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The debut album release from Lilly Winwood, 'Time Well Spent', chronicles this journey through earnest coming-of-age narratives and a sound that—much like her father’s work—offers an English take on traditional American roots music. Backed by Nashville producers Allen Thompson (Lady Couch) and Alex Munoz (Margot Price) , the songs on “Time Well Spent” blend Bonnie Raitt’s world-weary vocals, My Morning Jacket’s ethereal twang, and Brittany Howard's no-bullshit bravado to create an album that pays homage to Lilly’s singer-songwriter idols (like John Prine) and establishes the then twenty-three-year-old as a writer that’s wise beyond her years. For evidence, look no further than standout track “California,” a slow-burning, soulful meditation on exploration of the bittersweet nature of travel and pursuing a city that you love. It’s no surprise that Lilly sounds at home on Time Well Spent, though, considering she’s played music for most of her life. She’s written songs since her early teens (she wrote “One Big Sky,” a song about growing up and crossing a teenage threshold when she was fifteen), and she grew up playing in bands with her brother, Cal. Shortly after she began touring at age sixteen, and in 2016, she recorded a duet of “Higher Love” with her dad for a 2016 Hershey’s commercial, which Adweek lauded as “a true anthem spot.”

Winwood has continued on to collaborate with fellow East-Nashville-based Americana artists such as Boo Ray, with the release of their A-side/ B-side vinyl collaboration series with the A side being an upbeat and whimsical single ‘Hard to Tell’ and the B-side being a cover of the late Kenny Rogers and Dolly Parton’s ‘Islands in the Stream’. Boo Ray describes Winwood to SideWays Media ‘as clever like a safe-cracker, cooler than a polar bear’s toenails, and has a wonderful uproarious laugh. She’s a world-class vocalist and smart soulful songwriter’.

Lilly also collaborated with Nashville based Americana artist Don Gallardo on his 7-track EP ‘In the Name of Good Intentions’ where Lilly’s vocals are featured on more than half of the songs. Rolling Stone deemed Winwood and Gallardo’s ‘Shine a Light on Me’ one of the ‘Top 10 Best Country, Americana songs to hear now’ in 2019, amongst Trisha Yearwood and Tanya Tucker. Winwood and Gallardo spent the majority of 2019 touring together in both the UK and the US, featuring on Chicago’s WGN-TV morning news as well as Nashville’s ‘Today In Nashville’.

In late December 2020, Winwood’s music video for her single “Few More Records,” entered into rotation on CMT'S CMT Edge. Throughout the video, Winwood expresses the story of the song by portraying someone burnt out on the road, struggling with inner demons, but knowing there is still a job to do. She wanted to show fans that it is a possibility to embrace demons by dancing with hers throughout the video.