Artists like Dr. Octagon

Keith Matthew Thornton, better known by his stage name Kool Keith, is an American rapper and record producer known for his surreal, abstract, and often profane or incomprehensible lyrics. Kool Keith has recorded prolifically both as a solo artist and in group collaborations. Kool Keith is generally considered to be one of hip-hop's most eccentric and unusual personalities.

Company Flow was an American hip hop trio from Brooklyn, New York City, consisting of Bigg Jus, El-P and Mr. Len.

Ultramagnetic MCs are an American hip hop group based in the Bronx, New York City. Founded by Kool Keith, the group also includes Ced Gee, TR Love, and Moe Love. Big D was brought into the group by his cousin Kool Keith as a hype man in 1988. Tim Dog became an unofficial member in 1989. In 1990, DJ Jaycee was added as a road manager and backup DJ. A former member, Rooney Roon, was fired following an assault arrest. Beat-boxer Rahzel was a roadie for the group early in its career. The group's work was associated with unorthodox sampling, polysyllabic rhymes, and bizarre lyrical imagery.

Blackalicious was an American hip-hop duo from Sacramento, California, made up of rapper Gift of Gab and DJ/producer Chief Xcel. They are noted for Gift of Gab's often tongue-twisting, multisyllabic, complex rhymes and Chief Xcel's soulful production. The duo released four full-length albums: Nia in 1999, Blazing Arrow in 2002, The Craft in 2005, and Imani Vol. 1 in 2015. Gift of Gab died in June 2021.

Hieroglyphics, also known as the Hieroglyphics Crew and Hiero, is an American underground hip hop collective based in Oakland, California. The group includes founder Del the Funky Homosapien, fellow rappers Casual, Pep Love, and all four members of the group Souls of Mischief—Phesto, A-Plus, Opio, and Tajai—as well as DJ Toure and producer/manager Domino.

Handsome Boy Modeling School is an American collaborative project between hip-hop producers Dan the Automator and Prince Paul. The collaboration originally lasted from 1999 to 2006 and resulted in two albums, featuring a vast cast of guest rappers, singers, comedians and DJs. In February 2018, the duo played a concert in New York City.

Teren Delvon Jones, better known by his stage name Del the Funky Homosapien or Sir DZL, is an American rapper.

Paul Edward Huston, better known by his stage name Prince Paul, is an American record producer, disc jockey and recording artist from Amityville, New York. Paul began his career as a DJ for Stetsasonic. He has worked on albums by Boogie Down Productions, Gravediggaz, MC Lyte, Big Daddy Kane and 3rd Bass, among others. Major recognition for Prince Paul came when he produced De La Soul's debut album 3 Feet High and Rising (1989), in which he pioneered new approaches to hip hop production, mixing and sampling, notably by including comedy sketches.

Jaime Stuart Meline, better known by the stage name El-P, is an American rapper, songwriter, and record producer. He began his career as a member of the widely acclaimed Company Flow, and has been a driving force in alternative hip-hop since the 1990s. He is now most widely-known as one half of Run the Jewels. He has produced for rappers including Aesop Rock, Cage, and Mr. Lif. He was a member of The Weathermen and was the co-founder, owner, and CEO of the Definitive Jux record label.

Jeffrey Michael Haynes, better known by his stage name Mr. Lif, is an American rapper from Boston, Massachusetts. While being praised because of his political lyrics, he has released two studio albums on Definitive Jux and one on Bloodbot Tactical Enterprises. Mr. Lif is also a member of the hip-hop group The Perceptionists with long-time friends and collaborators Akrobatik and DJ Fakts One.

People Under the Stairs was an American hip hop duo from Los Angeles, California, formed in 1997 and disbanded in 2019. Since their inception, the group consisted solely of Christopher Portugal and Michael Turner. The group employed a DIY work ethic of sampling, MCing, DJing, and producing all of their output.

Ian Matthias Bavitz, better known by his stage name Aesop Rock, is an American rapper and producer. He was at the forefront of the new wave of underground and alternative hip-hop acts that emerged during the late 1990s and early 2000s. He was signed to El-P's Definitive Jux label until it went on hiatus in 2010. In a 2010 retrospective, betterPropaganda ranked him at number 19 at the Top 100 Artists of the Decade.

Quasimoto was a side project of American hip-hop producer Madlib, from Oxnard, California. Quasimoto is composed of Madlib and his animated alter ego Lord Quas. Lord Quas is known for his high-pitched voice, which often interacts with Madlib's regular voice. Quasimoto was conceived one day in the studio, when Madlib decided to rap to his own beats. Madlib did not like the sound of his voice, so he decided to slow his recorder down, rap slowly, then speed the recording back up to produce Lord Quas' distinctive high-pitched sound.

Daniel Dumile, also known by his stage name MF Doom or simply Doom, was a British and American rapper, songwriter, and record producer. Noted for his intricate wordplay, signature metal mask, and "supervillain" stage persona, he became a major figure of underground hip hop and alternative hip hop in the 2000s, and has been widely regarded as one of the greatest and most influential lyricists in underground rap.

Daniel M. Nakamura, better known by his stage name Dan the Automator, is an American record producer. He is the founder of the publishing company Sharkman Music and the record label 75 Ark.

Czarface is an American hip-hop supergroup formed in 2013 by underground hip-hop duo 7L & Esoteric and Wu-Tang Clan member Inspectah Deck. They released their acclaimed debut album, Czarface, on February 19, 2013. The album was followed by Every Hero Needs a Villain in 2015 and A Fistful of Peril in 2016, both of which were also praised by critics.

KMD was an American hip hop trio active from 1988 to 1994, during the golden age. The core of the group was composed of brothers Zev Love X and DJ Subroc. The group's original third member, Jade 1, left before the group signed with Elektra Records, being replaced with Onyx the Birthstone Kid. The group dissolved in 1994 following the sudden death of DJ Subroc in 1993, the departure of Onyx and conflicts with Elektra that resulted in them being dropped from the label.

Gang Starr were an American hip hop duo, consisting of Houston-born record producer DJ Premier and Boston-based rapper Guru.

Dilated Peoples is an American Los Angeles-based hip-hop trio, composed of rapper and record producer Evidence, rapper Rakaa, and Beat Junkies deejay and record producer DJ Babu. The group is better known in the UK, where they reached the Top 40 of the UK Singles Chart with two tracks, "This Way" and "Worst Comes to Worst". Their songs were featured in the 2003 video games Need for Speed: Underground and NBA Street Vol. 2, as well as MLB 06: The Show.

Main Source was a Canadian-American East Coast hip-hop group based in New York City/Toronto, composed of Toronto-born DJs and producers, K-Cut and Sir Scratch, as well as the New York City natives, DJ J.O.D and record producer Large Professor. Later, another Queens MC, Mikey D, replaced Large Professor.

Regan Farquhar, better known by his stage name Busdriver, is an American rapper and producer from Los Angeles. He has collaborated with rappers such as Myka 9, R.A.P. Ferreira, Nocando, Open Mike Eagle, 2Mex, Aesop Rock and Radioinactive. His primary producers have been Daedelus, Boom Bip, Daddy Kev, Loden, Paris Zax, Omid, Kenny Segal, and Nobody. He has also worked with D-Styles on two albums.