Criteria Includes: Catalog, Creativity, Lyricism, Impact, Longevity.
Words by veteran journalist Shea Serrano, he’s written for LA Weekly, The Houston Press and other music publications.
49. The D.O.C.
Although he never got the credit he deserved for his behind the scenes work with NWA, D.O.C. was able to shine on his solo albums, where he showed the world his ability to rhyme. Despite a nearly fatal accident in 1989, he’s kept doing his thing, and is currently working on his fourth album.
Classics: Solo Album: Nobody Does It Better (Ghost-Wrote for Dre & Death Row)
Classics: The Low End Theory, Midnight Marauders
47. Immortal Technique
Felipe Coronel takes a page out of Chuck D’s book: telling the world the truth is his full time job and he won’t let get anything get in his way. He’s the model of righteous anger, a grumpy saint out to save the world from itself.
Classics: Revolutionary Volume 1 & 2.
The king of Hyphy, E-40 has been going strong for years. Always representing the Bay, E’s energy and fearlessness set him apart from the pack.
Classics: In a Major Way, The Hall of Game
45. Big L
The master of the punchline and one of the original freestyle kings, Big L was the nastiest MC to come from 139th and Lenox. His hyperbolic threats and kinetic wordplay made him a rhymer to be reckoned with.
Classics: Lifestylez Ov Da Poor & Dangerous, The Big Picture
Ras gets a lot of hate, for no particular reason. Another working man’s rapper, he sounds comfortable over almost any beat, and never seems at a loss for things to say.
Classic: Soul On Ice (Classic Track – Nature of the Threat)
Whenever you hear Jada’s signature cackle, you know that it’s more likely than not that you’re about to hear some memorable bars. Whether with The Lox or going solo, Jadakiss has proved himself to be a true representative of the New York rap pantheon.
Classic: The Kiss of Death
Guru’s passing came as a shock to the entire world of rap, partly because it was surprising that someone so talented could be lost so suddenly. As the rhyming half of Gangstarr, Guru spit some of the cleanest verses ever heard, making the best of the immaculate production he was always provided with.
Classics: Hard to Earn, Moment of Truth
Classics: Power, O.G. (Original Gangsta)
40. Bun B
Though he was most beloved (and most skilled) as one half of the illustrious UGK, Bun has been doing big things and honoring the member of his partner since 2007. One of the greatest Southern rappers, Bun can go from willfully ignorant to astonishingly brilliant in a single sixteen.
Classics: Ridin Dirty, Dirty Money
Classics: Supreme Clientele, Bulletproof Wallets
38. Busta Rhymes
A fast rap maniac, you could always count on Busta to spit the quickest, weirdest, craziest thing that you’d heard in a minute. A true original, he’s still spitting some of the only great guest verses you’ll hear on the radio.
Classic: When Disaster Strikes
Classics: Quik Is The Name, Safe + Sound
36. Lil Wayne
The oddball Louisiana native isn’t afraid to put out everything he records, whether it be good, great, bad, or just plain ugly (Rebirth). That said, he’s a fearless rapper who can compete with anyone when he’s on his game.
Classics: Tha Carter, Tha Carter III
35. Masta Ace
New heads are always surprised when they finally get around to listening to Masta Ace, and think for a second that they’re listening to Eminem. Their flows are similar but the Juice Crew member got there first, schooling hypocrites and haters when rap was just starting to gain popularity.
Classics: Take a Look Around, SlaughtaHouse
34. Spice 1
Too Short protege’ Spice 1 is likely one of the most underrated gangster rappers of all time. With a matter-of-fact delivery that serves to emphasize the intensity of his stories, Spice could, and would, rap about anything.
Classics: 187 He Wrote, Amerikkka’s Nightmare
Classics: The Infamous, Hell on Earth
This foulmouthed California legend has improved every project he’s been on, from his work with Dre and Death Row to his more recent albums with DJ Quik and Roscoe, not to mention his legendary ‘NY,NY’ verse from 95′
Classics: Dogg Food, Tha Streets Iz a Mutha
Canibus has lost the reputation he used to have, but anyone who was around for his peak will agree that the man can flat-out spit. Although he was blackballed out of the industry, the rapper still holds the crown of having the greatest verse in hip hop history: see 1997′s ‘Beast from the East’ remix
Classics: See: Any of his freestyle’s or guest appearances from 1997-2000 circa
Classics: Liquid Swords, (Appearances on Wu albums)
29. Too Short
Raw and nasty as all get out, Too Short said things on wax that we all wish we were imaginative enough to say to our friends in private. Vulgar and hilarious, he’s a testament to rap’s ability to be honest about the way men talk and think.
Classics: Gettin It’, Cocktails,
Nas’s unsung counterpart, and the man responsible for some of the illest collabos ever made in Hip Hop. With a flow that mediated the difference between old school and new, A.Z. paved the way for what we’ve come to recognize as the New York rapper.
Classics: Do Or Die, Aziatic
27. Snoop Dogg
Rap’s current cuddly teddy bear was once the most gangsterest dude ever to come out of the LBC. His debut album captivated the game and took it to new heights. His work on the Chronic, Doggystyle, and other Death Row projects solidified his spot as an all time great.
Classics: Doggystyle + his work on The Chronic, Dog Food
26. Lauryn Hill
Mz. Hill may not have made anything worthwhile recently, but The Miseducation of Lauryn Hill opened the floodgates for other female rappers, as well as a whole host of new topics and ideas that could be spit in a verse.
Classics: The MisEducation of Lauryn Hill, The Score
25. Black Thought
The frontman of the legendary roots crew, Black Thought spits intelligent rhymes so fast and thick that you’re liable to miss the next three while trying to figure out the first one.
Classics: Illadelph Halflife, Things Fall Apart,Phrenology
24. Chuck D
Public Enemy was probably the most groundbreaking rap group of all time, and Chuck D was definitely the reason. He told it like he saw it (and still does), which made for gritty, honest songs that all of America was forced to pay attention to.
Classics: It Takes A Nation of Millions To Hold Us Back, Fear of a Black Planet
23. Method Man
As the face of the Wu Tang Clan, Method Man was one of the most hyped and hottest rappers of the 90′s, appearing in classic Wu albums, Biggie’s Ready To Die, 2pac’s All Eyez on Me and more.
Classics: Tical + Wu Tang Appearances
22. Talib Kweli
The consummate rapper’s rapper, the underground legend has been tearing it up ever since he and Mos Def teamed up to form Blackstar. Since then he’s been a mainstay, consistently releasing albums that show his dedication and hard work.
Classics: Mos Def & Talib Kweli Are Blackstar, Quality
Although he didn’t start weed rap, Redman is one of the most notable dudes ever to proudly proclaim his love for the herb. Hilarious and offbeat, Red keeps us laughing even as he drops knowledge.
Classics: Whut? Thee Album, Muddy Waters
20. Mos Def
Whether rapping with fellow great Kweli, or deftly illustrating the struggles of black folk on his solo albums, Mos Def has proved himself to be just as talented at rapping as he is at everything else.
Classics: Mos Def & Talib Kweli Are Blackstar, Black on Both Sides
Whenever you hear barking to start off a track you know you’re about to get yelled at by none other than DMX. The Ruff Ryder’s career has slowed a bit due to jail trouble, but for his early listeners, they know he altered the entire landscape of hip hop with his debut classic ‘It’s Dark and Hell is Hot’.
Classics: It’s Dark and Hell is Hot, Flesh of My Flesh
Classics: Built for Cuban Linx + Appearances on Wu Tang Albums
17. KRS One
Although he wasn’t a lyrical heavyweight, KRS One was one of the first guys to bring a real insight and consciousness to his lyrics, a development which makes him as important to rap’s history as nearly any other MC.
Classics: Criminal Minded, By All Means Necessary, Return of the Boom Rap
Classics: Radio, Mr Smith, Mamma Said Knock You Out
15. Kanye West
Ye may not be the best lyricist alive, but he is improving. Combine that with the impact of his music, his heart and work ethic, and the way he utilizes the talents of other rappers and you have to give Yeezy his dues.
Classics: College Dropout, Late Registration
14. Andre 3000
The unpredictable and outrageous half of the best rap duo of all time, Andre’s eccentricities are all forgotten when he steps up to the mic. Outraged or reflective, pensive or pissed off, dude’s bound to spit something ill, whatever his mood.
Classics: ATLiens, Aquemini,
13. Slick Rick
Unfortunately now better known to this generation as “the guy with the thing on his eye” Rick is the patron saint of offbeat rappers everywhere. The Ruler is a gifted storyteller, whose characters and voices create worlds for his listeners to inhabit.
Classics: The Great Adventures of Slick Rick, The Rulers Back
Common’s introspective neo-soul was a breath of fresh air, a fact that he was aware of himself when he told listeners and rappers alike about the right way to treat H.E.R. When he’s not modeling for the Gap, he still spits some of the freshest, most intelligent rhymes you’re likely to hear.
Classics: Resurrection, Be’
11. Kool G Rap
The second member of the legendary Juice Crew to make the list, Kool G Rap was one of the first hyper-lyrical rappers; a guy who inspired the second generation of lyricists who top this list.
Classics: Road To Riches, Wanted Dead or Alive
10. Big Pun
Pun was one of the most flat-out fun rappers ever to spit a sixteen. He could go from party rap to street talk in the blink of an eye but whatever he was talking about he always represented where he was from and what he was about.
Classics: Capital Punishment + Legendary Guest Verses & Freestyles
Classics: Long Live The Kane, It’s A Big Daddy Thing.
At his peak, Em made some of the most original, funniest, angriest songs in the history of the art form. Vicious flows occasionally can’t obscure the ferocious intellect seething just under the surface.
Classics: Slim Shady LP, Marshal Mathers LP
Southern rap’s scratchy voiced elder statesman, ‘face can be as hard as nails if he wants to but when he gets introspective, there’s no one else on Earth who can express the things he can in a verse.
Classics: We Cant Be Stopped (Geto Boys), The Diary, The Fix
6. Ice Cube
The illest member of NWA, Cube was as talented with the group as he was when he went solo. He went from controversial to family friendly, but if you listen closely to his catalogue, it’s clear that the business savvy always coexisted with the gangster shit.
Classics: Straight Outta Compton, The Predator, Amerikkkaz Most Wanted, Death Certificate,
5. Notorious B.I.G
The black Frank White had more flows than anyone, was a storytelling genius and expressed paranoia and fear with the kind of precision that you can usually only find in great literature. A true American original.
Classics: Ready 2 Die, Life After Death
The King of New York may have sullied his reputation with his recent output (BP3), but with a trio of classics and elven number one (solo) albums under his belt, Jigga still qualifies as one of the greatest MC’s of all time.
Classics: Reasonable Doubt, The Blueprint, The Black Album
He’s known as the God for a reason; no one does it like Rakim. The first of the truly great MC’s, he and Eric B made some of the most classic albums of all time together. Anything your favorite rapper does well, you can probably trace back to this guy.
Classics: Paid In Full, Follow The Leader, Don’t Sweat The Technique
Thug poet. Thug Martyr. Introspective rider and sensitive gangster. Pac was built of contradictions, all of which only furthered his myth as one of the lost giants of the game. Pac may be the only rapper to be bigger than the culture itself.
Classics: Me Against The World, All Eyez On Me, The 7 Day Theory
The best pure writer the game has ever seen, Nas easily takes on the role of any and every character he attempts to inhabit. He first introduced himself on Illmatic as a poetic observer of the street but he’s evolved seamlessly from there, to Escobar the kingpin, to Nasir the Teacher, to Nasty the villain, and others, always able to sound comfortable while spitting the truth as he sees it. Intelligent but not pretentious, proud but open-minded without ever revealing a single weak spot in his flow, he made the best album and the best diss song of all time and changed the way we think about modern rap. Who said Esco lost?
Classics: Illmatic, It Was Written, The Lost Tapes, Stillmatic, God’Son
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