Lyfe Jennings

City Winery Pittsburgh presents Lyfe Jennings live on Friday, October 30th, at 6:30 PM, part of a multi-show series. View all their Pittsburgh dates and times here!(opens in a new tab)

Lyfe Jennings brings his unmistakable voice and deeply personal songwriting to City Winery Pittsburgh for an unforgettable night of soul, honesty, and connection.

Known for his gritty delivery and raw storytelling, Lyfe Jennings blends classic R&B with elements of soul, gospel, and hip hop, creating music that feels both intimate and powerful. Often performing with live instrumentation including guitar, bass, and piano, his shows capture the emotional weight of his songs while keeping the energy grounded and authentic.

Rising to prominence with his acclaimed debut album Lyfe 268-192, named after his former prison identification number, Jennings made an immediate impact with standout tracks like “Must Be Nice” and “Stick Up Kid.” He followed that success with The Phoenix, a Gold certified release, and Lyfe Change, further cementing his reputation as one of R&B’s most socially conscious and emotionally honest voices. His music draws directly from lived experience, offering reflections on love, redemption, struggle, and growth.

Join us for an intimate evening where powerful stories meet soulful melodies, paired with City Winery’s signature wine and dining experience. This is a rare chance to see Lyfe Jennings up close in a setting designed for true music lovers. Reserve your seats early and be part of a night that promises depth, passion, and unforgettable performances.

🍽️ 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.

(opens in a new tab)🎶 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)(opens in a new tab)(opens in a new tab)