Jolie Holland grew up in Texas, where from a young age she experimented with writing, playing, and singing music. By her teens she had learned piano, guitar, and fiddle, and was performing as a traveling musician. San Francisco was home for a time in the mid-'90s before Holland was on her horse again, ambling to Vancouver and founding the neo-traditionalist folk outfit Be Good Tanyas. She contributed to the Tanyas' Blue Horse LP (Nettwerk, 2001) before moving back to San Francisco. There a series of solo demo recordings started making the rounds. Stark yet filled with imagery, Holland's work was folk in an American, Texas tradition, but accessed the fractured hope and gathered darkness of the country's past in beautiful and affecting new ways. The buzz surrounding the demos grew and grew, with national mags lining up with applause and Tom Waits nominating Holland for the esteemed Shortlist music prize. All of this led to Anti's signing Holland in August 2003; that November, the recordings were officially issued as Catalpa.
In April 2004, Holland returned with her actual studio debut. Entitled Escondida, the LP was a skillful blend of blues, folk, gospel, and musky vocal jazz, and immediately established Holland as one of the nation's most important young songwriters. It was followed in 2006 by the equally impressive Springtime Can Kill You. The Living and the Dead appeared in 2008. Holland toured extensively and collaborated on other artists' recordings for the next couple of years. She also relocated to New Orleans. She and co-producer Shahzad Ismaily recorded her next effort, Pint of Blood both in New York and in her home studio and other intimate spaces. It's credited to the quartet Jolie Holland & the Grand Chandeliers, whose other members included Ismaily, guitarist Marc Ribot, and Grey Gersten. The set featured nine new originals and a cover of Townes Van Zandt's "Rex's Blues" as its closer. Pint of Blood was released by Anti in June of 2011. After a three-year hiatus, she announced details of her fifth studio album, Wine Dark Sea, which was released via Anti in May, 2014. In 2017, Holland reunited with her former Be Good Tanyas bandmate Samantha Parton for the LP Wildflower Blues, which featured a powerful cover of Townes Van Zandt's "You Are Not Needed Now."