Olivia Rodrigo and Chappell Roan's 'Expectations' Remix Takes Over

Olivia Rodrigo and Chappell Roan have collaborated on a highly anticipated remix of Rodrigo's song "Expectations," which debuted on Thursday, October 15. The original track is featured on Rodrigo’s third album, You Seem Pretty Sad for a Girl So in Love, which previously topped the Billboard 200 chart. This 1980s-esque synth-pop anthem, known for its theme of setting high standards in the dating world, was a natural fit for Roan, whose presence significantly enhances the updated version. The Grammy winners emphasize their evolved perspective, singing, "Past mistakes are just new information. These days, I’ve got expectations."

The collaboration marks a significant moment for both artists. It is a rare feature for Olivia Rodrigo, who has only previously officially duetted with Robert Smith on "What’s Wrong With Me" from You Seem Pretty Sad. For Chappell Roan, this is her first-ever feature on another artist’s track, making it a particularly special contribution. Both pop stars share a creative connection, as they both work with producer Dan Nigro. Their long-standing friendship is evident, with Roan having opened for Rodrigo on both her Sour Tour and Guts World Tour. During the latter, Roan returned to the Guts stage to perform "Hot to Go!" with Rodrigo, and they reunited in August at Daisy Chain Fields, a festival founded by Rodrigo to raise funds for women and girls' charities. Roan expressed her admiration for Rodrigo on Instagram, acknowledging her as an inspiring artist who uses her platform for good.

The creative process behind the remix was discussed by the artists in an interview with Apple Music’s Zane Lowe. Roan revealed her intention to "spice things up" by introducing a queer perspective into her new verse. "I love making things a little gay," Roan stated, explaining that she imagined the figures in the song as "all wives." This new lyrical content specifically addresses an unimpressive female suitor, contrasting with Rodrigo's original lyrics that spoke to underwhelming men. Rodrigo shared a vivid memory from the studio, recalling how she recounted "crazy stuff that boys have done to me," leading Roan to playfully suggest, "Oh my god, you need to start dating girls. This is crazy." Roan praised Rodrigo's original songwriting for its ability to explore a relatable and "pretty difficult concept within a pop song."

Rodrigo elaborated that she initially conceived "Expectations" as a mantra song, aiming to create a track that listeners could repeatedly affirm, drawing inspiration from songs like Kendrick Lamar's "HUMBLE." She also noted that Roan’s "attitude and swagger" had already influenced her during the original song's creation, making Roan's eventual lyrical contribution a full-circle moment.

Accompanying the song is a visually striking music video, teased by Rodrigo hours before its release. The video embraces a campy game-show theme, featuring Rodrigo and Roan as contestants on "The Big Expectations Show." Dressed in various retro-chic outfits, they appear in different vintage game shows, including a "Family Feud" spoof titled "Sister Squabble," where they compete head-to-head with their "families." The fictional emcee, Johnny Johnson, is portrayed by Talking Heads frontman David Byrne, adding to the retro charm.

"Expectations" achieved chart success, debuting at No. 20 on the Billboard Hot 100 in June 2026. Rodrigo's album, You Seem Pretty Sad for a Girl So in Love, also debuted at No. 1 on the Billboard 200. Chappell Roan has also enjoyed chart success with her own hits, including "Good Luck, Babe!" and "The Subway," both of which reached the Hot 100 top 10 and explore themes of queer experience and rocky relationships.