Self-produced R&B artist Lyfe Jennings set himself apart from his contemporaries by documenting his personal struggles in a way that feels both genuine and inspiring. Born Chester Jermaine Jennings on June 3, 1978, in Toledo, Ohio, he grew up in a working-class family and lost his father at a very young age. He took his first steps in music as part of The Dotsons, a group he formed with his brother and two cousins, but an arson conviction cut his career short and sent him to prison for a decade. Shortly after being released in 2002, Lyfe Jennings cut out a demo and made his live debut at the Apollo, where he won amateur night five nights in a row. This inspired him to relocate to New York City, landing a deal with Columbia Records and releasing his first full-length, Lyfe 268-192, in 2004. The album, whose title referenced the inmate number he was given in prison, climbed to Number 7 on Billboard’s Top R&B/Hip-Hop Albums chart and spawned the Top 5 single “Must Be Nice.” Featuring guest spots by Three 6 Mafia and Young Buck, a second album titled The Phoenix came out in 2006 and went straight to the top of the R&B chart in the US, achieving gold certification. Following the release of Lyfe Change (2008) and I Still Believe (2010), Lyfe Jennings was forced to serve another prison sentence over a domestic dispute. In 2013, he returned with Lucid, which also cracked the R&B/Hip-hop Top 10 thanks to hits like “Busy” and “Statistics.” Subsequently, Lyfe Jennings dropped one more album, 2015’s Tree of Lyfe, before announcing his retirement with the LP 777 in 2019. Two years later, he broke the silence and released The Six Pack EP, Vol. 1, recorded in collaboration with singer Amina Buddafly. “Flawless Diamond,” the EP’s first single, climbed to Number 30 on the Adult R&B Songs chart.