Arrested Development released their debut album, 3 Years, 5 Months & 2 Days in the Life of..., in 1992. Thomas performed lead vocals and produced the entirety of the album. It produced several hit records and earned the group two Grammy Awards: Best Rap Performance by a Duo or Group for "Tennessee" and Best New Artist. In 1994, the group's follow-up, Zingalamaduni, did not perform as well commercially, and the group subsequently split. That same year, Thomas formed his own production company Vagabond Productions and became a promoter of neo-soul, hip hop and rock concerts in Atlanta. Thomas embarked on a solo career with the release of his self-titled debut album in 1996, which sold well in Japan and Europe but not in the United States. From 1998 to 2009, Thomas released an additional six solo albums, many of which were released exclusively in Japan.
Arrested Development reunited in 2000, and Thomas has toured and recorded with the group extensively since then.