After relocating to Los Angeles, Chesnutt found work with Death Row records, writing and producing five songs for the male R&B group Six Feet Deep.

Chesnutt and his former band, The Crosswalk with James (Jaime) O'Connell, John Maggio and Jay Gordon, had a brief stint with Hollywood Records, but they were later released from the label.

Chesnutt plays guitar and sings vocals on the track, and appears in its music video, which received heavy airplay on MTV and BET.

In 2006, Chesnutt appeared in the music documentary Dave Chappelle's Block Party, which was originally recorded in September 2004.

In 2020, Chesnutt wrote and performed an original song for the Pixar movie Soul called "Parting Ways".