Lyfe Jennings
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.(opens in a new tab)
🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.(opens in a new tab)
Reserve your preferred wine by filling out this form(opens in a new tab) and have a bottle waiting at your table when you arrive at your show. No more waiting for your first drink! We will save your wine preference and have a bottle at your table for all future shows. When you want to change your wine, come back to this form and update your preference.
🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.
The good news: we think you’ll love the food and wine just as much as the show.
🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile Plus members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.(opens in a new tab)
