A native of Costa Mesa, California, Cunningham was introduced to the guitar at age seven and grew up singing along with her four sisters in church, where her father was a worship pastor. By her teens, she was performing regularly as well as writing her own songs, drawing inspiration from artists like Joni Mitchell, Bob Dylan, and Jeff Buckley. In 2017, she recorded her debut EP, Love, Lose, Remember, with producer Tyler Chester (Blake Mills, Sara Watkins), following up in early 2018 with the EP For the Sake of the Rhyme. Those records, along with regular shows in Los Angeles and opening spots on tour with Punch Brothers, helped widen her audience. She soon signed with Verve Forecast and began appearing regularly as a bandmember on the Chris Thile-hosted public radio show Live from Here.
A slot at the Newport Folk Festival preceded the August 2019 release of Cunningham's debut album for Verve, the Chester-produced Who Are You Now. The record was nominated in the Best Americana Album category of the 62nd annual Grammy Awards. A covers EP, Wednesday, arrived in 2020 and found Cunningham putting her distinctive stamp on songs by Tom Waits, Radiohead, John Mayer, and others. An expanded version of Wednesday followed in January 2022 and earned a Grammy nomination for Best Folk Album. That July, she delivered her sophomore full-length, Revealer, which found her working with an intimate cadre of producers, including longtime collaborator Tyler Chester, Mike Elizondo, and Tucker Martine. ~ Matt Collar, Rovi