Talib Kweli started his rap career in a group called Mood with DJ Hi-Tek as the group's producer, Main Flow and Dante, back in Cincinnati. They had problems dealing with record labels and they never got major distribution and promotion for their only album, Doom.
Along with Mos Def (the pair are known as Black Star), Kweli achieved some mainstream success with Black Star (1998) on Rawkus Records. Mos Def went on to a successful solo career. Black Star and its individual members made numerous appearances on Chappelle's Show, a popular show on Comedy Central hosted by comedian Dave Chappelle. Chappelle himself hosted a Block Party featuring Kweli, Kanye West, Dead Prez, The Roots, The Fugees, Erykah Badu and other hip-hop and soul icons. Kweli and DJ Hi-Tek released the album Reflection Eternal in 2000, also on Rawkus.
Kweli has since released a critically acclaimed solo debut, Quality, in 2002, which received some mainstream attention thanks to the Kanye West-produced single "Get By." Quality also had tracks produced by successful producers Just Blaze and DJ Quik. In 2004, he released his second solo album and final Rawkus release, The Beautiful Struggle. The album features commercial production, and Kweli's lyrics retain their socio-political content. Also in 2004, Talib Kweli, along with Bob Moore's Amazing Mongrels, supported the Beastie Boys on their "Challah At Your Boy World Tour". In the same year, Kweli participated in a photo shoot by the renown fashion/celebrity photographer Ben Fink Shaprio. He also appeared in a few Dilated Peoples songs, including a live remix later featured on the video game NBA Street Vol. 2.
Kweli has created his own record label, Blacksmith Records and has recently signed acclaimed rapper Jean Grae and the group Strong Arm Steady (Kweli also appeared on the MF DOOM/Danger Mouse collaboration The Mouse and the Mask, on the song "Old School"). He left Geffen Records and has signed with Warner Bros. Records(to distribute for Blacksmith).
He has since broken through slightly more towards the mainstream, thanks in large part to an appearance on MTV's Wild 'N Out, and several performances on Chappelle's Show with long-time collaborator Mos Def; these performances were a product of host Chappelle's friendship with Kweli. Chappelle also participated in a number of skits on Kweli's albums "Train of Thought" and "Quality"- impersonating several people including Nelson Mandela. He also had a guest spot on West's widely successful debut album The College Dropout on the track "Get 'Em High". West has produced some of Kweli's songs, including his biggest commercial hit "Get By". Kweli can be seen in a commercial for the NCAA's Big Ten Conference, rapping about the league's basketball teams. He also provided the voice of the protagonist in the graffiti-themed video game Marc Eck's Getting Up: Contents Under Pressure, released in 2006.