Jennings' second album The Phoenix was released in August 2006. The album featured his hit single 'Must Be Nice'.

His first single was Stick Up Kid, which didn't see much sucess until after the album was released. He signed with Columbia Records and released his debut album Lyfe 268-192 (268-192 was his inmate number) in August 2004. To further pursue his career, Jennings moved to New York City where he performed at rapper Nelly's concert at Radio City Music Hall, at an NAACP convention where he performed an original song called 'Thank God for the NAACP', and at the Cafeteria in Chelsea, Manhattan during the blackout on August 14. The same year, he also independently released his first EP, What Is Love. In January 2003, he performed in Harlem at the Showtime at The Apollo. Jennings was released from prison in December 2002 and started to pursue a solo career in music. He has cited Erykah Badu's 1997 album Baduizm as one of the reasons for his rediscovery. The group separated in the early 1990s, and Jennings rediscovered music and started a music program at an Ohio prison where he was serving a ten-year sentence on an arson-related charge.

He later joined a group called The Dotsons with two of his cousins and his older brother, Jay. Your second album needs to show consistency. 'I think your first album is your introduction. Jennings told Farai Chideya on NPRs News & Notes that the name was chosen to reflect his growth as an artist. Jennings began singing at a young age in a Toledo church choir. The third album, Lyfe Change, was released in April of 2008 and debuted at 2 in Billboards Top 200 albums. He plays the guitar, bass, and piano which he integrates into his music. Lyfe Jennings (born Chester Jennings in Toledo, Ohio) is an African American R&B and soul singer-songwriter, record producer, and instrumentalist.

Lyfe jennings first album