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Jun 01, 2023

50 Best New York Rappers, Ranked

From Jim Jones to Jay-Z and more, here is our ranking of the 50 best rappers from New York. In the ever-evolving landscape of hip-hop, few places have played a more pivotal role in the genre’s legacy

From Jim Jones to Jay-Z and more, here is our ranking of the 50 best rappers from New York.

In the ever-evolving landscape of hip-hop, few places have played a more pivotal role in the genre’s legacy than New York. Thousands of rappers have grown from hip-hop’s birthplace throughout the course of its 50-year history. From Big L, whose gritty bars echoed through Harlem’s streets to the meteoric rise of Pop Smoke that electrified Brooklyn’s drill scene, New York’s rap scene boasts a wide array of voices that have been instrumental to the genre’s evolution and dominance throughout the decades. Others like Nicki Minaj shattered gender norms and redefined female empowerment, while Jay-Z, a self-made artist who elevated himself from Brooklyn’s Marcy Projects to a global mogul, has cemented his name in the history books forever.

In homage to New York’s impact on hip-hop, the Complex Music team has curated a list ranking 50 of the greatest rappers from the city (and its surrounding areas)—from some of its founding fathers and mothers to young bloods who have injected new energy into the city’s sound in the last five years. Skill, lyrical ability, and impact on the genre and culture in New York and beyond, were key factors in determining who made the cut. There are a few names on this list who may not have originated from New York, but their formative years were spent within the city, and their music certainly channels the essence of New York’s culture and sound.

Here are our picks for the best New York rappers of all time, so far:

In the ever-evolving landscape of hip-hop, few places have played a more pivotal role in the genre’s legacy than New York. Thousands of rappers have grown from hip-hop’s birthplace throughout the course of its 50-year history. From Big L, whose gritty bars echoed through Harlem’s streets to the meteoric rise of Pop Smoke that electrified Brooklyn’s drill scene, New York’s rap scene boasts a wide array of voices that have been instrumental to the genre’s evolution and dominance throughout the decades. Others like Nicki Minaj shattered gender norms and redefined female empowerment, while Jay-Z, a self-made artist who elevated himself from Brooklyn’s Marcy Projects to a global mogul, has cemented his name in the history books forever.

In homage to New York’s impact on hip-hop, the Complex Music team has curated a list ranking 50 of the greatest rappers from the city (and its surrounding areas)—from some of its founding fathers and mothers to young bloods who have injected new energy into the city’s sound in the last five years. Skill, lyrical ability, and impact on the genre and culture in New York and beyond, were key factors in determining who made the cut. There are a few names on this list who may not have originated from New York, but their formative years were spent within the city, and their music certainly channels the essence of New York’s culture and sound.

Here are our picks for the best New York rappers of all time, so far:

When “Munch” took over the streets of New York a year ago, the quicksand quality of Ice Spice’s rhyme and rhythm—courtesy of her sound crafter, RIOTUSA—amassed a crowd of head-scratchers and boppers alike. Ice was, and is, having fun with it, and many assumed the moment would equate to an evanescent, flat-lined ascent. What instead followed is a speedy, steady rise sustained by a distinct flow, alluring sexy drill sound, unsuspecting bars, and somehow both airy and hard-hitting delivery. Like a woman with something to prove, Spice released her first EP, Like..? five months after that single. Tracks like the later Nicki Minaj-assisted “Princess Diana,” and “Gangsta Boo” with fellow promising young spitter Lil Tjay best exhibit her pen’s cheeky wit with lines like, “Wanna be me, so she do my emotes/And my name in her mouth so I bet she gon’ choke.” Rather than sit comfortably on the princess throne once knighted by the queen, Spice has kept her foot on our necks and exhibited a special gravitational pull. In under 10 months, she has collaborated with everyone from London’s PinkPantherress to US pop sensation Taylor Swift and now-mentor Minaj—twice. Although we often see artists with distinct New York energy take off, seldom does that buzz translate to a massive national stage with this swiftness. And despite a couple of crossover moments, the deluxe version of her debut reminds us that she’s still that girl at the “Deli.”

In the foundational year of their rise, women in this space are historically held to a higher, impossible standard. The legendary Lil Kim was initially dismissed and comically reduced to a “botched” fashion statement. Cardi B’s longevity was ferociously doubted. Queen Latifah was judged for carrying the same toughness as her macho peers. Ice Spice will not be the exception to the rule; still, however she evolves from here, the rookie of the year will go down as the epicenter of this blissful, deliciously women-led moment in New York rap. Despite the nostalgic nature of an all-time list like this, it’s important to remember that in time’s totality exists the beauty of now, and Ice Spice’s impact on her generation of New York rap is undeniable. —Ecleen Luzmila Caraballo

Underground-rap legend Pharoahe Monch emerged as a leading act in the late ’90s after his rap duo with Prince Po, Organized Konfusion, had a temporary breakup. Armed with technical rhymes and animated delivery, Monch reintroduced himself on his 1999 solo debut, Internal Affairs. On the project, the South Jamaica, Queens native offered dexterous and poetic verses over abstract jazz samples from saxophonist Oliver Nelson and multi-hyphenate musician Quincy Jones. The sounds were fitting, as Monch has pointed to jazz greats Miles Davis and John Coltrane as his childhood musical guides. What solidified Monch’s artistry was his grim storytelling ability, metaphorical precision, and deft chopper flow, which made him a fitting collaborator with East Coast contemporaries such as Busta Rhymes, Method Man, Redman, M.O.P., and Talib Kweli. The rapper remains a cornerstone in hip-hop, as he still pushes music independently. His talent and impact have also earned him recognition from contemporary legend Eminem, who name-dropped Monch in his Rock and Roll Hall of Fame induction speech and the final verse of 2013 single “Rap God.” —Jaelani Turner-Williams

Diddy's rise to fame as a producer and entrepreneur is undisputed, but his reputation as a rapper, especially one of the finest from New York, sparks debates. Coming up in the pivotal '90s hip-hop era, Diddy founded Bad Boy Records in 1993 — a home to legendary acts like The Notorious B.I.G. and Mase. As an executive producer, he played a pivotal role in shaping the East Coast's distinct sound at the time, blending top-tier lyricism with catchy hooks and smooth R&B samples. While he first showed glimpses of his own artistry on tracks like "All About the Benjamins," it wasn’t until the late '90s and early 2000s that he emerged as a formidable solo artist, with No. 1 albums like No Way Out and Press Play. His starpower also shone through on classic love songs like “I Need a Girl (Pt. 2),” and heartfelt, timeless singles like “I’ll Be Missing You.” Though Diddy may not match the skillfulness of the artists he nurtured on Bad Boy, he is widely acknowledged as a visionary and tastemaker, with more impactful hits and memorable verses as an artist than you might realize. —Jessica McKinney

Biz Markie and my grandmother passed away on the same day, July 16, 2021. Growing up, my cousin and I would watch music videos on the Box, MTV, and BET in her living room for hours. One of the videos we watched the most was Biz Markie’s “Just a Friend.” We’d be in that living room singing our little hearts out just like Biz did on the hook. His undeniable charm and humorous approach reminded hip-hop fans that as West Coast “gangsta” rap was starting to take over the airwaves, music could be fun too. Biz was always like that though. A couple years prior, he released songs like “Make the Music with Your Mouth, Biz” and “Pickin’ Boogers,' which featured the unique beatboxing skill set that made him a fan favorite. His influence on the game is major. Snoop remade his song “Vapors,” which put Biz’s storytelling skills on front street. His music has been sampled a ton too — most notably by Mary J. Blige on “I Love You.” And the comedy he featured in his videos influenced the likes of Busta Rhymes and Ludacris. He was a dancer, a beatboxer, a singer, a rapper; all in all, Biz was hip-hop. —Angel Diaz

Think of the great Yonkers trio 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 wisened soul (a ripe 20 years old when they got started). As a whole, The Lox have 30 years of unbroken brotherhood as a legendary group that released classics on New York’s two dominant late ’90s labels. Styles was dynamic within the group, 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. He also had great prolificacy over the years in the mixtape scene (for younger inquisitive readers, I implore you to begin with the 2006 classic The Ghost in the Machine). But 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

Don’t underestimate Jim Jones’ ability to stay relevant. Everyone knows his biggest solo hit, “We Fly High (Ballin'),” but he’s impressively strung together countless defining moments in addition to those commercial peaks. If you ask Jim, he’s had "three careers" by now, recently explaining to Complex that his "first career" was his early days coming up with Cam’ron and starting the Diplomats, followed by his own solo career. And in the 2020s, he says he's in a "whole other zone" in the midst of a third career chapter. As a result, 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. He can also complement the hits by dipping into his lyrical bag when inspiration strikes. Whether he’s rapping with the Diplomats, recording his own solo material, or jumping on remixes with A-list stars, Jim Jones is always as New York as they come. —Eric Skelton

Though he doesn't have the Billboard accolades to show for it, Grand Puba was one of the most influential New York rappers of his era. The New Rochelle native first emerged as an artist in the ’80s, but didn't really make a mark until 1990 as part of Brand Nubian. On the group's One for All album, Puba turned Five-Percent Nation teachings into catchy earworms, helping spark a rise of mainstream conscious rap.

But get a rapper who can do both. As a solo artist, Puba leaned less into rhetoric and more into the playful charm of a street-smart New Yorker with the gift for gab — 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)," his biggest hit. Tommy, you owe Puba a check or two for that. —Donnie Kwak

Any time you can viably say you redefined the function of an artform, you’re probably an undisputed legend. As a member of Grandmaster Flash and the Furious Five, one of rap’s first great rap groups, Melle Mel earned the status 41 years ago. Mel helped expand hip-hop’s thematic landscape with “The Message.” The 1982 single is credited with introducing the notion of conscious rap to the mainstream. While previous rap 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. He 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.” It’s a narrative approach that’s fueled everything from Nas’ Illmatic to Jeezy’s Let’s Get It: Thug Motivation 101, making Mel a stylistic ancestor for some of the most poignant songs in hip-hop history. —Peter A. Berry

Brownsville, Brooklyn rapper Sean Price wasn't a household name. He was more like the guy who does construction work on your house. He was a craftsman, a blue-collar rapper, born wearing a Carhartt jacket and Timberland boots. In the ‘90s, Price — under the moniker Ruck — made a name for himself as one-half of duo Heltah Skeltah and as a member of collective Boot Camp Clik. As New York rap changed dramatically every few years, Price fell into obscurity until he unexpectedly became a blog-era favorite, thanks largely to the efforts of NahRight founder Eskay. In the mid-2000s, with albums like Monkey Barz and Jesus Price Supastar, Price’s solo career took off thanks to his hard-hitting, no-nonsense lyrical style and gravelly voice that stood in stark contrast to the emergent styles of regionless rappers during New York’s an identity crisis. “Back smack a rapper for rapping with Auto-Tunes/Fucking rapping computer thug/Stick the hard drive in your ass, computer love” is typical of Price’s dark humor. Despite his untimely death in 2015, his legacy is that of a rapper who stayed true to himself. —Insanul Ahmed

ASAP Rocky emerged on the scene in the early 2010s as part of a new wave of hip-hop artists reshaping the genre with rap collective ASAP Mob, alongside the likes of ASAP Yams and ASAP Ferg. His unique blend of fashion-forward style, charismatic delivery, smooth cadence, and pretty-boy aesthetic set him apart as a standout talent. Rocky's debut mixtape, Live. Love. ASAP, released in 2011, quickly 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. But what truly solidified ASAP Rocky's artistry is his relentless pursuit of evolution and experimentation. 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." Whether it's his impeccable fashion sense, innovative music videos, or his knack for unique collaborations (like “Praise the Lord” with Skepta), ASAP Rocky's contributions to New York rap are undeniable. —Jessica McKinney

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, Kool Dee 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 (you can find it on YouTube), making it one of the first viral hip-hop moments.

Once the Treacherous Three disbanded in 1985, Moe Dee became one of the first rappers to leave a group and launch a solo career. He would go on to become the first rapper to perform at the Grammys and later won one for Best Rap Performance in 1991. Most of those things happened before he ran afoul of LL Cool J. In fact, How Ya Like Me Now isn’t just his best album; it’s a comeback album. It’s an OG sonning a young upstart. Hip-hop in the ‘80s was the Wild West, but few were as long in the saddle as Kool Moe Dee. —Insanul Ahmed

Noreaga is one of the most unique rappers in hip-hop’s history. We first heard the rapper, born Jose Luis Gotcha, in 1996, 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 Capone 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 as the shiny suit era began to close its grip on the game. 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. “Superthug” set their wave in motion with the rapper and production duo having multiple hits under their belts thereafter. He’s also rightly credited for embracing reggaeton stateside, ultimately helping the genre go mainstream. Today he hosts one of the more important podcasts in rap, Drink Champs. N.O.R.E. always knows how to stay relevant. —Angel Diaz

Albeit tiny in stature, East Flatbush rap veteran MC Lyte broke out with weighty bars. Lyte kicked down doors as the first woman to release a solo rap album. Her 1988 debut Lyte as a Rock showcased her rugged and feminist-leaning rhymes, akin to fiery Queens trio Salt-N-Pepa, Queens rapper Roxanne Shanté, and the Bronx’s Sha-Rock. 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” (aimed at former rap rival Antoinette), and “Paper Thin.” “On the topic of rapping, I should write a pamphlet better yet a booklet/Your rap is weak homegirl, and it's definitely crooked,” Lyte proclaims on “10% Dis.” Following the ’80s boom-bap, Lyte continued to leave a mark, showcasing her clever wordplay and quick-witted declarations on classic cuts like “Cha Cha Cha,” “Poor Georgie,” “Ruffneck,” and Brandy’s “I Wanna Be Down (Remix)” with female rap peers Queen Latifah and Yo-Yo. Unless women rappers were already in a group together, in the ‘90s, 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, who collaborated with Lyte on 1996’s “Cold Rock a Party.” —Jaelani Turner-Williams

Ja Rule found a way to make a lane for his melodic flows and R&B hits while still keeping it gangster. 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 notably collaborations with women vocalists like Jennifer Lopez and Ashanti, the latter of which is pivotal in one 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. His influence can be heard in the music of contemporary New York acts like A Boogie Wit Da Hoodie and Lil Tjay, commercially successful rappers who tap into melodic bags but still flex their lyrical ability. —Jordan Rose

Before eccentric artists like Danny Brown, Redman, Madlib, and the late MF DOOM took hip-hop by storm, there was Kool Keith. Hailing from the Bronx, the wordsmith founded local rap enclave the Ultramagnetic MCs in 1984. An indefinite hiatus nine years later, Keith set out on his own. He adopted alter egos like Dr. Octagon, Dr. Dooom, and Black Elvis (a list that has since grown to at least 58 in total), drawing inspiration from sci-fi and comic books to create his mind-boggling rhyme schemes. 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 oddly referenced pornography (“Girl Let Me Touch You”) and homicide (“Earth People”) over synthetic production, making Keith a pioneer in the comic book–inspired rap canon. Although mainstream rappers were gaining popularity with commercial-friendly and ‘gangsta’ appeal in the ‘90s, Keith’s unique formula and weird rhymes solidified him as one-of-one. —Jaelani Turner-Williams

Ol’ Dirty Bastard’s solo debut album shook the table of rap. Return to the 36 Chambers: The Dirty Version is a masterpiece because it distills ODB’s sporadic flows, New York madness, and pension for erratic rhymes into one air-tight 17-song serving. He solidified his legacy with his work in Wu-Tang, but some of his most memorable verses are in Return to the 36 Chambers, like the bombastic “Brooklyn Zoo” or hit record “Shimmy Shimmy Ya.” Only Ol’ Dirty Bastard would think to turn his EBT card into an album cover, subsequently making it a hip-hop artifact that has been replicated and turned into rugs for college dorm rooms across the country. Despite his troubled life, ODB’s uncontrollable spirit made his stories come to life in his raps. “Shame on you when you step through to the Ol’ Dirty Bastard!” —Jordan Rose

Foxy burst onto the scene in 1996 as a featured artist on a couple of hits. First she played Bonnie to Jay-Z’s Clyde on “Ain’t No” — the lead single to Jay’s debut album, Reasonable Doubt. 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 officially 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, Nature, and Cormega, with production spearheaded by Dr. Dre. The Firm album dropped in 1997 and was considered a flop, but that opinion has wavered over the years. They had a hit with “Phone Tap” and had unreleased gems like “La Familia.” Foxy has since released two other solo albums with relative degrees of success. Still, nearly 30 years since her debut, Fox Boogie stands not only as one of the most influential women rappers to ever live, but she's a style icon as well. Her signature thin eyebrows, dark lipstick, and high-end fashion pieces have made Foxy a favorite of internet hip-hop archivists and is a fixture on the moodboards of stylists and young girls alike. —Angel Diaz

The GZA is one of the most cerebral and understated rappers ever. While most ‘90s New York rappers (including his Wu brethren Raekwon and Ghostface Killah) were flashy and iced out, and others were didactic and preachy, GZA was neither. A student of Rakim, he was smooth on the mic, almost never 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. More likely to incorporate chess and complex metaphors into his rhymes than nice watches and straightforward punchlines, GZA is one of the unique voices to emerge from New York. —Insanul Ahmed

Before Fab, there was a clear delineation between “mixtape rappers” and “mainstream rappers.” It was like the divide between a hooper famous for gravity-defying in-game dunks, and a sturdy all-around player who wins championships. Mixtape rappers were well-respected, battle-tested assholes who traded in the currency of bars but couldn’t translate their talent to a (lucrative) commercial setting that would sell across regions and demographics. In came Fab, a Frankenstein-like monster created by mixtape king DJ Clue to destroy freestyles with witty and hilarious punchlines. He then shocked the world by packing his debut, Ghetto Fabolous, with addictive early 2000s mall rap that still highlighted all the elements of his style that made him great (See: “Superwoman,” “Can’t Deny It,” “Young’n,” and “Into You,” among others. All “106 & Park-core exemplars). 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

In an era predicated on bars and hit records, Fat Joe has the best of both worlds. There are few rappers on this list that have been able to notch a hit in nearly every decade they’ve been active, but Joey Crack holds that distinction, setting him apart from many of his contemporaries from the 90s. 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. And his work with Terror Squad proved that he was more than just a hit-maker. Even beyond his hit records, Fat Joe’s massive personality and stage presence embodies what it means to be a New York MC. —Jordan Rose

At the height of his powers as arguably the best rapper in the world, Jay-Z used a quick bar to pay homage to a titan of hip-hop’s golden age: “Yeah, hearing me rap is like hearing G Rap in his prime.” As great as Hov thought he was, he still found that comparing his own style to Kool G Rap was the best way to describe his abilities, a testament to a G Rap’s legacy as one of rap’s earliest, and most proficient, street-rap stalwarts. 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 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

Big L, like several artists on this list, had his life tragically cut short at a young age. Still, he left an undeniable legacy during his short career in New York, putting out records like "Put It On," “Ebonics,” and "98 Freestyle" that have stood the test of time. Big L had a smooth flow that appealed to the masses, which he used to deliver poetic, lyrically dense verses that inspired and motivated even his most accomplished peers. Nas once told Funkmaster Flex that Big L “scared me to death,” remembering, “I said, 'Yo, it's no way I can compete if this is what I gotta compete with,’” after hearing his music. And 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 (although Jay-Z later revealed that Roc-a-Fella was "about to sign him right before he passed away"). Still, Big L’s gifts as an all-time lyricist and storyteller could never be denied, earning praise by everyone from Hov to Eminem. —Eric Skelton

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 — "P. Diddy made me pretty" — 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. (See No. 32 for one example.) Mase's vocal delivery — deliberate, nonchalant, and perfectly in the pocket of the beat — almost feels like a lost art now, akin to a midrange jumpshot. But Mase put points on the board for years, and for that he will always be a great. —Donnie Kwak

Even with his life tragically cut short, Pop Smoke was still able to create waves in rap that will be felt for generations. The Canarsie, Brooklyn rapper 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, and still has motion to this day, 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. Following Pop’s death in February 2020, his posthumous debut album 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 songs like “Mood Swings,” “The Woo,” and “What You Know Bout Love” that explored new sonic territory. New York drill has expanded in the years that followed Pop’s death, but his influence can still be heard in ad-libs, bars, and beat selections across the subgenre, proving his undeniable impact on New York rap (and beyond). —Jordan Rose

The Chef should be in the Rock and Roll Hall of Fame twice — once as a member of the Wu-Tang Clan and once as a solo artist. The Purple Tape alone should be enough to get the god in. Along with his partner-in-rhyme Ghostface Killah, Raekwon ushered in a style of rap 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 28 years after its release. The concept of sampling John Woo’s The Killer movie throughout was a game changer. “Wu-Gambinos” had every rapper and fan coming up with nicknames and aliases. His fashion sense also stood out. The image of him wearing that Polo Snow Beach jacket in the “Can It Be All So Simple ” video is etched in the brains of hip-hop heads across the globe, making the pullover one of Ralph Lauren’s most sought-after pieces. —Angel Diaz

Cardi B is anything but a regular degular, shmegular girl. The Bronx native 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 Bronx roots. Even more impressive, she made it to the top 20 of this list with just one studio album, Invasion of Privacy. Standout tracks like "I Like It" and "Bartier Cardi" showcased her talent for creating infectious club bangers, skillfully blending her Caribbean and Latin influences. In addition to one studio album, Cardi has also been a part of chart-topping collaborations like “WAP” with Megan Thee Stallion, “Tomorrow 2” with GloRilla and “Put It on da Floor Again” with Latto. In a time when women rappers were rising in numbers, Cardi B stood out because of her authenticity. 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. Cardi B's legendary journey is a testament to her unwavering authenticity, determination, and resilience in the face of criticism and challenges. —Jessica McKinney

It’s hard to say any one entity created a particular aspect of rap culture, but 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, Tip is most responsible. In the years since the clique’s debut, Q-Tip and a Tribe Called Quest have become known as forefathers of backpack rap, opening the doors for folks like Yasiin Bey (aka Mos Def), Talib Kweli, Kanye West, and countless others who created outside-of-rap binaries.—Peter A. Berry

As a hip-hop forefather, Joseph “Run” Simmons played a defining role in the genre’s influence as part of the iconic trio Run-DMC. In the late 1970s, the Queens native, first known as “Easy D,” began as a DJ and hype man for fellow hip-hop pioneer Kurtis Blow before coming from behind the turntable and onto the stage in 1983. As a part of Run-DMC, 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 — and Jam Master Jay’s scratch technique — 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 hypebeasts. Run’s skill and enthusiasm opened the door for revolutionary predecessors LL Cool J, a Tribe Called Quest, Ice Cube, Public Enemy, the Beastie Boys, Eric B & Rakim, and Slick Rick. —Jaelani Turner-Williams

If Malcolm X had dropped a rap album, he might have sounded like Chuck D. Infusing songs with themes of Black nationalism, the Long Island native emerged alongside Flavor Flav and Professor Griff as Public Enemy, a radical rap group that helped change hip-hop forever. Operating as the primary lyricist, 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 rap stars Ice Cube and 2Pac to do the same. He even told Elvis to go fuck himself. Brazenly defiant, Chuck D is the “conscious rapper.” When other MCs were serving up lessons on ghetto economics or how to earn your right to party, Chuck D was teaching us how to fight the power. —Peter A. Berry

In a medium that has always been a young man’s game, where five years constitutes a good run, 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 annual silly, made-up, and all important title of “King of New York,” Clifford Smith Jr. was the definitive belt holder in 1993, preceding the reign of Biggie and Nas in ‘94. 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 the 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 his debut classic, Ready to Die in 1994, handing the crown down from one king to the next. —Abe Beame

Storytelling is the bedrock of hip-hop, and Slick Rick is one of the architects who made that foundation so sturdy. When hip-hop was still finding its identity (and New York was diving headfirst into its Golden Age) Slick Rick delivered The Great Adventures of Slick Rick in 1988 and put on a class 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. “Children’s Story” changed how rappers rap and affected the genre on a national scale thanks to how Rick was able to seamlessly weave high-level storytelling into the frameworks of his patented rhyme scheme. Couple that with his unique look—punctuated with an eyepatch due to a glass injury he suffered as an infant—and you get one of the most recognizable figures, and flows, in hip-hop. —Jordan Rose

There is arguably no rapper who is more important (alongside Rakim), in terms of their ushering in the modern era of New York rap, than Big Daddy Kane. On his first two albums, (Long Live The Kane in ’88 and It’s a Big Daddy Thing in ’89), over some of Juice Crew mastermind Marly Marl’s greatest loops, 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, among many others. 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

Mos Def, who now goes by his birth name Yasiin Bey, has a legacy defined by his bars. His debut solo studio album, Black on Both Sides, is considered a hip-hop classic thanks to its inventive wordplay, complex song structure, and unrelenting bars. “Ms. Fat Booty” is an undeniable hit that continues to be sampled on modern day standouts like JID’s “Surround Sound,” “Do It Now” showcases his versatility while rapping alongside Busta Rhymes, and “Mathematics” is widely revered as one of the most impressive displays of lyrical exercise. “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. There are classes being taught about Mos Def’s elite wordplay, and his lyrical prowess is why his legacy has endured beyond his career with Blackstar. —Jordan Rose

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. He was signed to Untertainment with the cosign of the late Notorious B.I.G. and had two hit singles, “357” and “Horse and Carriage,” featuring his then–best friend Mase. 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 decided to sign with his childhood friend Dame Dash over at Roc-a-fella in 2001 — and the rest, as they say, is history. 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. Dipset’s partnership with the Dynasty didn’t last long, though, as both sides had a memorable split around 2004. He’s probably known more to the younger generation as a reaction meme of the rapper who used to wear pink, but the real ones remember when he almost took the throne. —Angel Diaz

Years into his career, Jadakiss stands as the Carmelo Anthony of hip-hop. He’s never been a top-five player, but his dexterous skill set is breathtaking in such an obvious way that even a casual fan would notice. The OGs revere it. Having surfaced alongside Bad Boy 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 been one of rap’s most reliably electric 16s for decades now. He’s rapped with The Notorious B.I.G. and 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

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.” Sadly, he died in 2000 before getting to truly enjoy his success. The legacy of his debut, Capital Punishment, remains — few rap albums before or since are as lyrically dense yet playfully fun. —Insanul Ahmed

The myth of MF DOOM is just as complicated, interesting, and enduring as his lyrical legacy. While DOOM was technically born in London, his origin story started 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. As DOOM, he famously covered his visage, first with a stocking and later with a metal faceplate fashioned after the accessory Russell Crowe wore in Gladiator. With his blend of dense and imaginative lyricism, classic New York production, and comic book inspirations, projects like 1999’s Operation: Doomsday helped turn DOOM into one of the most influential artists of the era. DOOM’s legend transcends generations, with Madvillainy vinyl gracing the walls of NYU college dorm rooms and barbershops to this day, and his metal mask is one of the most recognizable hip-hop artifacts ever. Even his passing being revealed on New Year’s Eve in the final hours of 2020, several months after it happened, sounds like something nefariously crafted by the rapper to fit his self-written tale. DOOM’s origin story could get lost in the sands of time, and his legacy would still live on. “Just remember, ALL CAPS when you spell the man’s name.” Long live the villain. —Jordan Rose

The Wu-Tang Clan is arguably the greatest rap group of all-time,and the case for Ghostface Killah being the best member is based on the fact that his success is not limited to the Wu’s initial five-year run. 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. “That's the past, heavy ice Rollie laying on the dash/Love the grass, cauliflower hurting when I dumped the trash,” he spits on “One.” What does it mean? We’re not sure, but Ghost once explained his thoughts quite sufficiently: “I don’t give a fuck if you don’t know what I’m talking about — this is art.” —Insanul Ahmed

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 n**** 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. She crossed over into pop with the Grammy Award–winning “Lady Marmalade” alongside Pink, Mya, and Christina Aguilera. Lil’ Kim opened doors for each of the women rappers who came after her and helped the fashion world understand the power of hip-hop. Many have benefitted from the blueprint she laid. —Aria Hughes

Although he was born in Hempstead, Long Island, Prodigy is often 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 whon 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

In the late ’80s, KRS-One was known as "The Teacha," which suggests exploring his work is an act of vegetable eating that stands alongside the dour historical recountings and militant spit scriptures of the late ’90s/early aughts underground scene. But he stands the test of time because while he's one of the greatest conscious rappers ever, the label does a disservice to understanding how fresh Lawrence Parker was. 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, getting offered a top 3 all time live rap record with Live Hardcore Worldwide (1991). 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. —Abe Beame

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,” which exuded his now signature electrifying energy, rapid-fire flow, and clever yet thought-provoking lyrics. As time went on, Busta Rhymes 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 effortlessly switched between different styles and subject matter, proving he was not just a one-trick pony but a dynamic and well-rounded rapper. Busta Rhymes possessed a unique tone and vocal ability that was instantly identifiable — characterized by a fast-paced delivery and intensity. We can't talk about Busta without mentioning his futuristic and innovative visuals though. One of his most iconic albums, Extinction Level Event: The Final World Front, featured the mesmerizing hit "Gimme Some More." Not only did the song showcase his innovative storytelling, but the accompanying music videos were a visual feast. Beyond his solo endeavors, Busta Rhymes collaborated with a variety of artists, including hits like "What's It Gonna Be?!" with Janet Jackson, the timeless classic "I Know What You Want" with Mariah Carey, and the banger "Look at Me Now" with Chris Brown. Busta Rhymes' longevity in the rap game speaks volumes about his exceptional talent and unwavering artistry. —Jessica McKinney

No one has had more visceral passion behind the mic than Dark Man X. While born and raised in Yonkers, DMX’s impact on New York City 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.” X followed this with Flesh of My Flesh, Blood of My Blood and …And Then There Was X, which all went No. 1, making for one of the most successful and impactful album runs in hip-hop history. These three albums in particular stand out because they all sound distinctly like X—he didn’t compromise his rapping style to fit the Shiny Suit era or any industry trend. DMX’s distinctly vaw rapping style is synonymous with New York City. His immediately recognizable raspy tone made his bars sound lined with rust, and his gritty delivery influenced future standout rappers like Pop Smoke and Scar Lip to lean into their own natural voices. X made even his most aggressively personal stories and bars (like “I’ve been through mad different phases like mazes to find my way”) feel relatable, and his own turmoil, as well as moments of redemption over the years made his music raw, real, and timeless. —Jordan Rose

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, Nicki's 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 goes far beyond her chart-topping hits. Nicki has opened doors for countless rappers and empowered an entire generation of young women to be unapologetically themselves. There is no New York rap list without Nicki Minaj. Her legacy is written in bold, pink letters. —Jessica McKinney

In the summer of 2002 in New York City, the soundtrack was as consistent as it could be in hip-hop. 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 rap 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 evidence of his staying power is his current city-to-city Final lap tour that’s selling out arenas around the world over 20 years later. Sometimes it’s fun to root for the bad guy. —Joe La Puma

LL Cool J, born James Todd Smith, emerged onto the rap scene in the mid-1980s during a pivotal era for hip-hop in New York City. Just a decade after hip-hop came to life in the city, the genre evolved rapidly with a new class of artists who were eager to flex their creativity and talent. LL Cool J was a standout act. His infectious enthusiasm and razor-sharp bars set him apart very early on in his career, best exhibited in his early singles. His 1985 debut, Radio, released to critical acclaim, and at just 17 years old, the young rookie captured the vibrant spirit of teenagers at the time, showcasing an unparalleled charisma and delivery. Songs like “I Can’t Live Without My Radio” and “Rock the Bells” quickly became anthems for the new school. Classic singles like “Mama Said Knock You Out” and “Headsprung” showcased his aggressive and compelling style that’s kept him relevant for many decades and shifts in the industry. While rap during this period was dominated by battle-rap aesthetics and hardcore sounds, LL Cool J will go down in history as one of the best (and most influential) because of his versatility. The Queens rapper introduced a softer, more seductive approach to the genre that effortlessly blended his fierce rap skill with smooth, melodic hooks and R&B influences. Songs like “Doin’ It,” “I Need Love,” and “All I Have” abandoned combative bars in favor of romantic and sexually charged lyrics. LL Cool J was one of the first rappers who made it cool to appeal to women by showing a more vulnerable side, paving the way for artists like Drake. While there are several pioneers who contributed to the melodic rap subgenre we hear on the radio today, LL Cool J undoubtedly deserves his flowers as a standout trailblazer. —Jessica McKinney

Most artists on this list can be described as “your favorite rapper’s favorite rapper,” but few hold that distinction over three rap generations like Rakim does. He came up during the heart of the Golden Era of hip-hop, where bars reigned supreme, and he cemented himself as one of the greatest MCs to hold a mic, in large part thanks to his technical ability. Rakim’s early work with Eric B. in the late ‘80s and ‘90s became gospel for future rap legends to emulate. Their debut album, Paid In Full, still gets referenced today despite coming out nearly four decades ago, with songs like “I Ain’t No Joke” and “Paid In Full” still frequently heard on commercials and New York street corners alike. Their sophomore tape Don’t Sweat The Technique had a similar effect on the culture, influencing not only New York rap but the entire East Coast sound that was still forming at the time. Rakim’s influence in rap extends far beyond his era. ASAP Rocky (another entry on this list) is literally named after him and DMX famously studied his rapping style when he was learning the craft. And the list goes on. Rakim will go down in history as a staple creator of the smooth signature New York rapping style that the region is known for today. Rakim was the original “God MC,” and his gospel of classic records will live in the zeitgeist of hip-hop forever. —Jordan Rose

The true testament of a great rapper is their ability to contextualize experiences and make them relatable (or at the very least compelling) to all. Nas is one of the best to ever hold a mic because he repeatedly wrapped the world around his vivid bars. On Illmatic, one of the most iconic debut albums of all time, or the prophesyings on It Was Written two years later, and the blasphemous challenges of the status quo on Hip Hop Is Dead (shared a decade after that), he never faltered in painting pictures that were true to his story and lived experiences, regardless of how they might be perceived by the world around him.

Beyond his classics, what’s impressive about Nas’ career is how he’s been able to adapt to the changing times and remain a noted inspiration for rappers who came after him. “Nas was like Jesus, Pac wrote the bible,” Cole raps on “Let Nas Down,” interpolating the I Am… track “Nas Is Like.” Nas didn’t just reimagine the rap game, he rewrote it—turning diss track titles like “Ether” into verbs. The Queensbridge rapper linked with Hit-Boy, one of the biggest producers of this current generation to make their King’s Disease trilogy and Magic 1 & 2, a testament to the limitless opportunities for reinvention that rap can offer if your pen is nice enough. With those projects, and collaborations with artists like Cordae, 21 Savage, The Weeknd, and more, Nas has figured out a way to evolve rather than aimlessly chase the modern sound. Only Nas has had the poise to rewrite his destiny thrice over. He defied the rap gods, sparred with the God MC, and still stands three decades later with more stories to tell. —Jordan Rose

Biggie could have been comfortably sitting atop this list if time would’ve allowed for it. In 1997, at 24, with two studio albums in his pocket—the latter of which was preemptively, eerily titled Life After Death—Biggie had the East Coast under his wing. He is one of the most New York-synonymous names of all time, with a pointed pen that dovetailed into the violent realities and layered lived experiences of his communities. And he did so in a way that was gritty—sometimes raw, and always nuanced. A true original gangsta rapper, B.I.G. was a mentor and pack leader of Junior M.A.F.I.A., a group from which the likes of Lil Cease and Lil Kim rose to prominence alongside tracks like “Players Anthem.”

The Brooklyn rapper, signed to Diddy’s Bad Boy Records, was a skillful storyteller who was proud of the art 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 nature. No other rapper could emote the feeling and sound of an entire city with just five words like “It was all a dream.” Rap fans of all ages quote and study him to this day, and, although his career was tainted and bookended by strife and disharmony, Biggie grew with a stillness and desire for peace felt in his final public addresses; in an interview with Angie Martinez in 1996, The Notorious B.I.G. declared it the year of love, and that year’s been going ever since. Biggie will go down in history as one of the most beloved New York rappers of all time. —Ecleen Luzmila Caraballo

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

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