Lyfe's debut album, Lyfe 268-192 in August 2004 (268-192 had been his inmate number). He eventually moved from Toledo to New York City to further pursue a music career, and wound up signing with Columbia Records. Later in 2003, Lyfe independently released a four-song EP, What Is Love. Although he was booed when he walked onstage, he eventually won the crowd over and eventually won five amateur night victories in a row. In January 2003, he performed on amateur night at the famous Showtime at The Apollo in Harlem, New York. Jennings was released from prison in December 2002 and pursued a music career. Lyfe began playing music in prison and even started a prison music program. During his time in an Ohio prison, Lyfe discovered Erykah Badu's 1997 album, Baduizm, and it rekindled his love for music. In October of the same year, when he was 19, Lyfe was sentenced to a 10-year prison term on arson charges.
In February 1993 he was arrested on drug charges.
He later joined a group called The Dotsons with two of his cousins and his older brother, Jay.
Lyfe began singing at a young age in a church choir in his hometown of Toledo.
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