The Best Underground Hip Hop Albums of All Time

Underground hip hop is all about being true to yourself and breaking away from the mainstream. It’s a subculture that values creativity, independence, and keeping it real.

Underground artists aren’t trying to fit into a mold or chase mainstream success. They’re all about experimenting with new sounds, exploring unique ideas, and expressing themselves in ways that might be too edgy, too personal, or even too creative for the mainstream sound.

Here real heads vote to rank those underground hip hop albums that stand the test of time, featuring some of the most iconic artists in the scene. From El-P and Company Flow to MF DOOM, J-Live, Cannibal Ox, and Kool Keith, these artists have been pushing the boundaries of the culture for decades.

Released: March 23, 2004

Label: Stones Throw

This legendary collaboration almost never saw the light of day. A bootleg copy of the record leaked to the public while West Coast DJ and producer Madlib (Otis Jackson Jr) and late British-American rapper MF DOOM (Daniel Dumile) were still laying tracks. Frustrated by the development they put the project on the shelf for a year and half. Fortunately the duo did eventually get back into the studio. They dropped the one and only Madvillain album on March 23, 2004. Though the record never achieved widespread mainstream success, it is heralded as one of the greatest underground hip-hop records of all time.

Affiliate disclaimer: Some links on this website are affiliate links. We may earn a small commission if you make a purchase through these links, but only promote products we truly believe in. We disclose affiliate links and give honest reviews.

Released: May 15, 2001

Label: Definitive Jux

Brooklyn’s Cannibal Ox made waves in the Hip-hop community when they dropped their debut album in the Spring of 2001. Eliciting comparisons to early Wu-Tang Clan records, The Cold Vein paired hard tales of life on streets with groundbreaking beats on a record that still hit hard after 20 years. Producer, label owner and DJ El-P (Run the Jewels) was universally heralded for the record’s cutting edge sound. On the mic, emcee duo Vast Aire and Vordul Mega tell hard tales of life in poverty-stricken New York City neighborhoods. El-P’s gritty beats proved the perfect backdrop to their real-life narratives.

Released: September 29, 1998

Label: Rawkus, Priority, EMI, MCA, Universal

This legendary record is the one and only album to be produced from the collaboration of two superstar rappers at the dawn of their careers. Released at the height of gangsta rap’s popularity, on Black Star Mos Def & Talib Kweli flipped the script with intelligent rhymes, an empowering message and a raw production style. With lyrics that focused on Afrocentric themes and black positivity, they disposed of materialistic, sexist and violent tropes that were popular in hip-hop at the time. The record harkened back to the late 80’s cerebral rap of artists like Public Enemy’s Chuck D.

Released: May 23, 2000

Label: 75 Ark

With their eponymous debut album, Deltron 3030 introduced an alternative hip-hop science fiction concept that uses futuristic settings to make modern social commentaries. Producer Dan the Automator (as the Cantankerous Captain Aptos), rapper Del the Funky Homosapien (as Deltron Zero/Deltron Osiris), and DJ Kid Koala (as Skiznod the Boy Wonder) build a world. With a cast of characters and cinematic musical backdrops, Del and his companion ‘the Automator’ travel time and space to battle with evil corporate forces. The record uses future fantasies to comment on present day commercialism.

Released: May 7, 1996

Label: Bulk, Mo’ Wax

One of the many alter-egos of Bronx emcee Kool Keith (Keith Thornton), the Dr. Octagon record marked the rapper’s 1996 debut as a solo artist. He had previously made a name for himself as a member of the NYC crew Ultramagnetic MC’s. The influential group played a pivotal role in the formative years of East Coast hip-hop. The 20-track Dr. Octagonecologyst mixes science fiction themes with stories from the hood told in Kool Keith’s distinctive flow. The eccentric and prolific rapper retired the Dr. Octagon character for nearly a decade, choosing to work as Kool Keith, until the 2006 album Return of Dr. Octagon.

Released: July 17, 2007

Label: Sound in Color

Emcee Blu and DJ/producer Exile first made a splash in the hip-hop world with their debut 2007 album Below the Heavens . The critically acclaimed project from the two artists established the collaboration as a permanent installation. The LA duo has released a string of albums, singles and EPs over the years. Though their origins are West Coast, the sound on Below the Heavens owes as much to the NYC scene as anything coming from the West. The record has a timeless vibe, with old-school beats built on classic soul grooves.

Released: July 22, 1997

Label: Rawkus

Originally released on Rawkus Records in 1997, with their debut album Funcrusher Plus , Company Flow introduced a raw and real production and lyrical style that was years ahead of its time. The record was produced by group member El-P who re-released it on his own record label in 2009. Noted for dramatically minimalist beats and Mr Len’s equally raw and unaffected rhymes, Funcrusher Plus takes on society’s ills with a smart and unforgiving eye. The record was also El-P’s introduction to a production career that would continue to generate classics.

Released: October 19, 1999

Label: Fondle ‘Em

With Operation Doomsday , Daniel Dumile introduced his new masked persona MF Doom. The rapper was making his solo debut after the tragic demise of his brother and their influential hip-hop crew KMD. The new solo album was the start of a legendary career that continues to this day. The album mixed chill soul vibes, jazz moods and old-school beats. As MF Doom, Dumile adopted a harder lyrical style than displayed in his earlier work as  Zev Love X in KMD. With the shift he shook the hip-hop world. After Operation Doomsday the talented emcee embarked on a series of influential collabs, most notable of which was the one-album classic duo Madvillian with emcee madlib

Released: October 17, 2000

Label: Rawkus

Train of Thought is the first album to be released by the duo of MC Talib Kweli and DJ and Hi-Tek, also known as Reflection Eternal. They first made their names as two-thirds of Mos Def’s Black Star . That now iconic album dropped one year before Reflection Eternal made their debut. The album continues the socially conscious, afro-centric intellectual lyricism and gritty Brooklyn grooves of Black Star . However, this is no sequel. The record is a testament to Kweli’s skills on the mic and Hi-Tek’s pivotal role in the underground sound.

Released: May 14, 2002

Label: Definitive Jux

Fantastic Damage is the debut solo album from rapper, DJ, producer and label owner El-P. The record was the groundbreaking multifaceted artist’s first release after the breakup of his group Company Flow. At the time of its release the prolific producer was producing and releasing a string of influential records on his Definitive Jux label. Released in 2002, the album was highly praised for capturing the tension and angst of a post 9/11 New York. This, despite the fact that the album was largely recorded prior to the attacks. The record is regarded as a testament to a skilled rapper and producer at the top of his game.

Released: June 13, 2000

Label: GoodVibe

Although Detroit’s Slum Village first got together in the late 90’s, the group’s earliest recordings floundered under contractual record label problems for years. By the time the band made their debut, founding member J Dilla had become a successful producer, working with folks like A Tribe Called Quest and Janet Jackson. With a jazzy and organic vibe that recalled similarly minded hippie hip-hop troupes like Tribe and De La Soul, Fantastic, Vol. 2 finds the group at their artistic peak. The band would continue releasing new music into the 2020s, despite the passing of founding members J Dilla (2006) and Baatin (2009).

Released: September 18, 2001

Label: Definitive Jux

Now based on the West Coast, Aesop Rock (Ian Matthias Bavitz) came up in New York City’s cutting edge underground hip-hop scene of the late 1990’s. He had already made a name for himself with records like 1999’s Appleseed when he dropped his third album. However, it is Labor Days that solidified his place in the history of the genre. Released on El-P’s Definitive Jux record label on September 18, 2001, Labor Days finds Bavitz in top form, spitting his signature poetic twists and clever wordplay with chopping rhymes over raw analog beats. The album was co-produced by Aesop Rock, Blockhead, and Omega One.

Released: October 31, 2000

Label: Subterraneous Records

Masters of the Universe by Binary Star was actually a remixed and remastered version of the group’s debut self-released album Waterworld . Released in 2000 and produced on a $500 budget, the record features raw and real one-take freestyles from emcees One Be Lo and Senim Silla. The Michigan-based rappers first met in prison. Their tracks feature old-school lyrical rhymes and real takes of hip-hop life. Senim Silla would eventually leave the group. One Be Lo continued and re-released Masters of the Universe in 2006.

Released: June 11, 2002

Label: Rhymesayers Entertainment

Minneapolis hip-hop duo Atmosphere dropped their second album on June 11, 2002. Though the record never achieved any mainstream success, twenty years after its release the record is still considered a classic of underground hip-hop. The record succeeds largely on the quick-witted rhymes and machine-gun delivery of rapper Slug (Sean Daley). Throughout the record he challenges society’s obsessions with money and fame and dissects his own life with confessional bars. DJ/producer Ant (Anthony Davis) matches Slug’s hard rap with a mizz of Jazz vibes and old-school breakbeats.

Released: October 3, 2000

Label: Superegular Records

Jedi Mind Tricks dropped their sophomore album and final independent release in 2000. Led by emcee Vinnie Paz, with Violent By Design the Philly collective put their hometown on the underground map. Soon after its release they were signed to Babygrande, Chuck Wilson’s New York City-based record label. Stylistically the album is born of the classic lyrical East Coast rap that dominated hip-hop’s Golden Age, the 1990s. Like the legends of that era, Vinnie and crew mix tales of street life with social commentary on Violent by Design. Though the roster has changed over time, the group is still making records 20 years later.

Released: March 11, 2016

Label: Griselda Records

Westside Gunn’s 2016 debut full-length solo album came at a pivotal time in the artist’s life and career. Following a string of successful mixtapes, the Buffalo rapper was silenced for nearly five years while serving a prison stint. Flygod marked his return to the mic as well as his final indie release before he and Griselda were signed to Eminem’s Shady records. Jail may have temporarily shut down the Westside show, but he came out swinging. Flygod goes hard and stays there. With features from Griselda homies like Conway and Mach-Hommy, Gunn drops first person narratives of gang banging over gritty downtempo boombap beats.

Released: May 27, 2003

Label: Rhymesayers Entertainment

In 2003 Brother Ali introduced a hard and politically charged sound, and launched a career that would find him speaking at Princeton and being stalked by the US government. The ethnically caucasian artist is albino. Being oppressed by his white peers, growing up the rapper felt a closer kinship to the black community. Now he writes about the struggles of the poor and socially oppressed. Musically, Shadows On The Sun holds true to the raw analog boom-bap beats of the 90s pioneers who influenced him. The Minneapolis rapper cites New York legends Rakim, Chuck D, and KRS-ONE as early inspiration for his sound.

Released: April 16, 2002

Label: Anticon

Sage Francis dropped his debut solo album Personal Journals in 2002 and introduced an eclectic new sound. The record featured a mix of emo introspection and poetry slam lyricism, dropped on old-school boom-bap and breakbeat rhythms. The rapper got his start in Providence, RI’s thriving spoken-word community. The aptly titled Personal Journals reads like the innermost thoughts of a kid, too smart for his own good and trying to make sense of an illogical world. Sage Francis is a talented emcee who is able to spin those diary entries into compelling bars.

Released: May 1, 2001

Label: Triple Threat Productions

J-Live’s debut almost never happened. The artist and the album bounced from one record label to the next for five years, due to circumstances completely unrelated to the music itself. The record finally dropped in 2001. It was met with universal critical acclaim. However, the debut was bittersweet for J-Live. Though he was topping ‘best-of’ lists around the industry, the rapper left his record label out of frustration. He followed less than a year later with the indie release, All of the Above .

Released: May 22, 2012

Label: Fat Possum Records

By the time EL-P dropped Cancer 4 Cure in 2012, he had for more than a decade been regarded as a leader in the underground East Coast scene. His work as both producer and rapper with groups like Cannibal Ox and Company Flow, is now legendary. The excellent Cancer 4 Cure is a masterpiece of the gritty New York sound EL-P helped create years earlier. The record features epic sci-fi space grooves, old-school breakbeats and dancehall jams. EL-P’s style as an emcee matches his gritty production, as he delivers lyrical and raw, mic-in-hand freestyles and street-philosopher views of the world.

Released: February 25, 2003

Label: ABB

When they dropped their debut album The Listening in February 2003, North Carolina hip-hop duo Little Brother introduced a sophisticated musical sound paired with a classic lyrical flow. Cinematic beats meet a mix of old-school shoutout raps and sucka MC disses on this laid-back Southern masterpiece. Producer 9th Wonder layers the group’s sound with R&B vocals, classic Soul grooves and orchestral moods. Meanwhile rappers Phonte and Big Pooh call out casual hip-hop fans and lazy rappers, challenging them to bring some old-school quality back into the rap game.

Released: October 7, 2003

Label: Fat Beats, Rhymesayers Entertainment

Formed in 2001, Soul Position was a collaboration between two previously established underground hip-hop artists from Ohio. MC Blueprint and DJ RJD2 dropped their first EP in 2002 before introducing their full vision on 8,000,000 Stories a year later. Their sound paired RJD2’s organic breakbeat funk rhythms with Blueprint’s verbose lyrical freestyle and distinctive nasally voice, wrapped in an experimental and often psychedelic production. Defiantly independent, the duo tread their own path until they disbanded after the release of their sophomore album, Things Go Better With Rj and Al .

Released: February 7, 2020

Label: ALC

Boldy James and The Alchemist first hooked up in 2013 for the rapper’s debut EP My 1st Chemistry Set . The Alchemist was already a respected producer, responsible for hits like Mobb Deep emcee Prodigy’s 2007 solo album Return of the Mac .
A skilled emcee and lyricist, Boldy delivers gritty street rap tales with clever wordplay and the jazz phrasing of a beat poet. In 2020 he reconnected with The Alchemist for the full-length LP The Price of Tea in China . On the record the team pairs the rapper’s signature stream-of-consciousness freestyle with a masterful mix of cinematic beats and old-school boom-bap.

Released: October 7, 2003

Label: Stones Throw Records

Champion Sound is the sole album of Jaylib, the long distance collaboration of hip-hop artists Madlib and J Dilla. The project began in 2000 as the two artists sneakered tapes to one another via the US mail. Twenty years ago internet connectivity was not what it is today. The full-length Jaylib debut is heralded as an underground classic. Sadly, the record would be the last to come from the creative duo. In 2006 J Dilla died of complications from lupus. Madlib went on to a successful solo career, including his legendary collaboration with MF Doom, Madvilliany.

Released: May 15, 2012

Label: Williams Street

A year before his debut as one half of Run the Jewels, Atlanta underground hip-hop hero Killer Mike released his definitive solo album. The veteran rapper is in top form on the record as he drops his signature, verbose and socially narrative. With a cerebral and lyrical approach, his style is reminiscent of 90’s greats like Chuck D and KRS-One. Stylistically, R.A.P. Music covered the full spectrum of the genre at the time. The record matched dirty South vibes with hard old-school East Coast beats and plenty of West Coast synth-fueled funk. At center stage is Killer Mike with a legendary flow.

Released: April 30, 2002

Label: MCA, Quannum Projects

Blackalicious’ star was finally on the rise when they released their sophomore album Blazing Arrow . After nearly a decade of obscurity they had a major record label deal, and a successful debut album, Nia . The Sacramento duo of Gift of Gab and Chief Xcel came up near the end of the gangsta rap era. While their peers followed that trend into its various subsequent offshoots, Blackalicious took their cue from the socially conscious rap of the 1990’s. On Blazing Arrow , the alternative hip-hop pioneers paired smart lyrical rhymes with soul samples, funk grooves, pop hooks and old-school cutting and scratching.

Released: September 16, 2003

Label: Sound-Ink Records, Traffic Entertainment Group

Viktor Vaughn is one of the many alter-egos of the late-great British-American rapper, Daniel Dumile. Best known as the mask-clad MF DOOM, he debuted Viktor in 2003 with Vaudeville Villain . The record dropped a year before his iconic Madlin collab, Madvillain. Dumile teamed up with producer Sound-Ink for the concept album. The record follows a day in the life of villainous wiz-kid, Viktor Vaughn. It’s a musically rich record that incorporates elements of pop, rock and old-school hip-hop. On the mic, Doom is in top form with his signature smart and gritty flow.

Released: April 2, 2002

Label: Coup d’État

J-Live is a rapper, producer and scholar who has been dropping science on the underground since the 1990’s. A former public school English teacher, the cerebral emcee (aka Justice Allah) educates through his music and live appearances.
In a story that is all too familiar in the music industry, his career nearly ended before it began. His solo album gathered dust for years as record labels delayed its release. By the time The Best Part did hit stores, J-Live had left the label and was in production on his brilliant indie follow-up, All Of the Above .

Released: September 18, 2001

Label: Viper Records; Fontana, Nature Sounds

Spanish Harlem rapper Immortal Technique debuted in 2001 with the incendiary Revolutionary, Vol. 1 . The record was the first of two albums that delivered a one-two-punch to ‘the system’. Over lo-fi beats, the verbose emcee rapped and chopped smart, determined and angry rhymes about the sorry state of affairs in America at the turn of the century. Immortal Technique delivered a total of three albums before going mostly silent after 2008’s The 3rd World . Since then he has worked as a writer and activist for many of the causes he addressed in his powerful debut album

Released: June 22, 2018

Label: Griselda

As Supreme Blientele opens, Westside Gunn steps to the mic and says, “I’m ready for anything.” He may have been reacting to what he saw on the horizon for the Griselda crew. Arriving two years after his debut and a year before Giselda’s iconic WWCD. Supreme Blientele , helped establish the Buffalo collective as leading voices in the underground hip-hop scene. Sonically the album creates a vivid picture of life in the hood, with classic soul and jazz samples looped over hard old-school beats. In his signature high-pitched voice and loose, conversational flow, Westside Gunn relays stories of gang life, professional wrestling and the rapper’s own declared status as a rap god.

Released: July 22, 2003

Label: Mic Club, Babygrande

Canibus caught the attention of hip-hop fans in the late 1990s. A notorious battle-rap champion, the Jamaican-American emcee first appeared as a featured artist on high-profile collabs with the likes of Wyclef Jean. He followed with the debut Can-I-Bus and the commercially disappointing 2000 B.C. (Before Can-I-Bus) . In 2003 Canibus dropped his third and most successful release to date, a concept album which looks at modern life through the eyes of the title character. Rip The Jacker is one of Canibus’ alter-egos, a harder version of himself created in reaction to the harsh reality of the music business.

Released: May 21, 2021

Label: Griselda

One of the most elusive and unconventional artists in hip-hop, the otherwise anonymous Hatian-American rapper Mach-Hommy has created an entirely unique industry around his distinctly cerebral, multilingual and hardcore style. He has released over 20 albums in just five years, most kept off of streaming services and sold directly by the artist with price tags in the hundreds. 2021’s award-winning Pray for Haiti is a benefit album for the rapper’s home country. The record is a showcase for his uniquely verbose and poetic technique. Like a gangster Mos Def, he delivers clever and sometimes cryptic tales over wildly creative jazz-infused beats.

Released: March 23, 2004

Label: Definitive Jux

Murs has been a West Coast underground stalwart for over two decades. In that time he has released dozens of albums as a solo artist and with longtime genre-bending collaborative side-projects like The White Mandingos and his logtime duo Felt. In 2004 the rapper dropped Murs 3:16: The 9th Edition , his fifth album and his first with producer 9th Wonder. The record is widely viewed as a turning point for both artists, representing a maturity of style and content. Murs delivers thoughtful examinations of love, hip-hop and politics over bangin’ lo-fi beats.

Released: July 17, 2020

Label: Dirty Science, Fat Beats

Released thirteen years after their debut collaboration, Blu & Exile’s Miles: From an Interlude Called Life is a cerebral and artistic record built on jazz vibes and boombap beats. Downtempo grooves meet sweet soul samples and a cool jazz-hop mindset. Lyrically, Blu delivers a thoughtful mix of social commentary tributes to the musicians that have inspired the duo’s sound. As suggested by the title’s shoutout to jazz legend Miles Davis, his respect is not reserved for hip-hop heroes. Everyone from poet Langston Hughes to Michael Jackson get props.

Released: November 23, 2018

Label: Griselda, Black Soprano Family

When Benny the Butcher dropped his debut full-length solo album in 2018, he and the Griselda crew were already leaders of the underground hip-hop scene far beyond the Buffalo city limits. The record was preceded by a decade of mix tapes, but Tana Talk 3 blew things up for Benny as a solo artist. In his distinct lyrical flow, Benny the Butcher mixes mafia metaphors with autobiographical accounts of the street. The record is also a tribute to the rapper’s brother Machine Gun Black who was killed by a drive-by in 2006. A painting of Black as a child graces the cover of Benny the album.