Born and raised in St. Louis, Missouri, Olsen began performing in the city's coffee shops during her teenage years, soon branching out and tapping into a network of like-minded artists. She moved to Chicago in 2006, eventually working with California musician Emmett Kelly as part of his collective the Cairo Gang. Singing harmonies on Bonnie Prince Billy's 2010 album The Wonder Show of the World as well as its 2011 follow-up, Wolfroy Goes to Town, Olsen also released her own set of original acoustic-guitar songs, Strange Cacti, in 2010. The cassette was later reissued as a 12", both on Bathetic Records. Half Way Home, a spare album with understated arrangements and a homespun approach somewhere between '50s country crooners and her indie contemporaries, followed on the same label in 2012.
In early 2013, Olsen added drummer Josh Jaeger and bassist Stewart Bronaugh to flesh out her stripped-back sound, which added a brooding, garage rock appeal to her intimate music. Soon after forming the trio, Olsen returned to the studio with producer John Congleton to track sessions for her third album, Burn Your Fire for No Witness, which was released in early 2014 on Jagjaguwar. The record was critically well-received and spent a week at number 71 on the Billboard 200.
By then resettled in Asheville, North Carolina, Olsen expanded her sound still further on 2016's My Woman, touring as a six-piece to support its release. My Woman fared even better on the U.S. album chart, reaching number 47. Jagjaguwar followed it in 2017 with Phases, a compilation of Olsen rarities such as early demos and unreleased material from the My Woman sessions. In June 2019, Olsen contributed a featured spot on a track for Mark Ronson's collaborative Late Night Feelings, whose other guests included the likes of Alicia Keys, Miley Cyrus, and Lykke Li. Featuring production by Congleton and lavish chamber orchestra arrangements by Jherek Bischoff and Ben Babbitt, her fifth studio album, All Mirrors, arrived on Jagjaguwar in October 2019. That record also landed on the Billboard 200, peaking at number 52.
Olsen returned the following year with the stripped-down Whole New Mess, her first true solo album since 2012's Half Way Home. Captured in Anacortes, Washington, at the Unknown, a church that was converted into a recording studio by producer Nicholas Wilbur and Mount Eerie's Phil Elverum, it saw Olsen rework nine songs from the heavyhearted All Mirrors (alongside two originals) using only her voice and guitar accompaniment. The box set Song of the Lark and Other Far Memories followed in May 2021. It packaged All Mirrors and Whole New Mess with a set of related bonus material titled Far Memory and a 40-page souvenir photo book. Later the same month, the John Congleton-produced original song "Like I Used To" found her duetting with Sharon Van Etten. She returned just a few months later with the covers EP Aisles. It reimagined '80s tracks made famous by acts like Laura Branigan, Billy Idol, and Men Without Hats.
Olsen released a cover of Karen Dalton's "Something on Your Mind" in early 2022, following it with a cover of Bob Dylan's "One Too Many Mornings" for the soundtrack to the series Shining Girls that May. Her next studio album, Big Time, appeared on Jagjaguwar in June 2022. Infused with the prospect of new love as well her familiar heartache and loss, it was written during a period when she was coming out as queer. Co-produced by Olsen and Jonathan Wilson, the record included earlier country touchpoints as well as some of the lush orchestrations of All Mirrors. ~ Fred Thomas & Marcy Donelson, Rovi
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