting his start in the rap group Leaders of the New School, Busta released his debut album, The Coming, which featured high-octane singles like “Woo Hah!! Got You All in Check.” As time went on, Busta continued to raise the bar with albums like When Disaster Strikes, which included the hit single “Put Your Hands Where My Eyes Could See.”

He switched between styles and subject matter, proving he was not just a one-trick pony but a dynamic and well-rounded rapper with a delivery few could compare to. He possessed a unique tone and vocal ability that was instantly identifiable, from “Scenario” to “Look at Me Now.” That kind of longevity in the rap game speaks volumes about his exceptional talent and unwavering artistry. —Jessica McKinney

Birthplace: Mount Vernon, NY

Biggest Hit: "Ruff Ryders' Anthem"

Essential Deep Cut: "The Convo"

No one has given more visceral feeling on the mic than Dark Man X. Born and raised in Yonkers, DMX’s impact on New York and beyond is undeniable. He was not only able to compete with Jay-Z during his commercial peak, but outsell him. DMX’s first studio album, It’s Dark and Hell Is Hot, debuted at No. 1 on the Billboard 200 chart with classic songs like “Ruff Ryders Anthem,” nd in the same year he followed it with Flesh of My Flesh, Blood of My Blood. It was a feat no one had accomplished before. His opening three album run, including And Then There Was X in 1999, stand because they bucked the Shiny Suit era and other industry trends. His immediately recognizable raspy tone made his bars sound lined with rust, influencing future rappers like Pop Smoke and Scar Lip to lean into their own natural voices. X made even his most aggressively personal stories and bars feel relatable, and his own turmoil, as well as moments of redemption over the years made his music raw, real, and timeless. —Jordan Rose

Birthplace: Port of Spain, Trinidad and Tobago

Biggest Hit: "Super Freaky Girl"

Essential Deep Cut: "Itty Bitty Piggy"

When Nicki Minaj burst onto the scene, the Queens spitter immediately asserted herself as a powerhouse to be reckoned with. Sure, she had the support of Lil Wayne, but even without a cosign, her star power was undeniable due to her larger-than-life personality and lyrical prowess. Her 2009 mixtape, Beam Me Up Scotty, took the world by storm with tracks like "Itty Bitty Piggy," which showcased her fearless talent, razor-sharp lyricism, and cocky delivery. While other women before her had introduced sex-positive music, Nicki Minaj took it to another level, and became an idol that every girl wanted to emulate. Who wouldn’t want to rock a pink streak in their hair or a jet-black bob with bangs because of Minaj? To this day, the Queen embodies “versatility” like no other, shown throughout her four studio albums. Nicki pushed against societal boundaries and demonstrated her crossover power with hits like "Super Bass," "Starships," and "Bang Bang." From playful and provocative to hard-hitting and emotional, Nicki's got it all in her arsenal. She's a trailblazer, trendsetter, and force of nature, with a mark on hip-hop that can’t be measured by any chart.. There is no New York rap list without Nicki Minaj. Her legacy—complicated as it may be—is written in bold, pink letters. —Jessica McKinney

Birthplace: Queens

Biggest Hit: "In da Club"

Essential Deep Cut: “50 Bars”

In the summer of 2002 in New York City, the soundtrack was as consistent as it could be. 50 Cent’s 50 Cent Is the Future was playing on loop out of cars, and New Yorkers were sticking their chests out, knowing their city had the next universal star. At the time, 50’s music was inescapable in New York, but his run was just beginning. He was shot and shelved, and when he came back, he played bully ball. He had already revolutionized the mixtape scene, a hand-to-hand flooding of jewel CD cases that were often wrapped in cover art with 50, Lloyd Banks, and Tony Yayo dressed in matching color schemes. They were rapping over popular beats of the moment and dissing any other artists in their way.

The mixtapes had the streets, but it’s what 50 would do on his first studio album that propelled him into superstardom. The world was waiting for Get Rich or Die Tryin’, and with one quarter-drop and the sound of a gun being cocked, 50 released a classic, chock full of hits that would sell 12 million copies, one of the most successful hip-hop debuts of all-time. 50 would go on to release four more studio albums, and help carve out Banks, Yayo, Buck, and the Game’s solo career success before he transitioned into a television mogul, co-creating smashes like Power and BMF, and executive producing more than a dozen shows. We haven’t received a full album from Fif since 2014, but he always finds a way to stay in the conversation. He’s always egging on a fight, either through social media or, sometimes, documentary filmmaking. Like a shark, he smells blood. . Sometimes it’s fun to root for the bad guy. —Joe La Puma

Birthplace: Bay Shore, NY

Biggest Hit: "Loungin" (Feat. Total)

Essential Deep Cut: "Ill Bomb" (with Funkmaster Flex & Big Kap)

Really, you could make the argument LL Cool J is the prototype for every rapper. The bombastic teenager ("I Can't Live Without My Radio"); the pop-oriented loverboy ("I Need Love"); the coast-agnostic traveler ("Going Back To Cali"); the comeback kid ("Mama Said Knock You Out"); the battle-tested vet ("4, 3, 2, 1"); the older, relationship-based lover ("All I Have"); the slightly washed, slightly embarrassing old head who still gets inspired ("Headsprung"); the empire-minded businessman and hip-hop scholar (the launch of Rock the Bells and its commitment to honoring the pioneers).

And yet, with all his accolades, you shouldn’t look further than his name: Ladies Love Cool J. When hip-hop credibility demanded a harder exterior, LL introduced a softer, more seductive approach to the genre, one that didn't hide his fierce rap skill—should note, undefeated in rap beefs—but found ways to naturally blend it with smooth, melodic hooks and R&B influences. His malleability built the bridge to the more versatile, fully commercialized hip-hop that someone like Drake has fully capitalized on. —Jessica McKinney

Birthplace: Long Island, NY

Biggest Hit: "Juice (Know the Ledge)"

Essential Deep Cut: “New York (Ya Out There)”

Not to oversimplify, but you could separate rap into two phases: BR (before Rakim) and AR (after Rakim). When he emerged on the scene as a teen on "Eric B. Is President," not only was he fully formed as an MC, he was something the still-burgeoning genre had never seen before: a rapping machine, multisyllabic but dead serious, weaving Five Percent teachings with bravado and a cadence that had never been heard before. Kool Moe Dee once said Rakim invented the idea of flow.

In 1986, rap was a genre of party starters: chanting silly sayings on the 1s and 2s, songs like Run-DMC's "My Adidas" and Joeski Love's "Pee Wee's Dance" ruled. Rakim changed all of that. His debut with Eric B., Paid in Full, is a masterpiece, of course, maybe the crowning achievement of 1987, a year widely understood as one of the greatest in hip-hop history. But in a lot of ways, the God MC didn't fully arrive until Follow the Leader in 1988. It's the perfect rap performance—still maybe the single best the genre has produced—dazzling in its franticness, controlled internal rhymes, and sheer precision.

Like most rappers from the golden era, careers were shorter, and the genre was changing even too fast for the God to keep up. Don't Sweat the Technique, his fourth and last album with Eric B., arrived in 1992 and is easily the weakest in their catalog, with the production sounding a step behind what everyone else was doing. Within a couple of months, the more gangsta-oriented sounds of the West would take over with The Chronic. But Ra was still Ra—slightly more energetic, still as skilled ("Know the Ledge")—and still spreading conscious rap, as on "Casualties of War." And ultimately, his influence would win out, not only the God but the Alpha and the Omega for the rappers who we would eventually anoint as the GOAT. —Dimas Sanfiorenzo

Birthplace: Brooklyn

Biggest Hit: "I Can"

Essential Deep Cut: "N.Y. State of Mind Pt. II"

Nas is one of the best to ever do it, in part because he tried to fit the entire world into his bars. It became a weak spot during his beef with Jay-Z, but the image of Nas as the quiet observer, watching everyone and everything around him, feels true when you listen to his best records. On Illmatic, one of the great debuts in music history, or on the more polished prophecies of It Was Written two years later, he built a point-of-view that was often imitated but never replicated. He’s been a provocateur, challenging the status quo; he’s made crossover hits about empowerment; he’s rapped from the perspective of a gun and told a story in reverse. Hell, he called out Diddy before it was commonplace.

Beyond his classics, what’s impressive about Nas’ career is how he’s been able to adapt to the changing times. The Queensbridge rapper linked with Hit-Boy, one of the biggest producers of this generation to make the King’s Disease and Magic albums, a testament to possibilities of aging gracefully in a genre obsessed with youth. . With those projects, and collaborations with artists like Cordae, 21 Savage, The Weeknd, and others, Nas has figured out a way to evolve authentically rather than aimlessly chase the new. Decades later, he’s still got stories to tell. . —Ross Scarano

Birthplace: Brooklyn

Biggest Hit: “Hypnotize”

Essential Deep Cut: "You're Nobody (Til Somebody Kills You)"

In March 1997, Biggie Smalls had the East Coast under his wing. His new single “Hypnotize” was out and it sounded like a hit. His colossal, double-disc sophomore album Life After Death was basically finished….you know the story from here. He might be sitting atop this list if he’d had the time.

In his short, bright career, he used New York as the background for songs about the sometimes violent, sometimes jubilant realities of his community. Signed to Diddy’s Bad Boy Records, he proved a skillful storyteller who was proud of the craft, calling himself a writer more than anything. Lines like “Most of these niggas think they be mackin', but they be actin'/Who they attractin' with that line/'What's your name? What's your sign?… Things that make you smile, what numbers to dial,” on his grand debut, Ready to Die, showed that poetic quality of his language. No other rapper could capture the feeling and sound of an entire city with just five words: “It was all a dream.”

Rap fans of all ages quote and study him to this day, and, although his career ended amid strife and disharmony, Biggie wanted peace. In an interview with Angie Martinez in 1996, The Notorious B.I.G. declared it the year of love. —Ecleen Luzmila Caraballo

Birthplace: Brooklyn

Biggest Hit: "Empire State of Mind" (Feat. Alicia Keys)

Essential Deep Cut: "Allure"

In trying to steelman Jay-Z’s placement at the top of this here list—which declares him, *drum roll* please, the home of hip-hop’s greatest rapper—one discovers quite quickly that there simply is not a single coherent argument that can be made to the contrary. It’s undisputed; it's undeniable. Whether you’re talking technical proficiency, Billboard hits, realest stories, global influence, personal style, magnetic charisma, total sales, brand management, feature verses, artist co-signs, enlightening interviews, patronizing laugh or just sustained relevance—by any and every quantifiable metric or qualitative assessment—Shawn Carter is simply the best, better than all the rest.

However, what makes the Brooklyn king’s coronation that much more satisfying and virtuous, is that despite his masterful nonchalance and posture of inevitable rule, this position was unlikely and hard-fought. Jay released his first song, “HP Gets Busy,” in 1986, and it took a decade of rejection and reflection—working as a hypeman for Jaz-O and Kane, when not stacking his seed capital in the street—for Jay to find his voice and draft his brilliant, self-funded debut, Reasonable Doubt. And from that modest success he was then thrust into the loose ball scramble created by the vacuum of 2Pac and Big’s passing, and emerged on top…only to be challenged for supremacy by an anointed peer, Nas, who resented his improbable ascent. The fracas yielded a disputed split decision, but Jay pushed forward, luster intact. In the 20 plus years since, Jay-Z has projected an uninterrupted air of dominance on the culture despite having had to contend with a constantly changing guard of adversity—shifting sounds, young challengers, new technology, public indiscretions, and, frankly, just getting older in a young man’s game.

Still, no matter what has been thrown at Jay-Z he has persevered and prevailed, growing as an artist, a businessman, and a brand. And he has done it with an intensity, integrity and grace wholly unique to the Empire State. Whether it’s his hustler’s ambition, his cosmopolitan curiosity, or his commercial interest, the blueprint to Jay’s success is his supreme distillation of characteristics that have defined Gotham since its founding in the 17th century. So yes, he sits at the top of this list because of his litany of unprecedented and unduplicated accomplishments, but more, much more, because he did it, he did it all the NY way. —Noah Callahan-Bever