Before they teamed up, Deacon the Villain from Kentucky and Kno from Georgia were already well known among the hip-hop underground for both their skills on the mike and their abilities in the producer's chair. Celph Titled, Tonedeff, and Mr. SOS all made guest appearance's on the duo's 2001 debut, Will Rap for Food, which appeared on the small Urban Aces label and soon went out of print. Rave reviews and Internet message boards helped make the album a rare collector's item until it was reissued in 2005 by the Caroline-associated FreshChest label. FreshChest was also responsible for CunninLynguists' sophomore effort, 2003's Southernunderground, which found Mr. SOS joining the group, allowing Kno to switch his focus from rapping to production. The album featured guest appearances by Masta Ace and RJD2, as well as a few political songs in response to the September 11, 2001 attacks.

Two loose mixtapes featuring a parade of guest stars have also appeared, with Sloppy Seconds, Vol. 1 landing in 2003 and Sloppy Seconds, Vol. 2 following two years later. Mr. SOS had moved on by the time of their third album, A Piece of Strange, released by The LA Underground/QN5 Music in early 2006. The album featured newly recruited member Natti, as well as guest appearances by Cee Lo Green and Immortal Technique. The group toured extensively for the release, scoring high-profile opening slots for Kanye West, Pharrell Williams, the Strokes, and others. Fourth album Dirty Acres appeared on Bad Taste in 2007, featuring guest appearances by Devin the Dude, Phonte Coleman of Little Brother, and Witchdoctor of the Dungeon Family. In 2009, CL released two mixtapes, Strange Journey, Vol. 1 and Vol. 2. Kno released his debut solo album, Death Is Silent, in 2010.

CunninLynguists retured in 2011 with their fifth proper studio album, Oneirology, which featured guest appearances from Big K.R.I.T. and Freddie Gibbs. The group took a short break following this album, with Natti releasing solo album Still Motion in 2013, and Kno forming trip-hop group Built to Fade, who released debut full-length To Dust in 2013 as well. Strange Journey, Vol. 3 appeared in 2014, and was created with input from fans, who provided ideas for musical concepts as well as artwork. Later in the year, the group collaborated with the Grouch and Eligh for the tour-only release The WinterFire EP. ~ David Jeffries