Lilly Winwood makes it a habit of going to hell and back.
Sleepless nights, weary miles, broken hearts, and the occasional redemption are the hallmarks of her travels. Fortunately for us, she’s taking notes about her road to perdition and making albums teeming with the tension of possibility. Lilly finds power in her balancing act, the life of an artist at once in between and on the precipice. She’s Americana by way of the British Invasion: Her mother is from West Tennessee, and her father, famed blue-eyed rock n’ roller Steve Winwood, is from Birmingham, England. Lilly grew up in Gloucester, England, a childhood peppered with visits to the States, before finally making Nashville her home six years ago. She’s also an artist caught in the flux of self-discovery, navigating the tightrope between innocence and experience, youthful abandon, and the self-assuredness of adulthood.
Moving to East Tennessee and emboldened by friendships with artists like Don Gallardo and Boo Ray, Lilly released Silver Stage in 2017, a 5-song EP that found the 22-year-old dealing out old-beyond-her years heartbreakers like “London”, “The Hard Way”, and the title track. Last year, she released her debut full-length, Time Well Spent, a document of an already hard-lived existence. It’s a coming-of-age record that faces learning curves, whether it’s swallowing hard pills or making up the rules as she goes. TWP is a Nashville record, produced by her friend, then-rookie producer Allen Thompson, who enlisted a who’s-who ensemble– including engineer Alex Munoz, multi-threat Robbie Crowell (Deer Tick, Diamond Rugs, Vincent Van Gold) guitarist Laur Joamets (Lore, Drivin N Cryin, Sturgill Simpson), and drummer John Radford to realize Lilly’s songs.
The results are a breezy sway of meditations about making strides and mistakes, delivered with Lilly’s straight-faced, self-assured vocals. TWS is a culmination of experience. She wrote “One Big Sky”, with its declaration “I won’t come home for summer,” when she was 15 years old. There’s also “Few More Records”, which fell into CMT’s Edge rotation, her anthem for the road-exhausted performer whose starry eyes are beginning to glaze over.
Elsewhere, she acknowledges her self-sabotaging tendencies in “Bruno”, choosing the doomed over the same, confronts the anxiety of the guilty-but-never caught in “One Step Behind”, hits the road for lost weekends in “Indiana”, and sings an ode to “Whiskey”, where “whiskey unlimited made me not remember/the best weekend yet.”
In “Nameless”, Lilly wrestles with her family name and her own identity as an artist; appropriately, the song, down to its sax solo, echoes the soul-meets-jazz stylings of her father’s music as a solo artist and with The Spencer Davis Group and Traffic. The track feels like a declaration of independence from someone who finds something valiant in eschewing inherited laurels to write her own story. Yet it’s in the lazy burn of “California” where Lilly finds true deliverance: “Baby, I’m a rolling stone/ rolled over, and I found my home.”
Lilly’s latest single, “Sleep Issues”. finds her staring down every insomniac’s hell– time alone with themselves and the perpetual what-ifs that keep the dawn at bay.