Jenna Raine with Ava Liv Mabry at City Winery Pittsburgh

City Winery Pittsburgh presents Jenna Raine live on Sunday, September 27th, at 7:30 PM! Jenna Raine’s songs brim with hope, heart and wide-eyed wonder. The Dallas-born singer-songwriter turns life’s little lessons, moments of bliss and unforgettable memories into the kind of pop music you’ve got to sing with the windows down. She’s tallied more than 466M total streams to date, fueled by early hits like “It Is What It Is” and her breakout smash “see you later (ten years).” The viral favorite, which exploded on TikTok and helped earn her a deal with Warner Records, first appeared on her major-label debut EP see you later — a project filled with hope, growth and a bright-side view of heartbreak. Jenna’s breakthrough success has included performances at the 2023 MTV VMAs Block Party, recognition from Rolling Stone, Billboard and V Magazine, as well as two Girls’ Life Magazine covers. She has collaborated with artists including Joshua Bassett (“Don’t Let Me Down”) and Aodhán King (“Still Worthy”), and supported David Kushner on his European tour earlier this year — all while continuing to expand her sound with her Only Started Growing EP featuring the viral hit “Roses.” Jenna closed out 2025 with the release of “Just 15” and “Talk of the Town,” alongside supporting Avery Anna on her The Let Go Letters Tour. Jenna returns with new music this year, unveiling “It Takes A Village,” and “What Would I Say,” out now. Her new music once again showcases her signature blend of heartfelt storytelling, unforgettable hooks and resilient optimism as she looks ahead to her debut album, Jeans, Boys & Jesus, set to arrive August 14. With unstoppable momentum and a luminous outlook, Jenna Raine is poised to bloom into the new year — one loved-up ballad at a time.