Billy Strings and Molly Tuttle both learned to flatpick from their fathers, both moved to Nashville in their mid-twenties, and both became the most decorated bluegrass guitarists of their generation. For a brief stretch around 2015, they shared a house on Petway Avenue in East Nashville, each in a separate room, each working toward something the other could hear through the wall. The careers that followed were built on the same foundation and pointed in opposite directions. That gap between them, more than any single record either has made, is the most interesting thing happening in bluegrass right now.
The biographical parallels are almost implausible in their precision. Strings, born William Lee Apostol, grew up in Muir, Michigan, learning Doc Watson and Bill Monroe from his stepfather, Terry Barber, a local bluegrass picker who also introduced him to the heavier end of the American guitar tradition. Tuttle grew up in Palo Alto, California, the daughter of Jack Tuttle, a multi-instrumentalist and music instructor who led a family band and immersed his children in the same tradition. Both were prodigies before they were teenagers. Both arrived in Nashville with vans and small followings and the kind of technique that makes other musicians stop mid-sentence. When Tuttle moved to Nashville in 2015, she landed in a house Strings was already renting. As Tuttle later told Rolling Stone, the two were rarely home at the same time: "We were both always on the road." On the rare nights they were, they walked across the street to jam on a neighbor's porch. The friendship that formed there has never fully separated their careers, even as those careers diverged.
The divergence is audible. Strings has always played with one foot in the tradition and one foot somewhere harder to name, absorbing the Grateful Dead's improvisational sprawl and the physical attack of heavy metal and folding both into his flatpicking without apology. His 2021 Grammy win for Best Bluegrass Album for Home came on the strength of a record that moved between mountain music and psychedelic drift with an ease that felt less like genre-blending than like a man playing the only way he knew how. He has since won IBMA Entertainer of the Year three consecutive times, in 2021, 2022, and 2023, the first artist to accomplish that since Earls of Leicester ran the same streak from 2015 to 2017. His audiences now fill amphitheaters. Tuttle first recorded with Strings on his 2017 debut album Turmoil & Tinfoil, and even then the contrast was clear: his playing reached outward, hers pulled inward.
Tuttle's Crooked Tree, released April 1, 2022, on Nonesuch Records, is the record that most clearly defines what she is reaching for. Produced by Jerry Douglas and Tuttle herself, recorded at Oceanway Studios in Nashville, the album is a bluegrass record that insists on being a songwriter's record at the same time. Douglas's dobro is present throughout, and the band Golden Highway, featuring Bronwyn Keith-Hynes on fiddle, Dominick Leslie on mandolin, Shelby Means on bass, and Kyle Tuttle on banjo, plays with the kind of locked-in precision that comes from musicians who have learned to listen more than they speak. The guest list reads like a deliberate act of positioning: Margo Price on "Flatland Girl," Old Crow Medicine Show on "Big Backyard," Sierra Hull on "Over the Line," Dan Tyminski on "San Francisco Blues," Gillian Welch on "Side Saddle." And on track three, "Dooley's Farm," Billy Strings. That placement, a third of the way through a record that is otherwise very much Tuttle's own argument, is as close as she comes to acknowledging the conversation directly.
The record's reach extended well beyond the bluegrass circuit. At the 65th Grammy Awards in February 2023, Crooked Tree won Best Bluegrass Album, and Tuttle received a Best New Artist nomination, the first time a bluegrass artist had ever been nominated in that category. The two recognitions together said something about the size of the audience Tuttle had found, and about the kind of artist she was becoming.
At the 34th Annual IBMA Bluegrass Music Awards in September 2023, the two careers occupied the same room in a way that made the comparison unavoidable. Strings won Entertainer of the Year for the third time. Tuttle, who co-hosted the show with Ketch Secor, won Album of the Year and Song of the Year for Crooked Tree, the title track co-written with Melody Walker. Strings was on tour that night and not present. Tuttle, accepting her song award, removed her wig on the live webcast and addressed the audience directly. The moment had nothing to do with guitar playing and everything to do with what kind of artist she is becoming. It was a songwriter's move, a storyteller's move, made on a stage that has historically rewarded virtuosity above all else.
The award the two have most visibly shared is IBMA Guitar Player of the Year, an honor Tuttle was the first woman ever to win, back in 2017. That award, and the fact that both have held it, is where the conversation between them is most legible. They are the two best acoustic flatpickers working in bluegrass today, and they have answered the same question, what do you do with that kind of ability, in ways that could not be more different. Strings has made his technique a vehicle for feeling, for the kind of extended, searching improvisation that connects bluegrass to the broader American tradition of playing past the end of the song. Tuttle has made hers a frame, something that holds the song in place while the words do their work.
In May 2025, Tuttle announced the dissolution of Golden Highway, the band that had been her primary collaborators since Crooked Tree. The decision closed one chapter of the argument she had been making since that record, and opened another. What she builds next, and whether it moves toward the song or away from it, will say as much about the state of bluegrass as anything Strings plays in an amphitheater. Two people who learned the same language, saying different things. That is the whole story.
