Conor Oberst and Phoebe Bridgers

Conor Oberst and Phoebe Bridgers On Their Surprise Joint Album 'Better Oblivion Community Center'

“We get pegged as being emo and death-obsessed,” says Conor Oberst, gesturing to singer-songwriter Phoebe Bridgers with his half-finished milkshake. “Things that we are,” she counters with a grin. On a dreary December day, Oberst and Bridgers are at a Pasadena, Calif., diner discussing Better Oblivion Community Center, their super-secret collaboration and the band’s surprise new self-titled album.

It’s not actually such a surprise that the former Bright Eyes boy wonder, 38, and the newly minted prodigy, 24, would decide to pool their respective sadness. But it is unusual for an independent rock act to drop an album unannounced. “We were trying to leave a trail of breadcrumbs,” says Phil Waldorf, co-founder and head of marketing for Dead Oceans, Bridgers’ and the band’s label. (Oberst is currently indie.) Those breadcrumbs included mystery-stoking social media missives, pamphlets left in record stores and one Los Angeles bus bench advertising the Scientology-esque name and a phone number where the outgoing message is from country-folk singer Christian Lee Hutson, with whom the artists worked, posing as a reverend.

Phoebe Bridgers & Conor Oberst Talk New Musical Project Better Oblivion Community Center | Billboard

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.)

Carissa Gallo
Oberst (left) and Bridgers

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.”

They had only one disagreement, over the tambourine-forward jam “My City.” Oberst heard it as early R.E.M. pseudo-funk, while Bridgers pushed for something more nuanced. Bridgers won. Having an elder statesman defer to her was a pleasant change of pace. “On my album, I [lost] a lot of arguments or didn’t stick with an idea because nobody else really saw it,” she says. (Her standout single “Motion Sickness” is about a regrettable fling with 44-year-old Ryan Adams, on whose label she released her first 7-inch in 2015.) “Men have a really special knack for being fucking assholes,” she says. “My bad experiences didn’t make me generalize, but it certainly taught me what sort of people to avoid.”

Carissa Gallo
Conor Oberst and Phoebe Bridgers photographed on Dec. 6, 2018, in Los Angeles. 

She likes that Oberst isn’t jaded, and learned from him not to worry about taking a formulated trajectory. He says that working with Bridgers taught him to slow down and be more discerning.

“I taught you patience?” she responds, laughing.

“Is that a meme?” he asks warily.

“It’s an Ariana Grande lyric,” she explains, referring to the chorus of “Thank U, Next.” He rolls his eyes.