Prior, he performed as a member of the hip hop group Lost Boyz from 1995 to 1999, and thereafter signed with Universal Records to pursue a solo career.

preceded the release of his debut studio album John P. Kelly (2001), which was met with moderate critical and commercial reception along with its follow up, Back Again!

Mr. Cheeks, who was mentored by his uncle Gil Scott-Heron, along with bandmates Freaky Tah (1971–1999), Spigg Nice and Pretty Lou made up Lost Boyz.

The Lost Boyz practiced a sincere, literate, non-sensational style of New York hip-hop and produced a number of singles including; "Lifestyles of the Rich and Shameless" (1994), "Jeeps, Lex Coups, Bimaz & Benz" (1995) and "Renee" (1996).

His debut solo album, John P. Kelly, named for both his cousin and his grandfather, featured the hit single "Lights, Camera, Action!".