A native of Toledo, Ohio, Lyfe Jennings — born Chester Jermaine Jennings — was in his church’s choir as a youngster, and by his early teens, he was singing in a family group called the Dotsons. An arson conviction sent him to prison for a decade. During his term, he worked on writing and playing music, inspired especially as a songwriter by Erykah Badu’s Baduizm. Within a few weeks of his release in 2002, Jennings cut a demo, made his live debut, and competed at Amateur Night at the Apollo. The Harlem theater’s notoriously unsparing crowd preemptively jeered Jennings as he strode to the mike with his acoustic guitar, but the performer’s natural grit and sincerity won them over for a five-night reign, during which he sold copies of his demo and generated interest across the music industry.
Courted by numerous labels, he signed with Columbia, and in August 2004 made his proper debut with Lyfe 268-192. Titled in part after his inmate number, the self-produced album reached number 39 on the Billboard 200, peaked on the R&B/hip-hop chart at number seven, and spawned three charting singles, including the platinum, Top 40 pop hit “Must Be Nice.” Jennings’ personal narratives were epitomized with “Greedy,” on which he sang of being wanted by police for child support he couldn’t pay.
The likes of Three 6 Mafia, Project Pat, and Young Buck were matched with Jennings for The Phoenix. While these collaborations were no doubt arranged to broaden the singer’s appeal to rap listeners — the debut contained no guest verses — it was a duet with another singer, LaLa Brown, that was most successful. A ballad regarding sexual pressures placed on teenage girls, “S.E.X.” topped the R&B/hip-hop chart and became Jennings’ second Top 40 hit. It pushed The Phoenix, issued in August 2006, to the top of the Billboard 200. The single and its parent release were both certified gold by the end of the year.