Nashville-based artist Bennett Woolsey is turning the complicated realities of love into song with his latest release, “Milan,” out now on all streaming platforms. The track serves as the fourth preview of his upcoming EP, scheduled to arrive later this year, and explores the emotional contradictions of maintaining a relationship across miles from the excitement of feeling close to someone to the difficult realization that love doesn’t always mean two people can keep moving forward together.
Woolsey describes “Milan” as an anthem for anyone who has tried to make a long-distance relationship work. Its central theme speaks to the uncertainty that comes with loving someone from afar, when moments of connection are often accompanied by separation, unanswered questions, and the challenge of figuring out what comes next.
The single continues a run of releases that includes “Chevy Chase,” “Cigarettes & Alcohol,” and “Spirit Wine,” each offering another piece of the story Woolsey is telling through his forthcoming project. Together, these songs introduce a songwriter willing to draw from personal experiences rather than shy away from the complicated emotions that accompany growing up and finding your place in the world.
Originally from Texas, Woolsey now divides his time between Nashville and Los Angeles, embracing a lifestyle shaped by movement, exploration, and a willingness to take chances. His experiences have taken him across the country, including periods spent living out of a camper and pursuing new adventures wherever they lead. Whether he’s traveling, reflecting on past relationships, or writing in the early hours of the morning, he approaches songwriting as a way to document the moments that leave a lasting impression.
That personal approach sits at the heart of his upcoming EP, which he considers his most revealing work yet. The collection examines the transitions that define early adulthood, including the excitement of first love, the sting of heartbreak, the difficulty of saying goodbye, and the growing independence that comes with discovering who you are. Rather than focusing solely on life’s major milestones, Woolsey draws attention to the smaller experiences that can quietly change the way we see ourselves and the people around us.
As a songwriter, Woolsey places particular importance on authenticity. He penned every track on the forthcoming release himself, using his own memories and experiences as the foundation for each song. While working with producers to shape the project’s overall sound, he has maintained a personal connection to the writing, allowing the music to grow without losing the stories that inspired it.
Before pursuing his solo career, Woolsey fronted indie rock band Brookside, contributing to the group’s breakout success with “Jimmy the Chameleon,” a viral single that has surpassed 12 million streams. More recently, he joined forces with rising artist Maryjo on “Used to You,” a breakup duet that explored the lingering emotions left behind when a relationship ends.
Now, Woolsey is establishing himself on his own terms, bringing together the warmth of modern Americana and the spirit of indie music with an emphasis on honest, lived-in storytelling. With “Milan,” he continues to explore the relationships and turning points that shape us, offering a reminder that sometimes the hardest part of loving someone isn’t the distance itself, but understanding what that distance reveals about the future.
As anticipation builds for his forthcoming EP, Woolsey is opening another window into his world one shaped by restless curiosity, personal reflection, and the experiences that remain with us long after a moment has passed.
LINKS:
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