The idea came from Bridgers, who acknowledges that surprise album drops have become a staple in hip-hop. Oberst points out that Radiohead did the same with its 2007 release of In Rainbows. But, he admits, “We are rolling the dice for sure. We’re not nearly as famous.” (Similarly, Robert Earl Keen and Randy Rogers independently released their secret collab as The Stryker Brothers in September.)
On their album, Oberst and Bridgers’ confessional storytelling is front and center, but amplified by contributions from Yeah Yeah Yeahs guitarist Nick Zinner and members of Dawes, it has a harder sound than one might expect. It’s wistful, but with bleating synths (“Exceptions to the Rule”) and distorted, guitar-driven duets (“Big Black Heart”). Oberst jokingly calls it “the 2019 version of the Sheryl Crow Tuesday Night Music Club,” referencing the ad hoc group of musicians who worked on Crow’s 1993 debut of the same name.
Oberst -- who has been releasing music since before Bridgers was born and whose 20-something albums with various outfits have amassed over 43.4 million on-demand streams, according to Nielsen Music -- first caught one of her performances in 2016 at a secret showcase he hosted at Los Angeles’ Bootleg Theater.
“I committed a cardinal sin that night,” he says, recalling how he dug the last song of her set without realizing it was a cover of Elliott Smith’s “Whatever (Folk Song in C).” She interjects: “He was like, ‘No, that’s not Elliott Smith. I know Elliott Smith’s songs.’” They both laugh at his botched attempt at mansplaining. They have a sibling-like rapport: Bridgers, with her typically platinum hair now tinted periwinkle, is playful and teasing while Oberst, smelling faintly of cigarettes, readily plays along. An L.A. native from a musical family, Bridgers discovered Oberst when she was in eighth grade, circa Bright Eyes’ 2007 album, Cassadaga. “I hope you paid for it,” says Oberst.
“No, LimeWire,” she quips.
After the showcase, Oberst guested on a track for Bridgers’ 2017 debut, Stranger in the Alps. Since then, they have been casually working on their own album in spurts in Los Angeles, even writing together -- a first for them both, despite past collaborations. For Monsters of Folk, Oberst’s group with Mike Mogis, M. Ward and Jim James, he would solitarily draft songs to workshop later; as would Bridgers for her boygenius side project with fellow singer-songwriters Julien Baker and Lucy Dacus.
“If I write when I’m really emotional, I’ll write one of the bad Taylor Swift songs,” says Bridgers. “I love Taylor, but every once in a while, she’s overly sincere.” And that’s where Oberst came in. “Once Christian and I were struggling with a song while Conor was tripping mushrooms in the other room,” she recalls. “Then he walked in completely out of his mind and wrote the entire thing.”