Los Angeles-based indie singer-songwriter Bennett Woolsey is stepping fully into the spotlight with his latest single “Tightrope,” out now via Third Generation Music Group. The track continues Woolsey’s ambitious release plan of unveiling a new song every five weeks, following “Used To You” and “Tsunami,” each offering another layer of his heartfelt storytelling and textured sound.
Woolsey’s journey began in Southlake, Texas, where he was known more for his speed on the track field than for his songwriting. It was there he first penned “Jimmy the Chameleon” for his high school band Brookside — a song that would unexpectedly take off online years later, amassing millions of streams and sparking the beginning of his solo career.
Since then, Woolsey’s path has taken him through Austin, Nashville, and now Los Angeles, where he’s honed his craft performing intimate shows that blend lyrical honesty with raw musicianship. One concertgoer described his sound best: “He can make a 12-string guitar cry.” Woolsey’s songs are grounded in real experience, shaped by his grandfather’s storytelling influence and inspired by lyrical greats like Passenger, Noah Kahan, and Billy Joel. “I find it easy to write things that are true… about real life experiences,” he says. “The progression usually informs the lyrics.”
Now collaborating with acclaimed producer Tonedeff (Pedro Antonio Rojas Jr.), Woolsey has recorded five new tracks that explore different emotional and sonic dimensions. “Tightrope” stands out as one of his most vulnerable releases yet, reflecting the balance between risk and restraint that defines both his artistry and his life on the move.
Despite his youth, Woolsey carries a reflective maturity. “I’ve done a lot of moving, a lot of leaving,” he admits. “I’ve gotten really good at leaving.” For him, every song captures a moment in time — a snapshot of emotion preserved in melody. As he continues to grow his audience, Woolsey is excited to expand his performances beyond solo sets. “There’s nothing like playing with a band—it’s a whole lot more fun.”
With his stirring voice, intimate lyricism, and cinematic folk-pop sound, Bennett Woolsey is quickly becoming one of indie music’s most promising new storytellers.