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Conversation: Lilly Winwood Claims Her Name On Debut ‘Time Well Spent’

Ed Rode

“I always tell people I grew up in midair,” says Lilly Winwood with a contemplative laugh. She’s speaking about her bi-continental upbringing between Nashville and Gloucestershire, England. Yet that’s not the only way the 25-year-old has hovered during her songwriting journey, between rock and country music, between youth and adulthood, between the star treatment and the self-driven solo tour.

The die was cast for her peripatetic life ten years before she was born, in 1985. English rock legend Steve Winwood caught a Junior Walker show at New York City’s Lone Star Cafe and happened to meet Eugenia Crafton from tiny Trenton in West Tennessee. In early ‘87, in the glow of the double Grammy Award success of his Back In The High Life album, Steve and Eugenia married and settled in their new home base of Nashville. That’s where Lilly was born, one of four, in 1995. And here she is once again, talking about her debut album Time Well Spent and the artistic life that led her to the East Side.


“We've had a home here, (but) I primarily grew up in England,” she says as she fills in her tricky backstory. “That's where I went to school, and we would come to Nashville in summers and spent vacation. High school is when I really wanted to pursue music, so me and my mom decided to move over here for a couple years, like around 16,17 years old.”

That’s when I first heard Lilly Winwood sing, at Music City Roots, and it was clear even then she had a nuanced feel for multiple roots genres and a voice beyond her years. There was promise in the air about her potential, but she had to graduate first, which happened back in the UK. “And that's kind of when I realized, okay I’m actually going to take this music thing seriously. So I moved back here when I was around 19. I've been here for like six years now permanently.”

Much of the living and growing she’s done in that time can be gleaned in the grooves and lyrics of Time Well Spent. In “California” she remembers her first road trip to the west coast during a stretch when she opened shows for father Steve. “Nameless” processes the burdens of that famous name and the resolve to claim it on her own terms. “Indiana” is about how the site of a dramatic breakup can become a place of temptation. While “A Few More Records” is a Steve Earle-tinged rocker inspired by road weariness and the unglamorous but necessary parts of the troubadour’s working life.

These coming-of-age and coming-to-terms songs are set to country leaning arrangements and textures produced by fellow East Nashvillian Allen Thompson. The band-leader and scene-maker had never made an album for another artist, but he’d been friends with Lilly for four or five years, and one night over beers the deal was struck. Thompson brought in pal Alex Munoz to engineer and play, along with a band of his close musical comrades, including drummer John Radford, guitarist Laur Joamets (Sturgill Simpson, Drivin’ N’ Cryin’) and multi-instrumentalist Robbie Crowell (Deer Tick), who plays keyboards and the surprising and refreshing sax solo on “Nameless.”

Thompson first met Winwood after booking her on a show at the 5 Spot years ago. “I was super impressed that anybody that young could write like that and perform well and have it that much together,” he told WMOT. “At that point she was 19 years old. And I guess this is me forgetting that her dad wrote “Give Me Some Lovin’” when he was like 14!” 

He says with her lacking family in town, she became like a “little sister” and a sounding board as she put together the beginnings of her writing, touring and recording career. Her wide range of influences, her low-timbred voice and her attention to lyric detail put her in a place Thompson understood. “She seems to be drawn to the storytelling aspects of straight country music, and she’s really good at it,” he said. “And she’s good at a lot of other stuff too. So I think whatever path this takes her on is going to be the right one.”

In the conversation presented here, you’ll hear a young artist whose life, choices and work direction have come decisively into focus in the past two or three years. Winwood is adaptable, comfortable in “midair” and the dichotomy that’s baked into her sense of place. “I definitely resonate with American life, if you will, more than I do England, but i feel like England will always be my home. It'll always be where my heart is and where my family lives. I am in tune with both places in very different ways.” 


Craig Havighurst is WMOT's editorial director and host of The String, a weekly interview show airing Mondays at 8 pm, repeating Sundays at 7 am. He also co-hosts The Old Fashioned on Saturdays at 9 am and Tuesdays at 8 pm. Threads and Instagram: @chavighurst. Email: craig@wmot.org