An R&B outlier, Lyfe Jennings has set himself apart as a self-produced singer and guitarist who balances love songs with acute societal observations, wisdom regarding day-to-day life and romance, and unflinching reflections on his personal struggles. Since achieving takeoff at Harlem's Apollo Theater, Jennings has hit the upper reaches of the R&B/hip-hop chart every two or three years with albums such as Lyfe 268-192 (2004), the gold-certified The Phoenix (2006), and Lyfe Change (2008). His third LP of the 2010s, 777 (2019), was promised to be his final statement. 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. Jennings sought more production collaborators as he made his third LP. While the Underdogs, Troop's Steve Russell, and Wyclef Jean all contributed to Lyfe Change, a number four Billboard 200 hit upon arrival in April 2008, it was driven most by "Never Never Land," a number 18 R&B/hip-hop single that Jennings wrote and produced himself. Jennings eyed 2009 for the release his next album, at one point provisionally titled Sooner or Later. He instead returned on Asylum/Warner Bros. in August 2010 with I Still Believe, a set with some of the production load carried by T-Minus and smaller contributions made by Troy Taylor, Bryan-Michael Cox, and Anthony Hamilton. Citing familial obligations, Jennings intended to make it his final LP as a lead artist. His third consecutive album to land in the Top Ten of the Billboard 200, it was nonetheless followed in October 2013 by Lucid, recorded for the Mass Appeal label after a second prison stint. Despite its lower profile and lack of big-name studio associates, the LP still cracked the R&B/hip-hop Top Ten -- promoted with the modest radio hits "Busy" and "Statistics" -- and proved that Jennings still had much to say from his everyman perspective. The artist's familiar output rate continued through a June 2015 release for Relativity, the number nine R&B/hip-hop entry Tree of Lyfe. In August 2019, he issued 777, announced as his last album. ~ Andy Kellman, Rovi