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After releasing her first EP, Strange Cacti, and a debut studio album, Half Way Home, on Bathetic Records, Olsen signed with Jagjaguwar, ahead of her first full-band record, Burn Your Fire for No Witness, which was released on February 17, 2014. The closing track of the album, « Windows », was featured in the final episode of the Netflix original series 13 Reasons Why in 2017.
Olsen’s third studio album, My Woman, was released on September 2, 2016. In a review for Consequence of Sound, critic Ciara Dolan described the album as a « startling record of unimpeachable strength and honesty », while Pitchfork’s Jenn Pelly described it as « her best record yet ».
In addition to her work with Bonnie « Prince » Billy and the Cairo Gang, Olsen has collaborated with a number of other notable figures of American indie rock, including Tim Kinsella of Cap’n Jazz, LeRoy Bach of Wilco and Cass McCombs. Her collaboration with Kinsella and Bach, as well as with Chicago poet Marvin Tate, resulted in the album Tim Kinsella Sings the Songs of Marvin Tate by Leroy Bach Featuring Angel Olsen which the group released on Indianapolis label Joyful Noise Recordings on December 3, 2013.
Olsen’s fourth studio album, All Mirrors, was released on October 4, 2019 to critical acclaim. Laura Snapes of Pitchfork described the album as « breathtaking », and a « strong wind » that blows in and « leaves you undone », while Alexis Petridis of The Guardian described it as « challenging and intriguing », and Luke Saunders of Happy Mag described it as a change of « theatric transcendency », when compared to her previous releases.
Olsen plays a vintage Gibson S-1 guitar from 1979.
In 2020, Olsen released several remixes of popular releases. On April 9, 2020, Olsen released a remix of « All Mirrors » her album All Mirrors Produced by Chromatics’ Johnny Jewel. On June 3, 2020 Olsen released a remix of « New Love Cassette » from her album All Mirrors produced by Mark Ronson with whom she collaborated with on Ronson’s song « True Blue ». 
On August 28, 2020, Olsen released her fifth studio album Whole New Mess through Seasick Records.