Jessica Woodlee

Jessica Woodlee is always getting lost—and writing songs about it. With a bold approach to pop, she combines modern pop lyricism and synths with hints of classic blues- and rock-infused instrumentation, creating a sound that feels fresh yet familiar. Influenced by artists like Maggie Rogers, Maisie Peters, and Taylor Swift, Woodlee channels emotional sensitivity and lived experiences into catchy hooks, vivid metaphors, and sharp storytelling.

Woodlee is all about fan connection. Her live shows feature big sing-along choruses, intimate acoustic moments, and personal anecdotes about the misadventures that brought her to each stage. First winning over audiences in local coffee shops, she has since become a staple of the underground college scene in the Northeast. She recently opened for Christopher at a sold-out show at Brighton Music Hall, a 500-cap venue, and joined rising LA pop artist Annie Omalley on her album release tour at the Mercury Lounge in New York City and again in Boston.

Through consistent releases, memorable live shows, and a grassroots sticker campaign, Woodlee has grown her following to over 15,000 across social media and nearly 11,000 monthly listeners on Spotify. Her music is regularly played on college, local, internet, and syndicated radio, and she’s made appearances on shows including Post Adolescence Glow, WICB, Bostunes, WCRX (Simmons College Radio), and WJDQ. Known for lyrics often jotted in the Notes app mid-train ride, Woodlee has captured the attention of listeners and critics alike. Abby Kenna of Indie Spoonful writes, “Her melodies are the image of pop perfection, immediately getting stuck in your head from the first listen. Even the rhythms of her lyrics are a hook within themselves, their cyclical flow mesmerizing.” 

Named one of Atwood magazine’s 50 Artists to Watch in 2023, Woodlee is just getting started.

A childhood spent listening to legends like Carole King, Jimi Hendrix, Eric Clapton, and Ella Fitzgerald inspired her debut EP, Karma, released in 2017. As she’s grown, her songwriting has explored the realities of young adulthood, from societal pressure to heartbreak and mental health. Tracks like “Whiskey” and “T.O.M.L.” reflect this evolution. In August 2024, she released JESS, a 13-song LP that cemented this chapter of her life. Indie Boulevard praised the album, writing that JESS “shifts styles and moods as effortlessly as a chameleon changes color, reflecting the ever-changing desires and events in the lives of twenty-somethings. This fleetingness, this search for self and place in the world, is beautifully captured in every track.”

Now hard at work on new music, Woodlee is gearing up for her next chapter. Follow her on social media and wherever you stream music.

Jessica Woodlee will be performing as part of Berklee’s Summer in the City 2025 concert series. View all concerts.