Bennett Woolsey isn’t romanticizing the kind of relationship that’s easy to walk away from. On his newest single, “Spirit Wine,” the Nashville-based singer-songwriter digs into the intoxicating and ultimately destructive connection between two people who know they’re hurting each other but can’t seem to let go.
Available now across streaming platforms, “Spirit Wine” serves as the third preview of Woolsey’s upcoming EP, scheduled for release later this year. Following “Chevy Chase” and “Cigarettes & Alcohol,” the track continues to reveal a songwriter becoming increasingly willing to turn complicated personal experiences into music.
Woolsey describes the song as the story of a relationship caught in a cycle of substance abuse, manipulation, and mutual addiction. But beneath those darker themes is something more complicated: the realization that sometimes what keeps two people together isn’t necessarily healthy love, but the inability to imagine life without the other person. That emotional contradiction sits at the center of “Spirit Wine,” giving the song a sense of vulnerability that feels grounded rather than manufactured.
The new single arrives with an accompanying music video, adding a visual component to Woolsey’s latest chapter.
For Woolsey, songwriting has become a way of documenting the moments that might otherwise disappear. Originally from Texas and now dividing his time between Nashville and Los Angeles, his life has been shaped by movement, curiosity, travel, and a willingness to chase experiences without knowing exactly where they will lead. That mindset also informs his forthcoming EP.
Written entirely by Woolsey, the project examines the messy territory of early adulthood, first loves, distance, heartbreak, independence, nostalgia, difficult goodbyes, and the realization that growing up rarely happens in a straight line. Rather than inventing stories from a distance, Woolsey pulls directly from his own life. He has collaborated with producers to develop the project’s sonic identity, but the songwriting remains firmly personal, with individual experiences transformed into songs that can resonate far beyond their original circumstances.
Woolsey is no stranger to finding an audience through honest songwriting. Before beginning his solo career, he fronted indie-rock band Brookside, helping lead the group behind the viral single “Jimmy the Chameleon,” which has surpassed 12 million streams. He later joined forces with rising artist Maryjo for the breakup duet “Used to You.”
Now, Woolsey is stepping further into his own artistic identity, combining elements of modern Americana and indie music with an approach to songwriting that puts lived experience ahead of polish. Currently, Woolsey is taking that new chapter on the road, touring across North America with Maryjo.
Tour Dates
August 28 – Houston, TX – Bad Astronaut
August 29 – Dallas, TX – Am/FM Dallas
August 30 – Nashville, TN – Cannery Hall
LINKS:
http://tiktok.com/@bennettwoolseymusic
https://www.instagram.com/bennettwoolsey
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