6:00 PM
9:30 PM

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Lyfe Jennings’ music is rooted in truth, resilience, and raw emotion. During a ten year prison sentence, the Toledo, Ohio native developed the deeply honest sound that would later define his career. Influenced by isolation, introspection, and the discovery of Erykah Badu’s Baduizm while incarcerated, Lyfe found his voice and committed to telling real stories through song.

Raised singing in church and performing with his family group, the Dotsons, Lyfe’s musical journey accelerated immediately upon his release in December 2002. Within days, he recorded a four song demo, began performing live, and earned a coveted spot at the Apollo Theater. Though initially booed for stepping onstage with only an acoustic guitar, Lyfe quickly won over the crowd with his gritty falsetto and soulful songwriting, going on to win Amateur Night five times in a row.

That momentum led him to New York City and a major label deal with Columbia Records. His debut album Lyfe 268 192, named after his inmate number, was released in 2004 and became a breakout success. A reissue featuring Fantasia on the hit single “Hypothetically” further solidified his rise.

Lyfe followed with The Phoenix in 2006, Lyfe Change in 2008, and I Still Believe in 2010, collaborating with artists including Three 6 Mafia, Young Buck, T.I., Ludacris, Jazmine Sullivan, Fabolous, and more. Each release showcased his ability to blend soul, hip hop, and unfiltered storytelling.

After returning to music in 2013 with Lucid, Lyfe once again landed in the Top 10 of Billboard’s R and B chart. His later release Tree of Lyfe, recorded largely in his home studio, continued that streak and reaffirmed his place as one of R and B’s most authentic voices.

Experience Lyfe Jennings live for an intimate night of soul, testimony, and timeless music at City Winery Chicago.