A random collection of my opinions on rap music (part 1 of several)
This post is designed to be very brief and not to go into very much detail, but this kind of thing is lots of fun for me to think about.
My friends G Holy and Adam Walsh have been asking random rap-related questions on Facebook lately, so you know I had to go in, baby. Y’all know how I get down. The survey I fill out here has gone around in a slightly
I have elected not to provide YouTube, Spotify, or Bandcamp links to specific songs to make the case for each individual call I’ve made here; I may yet reverse that decision later, but for now, I’ve decided to simply publish this piece, and I’m taking it on faith that enough of the people who read this newsletter love rap music that most of y’all will not be discombobulated by my choice not to hit y’all with 50, 000 links this time. Now then! Here we go!
Favourite rapper of all time: Ghostface Killah, although Scarface gets exceedingly close.
My vote for the objective “best” or “greatest” rapper of all time: Rakim, and I don’t even really think there’s a close second. That’s all I’ll say about this for now.
Favourite rapper of all time: Ghostface Killah, although Scarface gets exceedingly close. Some others who matter to me a lot include Chali 2Na, Mystikal, Bun B, Method Man, AZ, Black Sheep Dres, E-40, Raekwon, Suga Free, Bubba Sparxxx, Z-Ro, Young Bleed, Tragedy Khadafi, Devin The Dude, The Legend Adam Bomb, WC, Queen Latifah, Sauce Money, Jaz-O, Freddie Gibbs, Brother Ali, Shad, Monie Love, and Juvenile.
Favourite rapper who, as of April 2022, began their career recently enough that it makes sense to call them “current”: Probably Freddie Gibbs, although I also think highly of Benny The Butcher, 3D Na’Tee, Polo G, and Shad, as well as of Roc Marciano and Ka, whose careers have developed in such a fashion that I suspect they both count despite technically having been around since the ‘90s.
Favourite rapper of the ‘80s: I mean, it would have to be Rakim, even though ‘90s Rakim is better than ‘80s Rakim and even though I very much admire the ‘80s-era accomplishments and contributions of Big Daddy Kane, Kool G Rap, Slick Rick, Kool Moe Dee, Melle Mel, Grandmaster Caz, Ice-T, Chuck D of Public Enemy, Sir Mix-A-Lot, Schoolly D, Ice Cube, Dana Dane, Chubb Rock, King Tee, EST of Three Times Dope, Overlord Ice Dog of Tuff Crew, Wise Intelligent of Poor Righteous Teachers, MC Lyte, T La Rock, King Sun, Sir Ibu of Divine Force, Freshco, Superlover Cee & Casanova Rud, Doctor Ice of UTFO, the late Biz Markie, the late Heavy D, and many more.
Favourite rapper of the ‘90s: I’m used to thinking of what Bun B of UGK accomplished in the ‘90s and early 2000s as basically my favourite rapping anyone’s ever done, although obviously Rakim, Nas, Posdnuos of De La Soul, Q-Tip of A Tribe Called Quest, André 3000 of OutKast, Pharoahe Monch of Organized Konfusion, Mos Def, and various others put in work that made what I do still roughly think of as the “Golden Era” special.
Favourite rapper of the 2000s: My favourite who began their career around this time is probably Brother Ali, but Shad is important to me too, and I also need to give dap to ‘90s vets like Black Thought, WC, Busta Rhymes, Suga Free, Tragedy Khadafi, Devin The Dude, A.G., E-40, Young Bleed, Diamond D, and DJ Quik for making some of their best music during this era.
Favourite rapper of the 2010s or 2020s: Almost certainly Freddie Gibbs, who made an album called Midwest Gangsta Boxframe Cadillac Muzik that I really love sometime around 2009 or 2010. The runner-up is Big K.R.I.T., who released four stunning projects starting in 2010. Roc Marciano and Ka get honourable mention if they can be said to count! I also feel the need to acknowledge how good Big Boi’s music in this era has been. E-40, Black Thought, and many other vets have also kept improving.
I find it hard to keep the dates straight, but there are various rappers I think of as having entered the game relatively recently who have made important music in the last 15 years or so and who deserve to be acknowledged in contexts like this. I don’t necessarily listen to them all regularly, but they all demand acknowledgement for their meaningful contributions to the culture. There are many, but here are some of their names:
Black Milk, Ab-Soul, Blu, Yelawolf, Vince Staples, Earl Sweatshirt, Wax, Danny Brown, Kendrick Lamar, Phonte, Chance The Rapper, Rittz, Jay Electronica, Joell Ortiz, Royce Da 5’9”, Schoolboy Q, Noname, Crooked I, Lupe Fiasco, Currensy, Pill, J. Cole, the sadly late Nipsey Hussle, the sadly late Mac Miller.
Favourite female rapper: Monie Love or Queen Latifah – I can never choose between them; I love them both equally. My other favourite women rappers, in rough order, are Jean Grae, Bahamadia, Heather B, 3D Na’Tee, Mia X, Rah Digga, Foxy Brown, Shorty No Mas, MC Lyte, Sonja Blade, Ladybug Mecca, The Lady of Rage, and Roxanne Shanté.
I also very much respect and admire Salt-N-Pepa, Lady B, Sammus, Lex The Lexicon Artist, Eve, Sha-Rock, Keysha Freshh, The Conscious Daughters, Prowess The Testament, Haviah Mighty, Lil Kim, Phoenix Pagliacci, and Trina, among others. Lauryn Hill is not a personal favourite, necessarily, but she gets my vote as the best female rapper there’s ever been, and only Jean Grae challenges her for the title.
Favourite queer rapper: Prowess The Testament! And my second-favourite is probably Lex The Lexicon Artist. But there are several other good ones, including Le1f, Jesse Dangerously, Angel Haze, Invincible, Phoenix Pagliacci, Cakes Da Killa, Tunde Olaniran, Mykki Blanco, and the now-retired Duke Buzzy.
Favourite white rapper: Bubba Sparxxx at his best brings me more pleasure with his rapping than any other white rapper ever has, but some of the other white rappers I’m unashamed to call favourites are Brother Ali, The Legend Adam Bomb, Donny Yonder, Aesop Rock, Andy Cooper, Yelawolf, Roshin, Savilion, Jay Bizzy, Paul Wall, Tragic, and I Am Joseph.
I also feel the need to mention my respect for Spenny, Wax, Knamelis, Dopey Ziegler, Skizza, Big Daddy Rap Beast, Emotionz, Doseone, Action Bronson, Young Stitch, Blackboltt, Che Ruben, Illvibe, Notion, Jesse Dangerously, Ginzuintriplicate, and the now-retired Kehmak. I’m sure there are some I’m forgetting.
Favourite Latiné rapper: Definitely Son Doobie of Funkdoobiest, whose style I absolutely adore. Second would be Joell Ortiz, whose music I tend to find a lot of fun to listen to. I acknowledge that peers are probably better at rapping overall, but I find his music so much fun to listen to that I get more burn out of his shit than out of theirs. The late Big Pun was a titan as well, of course.
Black Sunday by Cypress Hill and Brothas Doobie by Funkdoobiest are both masterpiece albums, and the former is definitely the best rap album ever made by Latiné artists. I should probably spend more time with artists like Kid Frost, Lil Rob, and Mellow Man Ace, and groups like Delinquent Habits and A Lighter Shade of Brown.
Favourite Asian rapper: Lyrics Born is pretty clearly the greatest Asian rapper there’s ever been, but I also have a lot of respect for the Bay Area weirdo Rhythm X (who used to go by the sobriquet “the Mental Oriental”), for the South Asian-Canadian battle rappers Loe Pesci and Sam Osa, and for the in-on-the-joke, knowingly silly South Asian comedy rapper Haji Springer. I gather that there have been quite a few Hindu and Sikh artists emerging in the past couple years, especially in battle rap, but I don’t actually know any of their work well.
Favorite trap rapper: I used to say it was T.I., and I still think that man’s best music is superb, but I’m slightly less fond of him than I once was for whatever reason. (I assume it’s not the various sins and crimes he’s committed in his personal life, because I have no explanation for why that’d affect my view of him but not dent my love of Mystikal or Z-Ro in the slightest.)
Nowadays my answer might be Polo G, who is the best of the relatively new “sing-rapper” guys by a lot, although Morray, Roddy Ricch, Rich Homie Quan, NoCap, and Rod Wave all strike me as at least somewhat talented too. Polo G’s song “Finer Things” is really, truly one of my favourite rap songs ever.
I’m also a big fan of Young Dro, Gunplay, Boosie Badazz, and Kevin Gates – they can all REALLY bring it when the mood strikes them. All four of them are excellent traditional spitters who have made music that means a lot to me. And I feel obliged to acknowledge how much better of a rapper 2 Chainz is now then he was a few years ago – when he’s on, that man can really go in.
I’m also moved to mention Gucci Mane, Young Thug, and Future, even though I don’t listen to any of them terribly often. All three of them are very talented, and more than most other rappers of their ilk, they get a lot of hate from people who are not listening carefully and haven’t paid attention to the things they do well.
Despite my belief that Lil Wayne is overrated, I think he too is sometimes unfairly stereotyped by people who haven’t paid attention to how good he can be, and the same is true of Meek Mill to a lesser degree as well, and of Cardi B. I am less taken with Drake or with Nicki Minaj, but both of them have their moments as well.
Not all of these people are “trap” rappers, but I feel compelled to get on my soapbox about how “mainstream” rappers frequently get traduced and misunderstood by “true-school” Golden Era heads who don’t care to comprehend the ways in which the likes of Future or Gucci Mane are making good art because it appears at a glance to have so little in common with traditional “lyrical” rap, so here you go.
Favorite rapper under 30: I don’t have one specific answer, but some of the rappers I respect whom I’ve been led to believe are at least a little bit younger than I am include Polo G, DaBoii of SOB x RBE, Chippass, Morray, Xanman, Tink, G Perico, Eric Jamal of Coast Contra, Dave, Ezale, G Herbo, Marlon Craft, 42 Dugg, Navy Blue, Mick Jenkins, Payroll Giovanni, Maxo Kream, and Kur.
Favorite storyteller in rap history: Ghostface Killah or Scarface. Don’t make me choose.
Favourite featured guest appearance: Probably Bun B on “Tough Guy”, the song with OutKast and Sleepy Brown from the soundtrack to the Samuel L. Jackson/Jeffrey Wright Shaft flick from the year 2000. I also love him on “Bezzle” with T.I. and 8Ball & MJG, “Like Yesterday” with PSK-13, “‘Bout 2 Go Down” with Critical Condition, and “Big Pimpin’” with Jay-Z and Pimp C.
Some favourite guest shots that are NOT by Bun B include Raekwon on “Skew It On The Bar-B” with OutKast, Method Man on “N 2 Gether Now” with Fred Durst, AZ on “Life’s A B—ch” with Nas, Jaz-O on “N—-a What, N—-a Who” with Jay-Z, Guilty Simpson on “All In Together Now” with Skyzoo & Torae, both Brother Ali and Jean Grae on “So Wrong” with Joell Ortiz, Roc Marciano on both “Pouches of Tuna” with Action Bronson and “Horn Play” with Chan Hays, Tragedy Khadafi on “Astonishing” with Marco Polo, Busta Rhymes on “Do It Now” with Mos Def, and Sauce Money on “Bring It On” with Jay-Z and Jaz-O, among others.
Favourite posse cut (that is, favourite rap song with three or more rappers on it): The answer is definitely the original version of “Roll With The Flavor” with Treach, Chip Fu, Bumpy Knuckles, Queen Latifah, Heavy D, D-Nice, and Black Sheep Dres. Seven 16-bar verses, only one less than dope (D-Nice), and four of seven (Dres, Queen Latifah, Heavy D, and Treach) that are flawless all-time classic shit. Good luck finding it on the internet, although the perfectly serviceable Shandi S. Oxford mix is still floating around.
Honourable mention to The Luniz - “I Got 5 On It” [Remix], featuring Dru Down, Richie Rich, E-40, Shock G & Spice 1. I’m also really big on Jurassic 5 - “A Day At The Races” (ft. Big Daddy Kane & Percee P), NWA - “Parental Discretion Iz Advised” (ft. The D.O.C.), Master P - “Make ‘Em Say Uhh!” (ft. Fiend, Silkk The Shocker, Mia X & Mystikal), and OutKast & UGK - “Tough Guy” (ft. Sleepy Brown), among many, many others.
Most overrated rapper: By definition, I would say the most overrated rappers are Biggie, Tupac, Eminem, Jay-Z, Nas, and André 3000, because those are the six guys you generally can’t say anything even mildly critical about without being accused by at least a sizeable cohort of rap nerds of being some kind of traitor to the culture. I also think Kanye West is overrated as a rapper to a seismic, gargantuan degree. I feel a little weird about the cult of Lauryn Hill sometimes, too.
KRS-ONE is definitely one of the rappers with the widest gap between how much we’re all supposed to revere him and how much of his music I actually like. Common is also extremely overrated, in my view – his very best shit is about as good as rap music gets, but I think a lot of his most popular music is just kinda bad. And of course Lil Wayne and Drake are both overrated to absolutely hallucinatory degrees. So is Kendrick Lamar, even though, as is the case with André 3000 and Nas, I am an ardent supporter of his most of the time.
A few of the many other rappers I don’t care for whose fanbases among “real hip-hop!” types are substantial include Vinnie Paz, Apathy, The Game, Evidence, Joe Budden, Talib Kweli, Big Sean, Rapsody, Wale, Joey Badass, Juicy J, Travis Scott, Reks, Chino XL, R.A. the Rugged Man, Celph Titled, Jeezy, Classified, ASAP Rocky, Logic, Chris Webby, Madchild, Tech N9ne, Joyner Lucas, Logic, the Suicide Boys, and all three members of Non Phixion. There are some other popular cats I don’t like, such as Lil Pump, Playboi Carti, Blueface, and Tekashi Sixnine, but their fanbases among real rap heads are small.
I’m used to thinking of Talib Kweli, Joe Budden, and Kanye West as my three absolute least favourites among those who are considered legendary by at least a substantial subset of rap nerds. And I feel the need, for reasons that are very unfortunate, to also list Eminem and Ludacris, even though Ludacris used to be truly amazing and Eminem used to be one of the most talented ever, because they’ve both fallen off quite precipitously.
I feel like Termanology deserves some kind of special award for previously being one of the rappers whose music I hated the most but then improving so much that, as of 2022, I can no longer even try to hate. After 16 years, that guy is finally consistently good, and the duo album he put out with Paul Wall is, as of April 2022, my favourite rap album of the year. Credit where credit is due. And I feel like I should acknowledge Slug and Sage Francis, both talented rappers I generally prefer not to listen to.
Most underrated rapper:
Favourite producer: It’s DJ Premier, and with all due respect to everyone from DJ Quik to Diamond D to Clams Casino to RJD2 to Organized Noize to Buckwild to Fresh Kils to DJ Burn One to Harry Fraud to Timbaland to Notion to Large Professor to Rick Rock to KLC The Drum Major to The Stereotypez to The Beatnuts to Big K.R.I.T. to AVEREXXX to Statik Selektah to Bink! to Marco Polo to Mouse On The Track to Earthtone III to The J.U.S.T.I.C.E. League to The Legendary Traxster to Digs to (perhaps especially!) Pimp C, only Pete Rock comes even remotely close.
Favourite rapper from the region I’m from: If we’re talking the city of Toronto, it’s The Legend Adam Bomb. If we’re talking the entire province of Ontario, Shad and Donny Yonder both enter the discussion. I’m also a huge fan of D-Sisive, Roshin, Fraction, Savilion, Spenny, and Knamelis. The only Canadian rappers from outside Ontario that I truly love (among those I know of as yet) are Ultra Magnus, Jay Bizzy, Bonshah, Emotionz, Skizza, I Am Joseph, and Ginzuintriplicate. There are a variety of other Canadian rappers I respect, but my five personal favourite Canadians ever to do it are Adam Bomb, Shad, Ultra Magnus, Donny Yonder, and D-Sisive.
Favourite rapper from the American East Coast: This question is almost redundant, since about half my top 50 is from New York City and the surrounding areas, but Rakim is the GOAT, Ghostface is #2, and I also listen to Method Man and AZ every single day of my life. If you insist that I need a fifth man, I’d narrowly pick Raekwon.
Honourable mention to everyone from Redman and Mos Def to Queen Latifah and Black Thought to Nas and Wise Intelligent to Pharoahe Monch and Big Daddy Kane to Lil Fame and Inspectah Deck to Beanie Sigel and Roc Marciano to Black Sheep Dres and Joell Ortiz to CL Smooth and Killah Priest to Breeze Brewin and Chubb Rock to Freeway and MF DOOM to Grand Puba and Sauce Money to Bahamadia and Ka to Aesop Rock and Jadakiss to Monie Love and Young Zee to Grandmaster Caz and Freshco to Tragedy Khadafi and Vado to Capone of C-N-N and Percee P to Kool G Rap and Jean Grae to King Sun and EST of Three Times Dope to Cam’ron and A.G. to Treach and Jaz-O to Peedi Crakk and Divine Styler. And on and on forever!
Favourite rapper from the American West Coast: This is easy – the top three is Suga Free, E-40, and Chali 2Na of Jurassic 5. I also love WC, Lyrics Born, Saafir, DJ Quik, Casual, AMG, Xzibit, Kokane, Black C of RBL Posse, Andy Cooper of Ugly Duckling, Husalah, Turf Talk, San Quinn, Keak Da Sneak, MC Eiht, Busdriver, Andre Nickatina, Medusa, Longevity, Zaakir of Jurassic 5, Threat, King Tee, the late and extraordinary King Kahali, Self Jupiter and P.E.A.C.E. (both of Freestyle Fellowship), the homie Myka 9 (also of Freestyle Fellowship), and more.
Favourite rapper from the American South: Bun B at his best is my favourite rapper of all time, full stop, and Scarface at his makes the best rap music that’s ever been made. But I am also incapable of shutting up about how much I love Big Boi (André 3000 makes my top 10 greats but is not a favourite), Mystikal (despite everything), Z-Ro, Devin The Dude, Playboy Tre (aiyyo, this guy is AMAZING!), Juvenile, Young Bleed, Bigg Dawg C-Loc, my man 6 Shot, Bubba Sparxxx, MJG, or the late Big Moe.
Honourable mention to Yelawolf, Gunplay, Big K.R.I.T., Killa Kyleon, ESG, Kevin Gates, Boosie Badazz, Killer Mike, Paul Wall, T.I., Big Sant, Mia X, Playa Fly, Trick Daddy, Trae Tha Truth, Phonte, Pastor Troy, Kingpin Skinny Pimp, Tela, Fiend, and the late Lord 3-2, among others.
Favourite rapper from the American Midwest: Choosing between Freddie Gibbs and Brother Ali is impossible. I also really like Bizzy Bone, Krayzie Bone, Buk of Psychodrama, Mikkey Halsted, Black Milk, Guilty Simpson, Tree, Elzhi, Montana of 300, Twista, Saba, Smino, and Finale.
I run hot and cold on Eminem, Lupe Fiasco, Invincible, Vic Mensa, Royce Da 5’9”, Chance The Rapper, Esham, and Noname, but they’ve all made at least a small amount of music that blows my wig back, so I feel obliged to at least acknowledge them.
Favourite rapper from outside North America: Probably MC Solaar, who is from France and who is a goddamn beast – I hear he ain’t especially respected back home, but I’ve read some of his lyrics in translation, and I think he’s a genius.
I also like Shurik’n and Akhénaton, who are also from France, and I definitely dig Buggsy, Ocean Wisdom, Big Daddy Rap Beast, Akala, Stormzy, and Skepta, who are all British. Tommy Gunnz, from Australia, is super-dope, but he’s retired, alas.
Oh, and Faada Freddy – I hope I’m getting his name right, whoever the guy is from the Senegalese group Daara J who chops faster than Twista on their song “Boomerang”? That guy is a LEGEND!
Favourite rapper who has passed on: Big Moe! But I also love and respect Big L, Sean Price, Heavy D, Freaky Tah, Lord 3-2, Big Pun, Ol’ Dirty Bastard, Pimp C, Black Rob, DMX, Gift of Gab, and MF DOOM, among others.
Favorite rap group: It goes Wu-Tang Clan, then OutKast, then De La Soul, then A Tribe Called Quest, then UGK, then Goodie Mob, then the ranking becomes less important – but I do also love The Juice Crew, DITC, Camp Lo, 8Ball & MJG, Pete Rock & CL Smooth, M.O.P., and Digable Planets.
The rapper who makes the best musical decisions: As I’ve said before, I don’t see how it could be possible possibly be anyone except Kanye West, but I’d like to put in good words for Big Boi, Big K.R.I.T., Ghostface Killah, E-40, and DJ Quik.
The rapper with the best catalogue of great albums: Ghostface Killah! There are four classic Ghostface albums and no bad Ghostface albums. No one else really comes close, in my view.
The rapper who, in their prime, was the very best ever to do it:
The “best rapper alive“ as of April 2022:
The rapper who has had the biggest impact on the culture: A four-way tie between Eminem, Drake, Kanye West, and Tupac Shakur, although of course it also makes sense to acknowledge Biggie, Jay-Z, and Kendrick Lamar.
Favourite rap album of all time: Nas - Illmatic is the eternal answer, but I also love Scarface - The Fix, OutKast - Aquemini, Goodie Mob - Soul Food, Diverse - One A.M., Pete Rock & CL Smooth - Mecca and the Soul Brother, Wu-Tang Clan - 36 Chambers, Common Sense - Resurrection, Big K.R.I.T. - K.R.I.T. Wuz Here, Ghostface Killah - Supreme Clientele,
Favourite rap song of all time: It’s been De La Soul - “I Am I Be” for more than 20 years, but just for the hell of it, here are 19 more that mean a lot to me:
Favourite rapper of the ‘90s: Besides those listed above, Nas, Posdnuos, Pharoahe Monch, Method Man, Bun B, and Mos Def are some of those who made the ‘90s what I do still often refer to as the “Golden Era”. If you forced me to pick only one, Bun B. More on him later.
Favourite rapper of the 2000s: Brother Ali or Shad. Black Thought really came into his own in the 2000s as well, and several other vets who killed it in the ‘90s got even better in the 2000s – Raekwon, WC, Black Sheep Dres, E-40, Big Boi, A.G., Suga Free, Tragedy Khadafi, Diamond D, DJ Quik, Young Bleed.
Although their runs didn’t really start until 2010, I need to give it up to Freddie Gibbs, Rittz, and Big K.R.I.T. Yelawolf is a major talent too, although he’s kinda fallen off. Killer Mike’s best work came during this era as well.
And as far as the 2010s are concerned, I think Roc Marciano, Ka, and Kendrick Lamar are the chief contenders. Shouts as well to the cats who burned bright for a few years and then flamed out – Blu, Wax, Pill, Royce Da 5’9”, Elzhi, Joell Ortiz, Black Milk, Crooked I, Phonte, Lupe Fiasco, Ab-Soul, and Chance The Rapper all had respectable runs, and many of them are still quite good, notably the very underrated Joell Ortiz.
Favourite female rapper: My stock answer is Queen Latifah (I love her), although Monie Love is neck and neck with her (I love Monie too), and Lauryn Hill in her prime was clearly the dopest female rapper there’s ever been. Jean Grae is also easily one of the best ever to do it, and I have always loved various verses and songs by MC Lyte, Shorty No Mas, Bahamadia, Ladybug Mecca, Sammus, Rah Digga, Haviah Mighty, Lex The Lexicon Artist, Phoenix Pagliacci, The Lady of Rage, 3D Na’Tee, Mia X, Heather B, Trina, Keysha Freshh, Eve, Medusa, and Foxy Brown, among many others. I’m sure I’m forgetting some – respect to the legacy of women in hip-hop always!
Favourite queer rapper: It’s a tight race, but I’m giving the blue ribbon to the sadly retired Duke Buzzy. Runner-up is Lex The Lexicon Artist, closely followed by Jesse Dangerously, Le1f, Tunde Olaniran, Invincible, Prowess The Testament, Cakes Da Killa, Angel Haze, and Zebra Katz. Respect to that legacy too.
Favourite trap rapper: Depends who counts. Hesitant though I am to praise him on account of the fact that he’s a world-class scumbag, I think T.I. in his prime was by some distance the most talented rapper in that lane. You could also make a case for Young Dro, Trick Daddy, Gucci Mane, Kevin Gates, Young Thug, Boosie Badazz, Polo G, or Gunplay, all of whom have considerable skills and strengths.
Favourite rapper who’s passed on: This is hard – with all due respect to Biggie, Tupac, Big Pun, Big L, Phife Dawg, Prodigy, Guru, Ol’ Dirty Bastard, Nipsey Hussle, Shock G, Gift of Gab, DMX, Pimp C, Craig Mack, MF DOOM, Biz Markie, Proof, Soulja Slim, Mac Miller, and Sean Price, we’ve yet to lose any of the rappers I truly live and die by, although I’m tempted to say the Pimp just because I loved his beats and his singing voice so much. I guess my answer is Big Moe? I only know two Big Moe songs – “Barre Baby”, and “Confidential Playa” – but I jam the hell out of those two Big Moe songs.
I also really dug Black Rob, Freaky Tah of the Lost Boyz, Malik B. of The Roots, and Heavy D. Gift of Gab was hugely influential on Rhino the baby rap nerd, so he gets special dap. Lest we forget, Rammellzee is probably third behind only Tupac and Biggie as the most significant and influential legend we’ve yet lost as of October 2021 – he was the blueprint for abstract rap; it all traces back to him. He’s the alpha and omega of weird, freaky rap music.
If you dig deep there are a thousand interesting rappers who’ve passed on who were only marginal figures in their day but made an impact nonetheless – Lord 3-2 of The Convicts is a great example (you know him even if you think you don’t, or should, from his classic guest verses on UGK - “One Day” and The Geto Boys - “Straight Gangsterism”), but there’s also Charizma, Camu Tao, Eyedea, Alias, Big Mello, Fat Pat, H.A.W.K., Bender of Flight Distance, Grip Plyaz, The Last Mr. Bigg, Blade Icewood, Prince Markie Dee of The Fat Boys, Hood, Seagram, Jimmy Spicer, Professor X of X Clan, both Kangol Kid and The Educated Rapper of UTFO, Slang Ton of the Outsidaz, Lil Phat from Louisiana, both Skiano and Lil Snupe from Philly, Young Pappy from Chicago, King Reign from Toronto, and a zillion more. Ave atque vale to all the fallen!
Favourite rapper from the province in which I live: The Legend Adam Bomb, indisputably, unless Shad counts, in which case it’s a dead heat. Respect to D-Sisive, Donny Yonder, Tragic, Knamelis, Fraction, More Or Les, Roshin, LeZeppo, Savilion, Kehmak, Noah23, MisterE, Rel McCoy, Blackboltt, Maestro Fresh Wes, Keysha Freshh, Che Ruben, Dynamic, Spenny, Haviah Mighty, Charlie Noiir, Phoenix Pagliacci, Spek of Dream Warriors, Skitsofrenic, Arowbe, Young Stitch, Lex Talionis, Slick Mason, 3-Card, the now-retired Duke Buzzy, and (if he counts, which he may not because he grew up in the Maritimes) Ultra Magnus as well.
Kish, Dan-e-o, Nish Raawks, Kardinal Offishall, Thrust, Wio-K, Michie Mee, Grimace Love, Tona, Ghettosocks, and Choclair all get honourable mention. All of them are very good and are legends and OGs of the game, but it’s also true that I don’t love everything they’ve done equally.
Throw in Skizza, Emotionz, Jay Bizzy, I Am Joseph, Nilla, Ginzuintriplicate, Quake Matthews, Bonshah, and Nostic, who are all from elsewhere in Canada, and I think that’s most of my personal favourite Canadian emcees right there. I’m sure there are a few I’ve forgotten! I apologize for that!
Favourite rapper under 35: The answer is probably Kendrick Lamar, who is 34 as of October 2021. But I’m less passionate about him than most of the other rap heads I interact with are, and if not for him I would no longer have an answer to this question! At least not now that Chance The Rapper has fallen off and Shad and Freddie Gibbs have aged!
There are a couple strong newer artists – 3D Na’Tee, Kur, Marlon Craft, Navy Blue, Mad Squablz, Chris Crack, Lex The Lexicon Artist, Denzel Curry, A-F-R-O, Vince Staples, Stormzy, Earl Sweatshirt, Dave, Samm Henshaw, K.A.A.N., G Herbo, Morray, Piff Marti, Solosam, Che Noir, Ab-Soul, Maxo Kream – but no one who clinches this. So the award goes to Kendrick by default. I wonder if my answer might be different if and when I finally decide to give the time of day to the majority of the music made by Tyler, the Creator! I gather he’s very popular! And I think my favourite rap song by any artist presently under the age of 30 to emerge in the last several years is almost certainly “Finer Things” by Polo G. I genuinely, passionately love that song.
Favourite lyricist: The simplest answer is to just say peak AZ – God, I love the way that man puts words together – or peak Bun B, but there are so many. Mos Def in his prime is a good one. Black Thought at his best for sure. Eminem and Big Pun were both astounding at their respective peaks. Rakim, Ghostface Killah, and Raekwon are unassailable geniuses. Yelawolf at his best is an absolute beast. There are two or three Juvenile songs where I’d contend that he makes a case for himself as a great lyricist, notably “Gotta Get It”, which is a beautiful piece of comedy. E-40 when he feels like it is just ridiculous.
Royce Da 5’9”, Crooked I, Joell Ortiz, J. Cole, Lupe Fiasco, and Jay Electronica are all mostly just okay, but they also all have moments that make my eyes bug out of my head. Method Man at his best is utterly bonkers. MF DOOM was obviously an animal when he wasn’t fucking around. A lucid Cam’Ron, Young Dro, or Lil Wayne verse is always a thing of beauty. Both members of Clipse are dons. Chali 2Na of Jurassic 5 has the occasional clunky line but is about 90% mind-crushing assassin. Much as I despise his evil behaviours, Mystikal is a major contender in my view – he is extremely underrated as a writer of great lyrics.
Breeze Brewin, Aesop Rock, Jean Grae, Roc Marciano, Lyrics Born, Tragedy Khadafi, Ka, and Inspectah Deck are all titans. At his best, the late and deservedly beloved Gift of Gab was stunning. Tonedeff is a fine writer, certainly. Homeboy Sandman is hit or miss but has occasional moments where it’s like “WOO!” Brother Ali is a top ten overall lyricist to me. Bubba Sparxxx might be the most underrated pure rap lyricist of all time. Shad, The Legend Adam Bomb, D-Sisive, Ultra Magnus, Roshin, and Donny Yonder are all up there. There are so many.
Favourite underground rapper: Depends what or who you define as underground, ‘cause three-quarters of the greats probably count by some metric or other. Arbitrarily choosing my own, I’ll throw out some names: AZ, Saafir, Divine Styler, Breeze Brewin, The Legend Adam Bomb, Turf Talk, Son Doobie of Funkdoobiest, Kingpen Slim, the late King Kahali, Playboy Tre, Big Mike (with whom it was the honour of my life to work not long ago), Suga Free, Starlito, Lyrics Born, A.G. of DITC (whom I’m blessed to call a friend), Ka, Chali 2Na (who was the very first rapper I ever truly loved), DaVinci, Mikkey Halsted, Tonedeff, Z-Ro, Roc Marciano, Husalah, Young Bleed, 3D Na’Tee, Tragedy Khadafi, San Quinn, Busdriver, Self Jupiter, Andy Cooper of Ugly Duckling, Tribe One, Kokane, my friend Young Zee.
Most underrated: The entirety of the previous category, really, plus CL Smooth, Bubba Sparxxx (a major talent who deserved much better than he got), DJ Quik, Black Sheep Dres (especially now – he’s still outstanding in his middle age), Xzibit, Gunplay, Queen Latifah, Monie Love, WC, Wise Intelligent of Poor Righteous Teachers, Z-Ro, Chubb Rock, Juvenile, Peedi Crakk (and Beanie Sigel and Freeway and Young Chris), Aesop Rock (recognized by many, yes, but still sometimes unfairly regarded as too much of an egghead instead of as a pure genius), Twista, Young Dro, Mystikal, Devin The Dude, E-40 (who should be universally acknowledged as a legend and great), and probably a literal thousand more.
Most overrated: Talib Kweli, by far. That man is a reprehensible human being and a borderline incompetent rapper, and his legions of passionate fans are deeply mistaken.
Some of my other least favourites: Kanye West, Joe Budden, Evidence, Common (for the past 20 years at least – Resurrection is a classic, but I’m not big on anything else), Classified, Big Sean, Wale, Joey Badass, Logic, Joyner Lucas, Chris Brown (he could never rap at all), The Game, G-Eazy, ASAP Rocky, Macklemore, Jeezy, Travis Scott, Chief Keef, Lil’ Dicky (halfway talented, I admit, but I despise him anyway because he’s a self-impressed racist prick), Kid Cudi, Canibus, Juicy J, 50 Cent, Suicide Boys (ugh), Chris Webby, Unkle Adams (ugh), Madchild, Rapsody, Tom MacDonald (ugh), the late Zumbi of Zion I (God rest the departed), Lateef The Truth Speaker, Donald Glover (“Childish Gambino”), and Termanology.
Most of the very very new wave, too – Lil’ Pump, Playboi Carti, the Latiné pedo kid with the pink hair and the bad teeth… I don’t mean to come across as a crusty troglodytic old head, but I fuckin’ hate almost all those guys.
Also, don’t hate me for this, but a lot of the most popular underground rappers are talented enough but bore me to tears – Apathy, Vinnie Paz, Ill Bill, R.A. The Rugged Man, Reef The Lost Cauze, Necro, Chino XL, Celph Titled, Sabac Red, Goretex, Immortal Technique, Locksmith, and their hyper-aggro hardcore ilk on the one hand, and Slug, Sage Francis, Grieves, Prof, Sadistik, and their emo movement on the other. The vast majority of them are talented enough that they deserve to get paid and feed their families by rapping, but their work leaves me cold. (Brother Ali is the great exception who proves both rules. I’ve also slowly been warming up to both Esoteric and Copywrite, and I always kinda dug JoJo Pellegrino for whatever reason.)
Favourite producer: DJ Premier, forever and always. The rest of my top five is Pete Rock, Organized Noize, Pimp C, DJ Quik. Just outside the top five would be Digs, who happens to be my blood brother and one of the people in my life to whom I am closest and whom I most love – his beats are mindblowing.
Some of my other favourites, unranked, are Buckwild, Black Milk, Diamond D, Easy Mo Bee, DJ Burn One, Rick Rock, Clams Casino, Speakerbomb, Beanz N Kornbread, RJD2, The Legendary Traxster, Fizzy Womack, Jake One, Harry Fraud, Fresh Kils, Large Professor, Notion, Myer Clarity, Statik Selektah, Marco Polo, KLC, Kevin “Khao” Coates, Ant, Bink, The Beatnuts, Just Blaze, and Timbaland. I have a lot more to say about my favourite rap producers, but I’ll save that for another post.
Favourite rap album of all time: Illmatic by Nas is the eternal answer, but big shouts to The Fix by Scarface, Aquemini by OutKast, Soul Food by Goodie Mob, 36 Chambers by the Wu-Tang Clan, Mecca and the Soul Brother by Pete Rock & CL Smooth, Resurrection by Common Sense, Buhloone Mindstate by De La Soul, Supreme Clientele by Ghostface Killah, and Ridin’ Dirty by UGK. That’s my top ten, in that order.
Some others I love: One A.M. by Diverse, De La Soul Is Dead by De La Soul, Sir Luscious Left Foot by Big Boi, Black Sunday by Cypress Hill, Brothas Doobie by Funkdoobiest, Tricks of the Shade by The Goats, Below The Heavens by Blu & Exile, the self-titled Malibu Shark Attack album, The B. Coming by Beanie Sigel, Black On Both Sides by Mos Def, K.R.I.T. Wuz Here by Big K.R.I.T., Midwest Gangsta Boxframe Cadillac Muzik by Freddie Gibbs, Just Tryin’ Ta Live by Devin The Dude, Run The Jewels 2 by Run The Jewels, The Predator by Ice Cube, Trap Muzik by T.I., Taste The Secret by Ugly Duckling, Warriorz by M.O.P., Reasonable Doubt by Jay-Z, Midnight Marauders by A Tribe Called Quest (and also Beats Rhymes and Life and The Low End Theory), Uptown Saturday Night by Camp Lo, Reachin’ (A New Refutation of Time and Space) by Digable Planets, The Main Ingredient by Pete Rock & CL Smooth, Trauma by DJ Quik, ATLiens and Stankonia by OutKast, Deliverance by Bubba Sparxxx, the first two Organized Konfusion albums, all of the first five Ghostface Killah solo albums, and both installments of Raekwon’s Only Built 4 Cuban Linx series, among many others.
Favourite rap song of all time of today: My answer to this question is relatively firm. Feel free to peruse this list if you wish.
The objective “best” rap lyricist ever: I mean, it would have to be Rakim, right? He basically set the standard for everyone who came after him. I maintain that he’s still probably a top five writer in the history of the game, even taking into account every single rapper who’s come after him, all the 500 or so great rappers he and his forebears were responsible for birthing.
But you could also make a case for Pharoahe Monch, Black Thought, Mos Def, Brother Ali, or Shad. There are many dozens of others I respect – everyone from AZ and Tragedy Khadafi to Crooked I and Joell Ortiz to Jay Electronica and Elzhi to Roc Marciano and Ka to Inspectah Deck and Jadakiss to Cam’ron and Lil’ Wayne to Aesop Rock and MF DOOM to Jean Grae and Royce Da 5’9” to Lyrics Born and Gift of Gab to my personal #2 and #3, Ghostface Killah and Scarface. And, as I’ve said, there are a lot of rappers I respect as lyricists who never get brought up in these conversations because their styles are not traditionally “lyrical” – Suga Free! E-40! Young Dro! MJG! Bubba Sparxxx! Mystikal! Chali 2Na! Juvenile! CL Smooth! Andy Cooper! Black Sheep Dres! Yelawolf!
But I digress – the final answer is Rakim Allah. There’s only one God MC.
The rapper who has had the most impact on the culture: Probably Kanye West, but it might be a four-way tie between him, Eminem, Drake, and Tupac Shakur. My answer as to who has been most influential in the culture is the same. I’ll try to comment briefly on what I mean.
Rap music has always principally been an artform which belongs to the oppressed, the marginalized, and the dispossessed, particularly those who are people of colour. Tupac Shakur would probably get my vote as the single most influential rapper there’s ever been, as a result of the fact that, due to the complexities of his inner life and emotional makeup as someone wth both a richly poetic soul and an inclination towards self-destructive violence, he was in many ways the apotheosis of the “street rapper” ethos. His titanic charisma, keen intelligence, and remarkable sensitivity made him a global icon, especially among people who were themselves involved in “street” activity, but also in the wider culture. I would argue that no one has quite had an impact on rap music like he has, and it’s also notable that a significant subset of the rap community considers him an important figure in the history of Black American culture at large, on roughly the same level as people like Fred Hampton and Malcolm X.
Eminem is probably second, because although DJ Kool Herc explicitly made it clear from the very beginning that white people were welcome in hip-hop, Eminem is the main reason the floodgates burst open and white people are now prominently represented as not just consumers but makers of English-language rap music. Being a white rapper myself, I owe him and his mentor Dr. Dre a debt of gratitude for this, even though I think it could convincingly be argued that enough white rappers are engaging in vaguely appropriative cosplay that some of the consequences of the revolution Eminem ushered in have been deleterious.
Kanye West and Drake strike me as very important figures as well, because the violence-adjacent “street“ ethos that was represented by Tupac Shakur, Dr. Dre, Biggie, Snoop Dogg, 50 Cent, Jay-Z, Nas, and a wide variety of others was the dominant aesthetic and worldview in mainstream rap music for so long that when Kanye West came along and changed the rules of the game, he hit like an atomic bomb. I think Kanye West is a truly excrescent rapper, but there’s no denying that he made it acceptable for mainstream rappers to openly disavow “street“ behaviour in a way that resonated with the larger culture like no previous exponent of that idea ever had. It is also, of course, noteworthy that Kanye West’s astounding, staggering prowess as a producer and fine curatorial sense has done more to bolster the place in the culture occupied by open and self-conscious non-gangsta aesthetes than anyone else, although André 3000 of OutKast gets close.
And then Drake followed in Kanye’s footsteps and revolutionized the game again, to the point where his fundamental softness, toxic masculinity, and affinity for melody have set the tone of mainstream rap music for roughly the past ten years. I’ve already said more or less everything I have to say about Drake here.
Also, it occurs to me that it makes sense to mention Kendrick Lamar. He won the fucking Pulitzer! That’s gotta count for something!
The best rapper alive as of December 2021: I saw someone choose Conway The Machine as the answer to this question, which, I’m sorry, no, if you think that guy is the single best rapper doing it right now your standards are much too low in my opinion. I think the correct answer is probably either Ka, Roc Marciano, or Kendrick Lamar. I think my top five might be Marciano, Kendrick, Ka, Freddie Gibbs, and then either Stove God Cooks or Benny The Butcher, in that order.
Conway is intermittently spectacular, and I don’t have any problem with someone who wants to list him in their top 10 or 20, but in my subjective opinion he just doesn’t bring it hard enough often enough to be the single best rapper in the world at the moment. But he seems to be a case like Biggie, where everyone except for me is convinced that he’s one of the best ever and I’m left completely mystified because I think he’s pretty good (sometimes very good) and nothing more.
The rapper who has the best catalogue of great albums: Ghostface Killah! Pretty easily, in my humble opinion – there are five classic Ghostface albums and not a single bad Ghostface album. Honourable mention to UGK, OutKast, De La Soul, DJ Quik, Devin The Dude, Scarface, 8Ball & MJG, and, quiet as kept, Big K.R.I.T.! There’s a case to be made that Freddie Gibbs belongs in this discussion, but I don’t know that he’s quite consistent enough, even though when he’s at his best he’s very much one of my favourites ever to do it. Someone who loves Guru could make a great case for Gang Starr, but that someone is not me.
The rapper who, in their prime, was the very best ever to do it: Probably Mos Def – he has more talent in his pinky finger than most other rappers will ever have in their whole lives, and in particular he has always been (I am not remotely joking about this next point) about 50 times better than Talib Kweli, who is a borderline terrible rapper and is somehow even worse as a human being. (The Black Star album is virtually unlistenable to me for this reason. Kweli sucks.)
But if we’re talking exclusively about rappers in their prime – the peak of what they could achieve – then my favourite will always be Bun B. There are 20 or so Bun B verses released between roughly the years 1994 and 2003 that are emphatically, unequivocally my favourite rapping anyone has ever done. The best Bun verses are the Platonic ideal of technical precision married to unfuckwithable swag. The single saddest thing in rap music history to me, from the perspective of artistic loss (not human tragedy), was the fact that Bun B deliberately, intentionally chose to fall off at some point around the time when Texas rap had its moment in the international sun. What he does on “Tough Guy” is just… the perfect rap verse. There’ll never be a rapper quite like vintage Bun ever again.
Honourable mention to Rakim, Nas, Common Sense (another terrible artistic loss – I doubt he’s made even 15 great songs since about 1998), Pharoahe Monch, Black Thought, Kool G Rap, Method Man, Freddie Gibbs, Jean Grae, Royce Da 5’9”, Aesop Rock, MF DOOM, AZ, Tonedeff (another rapper whose talent is stratospheric but who makes musical decisions that don’t appeal to me), Roc Marciano, Redman, Big Daddy Kane, and Sean Price (who at his best was only rivalled by Pimp C as the rapper who did the best job of distilling the essence of rap music‘s time-honoured tradition of not giving a fuck), among many, many others.
The rapper who makes the best musical decisions: I ain’t sure I see any argument that it could be anyone other than Kanye West, but Big Boi (nota bene, not André 3000) deserves a shout, and so does Big K.R.I.T.!
Honourable mention to Rick Ross, The Game, Fat Joe, Talib Kweli, Evidence, Termanology, Classified, and Jeezy, all rappers I strongly dislike who consistently make music about which everything works beautifully except their own rapping.
Also, DJ QUIK, MOTHERFUCKER! And PIMP C, God rest the departed! And motherfuckin’ E-40, whose ear for beats is SPECTACULAR!
The best rapper who is a member of a group: Ghostface Killah by a lot (only Scarface gets close), but the competition for the rest of the top ten is a bloodbath – Uncle Brad is #2, and then I think my next four are Pharoahe Monch, Black Thought (Malik B. counts as another rapper in The Roots!), Posdnuos, and André 3000, in that order, but don’t quote me.
Then my next four (assuming the Juice Crew didn’t make enough music together to count) goes Raekwon, Method Man, Big Boi, Q-Tip. And I think that’s your top 10! Maybe? If the Juice Crew count, Kool G Rap and Big Daddy Kane are #9 and #10, and Big Boi and Q-Tip leave. God, this is difficult.
Honourable mention to Cee-Lo of Goodie Mob, who has had moments of rare and extraordinary power, and to Lil Fame of M.O.P., who has not spit even a single wack verse in 29 years! And if we’re counting The Juice Crew, shoutout to Tragedy Khadafi as well. Also, Big L, A.G., O.C., Lord Finesse, and Diamond D of DITC are all kings who shall walk in glory forever.
The best rap group ever: Picking between OutKast and the Wu-Tang Clan is like choosing between beloved children, but gun to my head I’m goin’ with the Wu-Tang Clan. Properly speaking, I think there are a very firm top six rap groups ever: Wu-Tang, then OutKast, then De La Soul, then A Tribe Called Quest, then UGK, then Goodie Mob, and only then can I even begin to think about anyone else.
DITC are #7, and M.O.P. are #8. If Pete Rock & CL Smooth count, they’re #9. If they don’t, your remaining few are Organized Konfusion, 8Ball & MJG, and Camp Lo. If The Juice Crew count, they’re #9, and Pete Rock & CL Smooth are #10, and that seals the deal. Shoutout to Digable Planets, the only rap group I love passionately enough that the impossibility of fitting them in after I’ve accounted for those I’ve already mentioned truly hurts.
I’m aware that my position is ludicrously disrespectful to Run-DMC, NWA, EPMD, Gang Starr, Public Enemy, The Geto Boys, The Roots, Mobb Deep, and The Pharcyde, among others, but I’m sorry, there’s nothing I can do about that. I can only be honest about how the music actually makes me feel. And if we’re talking about emotional impact on me in particular, UGK and Goodie Mob have to leapfrog all nine of them. The two near-perfect Goodie Mob albums (Soul Food and Still Standing) and the two near-perfect UGK albums (Ridin’ Dirty and Super Tight) necessitate it.