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Lyfe Jennings
City Winery LLC
Lyfe Jennings

Lyfe Jennings

08/15/2026
Sat 9:30 PM
Main Stage, City Winery Boston
80 Beverly Street
Boston, MA 02114
United States
from $57.60

City Winery Boston presents: Lyfe Jennings live on August 15 28th at 9:30pm, part of a two show series! See both shows here(opens in a new tab).

Not that he'd wish it on anyone, but it was during his ten-year sentence in prison that Lyfe Jennings developed his honest sound, thanks to isolation and Erykah Badu. It was an arson charge that put the Toledo, Ohio native in prison. His musical aspirations started in the church choir and grew up in the Dotsons, a teenage group that Lyfe formed with his brother and a couple cousins. Prison made his music deeper, according to Lyfe, and when a copy of Erykah Badu's Baduizm ended up in his cell in 1997, he was inspired and had the feeling that this introspective edge to his music was worth developing.

Two days after his December 2002 release from prison, he recorded a four-song demo CD. The day after that, he was performing live in a club. He had only a month of freedom before he was on-stage at the famous Apollo. He was booed when he walked on-stage with an acoustic guitar, but when the Apollo audience heard his gritty falsetto and lyrical songwriting, they were swayed -- swayed to the tune of five amateur-night victories in a row. Lyfe figured he'd sold 1,000 copies of his four-song demo CD during his Apollo "residency." That, along with a ton of calls from promoters and record label execs on his answering machine back in Ohio, influenced Lyfeto move to New York City and pursue a major-label deal. Columbia had the right offer and released his debut, Lyfe 268-192 (his inmate number), in August 2004. A year after its original release, the album was reissued with a new version of "Hypothetically," featuring American Idol winner Fantasia added as a bonus track.

The more hip-hop-oriented follow-up The Phoenix arrived in August 2006, with Three 6 Mafia and Young Buck making guest appearances. Lyfe Change -- released in April 2008 -- featured a handful of new production associates as well as a verse from T.I. Jennings. Lyfe moved to Warner Bros. and began working on another album, tentatively titled Sooner or Later, which he stated would be his last. It finally appeared in August 2010 as I Still Believe and featured guest spots from Bryan-Michael Cox, Warryn Campbell, Fabolous, Bobby Valentino, Ludacris, Anthony Hamilton, and Jazmine Sullivan. He did another prison stint for his actions in a 2008 domestic dispute and returned to music in October 2013 with Lucid, released on the Mass Appeal label. Like all of his previous studio releases, it peaked in the Top 10 of Billboard's R&B chart. Tree of Lyfe, recorded primarily in his home studio, following as a Top 10 hit R&B.


Dine At Your Show(opens in a new tab)

(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)


Wine At Your Table(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.


2 Item Per Person Encouraged

🎶 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.


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🍷 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)

Tickets start at
$57.60
Lyfe Jennings
Main Stage, City Winery Boston
08/15/2026
Sat 9:30 PM
Main Stage, City Winery Boston
80 Beverly Street
Boston, MA 02114
United States
from $57.60