The Mighty Rhino makes a cursory attempt at a definitive top 100 rappers list

At long last, a list I’m happy with!

I fucked around on a rap nerd message board a few days ago and ended up with a new top 100 rappers list that I’m very happy with! This list does attempt to take some consideration of who may be the “objective” greatest into account, in a way that the pure favourites list I posted a few months ago doesn’t, but although earlier iterations of this list, which those of you who know me well enough to have me as a friend on Facebook may have seen, focused a little bit more intently on trying to be “objective”, this list splits the difference between that kind of dispassionate “objectivity” and a genuine accounting of who exactly I personally listen to every day a lot more dextrously than previous iterations of this list have done.

I may at some future point post a version of the list that harmonizes this new top 100 with the commentary and other details that were a part of the original top 250 I started writing in 2015, but for now, all I have the “spoons” (that is, the energy) for is to roll with this new list. I’ve decided to provide a few sentences of commentary on why I’ve chosen each of the 100 artists selected for it.

The voluminous list of honourable mentions has also already been written about, but I’ve decided to move that to a separate document, in order that this one not become too long – it’s already at epistolary length. I’m cognizant that it may be a drain on some of you to read such a long post, but I’ve decided it’s worth doing this so that those of you who may not be initiated into the love of rap music can have at least a notional understanding of why I love each of these artists.

All that said, this actually took a lot less work than the original top 250 I wrote a few years ago did, and I’m surprised by how hard a time my obsessive-compulsive disorder is giving me about the fact that I’m skimping on detail by comparison to what I would usually do.

It’s also important to me to stipulate that I don’t expect those of you who don’t feel called to pay attention to rap music to care at all. (None of you owe it to me to share my passions!)

But I encourage those of you who do like rap music to take a look! And please feel free to supply me with feedback as well.

In (“Brackets”), we have one of the doubtless several songs that I believe make a good case for why each rapper is here.

I decided at the last second that rappers who perform in languages other than English would not be eligible, which disqualified the great MC Solaar, a French-language rapper with Senegalese and Chadian roots who is quite eloquent and dynamic – English is the only language I personally speak, but I’ve been able to read some of Solaar’s lyrics in translation, and his verbal dexterity and erudition are astounding. I’ve been a fan of his since childhood. The song below is worth your time.

I’ve been making sporadic updates to this list ever since I posted it in September of 2021, and I last made a major update to it on 1/12/2023.

CONTENT NOTE for the fact that I very effusively praise quite a number of artists who have committed terrible sins in their personal lives. If you can’t abide reading about amazing art by people who have done indefensible things, you may want to skip reading this document.

Now then! Here’s the new list:

101. Son Doobie of Funkdoobiest (“Lost In Thought”)

A wildly underrated Latiné dude whose mic-assasinating charisma, lyrical excellence, thoughtfulness, and raunchy humour make 1995’s Brothas Doobie an absolute classic of a rap album. Bonus points for the fact that he remains a very good rapper in 2023, although I moved him to #100 when I realized that I liked both his relatively mediocre 2003 solo album (Funk Superhero) and his debut, 1993’s Which Doobie U B?, a lot less than I hoped I would.

100. Bubba Sparxxx (“Jimmy Mathis”)

A Southern whiteboy from LaGrange, Georgia who makes weird lexical choices no other rapper would even dream of making, who is notionally affiliated with the legendary Dungeon Family, and who has made at least ten songs I feel the need to listen to almost every week. I am also quite fond of his fellow memorable and distinctive Southern whiteboys Paul Wall, Rittz, and Yelawolf, although the latter was unfortunately very reluctant to disown the Confederate flag.

99. Young Zee of the Outsidaz (“Thusly”)

A truly kind heart paired with a risqué sense of humour and a reedy voice. I can’t help it, I love him!

98. Joell Ortiz of Slaughterhouse (“Call Me”)

A cheerful Latiné rapper from Brooklyn who is equally adept at eloquent braggadocio, storytelling, and hit-you-in-the-feels music. Royce Da 5’9” from Detroit and Crooked I from Long Beach, who are two of his three groupmates in the pan-regional click known as Slaughterhouse, are both arguably even more talented and technically adept than he is, but I also find both of them are significantly less pleasurable to listen to, because they both occasionally say things I find badly written and/or simply uncomfortable, and also because his joie de vivre is so much more palpable than theirs, although I admit that one thing I enjoy about all three of them is that they all often sound like they’re having a blast rocking the mic. It just happens to be the case that because Joell’s personality is sunnier than Royce’s or Crooked’s, I find him a lot more engaging. As for the fourth member of Slaughterhouse, who is from New Jersey and whose name is Joe Budden, he’s terrible, and the less said about him the better.

97. Thirstin Howl III (“Brooklyn Hard Rock, Part 1”)

It’s been a real pleasure getting to know this wild and scuzzy but playful, hilarious, and good-hearted Puerto Rican vet!

96. Gift of Gab of Blackalicious (“First In Flight”)

I was initially tempted to exclude this fallen West Coast “true-school” legend, because the music of his that doesn’t work for me falls rather flat, but it’s true that his best work reveals a truly luminous and radiant heart and soul, and also that he was always extremely adept at making technically proficient rap music that expressed the contents of that open heart and beautiful soul without sacrificing exemplary craftspersonship.

95. Jaz-O (“Kings Kounty Drummer Freestyle”)

As of January 2023, he is the most recent addition to this list, but I love him too much to keep him off, even if he’s only really here on the basis of five or six staggering verses. His imperious élan has always struck me as dope and cool.

94. Sauce Money of Roc-A-Fella Records (“Bring It On”)

I love him even more than I love Jaz-O, and his record of outrapping their mutual associate Jay-Z is even stronger. His verse on “Bring It On” is a top 20 rap verse for me. I also respect that he has stayed sharp, hanging next to Raekwon and CL Smooth effortlessly on the 2011 mixtape cut “Silk” and various joints facilitated by the late DJ Kay Slay.

93. EL-P of Run The Jewels, Def Jux Records, and Company Flow (“Jeopardy”)

This sardonic white New York rapscallion’s music reflects such a jaded worldview that I find it hard to digest a lot of the time, but I can’t front on what an incredible rapper he is.

92. Chubb Rock (“Return of the Crooklyn Dodgers”)

A truly delightful figure, an obese straight-edge rapper with a deep, hearty voice who refuses to swear, who has made many a jam, and who is almost unstoppable on the rare occasions that he switches from his usual affability to a spittle-flecked, fired-up style all his own.

91. Krayzie Bone of Bone Thugs-N-Harmony (“Ridin’”)

I wish I had also found room in the top 100 proper for Bizzy Bone, the slightly more erratic figure who was one of two stars of this innovative, idiosyncratic, Grammy-winning five-man Cleveland crew, who pair hard technical rapping with gorgeous melodies. But in the end I had to relegate Bizzy Bone to a place just outside the top 100 and instead go with Krayzie Bone, who has remained a great rapper all these years.

90. Too Short (“Blow The Whistle”)

One of the OG “pimp” rappers, an Oakland mainstay who has stayed youthful and dynamic on the mic for about 35 years at this point and is still making great music in his lane as of 2023.

89. MC Lyte (“Ruffneck”)

One of the most venerable of all rappers who are women, and definitely one of the best – spunky, intelligent, charismatic, flavourful, dope.

88. MJG of 8Ball & MJG (“Throw Your Hands Up”)

“Pimp” rappers are a dime a dozen, but I can’t deny this kind of cleverness and savoir faire.

87. Del Tha Funkee Homosapien of Hieroglyphics (“Positive Contact”)

A syllable-bending and slightly curmudgeonly California iconoclast whose Hieroglyphics crew marches to the beat of its own drum and has made plenty of memorable music according to its defiantly “true-school” underground ethos. Casual, who appears in the top half of this list, is my favourite member of Hiero, but Del, Pep Love, Opio, and Tajai are all talented too. Del would be ranked much higher if he hadn’t spent roughly the last 20 years mostly making music I happen not to care for.

86. Biggie (The Notorious B.I.G.) (“Respect”)

This departed Brooklyn legend is easily one of the five or ten most popular rappers in the history of the artform, and I am significantly less keen on him than most for reasons I don’t fully understand how to articulate, but I acknowledge that he frequently packed his rhymes full of novelistic detail, told interesting stories, and knew how to brag so effortlessly and with such a surfeit of charisma that it’s no wonder he conquered the world. I am of the view that his five masterworks, unranked, are “Big Poppa”, “Hypnotize”, “Respect”, “Party and Bullshit”, and the posthumous jam “Rap Phenomenon” with Method Man, Redman, and DJ Premier.

85. LL Cool J (“Mama Said Knock You Out”)

He’s been making irredeemably corny music for what feels like several decades now, but he was the greatest rapper in the fucking world in roughly 1985, and that’s gotta count for something.

84. The GZA (“Liquid Swords”)

I have him ranked much lower than is typically fashionable; his formidable intellect is very revered, and so is his classic 1995 album Liquid Swords. I can’t claim to personally love everything he does, but I can’t deny his razor-sharp mind or the excellence of a line like “Emcees is weak, like clock radio speakers!”

83. Masta Ace of The Juice Crew (the original mix of “Jeep Ass N—a”)

One of the best-beloved “true-school” New York rappers, Masta Ace came out the gate hungry and engaging in 1988, and although his music got a lot more relaxed and distaff over time, to the point where I find it a little bit staid sometimes, he has always been an intelligent and honest rapper. I wish I had also found room for his friend Ed OG, who is from Boston and with whom he now has a certain “Yes, we’re both pushing 60 and we can both still rap, what are you gonna do about it?” chemistry. They both sometimes carry themselves like cranky old men, but they also both have a certain gravitas.

82. Ice-T (“Squeeze The Trigger”)

A veteran gangsta rapper and pop culture fixture who has always approached street rap with uncommon intelligence and sophistication, and has been particularly careful to disavow the misogyny and homophobia in which he lamentably trafficked in the early days of his career.

81. Playboy Tre (“Earline’s Son”)

A craggy-voiced, deeply soulful cat from Decatur, Georgia who is responsible for a handful of the very most emotionally potent rap songs it’s ever been my privilege to hear.

80. O.C. of DITC (“Time’s Up”)

His debut album, Word… Life, is excellent “Golden Era” East Coast “boom bap” rap music, and he’s been a workhorse for a full 27 years at this point. Only rarely does he blow my mind, but he also only very seldom comes less than correct. It’s also true that “Time’s Up” is one of the very most perfect of all rap songs. Any rapper would be lucky to get even one moment of such perfect chef’s-kiss one-single-tear lucidity across in their entire career.

79. Donny Yonder (“Roughneck”)

A good friend of mine, an Italian-Canadian man from Welland, Ontario whose gonzo style I adore – I consider him one of the most talented rappers in the whole world! He makes me imagine what would happen if the madcap absurdity that the New Jersey crew known as the Outsidaz brought to the game had been kept alive, but had also been rendered gentle and friendly rather than dirty. His style is magical.

78. Pusha T of Clipse (“Ain’t Cha”)

One of the most fiendishly clever of all rappers, even though he and his equally gifted brother No Malice generally don’t talk about anything except their history as drug dealers. Their extended crew features at least four more major talents – Ab-Liva, Sandman, Fam-Lay, and Roscoe P. Coldchain.

77. Tonedeff of QN5 (“Love Ain’t”)

Tonedeff is a Latiné rapper with roots in both New York and Florida who possesses what is quite simply the greatest flow in the entire 48-year history of the genre of rap music, and who also happens to be uncommonly good at writing, although he does not make sonic decisions for which I particularly care especially often. The rhythmic complexity of which he is capable is the kind of thing that sends my jaw racing to the floor.

76. Lyrics Born of Quannum Projects (the “Do That There” remix)

This towering Japanese-American underground king can rap faster than pretty much anyone, and also happens to be incredible at coming up with lyrics that are clever, intelligent, eloquent, and hilarious all at the same time. He is also rather good at making music that works in conventional “lyrical” rap terms while also incorporating funk elements. At one point, I had him ranked a full 20 spots higher than this; the reason his ranking has fallen is because I happen to subjectively consider some of the music he has made in the past ten years or so to be kinda bad. But the fact remains that when he’s on, very few rappers of any variety can touch him.

75. Juvenile (the original version of “Gotta Get It”)

I listen to the song I’ve recommended almost every single day, because Juvenile, who was raised on the subgenre of New Orleans party and club music known as “bounce”, makes every single line of that song sing by virtue of his hilarious wit. “Ha” is another brilliant moment.

74. Diamond D of DITC (“Rock Shyt”)

One of the very most charismatic, and also someone who has evolved into a superb writer. He has a certain élan very few rappers can match. He is also deservedly beloved for having made a great many excellent beats.

73. Lord Finesse of DITC (“Return of the Funky Man”)

Who or what is fucking with Lord Finesse’s charisma and his punchlines? No one and nothing, that’s who and that’s what.

72. Grand Puba of Brand Nubian (“Who Makes The Loot”)

Very much cut from the same clever, witty, charismatic, and personable cloth as Lord Finesse, but perhaps infinitesimally sharper, too. His two groupmates in Brand Nubian, Sadat X and Lord Jamar, are generally almost completely useless, but their friend Snagg Da Don is quite good and worthy of your attention.

71. Young Bleed of the No Limit tank (“Stamp On It”)

A dear friend of mine who has been a delight to work with and get to know and who, with his effortless charm and flow and bounce, is quite easily one of the most underrated rappers in the world.

70. Freeway of State Property (“Sun Don’t Shine”)

This devout Salafi Muslim from Philadelphia yelps and howls with more pure emotion than almost any other rapper, and he has what his friend Brother Ali famously called “a voice like an electric guitar”, as well as a flow, style, and approach to rhyme schemes that move in a thousand fascinating directions before resolving at exactly the right place every time. Not every Freeway verse is magic, but many are, and if he had a slightly better batting average, I would rank him much higher, because his best work is absolutely indelible.

69. Wise Intelligent of Poor Righteous Teachers (“Easy Star”)

I find this man’s beliefs about Jews and Zionism, as well as about Western civilization in general, truly reprehensible, but with his animated reggae-influenced style and nimble flow, he is nonetheless one of the most compelling Black nationalist rappers there’s ever been, especially among those who belong to the indigenous quasi-Islamic American sect known as “the 5% Nation of Gods and Earths.” It’s also true that there are several great Poor Righteous Teachers albums, of which he is always the anchor.

68. Breeze Brewin of The Juggaknots (“Clear Blue Skies”)

Aesop rock once said something to the effect that this hyper intelligent and relatively reclusive New York sophisticate was agreed-upon by every rapper in the East Coast Underground as being better at putting words together than any of the rest of them, and you don’t have to listen for long to discover why that’s true.

67. Divine Styler (the John Tejada Funky Precedent remix of “Make It Plain”)

This New York veteran, who has been active since at least 1987, is famous for making some of the least approachable abstract rap that anyone has ever made, but it’s impossible not to respect what a stirring, if also confounding, accomplishment his 1992 album Spiral Walls Containing Autumns of Light is, on top of which he has also made a lot of more conventional “boom bap” that bangs really hard, and he has always been underrated for his eloquence and sincerity.

66. Saafir (“Light Sleeper”)

A West Coast abstract rap titan. “Light Sleeper” is my favourite “singular statement from a weird mind” rap song there has ever been.

65. WC of Westside Connection (“100% Legit”)

Ice Cube’s longtime lieutenant has been dope since 1989, and in particular, “100% Legit” and “Frontline” are both unimproveable songs. There are many underrated California gangsta rappers – Kokane, MC Eiht, King Tee, and more – but he’s the cream of that crop.

64. Peedi Crakk of State Property (“Toyfriend”)

I can’t recommend the frenetic energy this squeaky-voiced Latiné dude brings to a song highly enough. He swallows every single track whole. He also tends to eat other rappers alive when he makes guest appearances. In particular, the song I have listed above is just him gunnin’ for two minutes and five seconds over an excellent club beat, rapping like his very life depended on his being able to spit the most brilliant shit he possibly could, and I’ve never heard anything like it in my life.

63. Queen Latifah (“U.N.I.T.Y.”)

I have loved her for a hundred thousand years and always, always will. She is not just a great rapper but a great actor, a natural born star, and one of the dopest all-around entertainers in the last 30 years of pop culture. Shoutout to her similarly charming friend Monie Love!

62. Chuck D of Public Enemy (“Brothers Gonna Work It Out”)

There will be those who are shocked that I have ranked this foghorn-voiced master of blistering Leftist agitprop so low – there are at least four genuinely good and culturally significant Public Enemy albums, and there’s no denying what an effective sloganeer he is. I’m also very charmed by his latter-day support for the great Bernie Sanders. The fact remains that what he does affects me less powerfully than it does many of his most ardent fans, and I also contend that he isn’t as good a rapper now as he once was, but I can’t deny his overwhelmingly important place in the culture.

61. Tupac Shakur (“Changes”)

I have gone on record to say I admire this almost universally beloved late cultural icon, particularly in light of the complexity of his persona and the vivid three-dimensionality of his emotional life, which he expressed artfully in many good songs.

60. Tribe One of Malibu Shark Attack and The Remnant (“Doing It Wrong”)

With apologies to Mega Ran, More Or Les, Mikal Kermit Hill, Jesse Dangerously, Prowess The Testament, Humpasaur Jones, Dopey Ziegler, Lex The Lexicon Artist, and Kadesh Flow (all of whom are very good!), this remarkably eloquent and perceptive biracial rapper from Atlanta has no competition at all as the most talented artist in the history of the much-maligned subgenre known as “nerdcore.” I admit that I mostly despise the subgenre apart from the artists I’ve listed, but Tribe almost justifies it by himself, not least because the album he made in 2014 with the Irish producer Rocky O’Reilly under the name Malibu Shark Attack contains at least two songs, “Doing It Wrong” and “Internal Organs”, that I think are quite clearly among the best songs in the history of rap music.

59. Ultra Magnus (“Duck”)

Thusano is the single greatest rap live performer I’ve ever seen, outpacing even Busta Rhymes and Big Daddy Kane; he is also lightspeed incredible at fast rapping, and his music is absolutely superb overall, such that I consider it a great honour and privilege to call myself his friend.

58. D-Sisive (“Golden Lullaby”)

Virtually no one can be more consistently relied upon to walk the road less travelled and come out the other side with a rap masterpiece. He is from Toronto, and I have the good fortune to call him a friend, so he and I have worked together and had a long and fruitful association, and I contend that songs like “Golden Lullaby”, “The Water”, “When We Die We Die Together”, “West Coast”, “I Love A Girl”, “Kneecaps”, and “Bozo Nightmare” should have made him rich and famous, or at least earned him the Juno Awards we all know he deserves. He is also responsible for putting an absolutely staggering verse on a song I made in 2018 called “Resplendent”, and he has great chemistry with The Legend Adam Bomb, on whom more later.

57. DJ Quik (“Jet Set”)

Hilariously ornery, but also capable of rich and penetrating emotional songs, not to mention that he is an outstanding producer whose work I strongly prefer to that of the much more revered and popular Dr. Dre. I also happen to be very fond of many of the rappers he hangs out with whom one can only really hear when they’re making guest appearances on his albums – not just Suga Free, who appears higher on this list, but also AMG, Blakkazz KK, Playa Hamm, Tweed Cadillac, and the late Mausberg, among others.

56. Percee P (“A Day At The Races”)

John Percy Simon was raised in the Bronx and has been rapping since at least 1988, and my friend Jesse Dangerously put it accurately when he said that “Percee P only ever really writes one verse, but he’s so consistent that all he has to do is turn on the tap and the same incredible verse comes out every single time, just with slightly different lyrics.” He is one of the undisputed masters of fast rap, with an unearthly, beautiful flow. My experiences with him as a human being have been sharply negative, but I can’t deny how completely my mind and my world broke in half when I heard him rap for the first time, so he has to be on this list anyway.

55. Killer Mike of the Dungeon Family and Run The Jewels (“God In The Building, Part 1”)

I don’t agree with every single one of his political opinions – I can’t emphasize how strongly I disagree with someone who supports both Jeremy Corbyn in the UK and the Second Amendment to the Constitution of the United States of America – but there’s no denying that this man is a blisteringly powerful rapper, possessed of the wisdom and insight to be able to speak accurately and movingly to the reality of the oppression experienced by so many Black Americans. His strength and fire are truly extraordinary to behold and witness.

54. Cam’ron of Dipset (“Down and Out”)

A street rapper from Harlem who absolutely loves playing with syllable combinations and rhyme schemes and who has a delightful and memorably gonzo sense of humour. I’m also very fond of his friends Hell Rell and Vado.

53. A.G. of DITC (“Infected”)

It took me a few years to realize how special this cat is – I wasn’t initially terribly fond of his work, although I always liked him well enough, but I eventually realize that he’s special and extraordinary, primarily because the rap critic Andrew Nosnitsky, whose writing and taste mean a lot to me, pointed out that he’s dramatically better in his middle age than the great majority of “elder statespeople” rappers are. The songs “Infected”, “Take It Back”, and “Here ‘Til Infinity” made me a fan for life. I have since had the opportunity to become Andre’s friend and work with him, and I’m very proud of that. He has been very kind to me, and I think he’s tremendously gifted and deserves all the praise he’s been getting.

52. Sean Price of Heltah Skeltah and the Boot Camp Clik (“Boom Bye Yeah”)

I’ve said it before – this guy is the purest distillation of the spirit of not giving a fuck in the history of rap. Pimp C of UGK and Ol’ Dirty Bastard of the Wu-Tang Clan are the only rappers who come even close to matching him in that respect. He was pretty good for most of the 1990s, but woke up one morning around the year 2004 and decided he would only ever exclusively crack hilariously filthy and disrespectful jokes in rap form ever again, and right from that eureka moment, right up until he sadly departed for the realm of the Spirit, he was one of the most electrifying rappers on the planet, to the tune of an adoring cult that considers him one of the greatest of all time. Bonus points for his chemistry not just with his old friend and Heltah Skeltah groupmate The Rockness Monstah but also with his fellow departed underground hero MF DOOM.

51. Freddie Gibbs (“Crushin’ Feelin’s”)

I’ve written about him at length here before – as I’ve said, I think he’s probably my favourite pure gangsta rapper ever to fuckin’ breathe: eloquent, clever, capable of moments of stunning emotional potency, and possessed of what Exclaim! magazine once referred to (speaking of a different rapper, but I’ve repurposed the remark because it’s so apt) as “a flow like liquid silk.”

50. Chali 2na of Jurassic 5 (“A Day At The Races”)

I’ve had the good fortune to meet and perform with this very fine man, and he will always get special props from me because he was my FIRST favourite rapper; I love his deep basso profondo voice, his incredibly charismatic mic presence, and his unconventional way with a rap lyric – he almost never goes the obvious route in terms of the lyrics he writes, and I find him absolutely mesmerizing because of it.

49. Jean Grae (“So Wrong”)

Not everything they do works for me, but when they’re on, they’re a mind-crushing assassin. “The Prestige” is another essential. They get the nod over several rappers who are arguably more consistent than they are, because their best material is simply that incredible.

48. Lil’ Fame of M.O.P. (“Blood, Sweat, Tears”)

The duo of Lil’ Fame and Billy Danze, who are collectively known as “the Mash Out Posse” (M.O.P.), are widely beloved for making some of the most invigorating hardcore rap music ever – they mostly just yell really loud, but the way they do so is electrifying. Fame, who is recognizable as the member of the duo with a voice so high that he almost sounds like a child, is notable for never having spit a weak verse that I’ve ever heard, not once in approximately 30 years. I particularly recommend the song I’ve mentioned above, which is an instance of him getting exceptionally vulnerable and revealing his heart on record, but he’s also absolutely superb at bone-hard shit-talk.

47. Casual of Hieroglyphics (the “Callin’ Out” remix)

Charisma, swagger, and wordplay from here to the moon.

46. Kendrick Lamar (“King Kunta”)

Roughly deserving of the tsunami of hosannas and accolades he’s received – a sharp and restless mind perpetually at work.

45. Shad (“Brother (Watching)”)

The only rapper of the relatively “new” generation whom I believe outpaces Kendrick, largely on the merits of even better lyrics, plus equally beautifully crafted albums. I’m blessed to be able to call him a dear friend.

44. Mystikal (“Hit Me!”)

The closest rap music has ever come to vintage James Brown, with an electrifying delivery, showstopping charisma, and a remarkable flow. He has committed worse crimes in his personal life than any other rapper has (with the lone possible exception of a relative nonentity named South Park Mexican), so I don’t blame any of you who choose to ignore him, but I need to listen to him regularly in order to be happy, because I love his music more passionately than I do almost any other artist’s in any genre.

43. The Legend Adam Bomb (“Show & Prove”)

A straight-ahead meat-and-potatoes technical rapper whose staggering eloquence makes my rap-nerd heart sing. Rivalled only by Shad and D-Sisive as the greatest rapper Canada has ever produced. My paean to him is to be found here, and he deserves every word of it and then some.

42. Jadakiss of The Lox (“We Gon’ Make It”)

Another relatively “mainstream” street rapper, but one with one hell of a pen – very few rappers have quite the gift that he has for vivid crime-drama imagery.

41. Ka (“Cold Facts”)

He’s been around since the mid-1990s, but has only become popular in the last ten years or so – he and his friend Roc Marciano have revived New York underground rap and taken it in some very beguiling directions. Ka is an unusually reclusive cult figure who burrows deep into his chosen subject matter (the samurai code, Greek mythology, whatever) and crafts fully formed and wholly sui generis rap albums on that basis. He’s a genuinely extraordinary artist and top-tier writer of rap lyrics who makes all of his music almost entirely himself, works fully independently, and has a day job as the captain of a firefighting team. Ka is very cool.

40. Aesop Rock (“None Shall Pass”)

There has never been a rapper like Aesop Rock before, and there may never be one again. It took me quite a few years to understand how to appreciate him, but once I did, I recognized that his extraordinary eloquence, intelligence, wit, and capacity for emotional depth deserve serious props. Amid an endless parade of terrible white rappers, he is one of very few who unquestionably justify their place in the culture. I’m very glad to have him representing us.

39. Brother Ali (“You Say (Puppy Love)”)

Narrowly gets my vote over The Legend Adam Bomb and Aesop Rock as the greatest white rapper ever to do it – an albino Muslim rapper from Minneapolis whom I regard as perhaps the best pure songwriter in the history of our beautiful genre. I wrote this tribute to him not long ago, and somehow it doesn’t feel quite rapturous enough.

38. Suga Free (“Angry Enuff”)

Probably the greatest of all “pimp” rappers, with a highly unorthodox flow that zigzags everywhere and a simultaneously dirty and verbally dexterous sense of humour that I find irresistible.

37. Slick Rick (“Children’s Story”)

One of the original storytelling rappers, sweet and charming and impossible to forget or not to love.

36. Tragedy Khadafi (“Astonishing”)

Just listen to the song above, which is a four-man posse cut organized by the Canadian producer Marco Polo – Tragedy, who is an affiliate of the legendary Juice Crew, goes last, and despite a valiant effort by the great Inspectah Deck, he steals the entire thing effortlessly. His verse on this is just… mind-boggling. After I had my brain assassinated by that verse, I went back and realized that he’s always been this good – he’s been rapping since about 1985, and only very seldom has he ever spit anything that hasn’t been remarkably vivid, memorable, and interesting. He is one of the best pure writers the rap game has ever seen.

35. CL Smooth (“For Pete’s Sake”)

With the exception of the aforementioned Chali 2na of Jurassic 5, CL was the first rapper I ever truly loved, and I still absolutely adore his nimble flow and effortless charisma and personability. The two proper Pete Rock & CL Smooth albums are both 9.5/10 classics, and although he is only seldom moved to rap anymore, I love a lot of his more recent work as well. In particular, he has such amazing chemistry with AZ that I would love to hear them make an album together.

34. Beanie Sigel of State Property (“Feel It In The Air”)

One of the best hardcore rappers, with a gift for plainspoken emotional honesty that hits devastatingly hard. The B. Coming is one of the greatest of all rap albums. Also, when he feels like just going off about how he’ll fuck his enemies up, his brash “Come at me, motherfucker!” bravado can be electrifying.

33. Black Sheep Dres (“First… and Then”)

His unflappable Bugs Bunny charisma and élan on the 1991 album A Wolf In Sheep’s Clothing have to be heard to be believed, because they’re that titanic of an achievement. And it also happens to be the case that, at the age of 54 as of October 2021, this cat may be the very best middle-aged rapper not named Ghostface or Scarface.

32. Z-Ro of the Screwed Up Click and Rap-A-Lot Records (“I Don’t Give A Damn”)

Arguably the single most underrated rapper in the universe – a Texas legend with a gorgeous singing voice whose music packs a metric fuckton of an emotional wallop.

31. Treach of Naughty By Nature (“Roll With The Flavor”)

Just a barnburner of a rapper. I’ll have to find some videos of Eminem talking about how Treach was so good in the early 1990s that he made him want to retire and hang it up because he feared he would never be as good.

30. Inspectah Deck (“Above The Clouds”)

Legendary as a guest-verse assassin, and if his 1995 debut album Assassination Day hadn’t been destroyed in a studio flood, I think he would probably rank even higher. His capacity for memorable imagery has rarely been equalled, and I love his fired-up delivery, too.

29. MF DOOM (“Saliva”)

One of the all-time best-beloved heroes of the underground – sadly departed now, alas (my anguished eulogy for him is here), but always prodigiously inventive, forever making interesting lexical choices and telling hilarious jokes. There’s never been anyone quite like him.

28. Big L of DITC (“Put It On”)

He really was a dynamo – I don’t see how any rap fan could deny just how completely it seemed like he was destined to conquer and swallow the world. Ave atque vale.

27. Big Pun (“Still Not A Player”)

This morbidly obese Latiné rapper had in common with Big L that he was taken from us far too soon and that if he had lived he would almost certainly have conquered the entire universe. I don’t much care for his two big albums, at least not at full length, but he gets the nod anyway because his best work (especially the delightful pop-flavoured single I recommend above) is so stratospherically good. His punchlines, breath control, and gully-ass delivery demand respect. He is allegedly responsible for mistreating his wife and young son, so I can’t vouch for him as a human being, but he was indisputably a remarkable rapper.

26. Roc Marciano (“Pouches of Tuna”)

There is no rapper who more consistently makes me want to cry tears of joy at their astounding combination of verbal eloquence and a magnificently funny sense of humour. His writing is high art.

25. Devin The Dude of Odd Squad and Rap-A-Lot Records (“Doobie Ashtray”)

A friendly, peaceful, deeply loveable, gently and playfully horny non-gangsta stoner who has been writing beautiful songs about human nature and the human condition since at least 1994. There’s simply no feeling in the world as wonderful as the way the ten or so best Devin The Dude songs make me feel.

24. Lauryn Hill of The Fugees (“Allies”)

There have been at least 40 dope rappers who are women, but I don’t know of any who have ever really approached the staggering brilliance of what Lauryn Hill can do, at least not in my opinion – Jean Grae, who as of 2023 has come out as a nonbinary person, got close, but they were the only one. At her best, Ms.Hill very easily one of the greatest and most talented ever to touch the mic. The Fugees as a group are overrated, in my view, but the ten or so best Lauryn verses… holy fuck!

23. Busta Rhymes (“Throw Da Water On ‘Em”)

He’s been making hits since 1991, and is very well-known for his lightning-fast flow, incredible live show, and remarkable catalogue of bangers. He has occasionally said disagreeable things about gay people (a matter on which he appears to have mercifully evolved since the ‘90s), and he’s never quite made a classic album, but there isn’t a rap fan on earth who denies the pizzazz he brings to the game.

22. Cee-Lo of Goodie Mob (“Still Standing”)

I’ll never defend him as a person, since he’s responsible for committing a rape, but there are moments of emotional power in his verses on the two classic Goodie Mob albums that are simply breathtaking. Bonus points for his brief sung verse on the song “Liberation” by OutKast, which might be my favourite individual thing about any song ever, in any genre. Like, just my favourite thing that has ever happened in the entire history of music. I really mean that.

21. E-40 (“It’s A Slumper”)

He’s one of the most polarizing and controversial of all rappers, because his voice and delivery are so unorthodox and because those who aren’t on his wavelength tend to find his writing corny as well, but I absolutely adore him and devour everything he does – Suga Free is his only competition as my favourite rapper in the history of the West Coast, and there are at least ten E-40 songs and probably even more individual verses that I find hilarious, or by the attention to detail in the lyrics of which I am gobsmacked, or by which I am somehow otherwise impressed. He’s a one of one, cut from whole cloth, and we wouldn’t be able to invent him if we didn’t already have him, but my God, am I ever grateful that we do.

20. Ice Cube (“When Will They Shoot”)

E-40 and Suga Free are my favourite West Coast rappers, but unless one prefers Tupac Shakur, Ice Cube has gotta be the “objective” greatest. He has made four strong solo albums, the best of which, The Predator, remains as powerful a statement of Black rage as has ever been put to tape. His verse on the song “Parental Discretion Iz Advised”, by his old group NWA, is also definitely one of my favourite verses in the entire history of the genre. It’s taking all my strength not to animatedly type out the lyrics in ALL CAPS right now.

19. Q-Tip of A Tribe Called Quest (“If The Papes Come”)

Almost certainly the single most charismatic rapper ever, and definitely among those who sounds the most friendly, which makes him approachable and renders his music almost endlessly relistenable. He is, in my view, the best thing about the three classic A Tribe Called Quest albums (Midnight Marauders, Beats Rhymes and Life, and The Low End Theory), all of which will live forever. He has also been pivotal in the careers of legends such as Nas, Organized Konfusion, and Mobb Deep. Hats off to one of the true Renaissance men of this shit.

18. Jay-Z (“So Ghetto”)

The man known as “Hov” has only a few rivals as the most overrated rapper of all time – Drake, Kanye West, Lil’ Wayne, Eminem, Biggie, Tupac, André 3000. But every single one of those artists is talented enough that it at least makes sense that they’re popular and famous and successful, and I can’t deny Jay-Z’s catalogue of wonderful songs. He has made at least four great albums (Reasonable Doubt, the first Blueprint, The Black Album, and American Gangster), and it’s also true that my favourite songs of his – “So Ghetto” first, last, and always, but also “Snoopy Track”, “This Life Forever”, “Lobster & Scrimp”, “Dirt Off Your Shoulder”, “Can I Get Open” with Original Flavor, and “N—-a What N—a Who?” with the great Jaz-O, plus about half of Reasonable Doubt – are about as perfect as rap music ever gets. The reason I see him as overrated even though he has accomplished so much extraordinary shit is because I think the worst Jay-Z music, of which there is rather a lot, is utterly execrable and unlistenable. If he didn’t have so much bad music in his catalogue, I would rank him a lot higher.

17. Big Boi of OutKast (“Fo’ Yo’ Sorrows”)

He’s just a microphone fiend, even though the fact that André 3000 was clearly better during the era of the four classic OutKast albums sometimes disguised that. He is wildly charismatic, routinely comes up with memorably inventive and playful punchlines, and has some of the finest swag in the history of the game. His first official solo album (Sir Luscious Left Foot: The Son of Chico Dusty) is my favourite purely party-focused rap album ever made. And in the years since, he has made a fuckton of great jams, notably “Mama Told Me” with Kelly Rowland, a perfect pop-rap song. He has some outstanding moments on the classic OutKast albums as well, and his Grammy-winning album Speakerboxxx is quite an achievement too (whereas André’s even more acclaimed The Love Below is not.) On top of which, he’s always engaging when discussing politics (much as I disagree with elements of his libertarian perspective), which he tends to do very artfully, sneaking political commentary into party tracks in “Easter egg” fashion. He also tends to give his all to featured guest appearances – his collaborations with Jay-Z, UGK, Run The Jewels, Janelle Monáe, and 8Ball & MJG have all been epic, and he’s also brought it to smaller-scale joints with artists like The Game, Kilo Ali, and The Youngbloodz, among others.

16. Mos Def (“Mathematics”)

I’ve said it before (notably here) – this man may be the single most naturally gifted rap artist ever to pick up a microphone, and neither his boneheaded political views, nor his frequently irritating public behaviour, nor his wildly inconsistent catalogue can torpedo that. There are ten or so songs and an additional seven or eight featured guest verses that make it clear as the noonday sun that he is one of the absolute best. “Mathematics” and “Hip Hop” are both reasonable suggestions as to what might be the single greatest rap song of all time, and they’re on the same fucking album.

15. Bun B of UGK (“Tough Guy”)

I’ve already discussed what makes this unfuckwithable don so special to me elsewhere, and I’ll doubtless do it again, especially when I eventually write a tribute post exclusively devoted to rapturous praise of him. The 20 or so best Bun B verses are simply my favourite rapping any artist has ever done, ever. He is, and I’ll quote myself to make the point, a master of “technical precision married to unfuckwithable swag.” I am not keen on most of the rapping he’s been doing for the past 15 years or so, but at his best, he is quite simply my favourite rapper ever.

14. Redman (“One Shot Deal”)

He’s been a pure beast for at least 29 years. His catalogue is imperfect, but his verses only seldom are. His charisma, live-wire energy, gift for memorably gonzo imagery, and swagger are untouchable.

13. Big Daddy Kane of the Juice Crew (“‘Nuff Respect”)

He hit the scene like an atomic bomb in 1988, and he is not only the quintessence of the flashy “don” rapper and the father of much of Jay-Z’s style, but he has also remained an excellent rapper and writer well into his 50s. His catalogue may not have as many bangers in it as some, but really, all you have to do is listen to the original version of “‘Nuff Respect” from the Juice soundtrack only once to understand why he will walk in glory forever.

12. Kool G Rap of the Juice Crew (“Fall Back”)

Amazing for many of the same reasons as Big Daddy Kane is, including the quality of his rapping in middle age, but buzzer-beats him by exactly one slot because his Donald Goines/Iceberg Slim crime fiction is even more vivid and writerly than anything Kane has done. Very few rappers throw you right in the middle of a compelling scene or story the way Kool G Rap does, and many dozens of important and influential and popular and talented rappers, from Capone to Jadakiss to Raekwon to Pusha T to Big Pun to Nas, have learned from him.

11. AZ (“I’m Back”)

Roc Marciano may have an even sharper pen than AZ does, but when I think of “lyricism” (which in the context of rap music refers to the art of coming up with poetic and eloquent and witty and memorable and beautiful rap lyrics), no one comes to mind faster than AZ. He is perpetually underrated as a result of the fact that very few of his albums are especially well-regarded, but I generally enjoy all of them, because I find him so mesmerizing that I care to investigate the contents of his mind whether the songs necessarily work or not. He is conversant with most of twentieth-century Black history, and I find his ability to make casually stunning reference to legendary figures and place himself within their lineage very impressive, on top of which he is perhaps more talented than virtually any other rapper at the art of the multisyllabic rhyme – he has many a rival for that title, but no clear superiors. His high, nasal voice makes him sound a little bit like a cartoon character, but for whatever reason, I find him substantially more compelling than virtually any three or even five random rappers put together. I listen to my ten or so favourite AZ songs pretty much every week of my life without fail, and I don’t remotely regret it.

10. Raekwon (“Staten We Go Hard”)

I’ve said this before – Raekwon‘s images are like “perfect jewels, piercing shards of glass.” There’s no better way I can articulate it. His pen is thoroughly unorthodox and unlike anyone else’s. Rap nerds generally revere his 1995 magnum opus Only Built 4 Cuban Linx, but I happen to think he got even better around the year 2010 – I love the air of wizened authority in his recent music, and the much slower and more laconic flow he’s adopted. Most of his best music is not on Spotify, in my opinion, which means it’s hard to find, but if you have an interest in hearing what I think is his best stuff, I’ll happily link you to it – he’s a very special and unique emcee, truly one of the greatest writers the game will ever know.

09. Method Man (“M.E.T.H.O.D. Man”)

Did I say Q-Tip was the most charismatic rapper of all time? My apologies, he’s a close second to Mista Mef. The man has never made a flawless album, but it hardly matters, because he just happens to possess, as a matter of his inmost essence, the most perfect imaginable natural charisma and mic presence for or of which a rapper could ever hope or dream. He’s also one hell of a clever and nimble writer, and his chemistry with Redman is dynamite. There are at least 20 Method Man verses that take my breath away, and I feel the need to listen to him constantly, almost every day.

08. André 3000 of OutKast (“Da Art of Storytelling Part 1”)

I’ve gone on the record to make it known that I am annoyed and creeped out by the large and sycophantic cult that thinks André Benjamin has never spit a wack syllable in his life, especially in light of the fact that I mostly very much do not enjoy his much-ballyhooed post-OutKast featured guest appearances. I tend to find his least effective work fatuous and pretentious, albeit sincere. However, there can be no denying that his performance on the four canonical classic OutKast albums (Southernplayalisticadillacmuzik, ATLiens, Aquemini, and Stankonia) is so incredible that he absolutely belongs in the top ten. His mind goes in a cornucopia of interesting directions, and his rare and beautiful poetic sense, keen jntelligence, and exquisite sensitivity deserve the wide-eyed, rapturous acclaim he has received.

07. Posdnuos of De La Soul (“I Am I Be”)

I once went on the record as saying that the erstwhile Kelvin Mercer’s work on the spellbinding tone poem “I Am I Be” is the single most indispensable performance in the history of abstract rap music, and I think that’s essentially obvious and indisputable. The magnitude of Posdnuos’ brilliance on the two near-flawless De La Soul albums, De La Soul Is Dead and Buhloone Mindstate, is so extraordinary that no one has ever quite caught up to him. He has also stayed exceptionally sharp on the mic well into his 50s, even though he’s never quite matched those soaring achievements. He’s one of those rappers that the entire game would be substantially lesser without; that’s how entirely unique and special the things he brings to the game are.

06. Nas (“New York State of Mind”)

Look, okay? Nas’ 1994 debut album Illmatic is just the best rap album ever fuckin’ made. Frankly, it’s one of only three 10/10 albums I’ve ever heard, in any genre, the others being the 1970s soul classics What’s Going On by Marvin Gaye and Curtis by Curtis Mayfield. It’s true that there isn’t even a single other Nas album that’s better than a 7.5/10 – Nas fans have mostly learned to accept the fact that he generally doesn’t know what he’s doing when he’s crafting an album, and frequently chooses bad beats or invests himself in silly song concepts. But it also remains true that scattered across that wildly inconsistent discography are about 30 other songs so incredible that, together with the nine impossibly perfect songs on Illmatic, it’s essentially impossible to deny that when Nas is lucid and on his game, he has the capacity to make staggeringly great rap music. His ex-wife, the talented singer Kelis, has accused him of spousal abuse, admitting that she beat him as often as he beat her but insisting that he would always instigate the physical confrontations between them, so I can’t necessarily vouch for him as a human being, aside from which some of his political and religious beliefs are truly strange. But the fact remains that he is far and away one of the most prodigiously gifted rappers ever to breathe, and that his 40 or so best songs are very much among the finest achievements in the history of the genre.

05. Black Thought of The Roots (“Funk Flex Freeverse”)

I am in the strange position of not ever having particularly cared for the very acclaimed rapping this Philadelphia don did in the 1990s, during which period he anchored at least three Roots albums that are widely considered classics. But around the turn of the new millennium, the man known to the government as Tariq Trotter somehow metamorphosed from a playful stylin’-ass yute who could always rap his ass off but whose work never really clicked with or for me in particular… into a fucking Black James Bond, an unstoppable secret agent who seemed capable of reaching new heights of eloquence with every verse. The apotheosis of this transformation into one of the most erudite and intellectually formidable rappers in the history of the game arrived in 2017, when he was invited to appear on his old friend Funkmaster Flex’s radio show and spit a “freeverse” – a series of rhymes that he had already written but that were not attached to any specific song – which cracked the whole world wide open, and which stands as perhaps the single best display of “lyricism” in the entire history of the genre. There isn’t a single moment in that entire thing in which you can’t or won’t hear and feel the whole world caving in. It’s the Mona Lisa. It’s The Brothers Karamazov. It’s the Eiffel Tower. It’s the Sistine Chapel. It’s the Hagia Sophia. It’s the entire contents of the Louvre. It’s “Spem in Alium”. It’s a fucking masterpiece.

04. Pharoahe Monch of Organized Konfusion (“Bring It On”)

Mr. Troy Jamerson is every bit as eloquent as Black Thought or Mos Def, and his contribution to abstract rap is roughly as significant as that of Posdnuos. The two classic Organized Konfusion albums are monumental achievements, but really, all you need to do if you’d like to get your mind assassinated by the towering genius of Pharoahe fuckin’ Monch is listen to two songs, “Releasing Hypnotical Gases” and “Bring It On”. If those two songs don’t fuck you up forever, I don’t know what to tell you. Oh, and you might as well also check out “Oh No” with Mos Def and Nate Dogg and “Situated” with Brother Ali, because that man works miracles. Really, there’s hardly a bad song in his catalogue, except the one with the awkwardly forced metaphor involving rape which I sincerely believe he didn’t intend to be misogynistic but which is nonetheless cringeworthy – it’s literally called “Rape”. Just avoid that one (and forgive him for occasionally hanging out with weak rappers like Talib Kweli and Shabaam Sahdeeq), and the rest of his catalogue will make you one hell of a happy rap nerd.

03. Scarface (“Who Do You Believe In”)

I’ve praised Brad T. Jordan to the skies on this blog before, and it’s always a pleasure to do it again, because Scarface is, as I never tire of saying, “the master of the gravitas of quietude”; he speaks softly and slowly, and there’s a smoke-burnished preacher’s quality in his voice that makes him sound like he’s been everywhere and seen everything, and he has the capacity to make such deeply wrenching, harrowing, heartfelt emotional songs that you can sometimes literally hear the tears in his eyes. The Fix is second only to Illmatic as the greatest rap album I know of, and it’s a whirlwind tour through the highs and lows of the human condition, with moments so staggeringly potent that they connect me to the simultaneous enormity and fragility of the experience of living more profoundly than any other rap music I’ve ever heard. I’m probably quoting or at least paraphrasing myself in saying much of this, but it never becomes even slightly less true. The whole entire genre of rap music would be substantially lesser without Scarface. I can very easily recommend 11 songs that make the case for his indispensability by themselves: in random order, “What Can I Do”, “I Seen A Man Die”, “Never”, “Who Do You Believe In”, “The Suicide Note”, “Safe”, “Someday”, “Heaven”, “Sorry For What”, “Smile”, and “This Can’t Be Life”. Every single one of those 11 songs is a staggering masterwork, and I will be grateful to him for them forever.

02. Ghostface Killah (“All That I Got Is You”)

If Scarface has made at least 11 masterpieces, there have got to be at least 20 Ghostface Killah songs that are equally as galvanizing, emotionally potent, clever, suspenseful, surreal, imaginative, electrifying, and/or delightful as not just anything Scarface can do, but anything that has ever been achieved by any other rapper ever. There isn’t a single rapper who has made great songs in as wide a variety of modes as Ghostface Killah has, and it’s also true that he has the best discography in the history of rap music by some considerable distance, having made at least five classic solo albums (Ironman, The Pretty Toney Album, Fishscale, Bulletproof Wallets, and the stunning surrealist masterpiece Supreme Clientele.)

Look – just do me a favour. Listen to the following songs in any order at all: “The Champ“, “All That I Got Is You”, “Be Easy”, “Shakey Dog Pt. 1”, “Underwater”, “Buck 50”, “One”, “The Grain”, “Love”, “The Sun”, “The Watch”, “Nutmeg”, “Toney Sigel”, “I Can’t Go To Sleep”, “Good”, “Yolanda‘s House”, “Save Me Dear”, “Daytona 500”, “Tush”, “Charlie Brown”. That’s 20 songs. Not all of them are equally as wonderful as one another, but taken together, they all give you an overall picture of his artistry. If you can still deny Ghostface Killah’s utter genius across a nearly infinite variety of songwriting modes and flavours after hearing all of those songs, then the way you approach not just rap music but music in general might simply be so different from mine that I can’t begin to fathom it. Ghostface Killah is quite simply one of the greatest all-around artists in the history of popular music.

01. Rakim Allah, baby! (“No Omega”)

The God MC is the one, man. The single greatest rapper. The one who, in my eyes, most defines what it is to be a great rapper at all. And his music is still such fun to listen to! To this day! He is a writer par excellence! There are at least 20 songs on which he absolutely goes bonkers and get sets the standard for what it means to rap well! I even enjoy his slightly less brilliant newer stuff, because the man's pen game remains impeccable – I just love both his writing and rapping voices so much. He's the alpha of this rap shit, with no omega, and it's beautiful.

There we go! That’s my new firm 100!

I have listed these rappers’ relevant group affiliations for the small number of those of you who probably don’t know that information, but I didn’t say outright that Ghostface Killah, Method Man, Raekwon, Inspectah Deck, and The GZA are four of the nine original members of the Wu-Tang Clan, which is probably the greatest of all rap groups – OutKast is their most significant competition for that title, although De La Soul and A Tribe Called Quest get close, and UGK and Goodie Mob ain’t too far off. (Scarface and Ice Cube are of course the most famous members of The Geto Boys and NWA respectively, but both of them are here for reasons primarily to do with their solo careers.)

Some of you may be wondering why certain established legends who are or were very significant in the history of hip-hop are absent; all I can say is that after many years of feeling “obliged” to rank Tupac Shakur, Biggie, Eminem, Chuck D, Common, KRS-ONE, Kurupt, Guru, Phife Dawg, Prodigy, LL Cool J, The GZA, Masta Ace, and even the execrable Talib Kweli (whom I despise!) highly because of their importance in and to rap history, I finally decided, “Fuck it, this is my list, it can contain whoever I want it to contain.” So I slipped most of those historically important figures into places that accurately reflect how I personally feel about their music, and filled the list with rappers I truly love instead. It did turn out to be the case that a few rappers I don’t personally listen to very often and who don’t figure especially prominently in my personal journey as a rap listener ended up on the list, but that mostly has to do with the fact that if I had left artists such as Biggie, The GZA, Chuck D, Masta Ace, and LL Cool J off the list completely, it would’ve required me to ignore the consensus about their achievements to a degree that I think might have been a little bit absurd. In short, in cases where I was willing to defy the consensus, several legendary emcees don’t appear on the list at all. In cases where I felt obliged to admit that the consensus has a point (even though I may not personally listen to the artist in question very often), they do eventually show up.

It is highly likely that I will come back to this post at some future point to explain why many these specific rappers I’ve just listed, all of whom are among the most acclaimed in the genre’s history, either didn’t rank highly on my list or weren’t mentioned at all. Far be it from me to contend that artists like Common, Guru of Gang Starr, Prodigy of Mobb Deep, Phife Dawg of A Tribe Called Quest, Kurupt, Ras Kass, and KRS-ONE are or were talentless; they are not. For various reasons, I simply don’t believe strongly enough in what they do or did to put them on my personal list.

Many of the most popular hardcore, “true-school”, and/or “emo” underground rappers, and a handful more who don’t fit into those categories, make perfectly serviceable (sometimes even good!) music that does very little for me, which explains the absence of various talented artists whose work leaves me cold, including (but not limited to) Esoteric, Copywrite, Ghettosocks, Locksmith, Slug of Atmosphere, Sage Francis, Ill Bill (and the other members of Non Phixion), Grieves, Prof, Sole, Reks, Reef The Lost Cauze, R.A. The Rugged Man, Ceschi, Gambit, Grip Grand, Astronautalis, Sa-Roc, Chino XL, RJ Payne, Tech N9ne, Westside Gunn, Your Old Droog, R.A.P. Ferreira, Saigon, Slaine, P.O.S., Sadistik, Snak The Ripper, Hopsin, Substantial, Cage, Dax, Mac Lethal, Merkules, Kristoff Krane, and, crucially, both members of the critically acclaimed duo Armand Hammer (Elucid and billy woods), who are both very sharp lyricists but whose music is too suffused with cynicism for me to have yet been able to much enjoy it.

There are also quite a number of popular “mainstream” rappers whom I think are neither terrible nor worth ranking on a list of the greatest, some of the most notable of whom are Drake, Nicki Minaj, Quavo, Offset, Meek Mill, Rick Ross, Cardi B, Fat Joe, Ja Rule, 2 Chainz, Lil’ Uzi Vert, and Lizzo. Although I have always been rather fond of the Cuban-American club-rapper Pitbull, whose skillset is quite limited but who is a very charming individual, as well as of the Los Angeles street cat YG, whose rapping is so simple that it’s surprising how well-crafted his first two albums are, and his friends RJ Mr. LA and Yowda. DaBaby from North Carolina is a deeply problematic figure, but I nonetheless find that he is is quite a good rapper, and he remains a major star. I also respect 42 Dugg and Shy Glizzy, a pair of squeaky-voiced dudes who are very popular these days, one from Detroit and the other from Washington, DC. And there are a handful of other “mainstream” rappers I’m still trying to figure out my view of, such as Tyler, the Creator (that’s his full stage name), Cordae, J.I.D., NBA Youngboy, and Goldlink. Lil’ Baby, who is among the very most popular working artists as of 2021, gets props from me for his excellent political song “The Bigger Picture”, but does little for me otherwise.

Then there are certain veteran rappers who are considered to have made significant contributions to the culture and who probably seem like major oversights to some but whom it happens for various reasons to be the case that I simply can’t claim to understand how to rank, namely Eazy-E and MC Ren of NWA, MC Serch of 3rd Bass, Salt-N-Pepa, The Beastie Boys, The Jungle Brothers, EPMD, Warren G, and Will Smith.

And, of course, it’s very commonly known to those who genuinely care about my opinions on this kind of thing that there are various popular rappers I happen not to like very much (or in some cases even at all), who include Talib Kweli, Big Sean, Joe Budden, The Game, Evidence, Canibus, Necro, Termanology, Kanye West, Kid Cudi, Joey Badass, Madchild, Tom MacDonald, Unkle Adams, 50 Cent, Rapsody, Vinnie Paz, Machine Gun Kelly, both members of Dead Prez, Classified, B.o.B., XV, Slim Thug, Apathy, Celph Titled, Jeezy, Immortal Technique, Wale, NF, Lil’ Dicky, Juicy J, Jarren Benton, Joey Purp, ASAP Rocky, G-Eazy, Lateef The Truth Speaker, Travis Scott, Macklemore, Wordburglar, Asher Roth, Megabusive, Chris Webby, Sammy Adams, Hoodie Allen, Damn Selene, Gunna, Russ, Lil’ Pump, Lil’ Yachty, Tekashi Sixnine, Playboi Carti, Mickey O’Brien (who is probably the worst rapper I’ve ever heard attempt a professional career), and the late Zumbi of Zion I, among others.

All due credit to the ‘80s pioneers I don’t fully understand how to rank, especially Kool Moe Dee, Sha-Rock, Grandmaster Caz, Roxanne Shanté, Melle Mel, Silver Fox, Steady B, Schoolly D, Chief Rocker Busy Bee, Spoonie Gee, T La Rock, Lady B, Coke La Rock, and both Reverend Run and Darryl McDaniels of Run-DMC! My favourite early-‘80s rapper is probably Grandmaster Caz, whom I know for a fact is still a very good rapper at the age of 60, but I also really like the nasally-voiced militant Sir Ibu of Divine Force, the vaguely dandyish Dana Dane, the clever duo of Superlover Cee and Casanova Rud, the hardhead energy-bomb Just Ice, and the Philadelphia OGs Overlord Ice Dog of Tuff Crew and EST of Three Times Dope.

Also, there are quite a few rappers I love whose styles are so abstract and/or unique that I don’t know how to rank them – I usually refer to them as “the children of Rammellzee”, those whose styles are so weird that ranking them on lists like this feels like a category error. Of the several rappers who fit this description, the ones I like the most are the two members of Camp Lo (Sonny Cheeba and Geechi Suede), as well as Fabo of D4L, a deeply strange sing-rapper from Atlanta who has made at least three songs I dearly love and consider essential listening, and my dear friend Witchdoctor, the latter of whom is probably the single weirdest rapper I listen to regularly. I also very much respect the most enduring weirdo rapper to emerge since the dawn of the new millennium, Lil B The Based God.

NGA FSH, Kool Keith, Godfather Don, the Bay Area “gangsta rap mystic” Andre Nickatina, the late Biz Markie, and the late Shock G are a few more strange, outré rappers who also get props over here.

Young Thug and Future, who are two of the rappers who are most popular among relatively young rap fans in the present age and who are similar to one another in that they’ve both made an impressive number of heartfelt and richly emotive songs despite constantly filtering their voices through the pitch correction software known as AutoTune and despite both working in the relatively strict confines of the Atlanta-based subgenre known as “trap music” (which I generally find thoroughly deadening and boring, except for the fact that it consistently uses the drum pattern known as the “808”, which I love), are two more important rappers whose styles are so distinctive that I wouldn’t know where or how to rank them – I ain’t sure they would make my list even if I did, but they strike me as important enough that it’s worth making mention of them in this context anyway. Both of them have made large quantities of music for which I don’t care, but both of them also have moments of startling lucidity and/or emotional depth that I believe more or less completely justify their massive popularity.

I would also single out my favourite of Young Thug and Future’s disciples, Polo G from Chicago, who is only 22 as of this writing but who has already made some stunningly emotionally potent music. His song “Finer Things” is truly one of my favourite rap songs ever – top 150 at least! There are also quite a few other young “sing-rappers” who have made at least some music I’ve enjoyed, including NoCap, Roddy Ricch, and Rod Wave.

After accounting for all these people, there are still about 150 rappers who would get honourable mention status in the context of this list! Some of the most important who very nearly made the list but didn’t quite, unranked, are Self Jupiter and P.E.A.C.E. of Freestyle Fellowship, Denzel Curry, Sada Baby, G Yamazawa, Toki Wright, Schoolboy Q, Ab-Soul, Kurupt and Daz Dillinger of The Dogg Pound, Black Milk, G Perico, Tobe Nwigwe, Saba, Vakill, 1TakeJay, Montana of 300 (that’s his full stage name), Chance The Rapper, Blaq Poet, the late Mac Dre, Danny Brown, Ab-Liva and Sandman, Fam-Lay, RBX, Kur, DaBoii of SOB x RBE, Vince Staples, the late Black Rob, G Herbo, Tree, Milano Constantine, David Banner and Kamikaze of Crooked Lettaz, Ali Vegas, Gucci Mane, Tela, Boosie Badazz, Dessa of Doomtree, Maestro Fresh Wes, Buk of Psychodrama, G. Dep, Planet Asia, Phonte Coleman of Little Brother, Fraction, the late Guru of Gang Starr, AMG, Alyssa Marie, Emotionz, Fredro Starr of Onyx, Bonshah, Playa Hamm and Tweed Cadillac of Penthouse Players Clique, Spodee, the late Mac Miller, LeZeppo of Chill Squad, Alpoko Don, Playa Fly, T-Mo and Khujo and Big Gipp of Goodie Mob (all three of whom are excellent and underrated!), the late Nipsey Hussle, Foxy Brown, San Quinn, Husalah, Shady Blaze, Rittz, Backbone, Turf Talk, Keak Da Sneak, Lex Talionis, Maxo Kream, Slaughter Rico, Guilty Simpson, Fatlip of The Pharcyde, both members of Dem Dirty Boyz, Kingpin Skinny Pimp, 8Ball of 8Ball & MJG, Killa Kyleon, Currensy, Big Sant, Blu, the late King Kahali, Le1f, Styles P of The Lox, the late Big Moe, Paul Wall, Nature, Vado, Cashus King, Bigg Dawg C-Loc, Young Chris and Neef Buck and Omilio Sparks of State Property, Bishop Lamont, Whitefolkz, the late Soulja Slim, Mac Mall, Finale, Paris, Kane Smego, Muja Messiah, Hell Rell of Dipset, Ras Kass, Capone of Capone-N-Noreaga, Jay Electronica, Fiend, Wax, Ahmad, Freshco, Bumpy Knuckles, the late Lord 3-2, Kingpen Slim, Lex The Lexicon Artist, Buggsy (the British cat, not the Philly battle rapper), Mega Ran, Skee-Lo, the late Freaky Tah of the Lost Boyz, Big Lo, Skepta, the late Big Mello, Longevity, Napoleon Da Legend, the late Killa Sha, Hell Razah, Boots Riley of The Coup, Kehmak, Duke Buzzy, J. Cole, Thought Provokah, Jabo, Tunde Olaniran, Dopey Ziegler, Tragic of Philly Moves, Kevin Gates, Homebwoi, Mick Jenkins, Homeboy Sandman, Mia X, Big Kwam, Sleep Sinatra, King EnZee, G Mane (the Alabama OG), Stephen Harris of G-Side, Savilion and Jay Bizzy and MisterE and Ginzuintriplicate and Jesse Dangerously and More Or Les (who are all members of the Canadian crew Backburner), Rob-O, Stormzy, Fabolous, 3D Na’Tee, Skyzoo, Dave (the kid from the UK), Psalm One, Trifecca, Mr. Funke of Lords of the Underground, Tame One of The Artifacts, Chill Rob G, Kokane, Action Bronson, Meyhem Lauren, Kwest Tha Madd Lad, Conway The Machine, Lloyd Banks, Edan, Snagg Da Don, Mikkey Halsted, Count Bass D, Trae Tha Truth, Invincible, Rel McCoy, The Lady of Rage, 6 Shot, Akala, Zeroh, billy woods and Elucid of Armand Hammer, Trick Daddy, Willie D of The Geto Boys, Godfather Don, Alfamega, Fuc That of Street Smartz, Keysha Freshh, Elete, Brewza, Eve, Bushwick Bill of The Geto Boys, Spenny, Marlon Craft, Pastor Troy, Big Daddy Rap Beast, Spek of Dream Warriors, King Tee, Mach Hommy, Ladybug Mecca and Doodlebug of Digable Planets, Sheek Louch of The Lox, DeDa Baby Pa, Phoenix Pagliacci, Slick Mason of Light It Up, 3-Card, Murs, J-Live, Heather B, Ludacris, Grap Luva, B-Legit, Young Stitch, Trina, Ed OG, Apani, Clubber Laing, Oatie Kato and Swayzack of The Goats, Haviah Mighty, Beans of Antipop Consortium, Doseone of Anticon Records, D.A. of Blac Monks, Big Reese of Parental Advisory, Thes One of People Under The Stairs, both members of Nice & Smooth, both members of The Beatnuts, both members of Das EFX, Mark Jordan, Tiye Phoenix, Choclair, Knamelis, Tona, Kish, Wio-K and Nish Raawks and Grimace Love and Dan-e-o (these four are all in the Toronto crew known as Monolith), Buck 65, Common (despite his work having largely sucked for roughly 23 years at this point), and, despite the multitudinous reasons my opinion of this man and his music is mostly very low, KRS-ONE. My OCD seems to be requiring me to provide a list of every other rapper I even remotely dig in the entire history of the game, but I’ll get to that later. This document is long enough as it is.

I’ve written out short blurbs regarding what I appreciate about each of my honourable mentions, but I realized at some point that pairing those blurbs with the rest of this document was making it so long that it might be impossible to read in one sitting, so I decided I wanted to write a separate post saluting the very many artists who get honourable mention. I’ll post that in the next couple days, inshallah.

If you’ve managed to read all this, I must tell you that I’m very honoured! I am periodically compelled to rant about my passions like this, especially when I can pair my rantings with lists, partly because it appears to be the case that I literally do have obsessive-compulsive disorder and partly because my enthusiasm is naturally very difficult to contain. Please don’t feel obliged to engage, but if you decide to, I will be entirely chuffed! Thank you all so very, very much!