Long before rap music existed, Nietzsche wrote, “Without music, life would be a mistake.”
This sentiment captures my feelings nicely.
Music might be my favorite thing about living.
The right music at the right time feels like literal magic.
My most beloved songs and albums have enhanced my existence immeasurably.
And, as you may have guessed, my favorite genre of music is rap music.
I discovered rap about 18 years ago, when I was 9 or 10 years old.
In it I found an enchanting synthesis of music and poetry. The combination of beats and rhymes was intoxicating, liberating.
As I delved deeper into the genre’s many caverns, I realized that most people’s idea of rap—based on what they heard on the radio—was extremely narrow.
That’s not to say that I don’t like any of the rap that gets airtime on the radio. I do like much of it.
But the overall sound and lyrical content of mainstream rap tends to be fairly repetitive and formulaic. Over time I came to learn that rap could be so much more. It could be anything.
Rappers might tell you the most tragically raw story you’ve ever heard. Or write a silly song about the importance of personal hygiene. Or contemplate the future of humanity through science-fiction. Or build intricate towers of abstract, cryptic poetry. Or name-drop writers, artists, scientists, and philosophers. Or explain their entire theory of reality. Or comment on global issues and the state of the world. Or paint horrifying pictures of the dark side of humanity. Or give you an intimate tour of the most vulnerable parts of their psyches. Or remind you of what it is to be human. Or explain why life is worth living and fighting for.
And they could do all this while flowing beautifully, in perfect rhythm, delivering elaborate rhymes over head-nodding, heart-thumping beats.
The best rappers had a superpower. The beatmakers too. Their style was entirely their own. Something deeply native to them—a pure expression of their individuality. And yet the music unites all the sorcerous individuals who make use of it; it is the underlying Substance, a kind of Tao even, in which all sound wizards swim and from which they derive their power.
The rap I’ve listened to and loved over the years has shaped my worldview and my approach to life more than almost anything else. I’ve now been freestyle rapping for about 10 years and making my own rap music for ~5.5 years. Other people, books, essays, nature, travel, and psychedelic experiences are the only other things that have had anywhere near the same impact.
Rap taught me the incalculable value of individuality, creativity, freedom of thought, liberated expression, whimsy and spontaneity, flow, passion, love, and the unending quest to understand the world and articulate one’s understanding.
It seems only fitting that I honor this art form that has given me so much, by passing on a list of the albums that sunk into my soul and taught me more than I could ever express.
So today, that is what I’m going to do.
Before we dive in, a note on the shadow of hip-hop: Rap music is not without its shadow aspects: Ego-aggrandizement, misogyny, romanticization of violent/hedonistic lifestyles, drug abuse, money/wealth worship, etc. Many albums on this list do not evince these aspects; some do. One need not support all the themes of a given album to enjoy the music, and one can view the shadow of hip-hop as providing invaluable insight into human psychology and the shadow of American/Western culture. I recommend listening with discernment, openness, and a deep curiosity to understand why different humans think the way they do.
111 Brilliant Rap Albums
I hereby dedicate this list to the late Mac Miller. I love you, Mac. Thank you for your gorgeous contributions to the human experiment. Your soul lives on.
This compilation contains my most beloved rap albums. I hope you will treasure them as I have.
For a sampling of many of the best tracks on these albums, listen to my Spotify playlist, ‘rap sages.’
And shoutout to Dennis Cloutier for taking the time to compile most all these albums into one giant ~100-hour Spotify playlist. : ]
All right, here we go.
1. I Wish My Brother George Was Here (1991) by Del the Funky Homosapien
Our story begins with Del the Funky Homosapien, one of my all-time favorites and 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. Smooth glory all the way through. Be sure to listen to Mistadobalina.
2. The Low End Theory (1991) by A Tribe Called Quest
If you don’t know Tribe, please acquaint yourself as quickly as permitted by the laws of physics. Basically the pure unadulterated essence of soulful head-nodding ’90s hip-hop.
3. Bizarre Ride II (1992) by The Pharcyde
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.
4. Midnight Marauders (1993) by A Tribe Called Quest
Midnight Marauders is, for me, quintessential Tribe—that jazzalicious, funkalicious, buttery aesthetic that just moves.
5. Southernplayalisticadillacmuzik (1994) by Outkast
Dear Lord, Outkast, man. Outkast was absolutely killing it in the mid-’90s. You’ll never hear another rap album like this one. Feel the funk.
6. Illmatic (1994) by Nas
Okay, okay, it’s Illmatic by Nas. One of the absolute classics of rap history. This is required listening for any serious student of the genre. Nas was hungry on this album; you can feel it in his voice and flow. He destroys every beat.
7. Dr. Octagonecologyst (1996) by Dr. Octagon (Kool Keith)
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.
8. ATLiens (1996) by Outkast
Andre 3000. Big Boi. That’s about all you need to know. I’m really not sure which I love more: this album or Southernplayalisticadillacmuzik. Both are life-changing.
9. Illadelph Halflife (1996) by The Roots
The Rooooots. Man. Black Thought has to be one of the most underrated rappers ever to do it. Did you catch his insane freestyle near the end of 2017? Dude’s still got it.
10. Music for Earthworms (1997) by Aesop Rock
Early Aesop Rock. Rare. Sacred. Collect this.
11. Overcast! (1997) by Atmosphere
Just hit play on the very first song on this album and you’ll forever be an Atmosphere fan. Some of the best rap ever to come out of the Midwest, or anywhere for that matter. True poetry that invigorates.
12. The Miseducation of Lauryn Hill (1998) by Lauryn Hill
Rap-heads tend to unanimously agree that Lauryn Hill was one of the best ever to clutch the mic, and I agree. Her rhymes hit you square in the soul. Kanye West gave a nod to her greatness when he rapped, “Lauryn Hill say her heart was in Zion / I wish her heart still was in rhymin’.” The song ‘Nothing Even Matters’ on this album, though not a rap song, is one of my favorite songs of all time.
13. Mos Def & Talib Kweli Are Black Star (1998) by Black Star
“The new moon rode high in the crown of the metropolis / Shining, like ‘Who on top o’ this?,'” Mos Def raps at the beginning of ‘Respiration.’ He and Talib Kweli formed the duo Black Star for this one album, and it’s an undeniable classic. This album sounds like New York City. It captures the spirit of the city in a way few other albums have.
14. Black Elvis/Lost in Space (1999) by Kool Keith
Just start listening to the hilarious intro to this album and you’ll be hooked. Kool Keith’s antics are truly one of a kind, and they’re on full display here. Not only does he bask in outrageousness in a way that no other rapper ever quite has, his lyrics also constitute some of the most potent poetry I’ve ever found. The man creates intricate literature that will show you the world in a way you’ve never seen it before.
15. Operation: Doomsday (1999) by MF DOOM
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.”
16. Nia (1999) by 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.
17. The Slim Shady LP (1999) by Eminem
Most Eminem fans I encounter don’t share my opinion that this is his best album. He was utterly ravenous at this stage—so ready to tear up any beat in order to make it. His energy here is so raw, honest, savage, frustrated, cutting. There’s plenty of horrocore here (rap containing dark, horror-themed lyrics), and while it might repulse some people, I find horrorcore important, as I think it’s likely cathartic for many people to listen to and can help us to illuminate/integrate our Jungian shadows—the taboo parts of ourselves that we reject and repress.
18. Deltron 3030 (2000) by 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.
19. Masters of the Universe (2000) by Binary Star
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 free, and started speaking their truth clearly and movingly. This album is widely acknowledged as an underground classic. Track one will have you bobbing along and thirsty for more.
20. The Marshall Mathers LP (2000) by Eminem
My second-favorite Eminem album. Few humans in history have ever channeled their emotional worlds into art(ifacts) as vividly and movingly as this man. Not to mention that his raw technical skill as a rapper is indisputably on par with the greatest MCs of all time.
21. Both Sides of the Brain (2000) by Del the Funky Homosapien
I had to include one more vintage masterpiece from Del. This dude’s voice and flow are just so damn iconic, and his lyrics are so spontaneous, off the wall, complex, abstract, and magical. I love the man.
22. The Cold Vein (2001) by Cannibal Ox
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. This is another one of those albums that just is New York City; the metropolis’ spirit is bottled within.
23. cLOUDDEAD (2001) by 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.
24. Labor Days (2001) by Aesop Rock
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.
25. Paullelujah! (2002) by 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.
26. Temporary Forever (2002) by Busdriver
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.
27. Full Circle (2003) by Hieroglyphics
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.
28. Madvillainy (2004) by 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.
29. MM…FOOD (2004) by MF DOOM
2004 was one hell of a year for the enigmatic legend, MF DOOM. MM…FOOD, an album with a title that’s actually an anagram of “MF DOOM,” dropped the same year as Madvillainy, and it’s another stunning staple of early art rap. Bottled creativity.
30. The College Dropout (2004) by Kanye West
Kanye motherfucking West. Dude catches plenty of flack for being somewhat of an egomaniac, but anyone who tells you that he hasn’t made some of the greatest rap music of all time is lying to you. College Dropout, his debut studio album, is where it all began. The album has everything: amazing beats, soulful flavor, insightful lyrics, humor, and plenty of Kanye’s inimitable creativity and personality. An album every rap fan needs to explore. Give ‘Family Business‘ a listen and try to tell me you still don’t like Kanye.
31. Elephant Eyelash (2005) by Why?
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.
32. Oxygen (2005) by Jazz Addixx
I don’t even remembered how I came upon this album back in the day, but it turned out to be one of the chillest rap albums I’ve ever heard. Seriously, if you’re just lounging around and need some vibe music, this is what you need.
33. The Carter II (2005) by Lil Wayne
Lil Wayne is one of the best ever to do it, and on this album he was truly in his prime. His iconic voice, flow, and whimsical lyrics are still fresh and satisfying 13 years later. If you haven’t heard this album, don’t hesitate.
34. Below the Heavens (2007) by Blu & Exile
Anyone who’s listened to this album knows that it’s a masterwork. Rapper Blu and the producer Exile came together in a way that seemed predestined and synthesized some kind of sublime alchemical smoothness. The beats are mesmerizing and Blu’s lyrics seem to erupt from a place of pure internal truth. A bona fide classic.
35. Graduation (2007) by Kanye West
Between this album, College Dropout, and My Beautiful Dark Twisted Fantasy, I really can’t decide which is my favorite Kanye album. All three are distinct and wonderful in their own ways. This album showcases Kanye’s provocative, deep, and emphatic lyrics over a wide array of spectacular beats. ‘Everything I Am’ might be my low-key favorite track.
36. Alopecia (2008) by 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.
37. Tha Carter III (2008) by Lil Wayne
It’s tough to say whether Tha Carter II or Tha Carter III was Lil Wayne’s pinnacle. Either way, you simply can’t go wrong here. Lil Wayne drops abundant clever and humorous metaphors over banging beats in his signature nasally, zany, emotive style.
38. Jet Files (2009) by Curren$y
Ah, good ol’ Curren$y. The dude has been so consistent over the years, putting out clever, goofy bars over breezy beats and making some of the best weed rap the world has ever known. Fun fact: I once cut my foot open at a Curren$y concert.
39. Man on the Moon: The End of Day (2009) by Kid Cudi
Fuck, this album means so much to me. No one has ever replicated Kid Cudi’s rap style. This is an album full of utter anthems for lonely angsty young humans. A couple years after its release I saw Kid Cudi live in Lincoln, Nebraska, and it was the best concert of my life to date.
40. The Swelly Express (2009) by Chiddy Bang
Damn, this brings back memories of walking around on my university campus on a bright sunny day feeling groovy about life and everything. Chiddy Bang is one of the most phenomenal hip-hop duos to do it in the last decade. Ridiculously unique beats combined with uplifting, punchy flows. Don’t miss this one.
41. The Warm Up (2009) by J. Cole
Fuck, this tape was so, so good. Takes me straight back to my later years of college when I was living in a rather wild party house with a few friends. We bumped this shit religiously. The song ‘I Get Up,’ in particular, is one of my favorite rap songs ever. J. Cole’s flow and wise, incisive lyrics truly shine on this project. Cherish it.
42. Shut Up, Dude (2010) by Das Racist
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-theory project, the first self-consciously postmodern rap music (probably?), and a bunch of other things. Das Racist forever.
43. Sit Down, Man (2010) by Das Racist
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.
44. Unapologetic Art Rap (2010) by Open Mike Eagle
Ah, yessss, Open Mike Eagle makes his first (but far from last) appearance on this list. Open Mike is one of my favorite rappers and the dude who originally coined the term “art rap” to describe what he was doing. He’s known for rapping over off-kilter beats about an extremely broad range of subject matter, from metaphysics to epistemology to the daily frustrations of being a “house husband.” His intellect, vulnerability, and off-the-charts talent combine to make him a superhero in my book.
45. Kush & Orange Juice (2010) by Wiz Khalifa
Had to throw this classic on the list. When I think of weed rap, this is probably the first tape that comes to mind. I honestly don’t know if Wiz could’ve nailed it anymore than he did with this project. The beats are hypnotically chill, and his lyrics are encouraging, soothing, humorous, and generally badass. I’ll never forget this album.
46. My Beautiful Dark Twisted Fantasy (2010) by Kanye West
God damn, this album was such a masterpiece. Definitely one of the most ambitious rap albums of all time, it often sounds like an entire symphony orchestra was used to produce these beats. If forced to choose, I would probably say that this album was Kanye’s magnum opus.
47. Man on the Moon II: The Legend of Mr. Rager (2010) by Kid Cudi
I didn’t think it was possible at the time, but I ended up loving this album as much or more than Man on the Moon I. The vibe on this album is even sadder and darker than the original Man on the Moon, and Cudi is back with the tremendous honesty of a giant-souled space king. The man’s a genius.
48. Escapism (2010) by SoulChef
SoulChef brings me straight back to my college days. Unlike a lot of the weed rap I was listening to in those days, SoulChef was bringing something that spoke to my spiritual depths.
49. Rappers Will Die of Natural Causes (2011) by Open Mike Eagle
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.
50. I Wish My Brother Rob Was Here (2011) by milo
Finally, milo, perhaps my favorite rapper. The title of this project pays homage to Del’s I Wish My Brother George 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 often, along with the rest of milo’s truly one-of-a-kind discography.
51. I’m in the Forest (2011) by Lakutis
The first thing you should know is that Lakutis takes a bit of time to get used to, but once you get there, he’s a rare delicacy. 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.
52. Family & Friends (2011) by Serengeti
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.
53. Section.80 (2011) by Kendrick Lamar
This will not be Kendrick’s final appearance on this list. Another one of my favorite rappers, Kendrick is widely regarded as one of the greatest rappers ever, if not the best. The man has managed to rise to the top of the hip-hop world, all while never sacrificing his hyper-meaningful lyrics and artistic integrity. This album is literally packed with great songs. I wouldn’t change a thing about it.
54. Ambition (2011) by Wale
This album transports me straight back to Lincoln, Nebraska, where I attended university from 2009-2013. I recently revisited this project after not listening to it in years and was absolutely blown away. The raw determined energy contained in this project is truly the very spirit of Ambition, the album’s perfectly fitting title. If you’re seeking motivation and inspiration to seize greatness, look no further.
55. Gift Raps (2011) by Chip tha Ripper
This is another album that brings me straight back to my college days. This album is just a totally classic masterpiece of stoner rap—a kind of fun, vibey, cartoonish tour through the prosperous and awesome life of Chip Tha Ripper. It’s easy to nod your head the whole way through.
56. Black Up (2011) by Shabazz Palaces
Shiiiit, when I saw these guys do their thing in San Francisco, it was a revelation, just as this album was when I first listened to it. This music is relentlessly innovative—fascinating and entrancing all the way through. Fun fact: Palaceer Lazaro of Shabazz Palaces was also a founding member of the jazz rap group Digable Planets, in which he went by Butterfly.
57. BIG FUCKING BABY (2011) by Big Baby Gandhi
Like LAKUTIS, Big Baby Gandhi is a dude associated with the Das Racist posse. Another NYC rapper, the dude has a knack for cooking up wildly unique beats and rapping over them with this really punchy, authoritative presence. His music is different from anything else you’ve ever heard, and this is his best project, in my opinion. Highly, highly recommended.
58. Childish Gambino EP (2011) by Childish Gambino
Childish Gambino!!!! Another all-time favorite rapper of mine, the rap alter-ego of actor Donald Glover is truly someone who has pushed the boundaries of what rap music is and can be. His passion and authenticity are so palpable on this album and in his oeuvre generally. The man has dropped some of the most inimitable, innovative, and beautiful rap music the genre has ever seen. I love him dearly.
59. Return of 4Eva (2012) by Big K.R.I.T.
Big K.R.I.T is one of the greatest and most authentic minds ever to make rap music. His soul-penetrating lyrics and Southern style make for a serious rap-music treasure chest. In particular, the song ‘The Vent‘ on this album is one of my favorite rap songs I’ve ever heard; I highly recommend listening to it if you want to feel the power and heart of the man known as K.R.I.T.
60. Duality (2012) by Captain Murphy
When this album dropped, no one knew who Captain Murphy was. Over time, it came to light that the legendary beat-maker Flying Lotus had decided to record some raps under an alias. And Holy Nature I’m glad he did. This odd album plays on themes of cult leadership and delivers intense lyrics over skyscraper-toppling beats the whole way through.
61. 1999 (2012) by Joey Bada$$
This was Joey Bada$$’s debut project and in my opinion his best (funny how that happens a lot of the time). Though it dropped in 2012, this album is like a time machine transporting the listener straight back into the bouncey, vibey soundscapes of ’90’s hip-hop, but with a modern twist. Joey Bada$$ demonstrates his articulate, on-point flows all the way through.
62. 51 (2012) by 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 in which his music has soothed me and saved me in a way that nothing else can.
63. NO 1 2 LOOK UP 2 (2012) by Big Baby Gandhi
A few years ago rumor had it that Gandhi 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.
64. Good Kid, M.A.A.D. City (2012) by Kendrick Lamar
Most any rap fan will know that this album is a quintessential modern classic of the genre. It’s a concept album that tells the troubling, eye-opening story of Kendrick’s life growing up in Compton, California. The album is dense with insight and addresses everything from the woes of poverty and dysfunctional education to gang violence and corruption in the criminal justice system.
65. Habits and Contradictions (2012) by Schoolboy Q
This album brings me straight back to the end of 2015 in San Francisco, California, a time when I was living in this crazy nice house overlooking SF with like seven amazing people. It had an indoor swing, retractable roof, musical instruments, cannabis-torching implements everywhere, Nerf guns, beanbags, lots of technology, and more. It was basically the closest thing to a utopia I’ve ever experienced. But I digress. This grimy, bass-heavy, intoxicating, vitalizing album is my favorite of Schoolboy Q’s. It truly slaps.
66. Control System (2012) by Ab-Soul
“I don’t even know what’s real, I’m just bein’ real,” Ab-Soul raps on ‘Pineal Gland.’ This lyric sums up this DMT trip of an album pretty well. It’s basically an inquiry into the nature of reality and society with a bit of a conspiracy-theory bent. Undoubtedly my favorite Ab-Soul album.
67. Nothing’s Really Real (2013) by J. Jones
This is one of the most interesting and psychoactive rap albums I’ve ever heard. Edgar Allen Poe’s quote, “Everything we see or seem, is but a dream within a dream,” seems like an accurate epithet to sum up the surrealistic nature of this project. I actually had the privilege to meet J. Jones while living in South Korea and did a couple shows with him. He’s a great dude and a seriously talented, mind-bending rapper.
Listen / buy: BandCamp
68. Things That Happen at Day/Things That Happen at Night (2013) by milo
This was actually the first project of milo’s that I encountered and so will always hold a special place in my heart. 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.
69. poplar grove (or how to rap with a hammer)(2013) by scallops hotel
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 beats on this project.
70. Wild Water Kingdom (2013) by Heems
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.
71. Because the Internet (2013) by Childish Gambino
This is hands down my favorite Childish Gambino album, and that’s really saying something. I consider this album an instance of True Art, an absolute ruby that captures the disorienting experience of being human in the age of the Internet and exponential technology in a way that few, if any, other rappers have managed.
72. Watching Movies With the Sound Off (2013) by Mac Miller
I’ve been a fan of Mac Miller since the KIDS days, but my engagement with his work reached new depths after digesting this project while living in South Korea circa 2013-2014. This was a new incarnation of Mac Miller, a kind of darkly psychedelic ‘based’ Mac who was testing the boundaries of rap with some of the most absurd, quirky lyrics ever recorded. This album initiated a true love affair with Mac that resulted in my now considering him perhaps my most beloved rapper of all time.
73. Acid Rap (2013) by Chance the Rapper
Chance the Rapper released one great mixtape prior to Acid Rap, but this was the moment in which he seriously exploded onto the rap scene and made a lasting name for himself. He was exceptionally innovative with this project, painting wacky, uplifting, jazzy soundscapes filled with his striking voice and personality.
74. Nothing Was Quite the Way it Used to Be Before (2013) by Lil Dicky
Lil Dicky has ascended rapidly to widespread popularity in the last couple years with hilarious music videos like ‘Lemme Freak‘ and ‘Ex Boyfriend.’ His signature combination of sharp wit, relentless creativity, and flawless flow have won over millions of fans, myself included, but fewer people are aware of some of the songs he did a few years ago. ‘Nothing Was Quite the Way it Used to Be Before’ is a 2-song, 13-minute EP that packs a serious wallop. The second song in particular is, to me, an absolutely breathtaking masterpiece of a rap song, my favorite song by Lil Dicky, and one of the most inspiring songs I’ve ever heard.
75. Doris (2013) by Earl Sweatshirt
I remember listening to this album while wandering around, feeling kind of lonely, in my neighborhood in South Korea, when I was a teacher there. Like all great poets, Earl has a gift for cutting through the artificial to illuminate something Real. His flow is one of the best of all time, and his voice and lyrics seem to bellow forth from some part of your own mind that you rarely visit. This album, my favorite of his, is a gift cloaked in shadow.
76. Long.Live.A$AP (2013) by A$AP Rocky
A$AP Rocky achieved something monumental with this album. Truly a brilliant curation of a wide variety of soundscapes, all doused in lyrical propane and ignited by a gripping flow and voice that demand our ears. An intensely honest look at what it was like for Rocky to come of age amidst gritty conditions in New York and Pennsylvania.
77. Rejovich (2013) by Rejjie Snow
Rejjie Snow is an extraordinary Irish rapper who you should know about. This short project is an excellent introduction to his masterful flow and lyricism.
78. D.A.I.S.Y. rage (2013) by kitty
Kitty is one-of-a-kind. Her confessional, sorta-seductive-sounding vocalizations are saturated with vulnerability and honesty. Disarming.
79. Nothing Was the Same (2013) by Drake
Had to throw a little Drizzy in here somewhere. Drake catches a lot of hate for whatever reason, but I think he makes great fucking music. His sensitive, heart-bearing lyrics were an important puzzle piece contributing to a gradual paradigm shift in the nature of mainstream rap. And let’s be honest, his songs tend to sound silky dope.
80. NOT O.K. (2014) by KOOL A.D.
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. 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.
81. Dark Comedy (2014) by Open Mike Eagle
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.
82. 3 Seashells (2014) by Lakutis
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.
83. Faces (2014) by Mac Miller
This is one of my absolute favorite rap projects of all time. Possibly my favorite. A genius exploration of universal human themes and the dark underbelly of (modern) life. I love you so much, Mac. May your spirit be at peace.
84. MTV1987 (2014) by Kevin Abstract
This album initiated a serious infatuation with the brilliant creative mind of Kevin Abstract. Heavily inspired by Childish Gambino, Kevin’s confessional, highly emotive style is cathartic to absorb. A definite poet whose penetrating lyrics allow you to spend time inside his inimitable mind and heart.
85. Run the Jewels 2 (2014) by Run the Jewels
RTJ, man, damn. Perhaps the rawest, most unchained and untamed rap duo in history? In certain intense moods, this music is nothing short of glorious. Hard-hitting, uncompromising, a dark earthquake.
86. Bad Habitat (2014) by Sayth
Sayth is a hella overlooked art rapper who burst onto the otherground scene around the time milo was first gaining visibility. From Wisconsin, Sayth uses his confessional lyrics to reveal slivers of modern America rarely seen.
Listen / buy: BandCamp
87. SADE EP (2014) by OKINAWA EIGHTY EIGHT
This album will always bring me straight back to Atlanta circa early 2015 when I discovered Okinawa Eighty Eight randomly at a rap show. It turned out they were fucking awesome. Live, funky instrumentation and a mega-soulful lyricist set them apart from other rap acts. This EP is a heart-stirring classic.
Listen / buy: BandCamp
88.The Waters (2014) by Mick Jenkins
THE WATER[S]. YES. Damn, this was such a dope tape. Mick Jenkins killed it with the flows and lyricism. A bard from Chicago who deserves your attention.
89. plain speaking (2015) by scallops hotel
90. (Boyle) and Piles (2015) by Red Wall
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.
91. A Special Episode Of (2015) by Open Mike Eagle
92. Jonwayne is Retired (2015) by Jonwayne
This list wouldn’t be complete without a little Jonwayne, an unassuming California rapper who knows the meaning of the word “honesty.” Formerly a Gamestop employee, Jonwayne found his true calling in beatmaking and rapping and presumably hasn’t looked back since. Lyricism + next-level beats make this project unforgettable.
93. GOOD:AM (2015) by Mac Miller
Another masterpiece from the legend, Mac Miller. Punchy, slapping beats, clever lyrics, and impeccable flow combine to make this a high-power middle-finger-to-the-haters type of album. Perfect for bumping in the car in certain “watch me do me”-type moods.
94. Thumbs (2015) by Busdriver
For me this is Busdriver’s magnum opus. Astoundingly ambitious and relentlessly creative, the album is a marvelous achievement. Anthems like ‘Much’ and ‘Worlds to Run’ occupy a sacred place in my heart.
95. fear, uncertain (2015) by Safari Al
Originally known as Safari Al, s.al is a long-time best friend and musical collaborator of/with milo. Criminally underrated, this project will ease your soul in the midst of dark times. Listen to ‘5 MILES’ and allow an uncanny peace to descend upon you; feel yourself expand into a space of deeper acceptance of life’s “strange cycles.”
Listen / buy: BandCamp
96. garage raps vol.1 (2015) by Signor Benedick the Moor
OMG, I fucking love this project. Sometimes I forget about it for a while and then I eagerly re-listen when I remember it exists. Unlike anything else out there. Raw, frantic raps over garage-band-sounding beats—gah! Just so, so good.
97. so the flies don’t come (2015) by milo
Ahhhh, damn, it’s like every single one of milo’s projects is his best project in its own way. This one absolutely blew my tiny monkey mind when I first heard it in SF back in 2015. INNOVATIVE. FLOW. The Zen Scientist has no equivalent…
98. Jarvage Vol. 1 (2016) by Jarv
Jarv was an immensely pleasing surprise when I discovered him a year or two ago. On this album he sounds like a high school kid (which he may have been when he made it?) who has just discovered that he can rap as fast as Twista and is incredibly happy to demonstrate his skill. Just downright charming and fun to listen to.
99. Bobby Tarantino (2016) by Logic
Logic. Logic. Logic. Fuck yes. He had to be included in this list. Dude is one of the modern greats. Top-level flow, lyricism, beats, production: Like butter. Play ‘Super Mario World’ and see what I mean.
100. FRAGMENTED (2016) by LOSTBOYEVSKY
All right, I’ll throw one of my own albums in here. FRAGMENTED is an EP about uncertainty, cognitive dissonance, fragmentation of identity, suffering, heartbreak, and the oft-overwhelming process of attempting to synthesize a coherent worldview or life-meaning from the various intermelding oceans of context and culture through which we swim in the 21st century. Ideal to listen to when feeling disoriented by modern life.
101. Essentials (2017) by Oliver Francis
OLIVER!!!!! I discovered Oliver Francis years ago on Soundcloud and it’s been beautiful to witness him transform from a master beatmaker/flipper of other rappers’ verses into a formidable rapper in his own right. In the past year or so he’s become one of my all-time favorites; I can’t tell you how much I’ve listened to this guy. His music can be replayed endlessly; it’s so soothing. He’s one of those artists who makes songs that make the highs higher and the lows more tolerable. Somehow his songs capture a mood that is both celebratory and melancholy. Particularly when you’re feeling up, Oliver will make you feel like the world is yours and you can accomplish anything you dream.
102. SATURATION (2017) by BROCKHAMPTON
BROCKHAMPTON is one of the most unique hip-hop groups in history. When I saw that Kevin Abstract had started a ~13-person rap collective, I knew I had to check them out. And shit, I was not disappointed. There’s a contagious youthful “let’s get it” type of energy in these songs. I recommend listening to ‘STAR’ to see what I mean.
103. Passive Impressive (2017) by Dunzo Donalds
DUNZO!! Dunzo Donalds has become one of my favorite rappers in the last couple years. I’ve also had the honor of becoming his friend and collaborating with him. Dunzo is a sweetheart and a force of Nature. He’s undoubtedly got the Funk in his soul and a mystical ability to translate the Divine into the language of music. His music is utterly and unapologetically Free in such an admirable way. He is uncompromisingly experimental. A genius and sage-in-training masquerading as a plain-clothed Wisconsinite.
104. raw navel (2017) by Pink Navel
Pink Navel showed up on my radar a couple years ago, and when I checked out their music, I was stunned. They exhibit a certain Purity of Heart that infuses their music with a rare kind of enchantment. Their style blends spoken-word poetry and rap in a truly delicious way. Listen close.
105. DAMN. (2017) by Kendrick Lamar
My favorite Kendrick Lamar album, I think. A Da Vinci-level masterpiece. Somehow Kendrick assembled a collection of beats that sound simultaneously simple and visionary, antique and futuristic, then proceeded to frost the beats with some of the most savage and disgusting flows ever concocted. Kendrick’s technical delivery is on par with Eminem’s—i.e. flawless.
106. Who Told You to Think???!!!????!?!?! (2017) by milo
Yep, milo. Milo. Milo. Milo. He did it again. He’s done it so many times. Sorcerer, indeed. With this album he translated some of the most mystical dimensions of his mind/experience. Truly a joy to behold.
107. The Great Dunzo (2018) by Dunzo Donalds
This is probably my favorite project by Dunzo—a collaboration with the producer br()ke, who apparently took some a capellas from Dunzo and constructed all-new beats around them. An eyebrow-raising accomplishment, because the meld is flawless. This project has a truly satisfying coherence and completeness. Each of the three songs is a jewel, packed with infectious upward-moving energy and punchy lyrics that could only have emerged from Dunzo.
108. Swimming (2018) by Mac Miller
Once more, rest peacefully, Mac. This album was released shortly before Mac’s death, and after his passing the album truly started to feel like he had sent it back from beyond the grave. There’s an uncanny way in which the energy of the album seems to anticipate his departure. In my estimation this is one of the greatest albums ever made in any genre—an ingeniously and meticulously crafted mood-tapestry. It will cradle you when you feel lost and alone.
109. Infinity Boy (2018) by Oliver Francis
Damn, I love Oliver so fucking much. I really can’t express it. I don’t know if the dude has ever dropped a non-golden song. The title track on this project is probably my favorite song of his. I strongly recommend all his Spotify music and the collection of rare jewels on his BandCamp.
110. Mu (2018) by Offsite
And then there was Offsite. Fucking Offsite. Gah, I love this man. I adore him. He’s become one of my all-time favorite artists; at present I listen to him all the time. In an interesting parallel to my life, he moved to Asia (Japan in his case) after college, around the same time (I believe) that he started releasing rap music. Offsite’s music is a totally once-on-this-Earth experience. You just have to listen to it. The beats, the philosophical interludes, the stunning, mind-blossoming, koan-esque poetry. It’s perfect. Follow this one up with his album HEX.
111. I’ll Say This Once (2018) by Offsite
Yes, Offsite, yes. Thank you for this sacred music. ‘A Dull Teacher’ samples someone reading the Tao Te Ching. That’s all you need to know.
All right, whew, damn, let me catch my breath. 111 genius rap albums. Just like that. Here are a few more incredible albums for which I didn’t have space:
1. Ready to Die (1994) by Biggie Smalls
2. Between a Rock & a Hard Place (1994) by Artifacts
3. Liquid Swords (1995) by GZA
4. Lifestyles of the Poor and Dangerous (1995) by Big L
5. All Eyez On Me (1996) by Tupac Shakur
6. Third Eye Vision (1998) by Hieroglyphics
7. The Taste of Rain… Why Kneel? (1999) by Deep Puddle Dynamics
8. Let’s Get Free (2000) by Dead Prez
9. Mind Over Matter (2000) by Zion I
10. First Born (2001) by Eyedea & Abilities
11. God Loves Ugly (2002) by Atmosphere
12. Get Rich or Die Tryin’ (2003) by 50 Cent
13. E&A (2004) by Eyedea & Abilities
14. A Piece of Strange (2006) by CunninLynguists
15. The Cool (2007) by Lupe Fiasco
16. Wonky Beats (2011) by Darwin Deez
17. Bottle of Humans (2012) by Sole
18. Home – Phantoms of Summer (2013) by The Dirty Heads
19. Indigoism (2013) by The Underachievers
20. Old (2013) by Danny Brown
21. Rap Album One (2013) by Jonwayne
22. Atrocity Exhibition (2016) by Danny Brown
What more to say?
All glory due to the sages and wizards who created this art. Long live rap music. Thank you Nature for making this beauty possible!
Go forth, love music, be free, spread joy, be who you are, cherish existence.
All the Love,