Gift of Gab made his name as the technically adept MC in the vaunted underground rap duo Blackalicious, in partnership with producer/DJ Chief Xcel. Born Tim Parker, he grew up mostly in Pacoima, part of L.A.'s San Fernando Valley region, but attended high school in Sacramento. There he first met Chief Xcel (born Xavier Mosley) in 1987.
Parker, then calling himself Tiny T or Gabby T, was already developing keen skills as a battle MC, and he and Mosley teamed up the following year. After graduating, Parker returned to Los Angeles, but he and Mosley kept up their partnership by phone. While attending UC-Davis, Mosley fell in with a group of hip-hop eccentrics who became the SoleSides collective, and Parker moved up to the Bay Area to join him in 1991, now having settled on Gift of Gab as his hip-hop alter ego. Blackalicious issued their debut single, "Swan Lake," on SoleSides in 1994, and several more followed, establishing their underground reputation and leading to a tour of Europe. They began work on a full-length album, during which time SoleSides shut down and reconfigured itself as Quannum; however, the process was long and laborious, as Gift of Gab struggled with an alcohol problem that took several years to overcome. Finally, in 1999, Blackalicious re-emerged with the A2G EP, whose "Alphabet Aerobics" electrified the underground and marked Gift of Gab as a prodigious new talent. That talent was confirmed by Blackalicious' first two full-lengths, 2000's NIA and 2002's Blazing Arrow, which elevated him to the status of perhaps the most under-appreciated elite MC in hip-hop.