First things first, we’ll start with what we disqualified. No mixtapes. No major label stuff. No albums by the artist after they went mainstream. We know that many people hate the moniker “underground,” and that it sometimes feels demeaning to artists. And we know that, for some people, there will be a difference between “underground” and “alternative” Hip Hop. We know that more still will find a difference between those two and “indie.” And we know that can go on ad-nauseum because the “underground” is something different, maybe, to everyone. Of course, also, we are only considering albums made since the Y2K scare.

We also know that people will feel as though we left some of their favorite albums off this list, and for that we’d like to say to feel free to drop your own list in the comment section. But, for us, these were the albums that set themselves apart. In the early 2000s, it was about hitting the record shops and being part of the scene, supporting your favorite artists that didn’t have a major label machine behind them. Later on it became about blogspots and now defunct forums where people shared music and thumbed their noses at those who weren’t in the know. All the while crate digging and hitting shows outside of the know of many.

More importantly, the “underground” lives forever, because it represented artists who weren’t afraid of topics and structures and sounds normally left off the table at A&R meetings. Those who didn’t clamor for radio play or acceptance. Those that you had to find.

Busdriver –  Temporary Forever

The Project Blowed member’s debut was full of the most humorous and mind numbing free-associative rhymes one will ever hear. Looking deeper into Busdriver’s mind, themes on gun violence and major labels complications among others give a feeling of something deeper.

Quasimoto – The Unseen

Madness is the pleasure of the unseen, and Madlib’s pig-nosed hippo with the brick is everyone’s unseen. The lost thoughts of a rambling stairwell dweller, or the undine styled under-thoughts of a producer living in a basement studio, Lord Quas was our one and only pleasure of pure id. A bit of jazzy ultra-violence in a squeaky ass voice never felt so good.

Little Brother – The Listening

For many, The Listening could be considered one of the most groundbreaking underground Hip Hop records of the modern era. Before their more commercially successful sophomore follow-up The Minstrel Show, the North Carolina trio felt like a polished major label act with a level of creativity that could only come from within the underground. Phonte and Big Pooh’s chemistry was undeniable while 9th Wonder held everything together effortlessly production wise.

Brother Ali – Shadows On The Sun

Mr. Ali Newman really hit his stride on his sophomore album Shadows On The Sun. Besides Brother Ali’s way better than average beat selection, the album proved how lyrically far the Rhymesayers Entertainment emcee. Though he’s improved with every release,Shadows Of The Sun could be considered his best.

Blackalicious – Blazing Arrow

Blazing Arrow wasn’t appreciated when released in 2002. However, it’s only gotten better with age thanks to Gift of Gab and producer Chief Xcel. There wasn’t a topic the duo wouldn’t touch. For example, how many people did “Chemical Calisthenics” help through high school Chemistry?

Z- Ro – Let The Truth Be Told

Former Gorilla Mob member Z-Ro has a storied history in Houston Hip Hop. Several albums in, he dropped a bonafide classic in  Let The Truth Be Told. For the first time in his career, he made an album that felt more than something local. From the intro “Mo City Don” to “Respect My Mind,” Let The Truth Be Told is an honest Southern tale.

Edan – Beauty & The Beat

Beauty & The Beat was an unlikely critical smash in 2004, garnering the dark-dust-feather topped Edan Portnoy (not to be confused with Portnoy, the ballsy, corrupt main character of Portnoy’s Complaint by Phillip Roth) an 85% Metacritic score and cementing him as a dim forefather in the realm of middle-class rap. Think American Beauty, but no dads, no beauty, and mostly zaniness refined into a brainy, cathartic lilt.  

J – Live – The Best Part

Like forward, free-thinking Gods-among-men, DX gave this album the 4.5 it deserved in 2001 just months before the towers fell and everything changed forever. Looking at it through a lens of xenophobia, groupthink and recklessness, J-Live’s The Best Part reads like a tome from another world lamenting the lack of intellectual rigor that would inevitably follow.

Murs & 9th Wonder – Murs 3:16: The 9th Edition

Murs has been, and been quite well, an everyman with an edge. On Murs 3:16: The 9th Edition he found his very capable footing on Def Jux by ditching the skateboard and sliding into a kind of existential angst. 

Ka – Grief Pedigree

One of the hardest (that’s right, hardest) NYC Hip Hop albums ever released, Ka’s foray into the depths of Brownsville proved a bit too much for the tastes of the Internet intelligentsia, but that doesn’t mean the sheer propensity for verse and meanness on this album should be overlooked.

Madvillain – Madvillainy

Madlib and MF Doom joining forces were something that only could’ve happened under the Stones Throw umbrella. For it’s time, Madvillainy became the super rap album, reaching unforeseen creative heights. Since then, both esteemed producer and emcee have elevated themselves into Gods for many core Hip Hop heads. It’s an album so good, some doubt its brilliance out of the right to be contrarian. A bonafide classic, either way.

Blu & Exile – Below The Heavens

Blu & Exile’s classic LP barely found an audience in 2007 when it was released. What a shame. This deeply visceral, almost perfectly executed album featured two amazing artists surpassing themselves to create this piece lightening in a bottle. Just the first 16 bars on “Greater Love” make it one of the best rap love songs of all-time, and that’s just the tip of the iceberg. Blu rollicked through a lush field of production, and it stands a testament to how good Hip Hop can be.  

El-P – Fantastic Damage

El-P’s debut Fantastic Damage was an unrelenting kick to the rap nuts of fuckboys everywhere before there was even a term for that level of human soap scum. What a year that was! Production for Cannibal Ox’s classic Cold Vein and then an abstract turn at lighting a molotov cocktail and calling it music. It blew almost everyone away, and it still does.

Aesop Rock – Labor Days

Def Jux tumbled out of the lost days at Rawkus ready to incite, well intelligent shit into the Hip Hop meta-sphere. Who better than Aesop Rock to do just that? Surgical is the only term you need for this album, as it tackles the topic of labor of all forms in concentrated bursts of brilliance. Produced mostly by Blockhead with a few self-produced cuts, Labor Days serves as a companion piece to The Cold Vein’s concentrated fury at the state of rap.

Cunninlynguists – A Piece Of Strange

A Piece Of Strange is when Cunninlynguists got serious. Kno hung up the mic for all but one verse, but what he dragged to the grave with him in the way of humor he more than made up for behind the boards. Deacon lit the intricate production ablaze with Natty this time, as Mr. S.O.S went back to his solo career. No one missed a single, solitary beat, and the album suffers from little to no real flaws. The emceeing is superb, and the high concept is done so well that it melts away and deeply lodges itself into your veins.

Oddisee – The Good Fight

Oddisee came all golden skinned out of his last record and created The Good Fight. The album almost completely avoided the status quo, bringing to light a rap realism that hadn’t been really traversed since The College Dropout. His is the other side of the coin, though, having graduated into how a dream takes hold only after wild efforts. The Good Fight, then, is a manual on how to join your luminescence with reality in a way that gets you closer to your dreams.

Atmosphere – God Loves Ugly

Unrelentingly angry, God Loves Ugly is a journey into the deep unconscious mind of Slug and all his issues with women and with people in general. It defined the angsty tug-of-war many people feel with the opposite sex, and then it lit a cold blue flame of despair to your mind as you listened.

Jedi Mind Tricks – Servants In Heaven, Kings In hell

If the mainstream bet its money on longing as the way to people’s wallets, then the Jedi Mind Tricks truly could not have cared less. Although this was their first album to chart on the Billboard 200, JMT had already secured a cult following at this point due to their ability to explore topics normally shoved under the rug. A masterpiece of pacing, lyrical variety, and fervor, Servants In Heaven, Kings In Hell stands as one of the group’s most mercurial pieces of work.

Cannibal Ox – The Cold Vein

Easily one of the best Hip Hop albums of all time, The Cold Vein is full of the stuff everyone was trying to avoid. You’ll hear all manner of sounds flood your consciousness and you’ll miss them when they fade away into a kind of mechanical abyss. It is the Ghost In The Shell of Hip Hop, contorting and examining just long enough to force you to understand the stark reality of your universe.

Zion I – Mind Over Matter

The Source gave this album three stars out of five when it dropped in May of 2000. Baba Zumbi and Amp Live melted down eclectic production and socially conscious lyrics into a maelstrom of sonic variability. Oh, and then The Source nominated them for independent album of the year. Too late.

Eyedea & Abilities – First Born

One of the most obscure records out of Rhymesayers Entertainment’s catalog is probably Eyedea & Abilities’ First Born. Production is an interesting blend of contemporary boom bap and experimental. Thankfully, there are some great conceptual tracks including “Color My World” and fan favorite “Big Shot.”

Roc Marciano – Marcberg

Phenomenal debut albums from rappers/producers are rare. Roc Marciano managed to accomplish that and more for his first go-around Marcberg. The Fat Beats release featured stellar tracks ranging from “We Do It” and “Thugs Prayer,” all doing a pretty great job of displaying vibes of dread.   

Masta Ace – Disposable Arts

Brooklyn’s own Masta Ace could be considered one of the most underrated emcees out of New York. Disposable Arts is an unfortunate reminder that sometimes, great conceptual bodies of work and lyrical excellence didn’t earn mainstream acceptance. Doesn’t stop the album from featuring some dope guest features from Jean Grae and Greg Nice.

Sean Price – Jesus Price Supastar

There’s a reason why Jesus Price Supastar was the first album from DuckDown Records to chart in years. His solo debut Monkey Barz felt more than a proper debut. However, Jesus Price Supastar couldn’t have been grander on all aspects. Beat selection and bars were better than ever. Plus, the usage of Reverend X samples put things over the top.

Homeboy Sandman – The Good Sun

Five years ago it was impossible to find an emcee who approached a track with the same style as Homeboy Sandman. The Queens native flossed an uncanny, beat embedded, often-rapid-fire-but-just-as-effective-when-slowed flow that came impossibly close to singing without actually singing. It was singular and absolutely appreciated, especially when merged with a range of concepts and production. The Good Sun tackled homelessness, heartbreak, mean mugs, environmental sustainability and the art of emceeing like a lyrical J.J. Watt—and he did it while leaving all profanity on the cutting room floor.  

dead prez – Let’s Get Free

Let’s Get Free became the wake up call Hip Hop needed at the turn of the millennium. Especially with tracks ranging from the now standard revolutionary cut “Hip Hop” and black nationalist themed “I’m a African.” It’s not all fist pumps and activists sonics thanks to sinsual cuts like “Mind Sex.”

J. Dilla – Welcome 2 Detroit

While many count Donuts and The Shining as seminal works from J.Dilla, his debutWelcome 2 Detroit is the perfect display of the Motor City’s crowned jewel. While later acclaimed projects felt more like showcases of his production skills, Welcome 2 Detroitinclude some of Dilla’s best bars as an emcee. This meant something more in line of a “from scratch” album than incredible unfinished material.

¡MayDay! – Take Me To Your Leader

Strange Music’s resident band reached rarefied air with Take Me To Your Leader. Rap/Rock hybrids usually buckle before finding a balance between dope rhymes and dope live percussion. Either the rhymes are awesome or the music’s awesome, almost never both at the same time. Three years since TMTYL’s release and ¡MayDay! still resonates righteously on-all-fronts. The Miami natives’ witty social commentary viscerally captures American plight post-Great Recession, all over production rich enough to be described as wealthy.

Reflection Eternal – Train Of Thought

Considered by some as one of the best album Rawkus Records produced during their heyday, Reflection Eternal: Train of Thought featured everything that Talib Kweli and Hi-Tek such a fierce Hip Hop duo. Kweli’s smart aggression matched Tek moody production. While the follow-up Revolutions Per Minute didn’t match their debut, their introduction as aged pretty well.

Jaylib – Champion Sound

Half the album was Jay Dee rapping on Madlib beats and the other half was Madlib rapping on Dilla beats and never was there a concept more arduously loved. The rhymes and beats, of course, are stellar, but they transcend themselves in little genius ways that redefine the way you look at production.