Art Rap Syllabus: 42 Rap Albums That Evidence Artistic Genius

A while back, I published an essay titled “What is ‘Art Rap’?” in which I argued that the “art rap” movement—spearheaded by rapper Open Mike Eagle and his cohort—is decidedly not a pretentious circle-jerk, but rather, a movement which seeks to elevate the entire genre of rap “to the status of a legitimate art-form of extraordinary richness, depth, and relevance, valuable as other canonized, Ivory-Tower-prioritized art-forms, evidencing the work of numerous artistic geniuses.”

I noted that “art rap” has been defined as “hip-hop as high art” and expanded this definition to the following: “a type of rap music that possesses a meta-awareness of itself as a divergent movement in the lineage of rap and broader art history, as a force that seeks to draw upon a wide array of lenses that have historically been underrepresented in rap music or art generally.”

I could probably delve deeper into discussions of what art rap means (let me know if you have ideas), and in the future I probably will. For now, though, this working definition will suffice.

Screen Shot 2015-04-14 at 2.46.46 PM

Art Rap 101

I’ve been thinking lately: if at some point I were to teach a class on art rap (something I would love, eventually, to do), or just rap, what would I include in the syllabus? Which albums (or EPs or mixtapes) would I be most excited to share, celebrate, discuss, and critique, in that order?

It’s hard to imagine offering a course on rap that didn’t start with its origins—in the New York hip-hop block parties of the 70s where rap music Jes Grew (to invoke the name of the metaphorical culture-virus in Ishmael Reed’s novel, Mumbo Jumbo) out of rhythm, creativity, beat machines, and its musical predecessors. I like to imagine those early pioneers, having little idea what it was that they were innovating, simply flowing with a feeling, winging it, freestyling, and spontaneously birthing what is arguably the most globally influential cultural phenomenon of the past 40 years.

But those guys aren’t really my main interest or specialty. I’ve listened to DJ Kool Herc, Afrika Bambaataa, Spoonie Gee, Grandmaster Flash, Rammellzee & K-Rob, and The Funky Four Plus One More, sure, yes, I have. I’m familiar with that raw, frenzied, yeah-we’re-really-doing-this-but-what-exactly-is-this, garage-band kind of energy that characterized the aesthetic of early rap, and I dig it. A lot. Any class of mine would necessarily begin with a YouTube-quest through inception-era rap, a tour of the cornerstones of the castle, as it were. (This would almost certainly lead to an obligatory sampling of some of the most influential, widely recognized rap-giants: Biggie, Tupac, Nas, Big L, etc.)

But I’ve admittedly not immersed myself sufficiently in the genesis-years of rap to be able to do much more than list a few of the mid-70s originators and pull up some YouTube videos. For the past five years or so, my interest in rap has revolved around the avant-garde. That is, I have been most interested in the radically odd and deliciously original artifacts that various artists have made by re-imagining that primordial sludge of early rap music.

So it seems that I have gravitated toward art rap—the deliberately subversive, expansive, and experimental—since long before I ever heard the term. And if I were to teach Art Rap 101, these are the albums, mixtapes, and EPs to which I would expose your progeny. I’ve presented them from oldest to newest, creating a neat timeline tracing one person’s idea of art rap from 1989 – 2014.

1. 3 Feet High and Rising (1989) // De La Soul

3 feet high and rising

I actually can’t even believe this album was released in 1989. So many zany, funky vibes. As Phife Dawg of A Tribe Called Quest later rapped: “Can’t forget the De La, due to originality.” This is some of that original backpacker hip-hop—the strain of rap that began to diverge from and subvert the mainstream genre in the late 80s. For De La Soul, rap was a light, chucklesome, spiritual celebration of love, camaraderie, and art.

Favorite track: Eye Know

Favorite lyric:

“It’s I again and the song that I send
Is taking steps to reach your heart
Any moment you feel alone
I can fill up your empty part”

2. To Whom it May Concern (1991) // Freestyle Fellowship

to whom it may concern

Open Mike Eagle’s protégé milo has actually identified Freestyle Fellowship as the origin of his particular lineage of rap music (or, art rap). The Fellowship, aka the “Sunshine Men,” makes it known at the beginning of this album that they acknowledge “rap as an art-form,” “break the rules,” and “set new standards in the vocal arena.” On the rest of the album, they back up that claim, combining mellow vibes with social commentary and off-the-wall ideas to form a unique elixir.

Favorite track: Sunshine Men

Favorite lyric: 

“As a sunshine man, with plans and a pen in my hand
Recordin’ thoughts and beats for the next man
Even those who live without a clue
I bring the truth to you, it’s not new”

3. I Wish My Brother George Was Here (1991) // Del the Funky Homosapien

i wish my brother george was here

Del is one of my all-time favorites and was probably one of the first rappers to totally rearrange and expand my notion of what rap music could be. This project, his first album, is, in my opinion, a bona fide classic. The sonic vibes throughout are consistently funky, and Del laces the album with a slew of ridiculous rhymes and unorthodox song topics ranging from chilling in a magical meadow to dealing with harassment on the bus. This shit is smooth glory.

Favorite track: Sunny Meadowz

Favorite lyric: 

“In the region of the forest where the march hare dwells
I sit and write scriptures by the old wishing well
Collect all my notes and sail a boat back to Berkeley
Tribes feel my vibe cause my style is rather earthly
Some say it’s whack but I ain’t trying to hear it
As long as what I do contains my soul and my spirit
It’s cool, I use this as a rule of thumb”

4. Bizarre Ride II (1992) // The Pharcyde

bizarre ride ii

Pharcyde, along with De La Soul and A Tribe Called Quest, is one of those groups that immediately comes to mind when I think of early-90s, genre-bending, soulful rap. With Pharcyde, though, there’s an element of extremely-stoned, high-energy wackiness that is distinctive and palpable and different than anything I’ve ever listened to.

Favorite track: Passin’ Me By

Favorite lyric: 

“Now there she goes again, the dopest Ethiopian
And now the world around me be gets moving in slow motion when
Whenever she happens to walk by — why does the apple of my eye
Overlook and disregard my feelings no matter how much I try?”

5. Midnight Marauders (1993) // A Tribe Called Quest

midnight marauders

Ah, A Tribe Called Quest—the third corner of that trifecta I mentioned in the previous blurb. If you don’t know Tribe, please acquaint yourself as quickly as permitted by the laws of physics. Midnight Marauders is, for me, quintessential Tribe—that jazzalicious, funkalicious, buttery aesthetic that just moves. 

Favorite track: God Lives Through

Favorite lyric: 

“Yo Tip I tell you man the devil’s tryin it
But I’m gonna stay strong cause I ain’t buyin’ it”

6. Dr. Octagonecologyst (1996) // Dr. Octagon (Kool Keith)

dr octagonecologyst

I once read somewhere that Kool Keith’s raps sound like those of a ranting homeless man who’s missing a few marbles (no offense to homeless people or those missing a few marbles, much love). I’ve also seen Kool Keith called “the original BasedGod.” I don’t disagree with either of these claims. You should probably go listen to Kool Keith’s whole discography (not that I have; it’s pretty extensive), though I recommend starting here then maybe moving on to Sex Style or Spankmaster. 

Favorite track: Earth People

Favorite lyric: 

“First patient, pull out the skull, remove the cancer
Breaking his back, chisel necks for the answer
Supersonic bionic robot voodoo power
Equator ex my chance to flex skills on Ampex”

7. Operation: Doomsday (1999) // MF DOOM

operation doomsday

The first time I heard the song “Doomsday” off this album I knew it was going to be a long, long love affair with the enigmatic MF DOOM. DOOM arguably innovated an entirely new sub-genre of rap—a cartoonish, comic book-ish realm of silly-yet-serious alter egos and general mystique. This album was where it all began. Say a prayer before listening. “Remember, ALL CAPS when you spell the man name.”

Favorite track: Doomsday (+ all of them)

Favorite lyric: 

“Known amongst foes for flow without no talking orangutangs
Only gin and Tang
Guzzled out a rusty tin can
Me and this mic is like yin and yang”  (+ all the lyrics)

8. Nia (1999) // Blackalicious


When rapper Gift of Gab and DJ Chief Xcel teamed up to create Blackalicious, I wonder if they had any sense of the wizardry that was about to ensue. I don’t hear Gift of Gab mentioned nearly as often as other late 90s/early 00s-era underground rappers, and that’s a shame really, because anyone who’s listened to Blackalicious knows that Gab’s speedy flows, exceptional articulation, and commanding voice over Xcel’s beats are truly a gift to this Earth. The best word I can think of to describe this album: spiritual.

Favorite track: Deception

Favorite lyric: 

“Now the moral of the story is that some go
Why would money make the inner vision crumble?
So if you’re blessed with the talent, utilize it to the fullest
Be true to yourself and stay humble

Don’t let money change ya!”

9. Deltron 3030 (2000) // Deltron 3030

deltron 3030

In 2000, Del the Funky Homosapien teamed up with Kid Koala and Dan the Automater to create something that hip-hop hadn’t quite seen before—a dystopian, intergalactic space opera starring Deltron Zero (Del) as rapping superhero who must travel light-years to win rap battles against extraterrestrials and restore balance to the cosmos. If you’re not sold, go fuck yourself. Jk, but rly, this.

Favorite track: Madness

Favorite lyric: 

“Simple minded people always poin’t the finger
To bring it to a close as if life is their role, their path
When all paths are intersections
It all depends on the person’s perception”

10. Masters of the Universe (2000) // Binary Star

masters of the universe

One Be Lo and Senim Silla are the two halves of Binary Star. The two MCs met in prison where they both seemingly went through Malcolm X-esque transformations to become razor-tongued preachers of the good word of hip-hop. Not even trying to be funny or anything—these guys reinvented themselves, got out of their correctional facility, and started speaking their truth clearly and movingly. This album is widely acknowledged as an underground classic.

Favorite track: Reality Check

Favorite lyric: 

“Who said you (w)rap tight? You come unraveled by
A slice of this rap scalpel guy, quick as apple pie
I’m learned in all schools of thought and shit you baffled by
Conceptual intellectual fox sly
Silla oxide rhymes flow like a rockslide
You must’ve forgot I’d, slap your ass knockneed and cockeyed
Bruised, battered, broken up, open cut, dipped in peroxide”

11. The Cold Vein (2001) // Cannibal Ox

the cold vein

Vordul Mega and Vast Aire, the two rappers who make up Cannibal Ox, are known for their dense subject matter and grimy, abrasive vocals and soundscapes that are quintessential of East Coast hip-hop. This album rewards repeated listens, as there’s simply so much packed into each verse.

Favorite track: Iron Galaxy

Favorite lyric: 

“Life’s ill, sometimes life might kill
Vordul Mega, five digits grab mics, mic strike, type: ill
Is life real? Yo ock he builds
When life feels like Earth don’t spin, whirlwinds might blend
Life’s at a standstill, dangerous cause man kills
And still cats visualize life ghetto like
One mind, sometime these cats see life
Street life in complete light and be like
I’m a live life after this one crime
One line from the Megalah blow spines
Everyone knows the city’s ill, cats kill . . .”

12. cLOUDDEAD (2001) // cLOUDDEAD


cLOUDDEAD was an experimental hip-hop group consisting of Doseone, Why? (Yoni Wolf), and Odd Nosdam. “Experimental” is truly the correct adjective, as anyone knows who has listened to this album. It’s very different from most any other rap—disjointed lyrics with mundane or unexpected subject matter whisp along, breeze-esque, through pulsing cloud rap soundscapes.

Favorite track: Apt. A (1)

Favorite lyric: 

“There’s something
To the fading of faith
My whole childhood
Was the broken guitar
And my sister’s silly
Yellow blanket
Now I carry
Slender and sexy curved
Sledge hammers
To break the bricks
I bought
I should have never went to college”

13. Labor Days (2001) // Aesop Rock

labor days

Aesop Rock. Need I say more? If you’re somehow unaware, Aesop Rock’s raps sound like some kind of seemingly menacing but actually deeply sensitive and troubled gargoyle walking through city streets spraying intricate non sequitur multisyllabic lyrical impressionism. There’s no way to capture the style in words, so just listen to this project.

Favorite track: Daylight

Favorite lyric: 

“Life’s not a bitch, life is a beautiful woman
You only call her a bitch because she won’t let you get that pussy
Maybe she didn’t feel y’all shared any similar interests
Or maybe you’re just an asshole who couldn’t sweet talk the princess”

14. Paullelujah! (2002) // MC Paul Barman


KOOL A.D. once rapped, “I’m the best white rapper, call me Paul Barman.” MC Paul Barman is hardly your stereotypical rapper—in fact, he’s basically the opposite. A nerdy white dude who basks in his own nerdiness, Paul is just beautifully different. And he’s innovated some of the cleverest wordplay rap has ever seen, not to mention a few new poetic forms. Don’t believe me? Check out his marvelous LinkedIn profile.

Favorite track: Excuse You

Favorite lyric: 

“Jesus H. Christ, where H stands for Holy crap
To boldly rap into the outer reaches, this doubter teachers
Defining God as aligning a divining rod with your reclining bod
Cause life is fickle, hellish, anemic, sickle-cellish
Dude, you’ll get chopped up like pickle relish
And when we perish, we’re, what’s the term dude, worm food
Worm food, friends’ memories fade,
You’re remembered by what you’ve made
So I intertwine my mind and my rhymes in a braid”

15. Temporary Forever (2002) // Busdriver

temporary forever

The first time I heard Busdriver I was thinking, “WTF IS GOING ON???” The dude’s known for his ostensibly strained voice, rapid-fire delivery, and labyrinthine lyrics that combine to produce something totally inimitable. He’s also part of Hellfyre Club, along with milo and Open Mike Eagle. Driver’s the man, basically.

Favorite track: Imaginary Places

Favorite lyric: 

“I’m just here to hold your hand when you die
And to show you around imaginary places
Put money lumps in my bloody stump
And I will have a smile that’s a perfect circle
Die in your sleep with the sky at your feet
I’ll shoot you when you’re happy, on the day that you will find peace
How do you do? I don’t know I’m okay
Every person I know is a secret service agent”

16. Full Circle (2003) // Hieroglyphics

full circle

Hieroglyphics is an Oakland-based rap collective consisting of Del the Funky Homosapien, Casual, Pep Love, Domino, DJ Toure, and the four individual members of the rap group Souls of Mischief: Phesto, A-Plus, Opio, and Tajai. Yeah, it’s a family affair. Hieroglyphics, to my knowledge, busted onto the scene in the early 2000s doing something that hadn’t quite been done in rap prior—i.e. overtly making spirituality and wisdom the primary focus of their sounds and lyrics, almost coming across as gurus of a sort. Much love.

Favorite track: Powers That Be

Favorite lyric: 

“Velcome all vulnerable vocalists
Visualize vivid verb play in my vortex
Virtually, no verse’ll be vinnin ova me
They vapor
My verbal voltage vanquishes
Parental advisory
Vamoose! I’ll vick your vitality
Vindictive with voodoo
Valiantly save the virgin from the viper
Vanglorious vide vorld of volcanic violence”

17. Madvillainy (2004) // Madvillain (MF DOOM & Madlib)


This project is certainly legendary and is arguably MF DOOM at his absolute best, which is probably in no small part due to his working with Madlib, one of the greatest hip-hop producers of all time. Madvillainy continues the MF DOOM theme of cartoonish rhymes set over jazzy instrumentals and here it’s just oh so beautiful.

Favorite track: Accordian

Favorite lyric: 

“Villain get the money like curls
They just tryin’ to get a nut like squirrels in his mad world
Land of milk and honey with the swirls
Where reckless naked girls get necklaces of pearls
Compliments of the town jeweler
Left back now-schooler tryin’ to sound cooler
On the microphone known as the crown ruler
Never lied to ma when we said we found the moolah”

18. Elephant Eyelash (2005) // Why?

elephant eyelash

I mentioned Yoni Wolf a bit earlier. After spending the earlier part of his career collaborating in a couple different rap groups, Yoni broke off as a solo vocalist, teaming up with his brother Josiah, Doug McDiarmid, and Matt Meldon to start a band called Why?. This is Why?’s first album and one of my favorites of all time. I love every song on it. There’s this sense on this project of such a pure honesty and vulnerability and poetry that I have never quite encountered elsewhere in music. It’s just special, in my book. Also, this album isn’t purely rap. Deal with it.

Favorite track: Rubber Traits (+ all of them)

Favorite lyric: 

“Today I fell asleep in a bath of hair
Hair that once sprouted from my own white wet chalk follicles
I swallow a coal and follow my breath
And I did it with the grapefruit soap, thinking of you
Bathed, shaved, and oiled, your legs are two skinny dolphins swimming
Between the mattress and the layers of bedding
Turning in your drug dry sleep
When i ask you to kiss my pulse
You offer to start the shower
I want a verb and you give me a noun
What do you dream up while I tongue you down?”  (+ all of them)

19. Alopecia (2008) // Why?


My second-favorite Why? album. Truly another spectacular piece of art that nearly matches the candor and soulfulness of Elephant Eyelash, but not quite.

Favorite track: Fatalist Palmistry

Favorite lyric: 

“I sleep on my back cause it’s good for the spine
And coffin rehearsal
I know a psychic who reads her own palms
And her findings are personal
She keeps her fists shut tight
And she sleeps on her side
Well, maybe she knows something I don’t know
But I am still alive, in love and wide-eyed in my time
Not a mummy shrinking in its cloths
Your cat clawed out my eyes while I’s distracted by your smile
And now my sockets sit like empty catcher’s mitts waiting
And you ask me is there anybody else that I’m dating”

20. Shut Up, Dude (2010) // Das Racist

Das Racist 2 ol

Now, to move in a totally different direction, let’s talk about the post-ironic stylings of the now-defunct Das Racist. Das Racist was comprised of rappers KOOL A.D. and Heems and their hype-man, Dapwell. Das Racist, like other acts listed here, was something totally different that rap had never seen before. Das Racist was at once a pop-cultural blender, a parody of everything, a parody of itself, a medium for spiritual wisdom, a critique of capitalism, a critical race project, the first self-consciously postmodern rap music (probably?), and a bunch of other things. Das Racist forever.

Favorite track: You Oughta Know (+ all of them)

Favorite lyric: 

“This is panic attack rap
Eating four flapjacks
Trap raps, let ‘em free, they always come back to me
The Internet told me that that’s called love
I’m on the Internet cause I’m an Internet thug
Yes I’m in control, man
Pos vibe emanator
Yes I got my Soul Tan
Soul Shine”  (+ all of them)

21. Sit Down, Man (2010) // Das Racist

sit down man

Das Racist actually released back-to-back mixtapes in 2010, which kind of catapulted them onto a lot of people’s radars. In my opinion, Sit Down, Man is their best project. Just dive into it, read about it, do whatever you have to do to make sense of it, love it.

Favorite track: Amazing (+ all of them)

Favorite lyric: 

“Yeah, see, quit smilin’ and shut your silly traps
‘These zooted brown weirdos is wildin’… but they can really rap!’
They saw the cover of the tape, figured it’s pretty wack
Later on eventually admitted that it’s pretty crack
Snatched the beer can out your hand like ‘Gimme that’
I’m all up in the freezer at your crib like, ‘Where your Jim B at?'”  (+ all of them)

22. Rappers Will Die of Natural Causes (2011) // Open Mike Eagle

rappers will die of natural causes

This was the first project of Open Mike Eagle’s that I heard and the project that converted me to someone perpetually interested in what he’s doing musically and artistically. In typical Mike fashion, the project is an array of eccentric conceptual tracks with a healthy dose of wittiness, social criticism, and philosophizing. Only Mike Eagle could make this music.

Favorite track: Dishes (and, yeah, all of them)

Favorite lyric: 

“Immersed in the circus in service to the art
Circuits spark, then the worthless words start
To burst to the surface in a vertical march
Thus begins an irreversible arc
Resisting the urge to rip a person apart
Pitch in, the sensation’s intense
The switch gets turned and it burns like incense
But upward the subject inches” (+ all)

23. I Wish My Brother Rob Was Here (2011) // milo


The title of this project pays homage to Del’s I Wish My Brother Rob Was Here (mentioned earlier) and refers to milo’s friend Rob who passed away. The album can be seen as a tribute to Rob. Though this wasn’t the first milo project I heard, it was the first one that he released, bursting onto the art rap/nerd-hop scene with a rare and somehow abracadabra-y combination of “geeky” references and naked, human sensitivity and candor. I still listen to this project (just listened to it today actually) often, along with the rest of milo’s truly one-of-a-kind discography.

Favorite track: Thief of Always

Favorite lyric: 

“Catch me in kitchen with a veggie fajita
A dollar bill is a bookmark in my Bhagavad Gita
I’m probably your number one Facebook creeper
A nerd rapper who knows the words to ‘Hit Me on my Beeper’
It’s a false choice like the mind-body problem
I know I’m weird but I’m good at this like Dennis Rodman
I don’t ever want to be wealthy
Wearing squirrel fur so those PETA people will pelt me with
Fair trade local organic onions
I hope I can never afford a servant to sand my bunions”

24. I’m in the Forest (2011) // Lakutis

i'm in the forest

The first thing you should know is that Lakutis takes a bit of time to get used to. He sounds kind of like a combination of Danny Brown, Kool Keith, and some kind of deranged cyberpunk cult leader, in the best way possible. Lakutis actually gained recognition working with Das Racist and has since released a couple unforgettable solo projects, this being one of them.

Favorite track: I’m Better Than Everybody

Favorite lyric: 

“Born in a cyberpunk cesspool,
This cesspool is the best pool
Best kept cool in the test tube
Best dressed fool in the death cube”

25. Family & Friends (2011) // Serengeti

family & friends

I’m disappointed only that I didn’t discover Serengeti sooner, as he’s quickly become one of my all-time favorite artists. The dude’s oeuvre is seriously broader and more diverse than pretty much any other rapper I’ve encountered, and he, like Yoni Wolf of Why? (they’re actually both on the anticon label), possesses this ineffable authenticity that just makes everything he touches an absolute jewel. This album is like mainlining essence o’ humanity.

Favorite track: Tracks

Favorite lyric: 

“You’re sleeping outside, all our friends died
Our beautiful new apartment, turned into a dive
We used to speak Norse and pluck hairs from each other’s chests
Now I walk over you in the morning on the back steps
No goodnight: no more trots to and from the docks
No more window shopping for books or boutique clocks
But I do remember, the oceanic abyss
As beautiful as a kiss, as beautiful as the swiss” (+ all)

26. 51 (2012) // KOOL A.D.


When I first encountered Das Racist, little did I know that it would be the beginning of an eternal love affair with KOOL A.D.—you know, the member of Das Racist with the crazy-long beard? KOOL A.D. is like a Taoist-trickster-guru-chillmatic-wild-animal-Dadaist-thing, and there have been periods of my life the last couple years where his music has soothed me and saved me in a way that nothing else can.

Favorite track: La Piñata

Favorite lyric: 

“Kool A.D. the dumb shiny
Come find me, young Hi-C commercial
I circle like sharks while y’all panic, I work magic
You probably wouldn’t understand it
The kid go, think fast, live slow”

27. NO 1 2 LOOK UP 2 (2012) // Big Baby Gandhi

no1 2 look up 2

Big Baby Gandhi is another dude who was tight with the Das Racist posse and sort of gained a following that way. Maybe a year or so ago rumor had it that he was retiring from rap to become a dentist, but I’m not sure that actually happened. Whatever the case, Gandhi brings something raw and honest but also biting and detached on this project.

Favorite track: Eulogy

Favorite lyric: 

“My aunt’s here today she’s so strong on the surface
Inside I know she’s strong like the Earth is
If you was here right now you’d call me a bitch
Like why you crying in front of all these people
Talking about your feelings and shit
You right
Come back for a week we do what you like

So now I’m grown and I wipe my own tears
Buy my own beers
Drink my own beers
Conquer my own fears”

28. Rap Album One (2013) // Jonwayne

rap album one

I think it was when I heard Jonwayne say, “Livin’ in a world that be written by Franz Kafka / He opened up my chakras,” that I was like, “Okay, this guy could be someone I might like.” Jonwayne is a West Coast dude that brings an almost East Coast gruffness and seriousness to the mic, simultaneously challenging listeners with cryptic, intellectual poetry.

Favorite track: Reflection

Favorite lyric: 

“Welcome to the Metropolis
Where we don’t even sweat an apocalypse”

29. 63 (2013) // KOOL A.D.


It’s another KOOL A.D. project. Need I say more?

Favorite track: Moneyball

Favorite lyric: 

“Cashing in chips, dining and dashing and shit
Minding a mansion, shiny, diamonds and ashes and shit
My ghosts blow in the shells and live hells and heavens for generations at a time, and climb
To the next host, the fresh toast, the heat electrical
Too hectical, half-ro-futurist, astro-truthfulness
Young Fidel Cashflow, using this
Music as whatever I really need to use it as”

30. NOT O.K. (2013) // KOOL A.D.

not ok

This project was supposedly comprised of the songs that weren’t good enough to make it onto KOOL A.D.’s album, WORD O.K. (farther down on this list). Yet, I may have dug it even more than WORD O.K. and it’s still classic KOOL and I love it. Did I mention KOOL A.D. is a guru who can show you the secret to life if you listen to his music for at least 100 hours? Reading his horoscopes helps too.

Favorite track: SWOLE

Favorite lyric: 

“Moving seven miles an hour like a forest fire
God’s speed, grow deep like the river, the gorgeous Nile
Fly like the arrow from the quiver, the golden child
The muscles that collude and make human speech equal Jihadi virgin policy
Fact check my ass, I serve quality plus quantity, peep the lush homily”

31. Peaceful Solutions (2013) // KOOL & KASS

peaceful solutions

KOOL A.D. was hella busy in 2013. In addition to all of that solo shit I just listed, he teamed up with Kassa Overall to form the duo KOOL & KASS and subsequently released this ruby of a project. This project is about silliness, improvising the moment, intrinsic enjoyment, and not giving a fuck mostly.

Favorite track: BELLRINGER

Favorite lyric: 

“I’m an idiot
The more I smoke yo the smaller the Philly get
I say big words like ‘Soliloquy’ and ‘Pirouette’
Rap James Joyce, change voice, brain moist, dames’ choice
Slang so bang bang no thang, a bay boy
Nobody in the same lane, kid sis
Slay toys, love moves in a world of hate
Display joy”

32. Things That Happen at Day/Things That Happen at Night (2013) // milo

things that happen at day:night

This was actually the first project of milo’s that I encountered and so will always hold a special place in my heart. Possibly my favorite project of his, it was technically released as two separate EPs, but the two seem to form a cohesive whole. As with all of milo’s stuff, there’s a lot going on here—vulnerability, social criticism, existential musings, esoteric references, etc. Just listen to milo, dammit bruh.

Favorite track: Monologion (et al.)

Favorite lyric: 

“I still dance when I hear that sweet chin music
Repeat the same sins fluid
Sit tight while the caveman de-thaws
Announce my presence like Bonesaw McGraw
Laid on my back, the bright lights circling
I am not Hercules, not even a distant relative
Open Mike tried to tell me that this is all relative
But I have found objective truths
In egg fried rice and fruits” (et al.)

33. Cavalcade (2013) // milo


Another project of milo’s that was, I think, a kind of tribute to milo’s grandfather who had recently passed away. Personally I think this project takes a little longer to get into, but once you’re there, it’s really something. There’s a grimness and darkness on this album that seems gradually to be transmuted into a hint of hopefulness and humanity.

Favorite track: ecclesiastes (et al.)

Favorite lyric: 

“My sadness crept up on an escalator
Looked in my granddad’s eyes and saw the life leave him
I have the super power to summon pipe dreams when I might need ‘em
There’s no point to fight the four seasons
I would’ve raised my hand but I’d make a poor deacon
I’d make a better Batman draped in black skin
I used to pour my guts out, but now I push ‘em back in” (et al.)

34. Wild Water Kingdom (2013) // Heems

wild water kingdom

As I mentioned earlier, Heems was the other rapper in Das Racist. After Das Racist disbanded, Heems, like KOOL A.D., started releasing some awesome solo stuff. This is my personal favorite of his solo releases so far. It’s kind of like a drug-fueled, anxiety-ridden, tongue-in-cheek, cloud-rap fiasco.

Favorite track: Soup Boys

Favorite lyric: 

“That drone cool, but I hate that drone
Chocolate chip cookie dough in a sugar cone
Drones in the morning, drones in the night
I’m trying to find a pretty drone to take home tonight”

35. poplar grove (or how to rap with a hammer) (2013) // scallops hotel

poplar grove

This might be my all-time favorite project of milo’s. Here, he adopts the moniker “scallops hotel” to bring us a variety of unorthodox sounds and poignant poetry. He also produced a number of the songs on this project.

Favorite track: bergamot gamut (+ the rest of them)

Favorite lyric: 

“Sometimes I walk home with a scarf on my face
I don’t have leprosy but I’m feeling out of place
I’m not really much of a small talker
Made a Faustian bargain with a group of bald bloggers” (et al.)

36. Perfect Hair (2014) // Busdriver

perfect hair

Busdriver’s most recent album is an amalgamation of distinctly memorable beats and Driver’s typically snarky, incisive, zany commentary.

Favorite track: Eat Rich

Favorite lyric: 

“I’m a frequent flyer
And a decent liar
And that’s a lie in itself but you knew that, come on
And still you never would admit how sick I’ve become

I eat my food raw
Grew up bourgeois
Never run game like a cue ball
But you knew that, come on
And so you’ll never admit how sick I’ve become”

37. WORD O.K. (2014) // KOOL A.D.

word ok


Favorite track: LIFE & TIME

Favorite lyric: 

“Even though a lot of people are not eating
And I’m seeing that and it sucks and I’m not feeling that
But what can one man do?
I don’t know, probably a lot”

38. Dark Comedy (2014) // Open Mike Eagle

dark comedy

Pretty much unanimously declared a masterpiece in secret corners of the Internet, Open Mike Eagle’s Dark Comedy is an ingenious exploration of the present historical moment and all of the ways in which it fails to be the “Golden Age” that it might have been.

Favorite track: Dark Comedy Morning Show

Favorite lyric: 

“I see the deepest greens
I hear the darkest blues
Might not be synesthesia
Might be apartment fumes
G-g-get up and dance
G-g-get up and dance
I w-w-wipe my son’s ass
And get shit on my hands” (et al.)

39. A Toothpaste Suburb (2014) // milo

a toothpaste suburb

Milo’s first full-length LP ambitiously strives to create an aesthetic that embodies the arguably drab and uninspired vision of life that has been realized in modern suburbia.

Favorite track: in gaol

Favorite lyric: 

“If I was a necromancer I would bring back Foster Wallace
If I was a necromancer I would bring back my friend Robert
If I was a necromancer I would bring back Schopenhauer
If I was a necromancer I wouldn’t be a fucking coward”

40. 3 Seashells (2014) // Lakutis

3 seashells

Lakutis’ 3 Seashells is inexplicably a work of genius. Comes complete with some of the filthiest, murkiest hip-hop sounds of the decade and a hailstorm of lyrics that tow the line between mindless babble and carefully orchestrated juxtapositions designed to challenge fundamental assumptions.

Favorite track: What The Fuck

Favorite lyric: 

“Skeleton, whole human race finna feel it.”

41. (Boyle) and Piles (2015) // Red Wall

boyle and piles

Milo’s first release of 2015, in which he teams up with long-time friend Safari Al to form Red Wall, a rap duo that expressly asserts that they are “not a rap group.” What most impressed me about this project was the way in which milo made such a clean break from the aesthetic of A Toothpaste Suburb to innovate something totally fresh-sounding. The beats, the lyrics—everything is novel and fascinating by virtue of total uniqueness.

Favorite track: H.A.P.P.Y. Brain

Favorite lyric: 

“It’s not enough to write a rap song
I should hire a choir of black moms
To reprimand me if I act wrong”

42. A Special Episode Of (2015) // Open Mike Eagle

a special episode of

Open Mike Eagle’s A Special Episode Of feels like a kind of epilogue to Dark Comedy. It’s another burst of brilliant, mega-relevant music from a brilliant man.

Favorite track: Ziggy Starfish (Anti-Anxiety Raps)

Favorite lyric: 

“Woke up thinking I’m Batman
Every town is like Gotham
I log into my twitter page
And start bending over like Gollum
This dumb cred is like crack rock
And I never seem to hit bottom”



Wacky, philosophical rap music.


Young existential crisis. I make rap music about the void.

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