Random Rules Playlist 005: The 100 Greatest Outré Artists in Hip Hop History

Our own way of celebrating 50 years of Hip Hop

Aug 25, 2023

With everyone from the NY Public Library to Hulu getting in on the fun, I wanted to celebrate the 50th anniversary of hip-hop in my own way (of course, this means a PLAYLIST). I had the idea to make a list of the more left of center artists from all eras of hip hop. Originally I was going to call it the Top 50 greatest Oddballs in Hip Hop, but that seemed a little insulting and I wanted it to be more of a celebration of weirdness and less about these artists being outcasts, so I settled on “outré” as the most accurate label to describe the aesthetic I wanted to highlight. As I started assembling the playlist, I quickly realized it would be impossible to limit it to 50 artists, as I wanted to include multiple tracks from people like Madlib, Kool Keith and MF Doom who have multiple personas / projects. So, what we have is a top 100 that still just barely scratches the surface of the history of outré rap, and gives a brief look at all eras of hip hop from old school to backpack to boom bap to cloud rap and the most important regions — NYC, LA, Bay Area, Chicago, the South, and the UK.

It’s important to note a few artists who you might expect to see on this list that we chose to omit, just to make room for some lesser known stuff. There’s no Outkast, Beastie Boys, Missy Elliott, Mystikal, etc. on here. Busta Rhymes and Kendrick Lamar make brief appearances (Busta’s early group Leaders of the New School is included and Kendrick has a guest verse on the Danny Brown track). I also avoided horrorcore as a genre for the most part, although it is represented by the inclusion of its originators, Geto Boys and Gravediggaz.

There are a few very mainstream artists who still made the cut - Public Enemy, A Tribe Called Quest, De La Soul, ODB, Lil Yachty, etc. I know everyone will have thoughts on this decision, and I welcome your comments. Who did I leave out? Who should I have cut? Let me know!

Please note: this playlist is in no particular order and I recommend you listen to it on RANDOM, of course!

Ultramagnetic MC’s - “Ego Trippin”
Tierra Whack - “4 Wings”
Biz Markie - “Nobody Beats The Biz”
Digital Underground - “Same Song”
Quasimoto - “Basic Instinct”
Bushwick Bill - “Ever So Clear”
Slick Rick - “Children’s Story”
The Pharcyde - “Drop”
Schoolly D - “I Don’t Like Rock ‘n’ Roll”
Busy Bee - “M.C. Battle At The Dixie”
Dana Dane - “This Be The Def Beat”
Leaders Of The New School - “What’s Next”
Black Sheep - “Flavor Of The Month”
Noname feat. Raury & Cam O’bi - “Diddy Bop”
Prince Paul feat. Breeze - “Steady Slobbin”
Organized Konfusion - “The Extinction Agenda”
Fatlip - “What’s Up Fatlip”
De La Soul - “Oodles of O’s”
Digable Planets - “Dog It”
Slum Village - “Look Of Love”
Madvillain - “All Caps”
Dej Loaf - “Try Me”
MC Shan - “The Bridge”
Lootpack - “Whenimondamic”
Mach-Hommy - “No Blood No Sweat”
Azealia Banks - “212”
Dizzee Rascal - “Brand New Day”
Earl Sweatshirt - “Chum”
Subtitle - “S Is For Summer”
Edan - “Fumbling Over Words That Rhyme”
Little Simz - “Venom”
Cannibal Ox - “Iron Galaxy”
Danny Brown feat. Kendrick Lamar, Ab-Soul & Earl Sweatshirt - “Really Doe”
Lil B - “Swag Like Ohio”
Main Source - “Snake Eyes”
Blackalicious - “Alphabet Aerobics”
MC Shy-D - “I’ve Got To Be Tough”
clipping. - “Story 2”
Shabazz Palaces - “Swerve…”
Armand Hammer - “Black Sunlight”
Charizma & Peanut Butter Wolf - “Ice Cream Truck”
Dead Prez - “Hip-Hop”
MF Doom - “Rhymes Like Dimes”
Jean Grae - “Going Crazy”
Son of Bazerk - “Change The Style”
Aesop Rock - “Sick Friend”
Jay Dee - “Y’all Ain’t Ready”
Leikeli47 - “Girl Blunt”
Kool Keith - “Livin’ Astro”
Your Old Droog feat. Heems - “Bangladesh”
Clipse - “Young Boy”
Freestyle Fellowship - “Bullies Of The Block”
JJ Fad - “In The Mix”
RXKNephew - “Critical”
SpaceGhostPurrp - “Bringing The Phonk”
Ol’ Dirty Bastard - “Shimmy Shimmy Ya”
Vince Staples - “Big Fish”
Lil Yachty - “… the ride-”
Bahamadia feat. Chops, Planet Asia & Rasco - “Special Forces”
dälek - “Distorted Prose”
Pink Siifu feat. BbyMutha - “Big Ole”
Moor Mother feat. Billy Woods - “Giraffe Hunts”
Jeru The Damaja feat. Afu-Ra - “Mental Stamina”
JPEGMAFIA - “HAZARD DUTY PAY!”
Big Freedia - “Booty-Whop”
Tyler, The Creator - “Yonkers”
Death Grips - “Get Got”
Themselves - “Poison Pit”
The Coup - “Me And Jesus The Pimp In A ‘79 Granada Last Night”
KRS-One - “I Can’t Wake Up”
Gravediggaz - “2 Cups of Blood”
Geto Boys - “Mind Playing Tricks On Me”
Freddie Gibbs & Madlib - “Crime Pays”
Public Enemy - “Brothers Gonna Work It Out”
Reflection Eternal - “Fortified Live”
Vast Aire feat. MF Doom - “Da Supafriendz”
The Beatnuts - “Props Over Here”
RATKING - “Snow Beach”
Mantronix - “Bassline”
Stetsasonic - “Paul’s Groove”
Angel Haze - “New York”
Das EFX - “Mic Checka”
Hieroglyphics - “You Never Knew”
Souls Of Mischief - “93 ‘Til Infinity”
Mykki Blanco feat. Princess Nokia - “Wish You Would”
cLOUDDEAD - “Rifle Eyes”
Busdriver - “Casting Agents and Cowgirls”
Sampa The Great - “Final Form”
Flatbush Zombies - “Bounce”
Jungle Brothers - “Tribe Vibes”
Denzel Curry - “Lay_Up.m4a”
Deltron 3030 - “Time Keeps On Slipping”
KMD - “Subrocs Mission”
Company Flow - “8 Steps To Perfection”
Injury Reserve - “Three Man Weave”
King Geedorah feat. Mr. Fantastik - “Anti-Matter”
The Fly Girlz - “Born 2 B Fly”
Rammellzee feat. K-Rob - “Beat Bop”
Dr. Octagon - “Blue Flowers”
The Koreatown Oddity feat. Sudan Archives - “Little Dominiques Nosebleed Part 1”
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