"One of the hardest parts was that people kept on telling me to shut up," Lyfe told the Baton Rouge Advocate. He joined a prison gospel group and also learned to play the acoustic guitar, one of the few instruments available to him. Lyfe made use of his time behind bars by working on his music. At 16 he was sent to prison for ten years on an arson charge. "I ran around, did a lot of nonsense, got in a lot of trouble," he told Corey Moore of National Public Radio. He began to drift away from his studies at Toledo's DeVilbiss High School. At the time, Lyfe was not in a position to pursue his ambitions. The group broke up after that, but local producers had already identified Lyfe's voice as something special, and encouraged him to work toward becoming a solo act. The group tried to follow in the footsteps of the phenomenally successful sibling ensemble New Edition they scored several talent show wins and got as far as making a demo recording. His brother Jay joined a group called Lade Bac that was featured on an album by R&B star Keith Sweat, and an uncle, Keith Dotson, formed a family group called the Dotsons. The "lyfe" spelling, according to a Toledo Blade article, indicated that his music often asks the question "why?" His first musical experiences came in church, and several members of his family went into musical careers. Lyfe was a stage name chosen after he restarted his career after prison and began writing songs, often about life's trials. Lyfe was born Chester Jennings in Toledo, Ohio, around 1976. After releasing his debut album, Lyfe 268-192, in 2004, he gradually but steadily gained a large fan base. And Lyfe's musical style, like that of the philosophical-minded vocalist Erykah Badu, hovers between hip-hop and R&B, with classically soulful vocals framed and interspersed by spoken interludes or brought up short by hip-hop's abruptness and humor. He plays an acoustic guitar, an instrument he learned in prison but one that is fairly uncommon in a contemporary urban context. Lyfe writes honest, emotional songs, drawn from his own experiences. The many attempts that have been made to describe it show how unusual it is: labels range from folk-rap (Lyfe's own description) to singer-songwriter (the Seattle Times) to "R&B/hip-hop/folk" (Billboard). The New York Times referred to him as a "socially minded R&B singer". He plays the guitar, bass, and piano which he integrates into his music. Lyfe Jennings (born Chester Jermaine Jennings) is a platinum-selling American R&B and soul singer-songwriter, record producer, and instrumentalist.