Arrested Development's debut album took its title from the amount of time it took the group to secure a record contract; Three Years, Five Months and Two Days in the Life of... produced the hit single "Tennessee," a strongly spiritual track inspired by the deaths of Speech's brother and grandmother and partially based on summer visits to the latter's home in Ripley, Tennessee as a child. The album garnered rave reviews and sold over four million copies, while "Tennessee" went gold and hit the Top Ten; its two follow-ups, "People Everyday" (a rewrite of Sly's "Everyday People") and "Mr. Wendal" did likewise. Accolades poured in; Arrested Development won Grammys for Best Rap Album by a Duo or Group and Best New Artist (the first rap act to do so) and were named Rolling Stone's Band of the Year.

The band played on the 1993 Lollapalooza tour, released an Unplugged album, and also contributed the track "Revolution" to supporter Spike Lee's Malcolm X. However, there was dissension in the ranks; Farris, whose vocals were a big part of "Tennessee"'s success, left the group for a solo career, and Speech shook up the lineup, switching Headliner to a co-rapping slot and replacing him with DJ Kwesi Asuo, also adding bassist Foley, singer Nadirah, and dancer Ajile. Their second album, Zingalamaduni (Swahili for "beehive of culture"), was released in 1994; while some reviews hailed it as a major work, overall response from both critics and record buyers was more ambivalent. Speech, who writes a column on racial issues for his mother's newspaper, the Milwaukee Community Journal, and occasionally lectures on his political views, was criticized for allowing his politics to become heavy-handed, while he himself was portrayed as a control freak unable to work with others after Farris's departure. Those rumors were lent credence in 1996 when, contrary to Speech's earlier assertion that the group would be around for ten or twelve years, Arrested Development officially broke up. Speech went solo and recorded a debut album, which failed to make an impact.