Olivia Rodrigo called Chappell Roan, her former tour opener, to help her remix “Expectations,” one of the standout songs from her new album, You look pretty sad for a girl so in love. Better yet, the two pop stars went all-in for its music video, in which they join a game show hosted by famous Rodrigo fan David Byrne. Rodrigo and Roan producer Dan Nigro also makes a special appearance. Watch the video below.
Rodrigo is currently on the Unraveled Tour supporting You look pretty sad for a girl so in love. His third studio album follows that of 2023 Tripe and marks even greater ambitions, both musically with songs like “The Cure”, “Serena Joy” and her Robert Smith duet “What’s Wrong With Me”, and externally with her live performances, having organized the first Daisy Chain Fields charity music festival with a star-studded line-up celebrating womanhood. Find out how it all played out in Shaad D’Souza’s Pitchfork cover story, Olivia Rodrigo: Blood on the Tracks.
Roan released his first album, The Rise and Fall of a Midwestern Princessin 2023, after a long and winding journey as a songwriter to that point. The following year, Roan quickly gained popularity, largely due to his gigs as the opening act for Rodrigo and his viral music festival performances. After winning Best New Artist at the 2025 Grammy Awards, she released “The Giver,” her first new single since her LP, and then a few months later followed it up with “The Subway,” which earned her two Grammy nominations at this year’s ceremony. Next week she will host a charity show, The Super Graphic Spectacular, with performances from Caroline Polachek, Tinashe, MUNA and more.
Read about Tripe And The Rise and Fall of a Midwestern Princess in The Best Pop Music of 2023.
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