[1] A mutual friend of theirs was helping organize the event and told Oberst that he was Bridgers' favorite songwriter in LA at the time, so he invited her to play and was so impressed that he immediately asked her to send him the record she was working on.

He brought her onstage to sing the Bright Eyes song "Lua" at WXPN's Xponential Music Festival that July, he sang on the duet "Would You Rather" from her debut Stranger in the Alps in September, they covered Sheryl Crow with Soccer Mommy at the Music Hall of Williamsburg in February 2018, and they worked together on a new version of his song "LAX" for Amazon Music in October, among numerous other joint appearances at each other's shows across the U.S.[5][6][7][8] The initial idea of forming the band apparently stemmed from Bridgers complimenting a cover Oberst had done of a Replacements song one night, and him replying that they should start a band and sound like the Replacements.

[10][11][12] The album was teased with "cryptic brochures" and a phone hotline, but was released with only a day of official notice and featured no promotional singles beforehand, which Bridgers explains was an effort to avoid people "[making] assumptions about what the entire record sounds like", since the songs are each so different.

[17] On January 29, 2019, the band announced their expansive concert tour of the U.S. and Europe, along with releasing a music video for their single, "Dylan Thomas," directed by Michelle Zauner.

[24] In August 2023, Bridgers performed a Better Oblivion song live for the first time since their 2019 tour when she sang "Chesapeake" with Christian Lee Hutson at a concert in Øya.