When we’re talking about ranking the best New York rappers of all time, we’re talking about the MCs who came up in the Mecca of hip hop.
With all due respect to L.A. , Detroit , Chicago , Atlanta , New Orleans , and all of the many fine cities that have produced great rap talent, there’s no place quite like New York. As the official birthplace of hip hop – when DJ Kool Herc threw a block party in his apartment at 1520 Sedgwick Avenue, The Bronx – the city has a long and illustrious history of rappers.
From Brooklyn’s Jay-Z, Big Daddy Kane and Biggie Smalls, to Queens’ 50 Cent, LL Cool J and Nas, over to Harlem’s Mase, Big L, and Puff Daddy and Yonkers’ Lox crew and DMX. Then there’s the Bronx which boasts legends like Fat Joe, KRS-One, and Big Pun; Shaolin’s very own Wu-Tang Clan; and Long Island’s Chuck D, Busta and Rhymes. The bottom line is: New York is the Mecca of hip hop for a reason.
From Nas, Jay-Z, Raekwon and Biggie, to Rakim, Big Daddy Kane, Kool G Rap and Slick Rick, here are the top 50 best New York rappers of all time.
50. Fat Joe
Discography: Represent (1993), Jealous One’s Envy (1995), Don Cartagena (1998), Jealous Ones Still Envy (J.O.S.E.) (2001), Loyalty (2002), All or Nothing (2005), Me, Myself & I (2006), The Elephant in the Room (2008), Jealous Ones Still Envy 2 (J.O.S.E. 2) (2009), The Darkside Vol. 1 (2010)
Running with the legendary Diggin’ in the Crates crew since the early ’90s, Joey Cartagena made his debut in 1993 with Represent , but it wasn’t until his 2001 album, Jealous Ones Still Envy (J.O.S.E.) , when he made a real splash in the mainstream. Known for his suave delivery and smooth flow, he knew exactly how to balance the intensity of ‘90s boom bap with catchy pop appeal.
While most rap fans recognise him for hits like “What’s Luv?” and “We Thuggin’,” hip hop heads understand that Fat Joe has always been about the culture from the beginning of his career to the present day. A legend of the city for three decades, Fat Joe is absolutely one of the best New York rappers of all time.
49. Mase
Discography: Harlem World (1997), Double Up (1999), Welcome Back (2004)
With his 1997 debut Harlem World , Mase defined the sound of late ’90s pop rap. Boasting one of the smoothest flows ever in rap and a signature nonchalant delivery, the Bad Boy rapper took hip hop to new commercial heights during his peak years. What he lacks in a lengthy discography, Mase has more than made up with his lasting influence. His melodic and indifferent style of rapping has become a hip hop staple, still heard today in names like Drake, Pusha T and Kanye West. Not only is this Bad Boy legend one of the most underrated rappers ever, he’s absolutely one of the greatest rappers from New York.
48. Havoc
Discography: Juvenile Hell (1993), The Infamous (1995), Hell on Earth (1996), Murda Muzik (1999), Infamy (2001), Amerikaz Nightmare (2004), Blood Money (2006), The Kush (2007), Hidden Files (2009), 13 (2013), The Infamous Mobb Deep (2014)
From the time he made his way into the rap game, Havoc helped carry boom bap into a darker direction. No other producer, other than RZA and DJ Premier, has had a bigger hand than in shaping the sound of ’90s New York era hip hop than Havoc. Part of the legendary duo Mobb Deep , he bounced well off Prodigy, encapsulating the bleak, grimy sound of New York gangsta rap.
From the iconic “Shook Ones, Pt. II” to the chilling “Hell On Earth”, his low-key lyrical style always painted a vivid picture of his struggle in the streets. Whether part of Mobb Deep or as a solo artist, Havoc is cemented as one of the greatest New York rappers in history.
47. Foxy Brown
Discography: Ill Na Na (1996), Chyna Doll (1999), Broken Silence (2001)
One of the greatest female rappers of all time , Foxy Brown competed with Nas and Jay-Z for the best verse on their own records, she pushed forward the sound of dancehall with hits like “Oh Yeah”, and went platinum with her first album in 1996, Ill Na Na . Whether it was a club hit and a grimy boom bap track, she knew how to make it. A vicious lyricist with the ability to sound comfortable across different genres, Foxy might be one of the most underrated MCs in the game, period. With her catalogue, influence and mic skills, there’s no denying Foxy’s legacy as one of the best NYC rappers of all time.
46. CL Smooth
Discography: Mecca and the Soul Brother (1992), The Main Ingredient (1994), American Me (2006), The Outsider (2007)
Hailing from New Rochelle, New York, CL Smooth has one of the slickest flows ever, and a sharp pen to match. With producer Pete Rock, the duo made some of the greatest songs in rap music such as “Straighten It Out,” “I Got a Love” and of course, the iconic “They Reminisce Over You”. While CL has stayed relatively inactive since the duo’s breakup, few rappers have come close to matching his effortless flow and poignant lyricism.
45. Phife Dawg
Discography: People’s Instinctive Travels and the Paths of Rhythm (1990), The Low End Theory (1991), Midnight Marauders (1993), Beats, Rhymes and Life (1996), The Love Movement (1998), Ventilation: Da LP (2000), We Got It from Here… Thank You 4 Your Service (2016), Forever (2022)
Phife was a pioneer in jazz rap and founding member of A Tribe Called Quest. His animated delivery and carefree lyricism gave his music an upbeat charm, setting it apart from other ‘90s hip hop. Tribe released classics like The Low End Theory and Midnight Marauders . While Q-Tip often gets more shine for those records as the group’s frontman, everyone knows that Tribe would not be the same without Phife’s contributions.
44. Biz Markie
Discography: Goin’ Off (1988), The Biz Never Sleeps (1989), I Need a Haircut (1991), All Samples Cleared! (1993), Weekend Warrior (2003)
Debuting in 1988, Biz Markie was a hip hop legend well-known for his 1989 hit, “Just a Friend.” That one song encapsulated everything that made Markie and his discography so appealing: he was a great storyteller, full of charisma, who carried that lighthearted sound of ‘80s hip hop through to the ‘90s and beyond. While Biz would never be regarded highly as a lyricist, he dropped undeniable classics during his time with the legendary Juice Crew, including Goin’ Off and The Biz Never Sleeps .
43. 50 Cent
Discography: Get Rich or Die Tryin’ (2003), The Massacre (2005), Curtis (2007), Before I Self Destruct (2009), Animal Ambition (2014)
50 Cent was a singular, driving force in 2000s hip hop. Combining a distinctive, laid-back delivery and unforgettable melodic hooks , he provided hip hop with ’90s street energy updated for a new audience. With his 2003 debut, Get Rich or Die Tryin’ , 50 sold over 800,000 copies in under a week, and produced iconic hits like “In Da Club” and “Many Men (Wish Death).”
With that momentum, the South Jamaica hustler-turned rapper led his G-Unit crew to taking over the rap industry. It took five years and the coming of Kanye West to pry the game out of 50’s hands. While he’s more occupied with taking over the entertainment industry these days, 50 will always be recognised as one of the kings of New York .
42. Buckshot
Discography: Enta da Stage (1993), War Zone (1999), The BDI Thug (1999), Total Eclipse (2003), Chemistry (2005), The Formula (2008), Survival Skills (2009), The Solution (2012), Backpack Travels (2014), Rise of da Moon (2019)
Buckshot has a fiery energy which keeps the listener hooked to every word, performing at his best over gritty boom bap beats. He’s a member of groups Black Moon and Boot Camp Clik, and has full collaborations with KRS-One, P-Money, and 9 th Wonder. From 1993 to the present, his discography has been packed with classic songs and albums. From the early ’90s to present day, Buckshot has maintained his longevity and cultivated a devoted fanbase by sticking to what he knows best.
41. Lil’ Kim
Discography: Hard Core (1996), The Notorious K.I.M. (2000), La Bella Mafia (2003), The Naked Truth (2005), 9 (2019)
Lil’ Kim is viewed as one of the most influential female rappers, rivalling her male Brooklyn contemporaries like Jay-Z and Biggie Smalls in impact and paving the way for female MCs to have a louder voice in the hip hop scene. Her raunchy, unapologetic debut in 1996, Hard Core , proved that hip hop wasn’t just a man’s game, providing the formula for a new generation of female rappers to come up after her, from Cardi B and Megan Thee Stallion to Nicki Minaj and Dojo Cat.
40. Canibus
Discography: Can-I-Bus (1998), 2000 B.C. (Before Can-I-Bus) (2000), C! True Hollywood Stories (2001), Mic Club: The Curriculum (2002), Rip the Jacker (2003), Mind Control (2005), Hip-Hop for Sale (2005), For Whom the Beat Tolls (2007), Melatonin Magik (2010), C of Tranquility (2010), Lyrical Law (2011), Fait Accompli (2014), Time Flys, Life Dies… Phoenix Rise (2015), Kaiju (2021), One Step Closer to Infinity (2022)
Revered for his freestyling ability and sharp lyricism, Canibus burst onto the scene in the early ‘90s and has never slowed down since. While his battle with LL Cool J stopped any momentum he had in mainstream hip hop, the highly respected MC has continued to grind away with underground releases. Unlike most rappers who prefer the studio, Canibus is known for his skills as a battle rapper, recognized for his lengthy discography and impressive freestyles.
39. Talib Kweli
Discography: Mos Def & Talib Kweli Are Black Star (with Mos Def as Black Star) (1998), Train of Thought (with Hi-Tek as Reflection Eternal) (2000), Quality (2002), The Beautiful Struggle (2004), Eardrum (2007), Liberation (with Madlib) (2007), Gutter Rainbows (2011), Revolutions Per Minute (with Hi-Tek as Reflection Eternal) (2010), Habits of the Heart (with Res as Idle Warship) (2011), Prisoner of Conscious (2013), Gravitas (2013), Fuck the Money (2015), Indie 500 (with 9th Wonder) (2015), Radio Silence (2017), The Seven (with Styles P) (2017), Gotham (with Diamond D) (2021), No Fear of Time (with Yasiin Bey as Black Star) (2022)
Talib Kweli is a legend in the conscious hip hop scene who made his debut in 1997 alongside Mos Def in the iconic duo, Black Star. With his youthful voice, Kweli is an elite lyricist with a cold delivery and nonchalant flow. He has strong political views, using his platform, whether it’s music or other media channels, to fight back against racial stereotypes and black oppression. With countless acclaimed releases across albums, mixtapes and collaboration projects, Talib Kweli is undeniably one of the best New York rappers of all time.
38. O.C.
Discography: Word…Life (1994), Jewelz (1997), Bon Appetit (2001), Star Child (2005), Smoke and Mirrors (2005), Oasis (2009), Trophies (2012), Ray’s Café (2014), Ray’s Café: The After Hours EP (2014), Dive In (2015), Same Moon Same Sun (2017), Perestroika (2017), A New Dawn (2018), Opium (2018)
O.C. has never shied away from switching up his style. He embraced the rough sound of boom bap in the ‘90s with Word…Life , and has since made aggressive, hardcore rap, as well as conscious hip hop with collaborators like Apollo Brown. As part of D.I.T.C., like its other members, he’s been widely regarded for his contributions to the underground. A dedicated lyricist best-known for the care and time he devotes to writing the best bars possible, O.C. is without doubt one of the greatest New York rappers to ever touch a mic.
37. Kool Keith
Discography: Dr. Octagonecologyst (1996), Sex Style (1997), First Come, First Served (1999), Black Elvis/Lost in Space (1999), Matthew (2000), Spankmaster (2001), Nogatco Rd. (2006), The Return of Dr. Octagon (2006), Dr. Dooom 2 (2008), Tashan Dorrsett (2009), Love & Danger (2012), Demolition Crash (2014), El Dorado Driven (2014), Feature Magnetic (2016), Moosebumps: An Exploration Into Modern Day Horripilation (2018), Controller of Trap (2018), Keith (2019), Computer Technology (2019), Saks 5th Ave (2019)
A god of the underground , Kool Keith is among the most creative rappers, renowned for his graphic and often nonsensical lyrics, as well as his warped ear for beats. Since his start in Ultramagnetic MCs, with their game-changing Critical Beatdown , The Bronx rapper has dropped classic after classic as his alias Doctor Octagon, amongst many other names. While Kool Keith’s lasting impact will be recognised more as time goes on, he is cemented as one of the greatest New York rappers of all time.
36. Cormega
Discography: The Realness (2001), The True Meaning (2002), The Testament (2005), Born and Raised (2009), Mega Philosophy (2014), The Realness II (2022)
“What up with Cormega? Did you see him? Are y’all together?” With that single line on “One Love,” Nas had the whole rap world eagerly awaiting the debut of this legendary Queensbridge name. Determined to pursue a rap career after his release in 1995, Cormega spent a short stint as a member of The Firm before going his own way. One of the most skilled rappers of his era, Cormega’s verses are always full of dense rhymes with a fierce yet composed delivery. His vivid street tales are always backed by deep moral lessons and poignant truths. Since his debut with The Realness in 2001, Cormega has continued to put out quality releases over the next two decades, cementing his position as one of the greatest rappers from New York.
35. Lord Finesse
Discography: Funky Technician (with DJ Mike Smooth) (1990), Return of the Funky Man (1992), The Awakening (1996)
One of the founding members of the Diggin’ in the Crates crew, Lord Finesse officially broke on to the scene in 1990 with DJ Mike Smooth for Funky Technician . A masterpiece in punchlines, wordplay and funky production, the record has gone down as a classic. After two solo records, Finesse dedicated the rest of his career to production work for the D.I.T.C. collective among other rappers. In that short time span, however, he proved himself a well-rounded MC, with an aggressive delivery that has inspired the likes of legends like Big L. Not only is Lord Finesse one of the finest New York rappers ever, he’s one of the most influential.
34. Guru
Discography: No More Mr. Nice Guy (1989), Step in the Arena (1991), Daily Operation (1992), Guru’s Jazzmatazz, Vol. 1 (1993), Hard to Earn (1994), Guru’s Jazzmatazz, Vol. 2: The New Reality (1995), Moment of Truth (1998), Guru’s Jazzmatazz, Vol. 3: Streetsoul (2000), Baldhead Slick & da Click (2001), The Ownerz (2003), Version 7.0: The Street Scriptures (2005), Guru’s Jazzmatazz, Vol. 4: The Hip Hop Jazz Messenger: Back to the Future (2007), Guru 8.0: Lost and Found (2009), One of the Best Yet (2019)
One of hip hop’s most underrated lyricists, Guru rocked a calm delivery and a flow so steady listeners would hang on closely to every word he dropped. With DJ Premier, as part of Gang Starr, he was responsible for some of the greatest New York boom-bap albums, from Step in the Arena to Hard to Earn , and also helped to push jazz-rap forward with his ground-breaking Jazzmatazz series. A thoughtful legend who always kicked knowledge in his rhymes, Guru was tragically taken from hip hop at the young age of 48, but his lyrics have continued to live on long after he departed.
33. Cam’ron
Discography: Confessions of Fire (1998), S.D.E. (2000), Come Home with Me (2002), Purple Haze (2004), Killa Season (2006), Crime Pays (2009), Heat in Here Vol. 1 (with Vado) (2010), Gunz n’ Butta (with Vado) (2011), Purple Haze 2 (2019), U Wasn’t There (with A-Trak) (2022)
Cam’ron was at his height in the early 2000s when he signed to Roc-A-Fella Records, dropping the blockbuster Come Home With Me as well as his cult classic, Purple Haze . With his nonchalant delivery and laidback rapping style, Cam was like a more street-hardened version of Mase who could spit dense rhyme schemes and complex multisyllabic rhymes effortlessly. Sounding best over hard-hitting, soulful production by Just Blaze and The Heatmakerz, Cam’ron made classic, powerful music and is absolutely one of the greatest New York rappers ever.
32. AZ
Discography: Doe or Die (1995), Pieces of a Man (1998), 9 Lives (2001), Aziatic (2002), A.W.O.L. (2005), The Format (2006), Undeniable (2008), Legendary (2009), Doe or Die II (2021)
The first time AZ ever stepped into a recording booth to drop a rap verse was when he stepped up to the mic for Nas’ “Life’s a Bitch.” It was one of the most stunning debut guest verses of all time and quickly set off a bidding war for the hungry Brooklyn rapper. Shortly afterwards, in 1995, AZ released the classic Doe or Die , showcasing his skills as a master lyricist who spat each verse like it was his last. Over the next few decades, he would maintain his butter-smooth flow and impeccable delivery as he dropped quality releases one after another.
31. Fabolous
Discography: Ghetto Fabolous (2001), Street Dreams (2003), Real Talk (2004), From Nothin’ to Somethin’ (2007), Loso’s Way (2009), The Young OG Project (2014), Friday on Elm Street (with Jadakiss) (2017), Summertime Shootout 3: Coldest Summer Ever (2019)
A braggadocio lyricist at heart with the nonchalant delivery of Mase and cold wittiness of Jay-Z, Fab was born to do this rap shit. One of the most staple New York rappers in the city’s history, Fabolous’ greatest strength lies in his versatility. Whether it was crafting shimmery R&B hits with Jagged Edge and Tamia or getting barred up on gully posse cuts with Lloyd Banks and Vado, the Brooklyn MC could attack it from all angles.
30. Nicki Minaj
Discography: Pink Friday (2010), Pink Friday: Roman Reloaded (2012), The Pinkprint (2014), Queen (2018)
One of the biggest and most influential female rappers of all time, Nicki Minaj has done enough this past decade to earn her GOAT standing. Born in Trinidad and Tobago, but raised in South Jamaica, Queens, the Young Money MC started grinding her way into the rap game way back in the 2000s with mixtapes like Playtime Is Over and Sucka Free .
However, it wasn’t until her third tape, Beam Me Up Scotty , that she struck gold. After that, with co-signs from Birdman and Lil Wayne as well as a history-making guest verse on Kanye’s “Monster,” Nicki was well positioned to become the biggest thing in hip hop. Save for a few bumps over the course of her rap career, the Queen of Rap has done exactly what she set out to do in the first place.
29. Inspectah Deck
Discography: Uncontrolled Substance (1999), The Movement (2003), The Resident Patient (2006), Manifesto (2010), Chamber No. 9 (2019)
While best-known for being part of the Wu-Tang Clan, Inspectah Deck has more recently experienced a resurgence in his rap career as part of the hip hop supergroup Czarface. Legendary for his complex rhyme schemes, strong wordplay, and storytelling abilities, Deck is often regarded as one of Wu-Tang’s strongest lyricists. His solo catalogue doesn’t receive the same praise as his group work, but as a feature artist and group member, Deck is absolutely one of the best to ever do it.
28. Sean Price
Discography: Monkey Barz (2005), Jesus Price Supastar (2007), Mic Tyson (2012), Imperius Rex (2017)
A core member of the renowned Boot Camp Clik as well as part of the Brooklyn duo Heltah Skeltah, Sean Price made his debut on Smif-N-Wessun’s gritty, underground classic Dah Shinin’ , and pretty much stuck to the hardcore rap formula for the rest of his career. With his animated style of rapping that blended witty lyricism and complex rhyme schemes, Sean Price was always a delight to listen to. The Brooklyn MC’s solo career made a huge impact on the underground scene until his untimely death in 2015.
27. Q-Tip
Discography: People’s Instinctive Travels and the Paths of Rhythm (1990), The Low End Theory (1991), Midnight Marauders (1993), Beats, Rhymes and Life (1996), The Love Movement (1998), We Got It from Here… Thank You 4 Your Service (2016)
No other hip hop artist has been able to transcend different rap eras, regions and sounds as Q-Tip has over the decades. Starting off as the frontman for A Tribe Called Quest, arguably the greatest rap group of all time, Q-Tip was responsible for quarterbacking three straight classics back-to-back in as many years.
But even putting aside his legendary work for Tribe, on the solo tip, the Queens rapper dropped one of the best rap albums of the 2000s with The Renaissance , showcasing his longevity and youthful rhyme style. A legend across rapping and production, Q-Tip is absolutely one of the greatest New York rappers of all time.
26. Slick Rick
Discography: The Great Adventures of Slick Rick (1988), The Ruler’s Back (1991), Behind Bars (1994), The Art of Storytelling (1999)
The greatest storytelling rapper of all time , Slick Rick got his start in the early ’80s as part of Doug E. Fresh & the Get Fresh Crew. After capturing the hip hop world with hits like “The Show” and “La Di Da Di” ( the most sampled rap song of all time ), Rick the Ruler struck it out on his own with The Great Adventures of Slick Rick .
Over the decades, Slick Rick’s influence on subsequent rap generations have grown more profound. He’s one of the most heavily referenced and sampled names in hip hop, showing he wasn’t only an incredible MC, but one whose legacy lives on through the countless rappers he’s inspired, from Nas and Jay-Z to Kanye and Snoop Dogg.
25. Busta Rhymes
Discography: The Coming (1996), When Disaster Strikes… (1997), Extinction Level Event: The Final World Front (1998), Anarchy (2000), Genesis (2001), It Ain’t Safe No More… (2002), The Big Bang (2006), Back on My B.S. (2009), Year of the Dragon (2012), Extinction Level Event 2: The Wrath of God (2020)
Busta Rhymes has one of the most animated deliveries in hip hop, with a booming voice and manic energy like no other. He started as part of Leaders of the New School but became a household name after his ferocious feature on A Tribe Called Quest’s “Scenario.” Once that track dropped, it was clear that Busta was destined for solo superstardom.
As one of the few rappers who came up in the ’90s still thriving in today’s rap world, Busta’s versatility is what’s kept him going for all these years – he can go from trading bars with Kendrick Lamar to jumping on a radio smash hit with Chris Brown effortlessly.
24. Styles P
Discography: A Gangster and a Gentleman (2002), Time is Money (2006), Super Gangster (Extraordinary Gentleman) (2007), Master of Ceremonies (2011), The World’s Most Hardest MC Project (2012), Float (2013), Phantom and the Ghost (2014), A Wise Guy and a Wise Guy (2015), G-Host (2018), Dime Bag (2018), S.P. the GOAT: Ghost of All Time (2019), Presence (2019), Styles David: Ghost Your Enthusiasm (2020), Ghosting (2021)
One of the hardest working New York rappers of all time, Styles P has spent the past two decades grinding out countless albums, mixtapes and collaboration projects independently. While his work with The LOX put him on the mainstream stage and gave him global recognition, it’s Styles’ more low-key releases that have made him one of the greatest MCs ever. As a rapper who thrives on grimy, hard-hitting production, the Yonkers rapper has a cool and collected way of rapping that bounces well off the more aggressive delivery of his brothers Jada and Sheek.
23. Big Pun
Discography: Capital Punishment (1998), Yeeeah Baby (2000)
It should be a criteria for any budding hip hop head to be able to recite Big Pun’s first verse off “Twinz (Deep Cover ’98),” no matter how old they are. Emerging in the mid-90s after being discovered by Fat Joe and welcomed by the Terror Squad, Big Pun quickly proved to be one of the most naturally gifted MCs of his time.
With a dynamic flow and incredible rhyme skills, he showcased his talents to the fullest on his grimy and hard-hitting debut, Capital Punishment , in 1998. While his life was cut too short when he passed away in 2000, Pun’s music continues to inspire rappers today as his name lives on as one of the greatest New York rappers to ever do it.
22. Raekwon
Discography: Only Built 4 Cuban Linx… (1995), Immobilarity (1999), The Lex Diamond Story (2003), Only Built 4 Cuban Linx… Pt. II (2009), Shaolin vs. Wu-Tang (2011), Fly International Luxurious Art (2015), The Wild (2017)
Chef Raekwon is one of the most iconic New York rappers ever. Sporting a distinctive, husky voice and killer slang that was so dense it probably helped create Urban Dictionary, Raekwon has been an OG of the city for quite some time now. With the legendary Only Built 4 Cuban Linx… setting the standard for what a street rap album could be, Chef, along with his partner-in-crime Ghostface Killah, has been foundational in defining hardcore East Coast hip hop.
21. GZA
Discography: Words from the Genius (1991), Liquid Swords (1995), Beneath the Surface (1999), Legend of the Liquid Sword (2002), GrandMasters (with DJ Muggs) (2005), Pro Tools (2008)
The OG founding member of the Wu-Tang Clan, there are few names in hip hop that command more respect than GZA. After going through the wringer with Cold Chillin’ Records where he released his debut album, the poorly received Words from the Genius , The Genius regrouped with his cousin RZA and formed Wu-Tang. With a cold, methodical rap style and unique ability to express complex ideas in the least amount of words, to this very day GZA commands attention whenever he appears on a track.
20. Pharoahe Monch
Discography: Organized Konfusion (1991), Stress: The Extinction Agenda (1994), The Equinox (1997), Internal Affairs (1999), Desire (2007), W.A.R. (We Are Renegades) (2011), PTSD: Post Traumatic Stress Disorder (2014), A Magnificent Day for an Exorcism (2021)
There are few MCs as unpredictable and unique as Pharaohe Monch. He’s a dynamic rapper with a fast flow and manic tone, working well over the jazzy production of Organized Konfusion, the grimy beats of his solo material, and more recently, the explosive rock instrumentals from his work in Th1rt3en. One of the most skilled rap talents we have ever seen, Pharoahe is also a conscious writer, crafting thought-provoking songs across modern day classics like W.A.R. (We Are Renegades) and PTSD .
19. Masta Ace
Discography: Take a Look Around (1990), SlaughtaHouse (with Masta Ace Incorporated) (1993), Sittin’ on Chrome (with Masta Ace Incorporated) (1995), Disposable Arts (2001), A Long Hot Summer (2004), The Show (with eMC) (2008), Arts & Entertainment (with Ed O.G.) (2009), MA Doom: Son of Yvonne (2012), The Turning Point EP (with eMC) (2014), The Tonite Show (with eMC) (2015), The Falling Season (2016), A Breukelen Story (with Marco Polo) (2018)
If you’re talking about the most underrated rappers in hip hop history, Masta Ace would be in the top five, at least. A highly-skilled veteran whose career kicked off in the late ’80s with his legendary verse on “The Symphony,” the New York rapper has been able to cut across different eras of hip hop better than most of his peers.
Whether it’s his golden age classic debut, Take a Look Around , the West Coast-satire project SlaughtaHouse or his collaboration with MF DOOM, MA Doom: Son of Yvonne , Masta Ace has consistently been able to reinvent himself while maintaining his love for the craft. Is there any wonder why fellow wordsmith Eminem shouts him out all the time ?
18. Big L
Discography: Lifestylez ov da Poor & Dangerous (1995), The Big Picture (2000), 139 & Lenox (2010), Return of the Devil’s Son (2010), The Danger Zone (2011)
Probably the most beloved MCs ever, Big L was one of the greatest freestylers and wordsmiths in hip hop, with almost every bar being a double or even triple entendre. He released his classic, Lifestylez Ov Da Poor & Dangerous , in 1995, cementing him as one of the most talented MCs of the era. The Harlem rapper tragically died way too soon, but his wordplay remains unrivalled, and he has remained a fan favourite from the first time we heard him. There is perhaps no other rapper who personifies New York rap attitude better than Big L.
17. Jadakiss
Discography: Kiss tha Game Goodbye (2001), Kiss of Death (2004), The Last Kiss (2009), Top 5 Dead or Alive (2015), Friday on Elm Street (with Fabolous) (2017), Ignatius (2020)
Jadakiss is the absolute definition of a New York rapper. With his raspy flow, memorable adlib, confrontational bars and Yonkers swagger, the LOX MC has strutted around these New York streets for the past 20 years, swapping rhymes with fellow legends like Hov, DMX, Big and Nas while always holding his own. Jada’s recent performance at Verzuz, where he almost singlehandedly crushed Dipset at Madison Square Garden cemented him as one of the rightful kings of New York.
16. LL Cool J
Discography: Radio (1985), Bigger and Deffer (1987), Walking with a Panther (1989), Mama Said Knock You Out (1990), 14 Shots to the Dome (1993), Mr. Smith (1995), Phenomenon (1997), G.O.A.T. (2000), 10 (2002), The DEFinition (2004), Todd Smith (2006), Exit 13 (2008), Authentic (2013)
Speaking of rappers who pushed hip hop culture higher than it had ever been, James Todd Smith aka LL Cool J was at the forefront of the new era of rappers leading the genre into the mainstream. With his accessible blend of gritty street anthems and radio singles, the Queens legend helped create the formula that so many rappers after him used to achieve incredible success, from Jay-Z to 50 Cent and Drake.
A truly versatile MC who could jump on posse cuts with murderous MCs like Prodigy, Method Man, Redman and Keith Murray, then perform duets with Jennifer Lopez, LL Cool J was really a one-of-a-kind artist and absolutely one of the greatest rappers New York has ever seen.
15. Mos Def
Discography: Mos Def & Talib Kweli Are Black Star (with Talib Kweli, as Black Star) (1998), Black on Both Sides (1999), The New Danger (2004), True Magic (2006), The Ecstatic (2009), Negus (2019), No Fear of Time (with Talib Kweli, as Black Star) (2022)
A legend of conscious, underground hip hop known for his introspective lyricism spoken with so much charisma and personality, Mos Def, who now goes by Yasiin Bey has always managed to transcend hip hop culture even from his early days. While albums like Mos Def & Talib Kweli Are Black Star and Black on Both Sides are certified classics, the Brooklyn MC has consistently popped up for devastating guest verses over the decades.
14. Run-D.M.C.
Discography: Run-D.M.C. (1984), King of Rock (1985), Raising Hell (1986), Tougher Than Leather (1988), Back from Hell (1990), Down with the King (1993), Crown Royal (2001)
Arguably the most impactful act in hip hop history, Run-D.M.C. played a huge role in driving hip hop forward while the culture was still in its infancy in the early ‘80s. With their debut single “It’s Like That” backed by the scathing “Sucker M.C.’s,” the Queens duo laid the foundations for the new hip hop era where disco beats and sparkling outfits were out and raw drum tracks and Adidas sneakers were in. It didn’t take long for Run-D.M.C. to rack up a number of milestone achievements, including:
- first hip hop gold record with Run-D.M.C.
- first hip hop platinum record with Raising Hell
- first rap act to appear on MTV, the cover of Rolling Stone and the Live Aid stage
- first rap act to be nominated for a Grammy Award
13. El-P
Discography: Funcrusher (1996), Funcrusher Plus (1997), Fantastic Damag e (2002), High Water (2004), I’ll Sleep When You’re Dead (2007), Cancer 4 Cure (2012), Run the Jewels (2013), Run the Jewels 2 (2014), Run the Jewels 3 (2016), RTJ4 (2020)
I’m frankly sick and tired of not seeing El-P’s name on these types of lists. What does the man have to do to get the flowers he deserves? One of the founding members of famed Brooklyn trio Company Flow, El-P went on to shape the sound of underground hip hop with his role in Definitive Jux, Cannibal Ox and Rawkus Records. Just his solo catalogue alone, from Fantastic Damage to Cancer 4 Cure would earn him a spot on a greatest underground rappers list. Now, as one half of Run the Jewels, El-P is taking his elastic flow and booming production to a whole new level. Not only has he cemented himself as one of New York’s legends, he’s one of the GOATs, period.
12. DMX
Discography: It’s Dark and Hell Is Hot (1998), Flesh of My Flesh, Blood of My Blood (1998), … And Then There Was X (1999), The Great Depression (2001), Grand Champ (2003), Year of the Dog… Again (2006), Undisputed (2012), Exodus (2021)
It can be hard to understand just how impactful DMX was when he first came out, but at one point in time, the Yonkers MC was the biggest thing in hip hop. With his first two albums, It’s Dark and Hell Is Hot and Flesh of My Flesh, Blood of My Blood , X helped shift hip hop back to the streets at a time when the culture was being paraded around champagne-soaked yachts by Puffy and his Bad Boy minions. Combining his gruff, booming voice with a melodic charisma and confessional-type tracks, DMX cultivated a strong fanbase who helped him become the first artist in history to have their first five albums debut at number one .
11. Chuck D
Discography: Yo! Bum Rush the Show (1987), It Takes a Nation of Millions to Hold Us Back (1988), Fear of a Black Planet (1990), Apocalypse 91… The Enemy Strikes Black (1991), Muse Sick-n-Hour Mess Age (1994), Autobiography of Mistachuck (1996), He Got Game (1998), There’s a Poison Goin’ On (1999), Revolverlution (2002), New Whirl Odor (2005), How You Sell Soul to a Soulless People Who Sold Their Soul? (2007), Most of My Heroes Still Don’t Appear on No Stamp (2012), The Evil Empire of Everything (2012), The Black in Man (2014), Man Plans God Laughs (2015), If I Can’t Change the People Around Me I Change the People Around Me (2016), Nothing Is Quick in the Desert (2017), Celebration of Ignorance (2018), What You Gonna Do When the Grid Goes Down? (2020)
One of the greatest voices in hip hop music, Chuck D always commanded attention with his booming rap style, where he almost shouts every bar with a passion rarely matched by his contemporaries. As the frontman of Public Enemy, one of the most influential rap groups in history, Chuck D was the glue behind defining hip hop albums like It Takes a Nation of Millions to Hold Us Back , Fear of a Black Planet and Apocalypse 91… The Enemy Strikes Black . Along with ’80s rap peers like Rakim, KRS-One, Slick Rick, LL Cool J and Big Daddy Kane, Chuck D showed future hip hop generations just how far the art form could go.
10. Prodigy
Discography: Juvenile Hell (1993), The Infamous (1995), Hell on Earth (1996), Murda Muzik (1999), H.N.I.C. (2000), Infamy (2001), Amerikaz Nightmare (2004), Blood Money (2006), H.N.I.C. Pt. 2 (2008), H.N.I.C. 3 (2012), The Bumpy Johnson Album (2012), The Infamous Mobb Deep (2014), Hegelian Dialectic (The Book of Revelation) (2017)
Recognised as one of the most important names of the ’90s New York era, Prodigy was instrumental, along with Havoc, in shaping boom-bap into a grimier, more sinister sound. A precise writer who used a slow, methodical flow, Prodigy couldn’t string rhymes together as effortlessly as Nas or deliver them as explosively as Big.
But what he could do better than anyone else was craft each bar as a standalone work of art delivered with his ice cold voice. It’s the reason why Prodigy is one of the most sampled hip hop artists of all time, you just couldn’t get the sound of his voice from anywhere else.
9. Big Daddy Kane
Discography: Long Live the Kane (1988), It’s a Big Daddy Thing (1989), Taste of Chocolate (1990), Prince of Darkness (1991), Looks Like a Job For… (1993), Daddy’s Home (1994), Veteranz’ Day (1998)
Big Daddy Kane is widely regarded as the ultimate Brooklyn MC. A master punchline artist with pristine technique and an ultra-smooth demeanour, Kane inspired future Brooklyn legends like Jay-Z and The Notorious B.I.G. with golden age classics like Long Live the Kane and It’s a Big Daddy Thing .
While his peer Rakim may get most of the accolades when it comes to revolutionising the rap landscape with multisyllabic, compound rhyme patterns, Big Daddy Kane was right there with him. Not only is the Smooth Operator one of the greatest New York rappers ever, he’s one of the best rappers of all time , period.
8. KRS-One
Discography: Return of the Boom Bap (1993), KRS-One (1995), I Got Next (1997), The Sneak Attack (2001), Spiritual Minded (2002), Kristyles (2003), Keep Right (2004), Life (2006), Adventures in Emceein (2008), Maximum Strength (2008), The BDP Album (2012), Never Forget (2013), Now Hear This (2015), The World Is Mind (2017), Street Light (First Edition) (2019), Between Da Protests (2020), I M A M C R U 1 2 (2022)
It’s hard to understate the importance of KRS-One to hip hop culture. Out of all his peers, including Big Daddy Kane, Kool G Rap, and Rakim, the Blastmaster has probably had the most success in terms of transitioning across multiple eras. From his Boogie Down days to the start of his solo career to his role now as the Teacha, KRS has consistently evolved his craft and content as the years have gone by. At 57 years old, and almost four decades into the game, Kris is still dropping quality releases – 2022’s I M A M C R U 1 2 is a strong release – and proving that hip hop culture wouldn’t be the same without him.
7. Ghostface Killah
Discography: Ironman (1996), Supreme Clientele (2000), Bulletproof Wallets (2001), The Pretty Toney Album (2004), Fishscale (2006), More Fish (2006), The Big Doe Rehab (2007), Ghostdini: Wizard of Poetry in Emerald City (2009), Apollo Kids (2010), Twelve Reasons to Die (2013), 36 Seasons (2014), Twelve Reasons to Die II (2015), Ghostface Killahs (2019)
There aren’t many rappers in history who can match the type of longevity and consistency that Ghostface Killah has displayed since the early ’90s. Off the top of my head, you’ve got Hov, Nas, Black Thought, maybe Busta Rhymes, and that’s about it. That’s a very exclusive members club you got right there.
Whether it was kicking down the door on “Bring da Ruckus,” playing the supporting role on Chef’s Only Built 4 Cuban Linx… , dropping one of the greatest Wu albums ever with Supreme Clientele , or just going super hard in general for all these years, Ghost is definition of a rapper constantly putting in the work on their craft.
6. Kool G Rap
Discography: Road to the Riches (with DJ Polo) (1989), Wanted: Dead or Alive (with DJ Polo) (1990), Live and Let Die (with DJ Polo) (1992), 4,5,6 (1995), Roots of Evil (1998), The Giancana Story (2002), Click of Respect (with The 5 Family Click) (2003), Half a Klip (2008), Riches, Royalty, Respect (2011), Once Upon a Crime (with Necro as The Godfathers) (2013), Return of the Don (2017), Son of G Rap (with 38 Spesh) (2018)
Quite possibly the most influential New York rapper of all time, apart from Rakim, Kool G Rap helped raise an entire generation of street rappers with his murderous rhyme book. From Nas, AZ, Raekwon, and Ghostface to Jay-Z, Big Pun, Biggie, and Black Thought, G Rap’s DNA can be found in most hardcore rappers from the ’90s and beyond. While most of his peers have slowed down in the later years, the mafioso don has stayed relatively active to this day, with collaboration projects with Necro and 38 Spesh keeping his name in the spotlight.
5. Method Man
Discography: Tical (1994), Tical 2000: Judgement Day (1998), Tical 0: The Prequel (2004), 4:21… The Day After (2006), The Meth Lab (2015), Meth Lab Season 2: The Lithium (2018), Meth Lab Season 3: The Rehab (2022)
When Method Man is completely dialled in and playing in his zone, I don’t think there’s a rapper on the planet who can fuck with him. It’s like the Shaolin MC was designed in a laboratory by scientists trying to create the perfect superstar rapper – he had the looks, the flow, the voice, he had the smash hit with Mary J. Blige, and he ran with the baddest crew in the game.
Why Meth didn’t become the biggest rapper of the ’90s is beyond me. That’s not to say he still isn’t going hard to this day. Whether it’s albums like Meth Lab Season 3 : The Rehab or feature verses for A$AP Mob and Conway the Machine, Method Man is one of the nicest rappers to ever grace a mic.
4. Rakim
Discography: Paid in Full (1987), Follow the Leader (1988), Let the Rhythm Hit ‘Em (1990), Don’t Sweat the Technique (1992), The 18th Letter (1997), The Master (1999), The Seventh Seal (2009)
The most influential rapper of all time, bar none. Hip hop would not be where it is if it wasn’t for Rakim Allah picking up the mic and changing the rap game with the one-two punch of “Eric B. Is President” and “My Melody.” It was like a light switch was flicked on, and suddenly screaming rappers with their simple rhyme schemes like Run-D.M.C. were considered old school and Rakim represented the new future of the art form.
With his musical partner Eric B., Rakim defined late ’80s golden age hip hop with their 4-album run, but Rakim didn’t stop there, dropping two very good albums in the late ’90s – The 18th Letter and The Master – as if to prove to these young bucks that he was the one and only God MC, one of the greatest New York rappers of all time.
3. The Notorious B.I.G.
Discography: Ready to Die (1994), Life After Death (1997)
The one and only Notorious B.I.G. had a catalogue of just two albums, but with those two releases, he accomplished more than most rappers could over the course of their entire career. Born and raised in Brooklyn, and influenced by ’80s rap greats like Big Daddy Kane, Slick Rick and Kool G Rap, Biggie Smalls honed his rap skills as a teenager rapping on New York streets while juggling a life of crack cocaine vials and book bags.
After linking up with Puffy and going all-in on the music business, Big quickly rose to the top of the food chain as he snatched the King of New York crown away from Nas and faced off with his friend-turned-enemy Tupac Shakur. Now, 25 years after he was tragically murdered out in L.A., The Notorious B.I.G. will always be remembered as one of the greatest New York rappers in history.
2. Jay-Z
Discography: Reasonable Doubt (1996), In My Lifetime, Vol. 1 (1997), Vol. 2… Hard Knock Life (1998), Vol. 3… Life and Times of S. Carter (1999), The Dynasty: Roc La Familia (2000), The Blueprint (2001), The Blueprint 2: The Gift & the Curse (2002), The Black Album (2003), Kingdom Come (2006), American Gangster (2007), The Blueprint 3 (2009), Magna Carta Holy Grail (2013), 4:44 (2017)
There perhaps isn’t another artist in history who has a stronger claim to rap greatness than Jay-Z. It’s not the fact that he’s an incredible MC, or has an extraordinary catalogue spanning multiple decades, or is one of the most impactful rappers ever, or has sold as many records as he has.
Whether you believe Hov is the GOAT or not, he was destined for the upper echelon of this culture from the very beginning. From selling copies of Reasonable Doubt out of his trunk to taking over the rap game with Vol. 2… Hard Knock Life and becoming the president of Def Jam, to now his elder statesman position, Jay-Z is like God to a lot of these rappers. In fact, Hov would be at the very top of this list, if it wasn’t for one rapper…
1. Nas
Discography: Illmatic (1994), It Was Written (1996), I Am… (1999), Nastradamus (1999), Stillmatic (2001), God’s Son (2002), Street’s Disciple (2004), Hip Hop Is Dead (2006), Untitled (2008), Life Is Good (2012), Nasir (2018), King’s Disease (2020), King’s Disease II (2021), Magic (2021), King’s Disease III
“Nasty Nas has to rise ‘cause I’m wise / This is exercise ’til the microphone dies.” When Nasir bin Olu Dara Jones made his recording debut in 1991 on Main Source’s “Live at the Barbeque,” there was no telling that he would become the greatest New York rapper of all time.
The talent was there, the rhyme skills were there, the stories were there, the pedigree of his forefathers Rakim, Kane, G Rap and Slick Rick were there, but no-one could have known the Queensbridge rapper’s career would turn out the way he did.
Nearly 20 albums later, beefs with Biggie, 2Pac, and Jay-Z all wrapped up, and over 30 years in the rap game, we’re here writing this article while we await King’s Disease III , his fourth album in two years. If that’s not GOAT shit, I don’t know what it is.
