Cheeks released the follow-up album, Back Again! The single off the album was 'Crush On You' and it featured Mario Winans. The album also included a collaboration with longtime friend and business partner, Stephen Marley, (son of reggae artist Bob Marley) featuring the ballad 'Till We Meet Again' (recorded in Freaky Tah's memory) and the reggae-flavored 'Mama Say”. Kelly, named for both his cousin and his grandfather, featured the hit single ' Lights, Camera, Action!'. Lost Boyz gained worldwide critical acclaim following the release of the albums Legal Drug Money in 1996, Love, Peace & Nappiness in 1997, LB IV Life in 1999, LB Next Generation in 2019 and Legacy in 2020. 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).
Cheeks, who was mentored by his uncle Gil Scott-Heron, along with bandmates Freaky Tah (1971–1999), Spigg Nice and Pretty Lou made up The Lost Boyz.
