Tuttle's father, Jack, was a well-respected bluegrass multi-instrumentalist and instructor who led a family band, the Tuttles, and encouraged his children to share his love of music. Born in 1993, Molly was eight years old when she began playing guitar, and by the time she was 11 she was good enough to play on-stage with her father. She recorded an album with her dad, The Old Apple Tree, when she was 13, and added banjo and mandolin to her repertoire, though her main focus was still on flatpicking and clawhammer guitar styles. In her late teens, Tuttle was recognized as a rising star; she was awarded merit scholarships to the Berklee College of Music for music and composition, received the Foundation for Bluegrass Music's Hazel Dickens Memorial Scholarship, won the Chris Austin Songwriting Competition at the Merlefest Music Festival, was named Best Female Vocalist and Best Guitar Player by the Northern California Bluegrass Society, and appeared on A Prairie Home Companion, all in 2012. By 2014, Tuttle had joined the all-female contemporary bluegrass group the Goodbye Girls, and she recorded a duet album with fiddler John Mailander. While she was widely celebrated as a bluegrass player, Tuttle was also influenced by the songwriting of Bob Dylan and Gillian Welch, and began writing songs that reflected a sensibility more akin to contemporary folk. In 2015, Tuttle launched a crowd-funding campaign to finance the recording of her first solo project: her seven-song EP Rise was released in 2017 -- the same year she signed with Compass Records and became the first woman to win the International Bluegrass Music Association's Guitar Player of the Year Award. Two years later, Tuttle released her acclaimed debut full-length effort, When You're Ready, and in 2020 issued the covers LP ...But I'd Rather Be with You. Early 2022 saw the release of the lively track "Crooked Tree," the lead single from the full-length LP of the same name. The album marked Tuttle's debut for Nonesuch Records and her first outing with her bluegrass collective Golden Highway. Featuring guest spots from Margo Price, Billy Strings, Old Crow Medicine Show, Sierra Hull, Dan Tyminski, and Gillian Welch, the album took home the prize for Best Bluegrass Album at the 65th Annual Grammy Awards. ~ Mark Deming, Rovi