He received a nomination for Best Rap Performance by a Duo or Group at the 49th Annual Grammy Awards for his guest appearance alongside Paul Wall and Ali on Nelly's 2005 single "Grillz", which peaked atop the Billboard Hot 100.

[2] He began rapping with Khujo, T-Mo and Cee-Lo forming the Goodie Mob, a group that became part of the musical collective Dungeon Family.

The following year, the trio of Gipp, T-Mo and Khujo reunited to release Goodie Mob's fourth studio album, One Monkey Don't Stop No Show, through Koch.

The single become a number-one hit in the United States and received a Grammy Award nomination for Best Rap Performance by a Duo or Group, but lost to Chamillionaire's "Ridin' Dirty" with Krayzie Bone.

This led Ali & Gipp to release a collaborative studio album Kinfolk in 2007, which made it to number 174 on the US Billboard 200.