Olivia Rodrigo partnered up with Chappell Roan to drop a new remix of Rodrigo’s song “expectations” from her album You Seem Pretty Sad For A Girl So In Love. And with it, the pop stars released an undeniably iconic music video. If having two of the biggest artists in the world right now collab on a song weren’t enough, the video also included a few iconic cameos.
The “expectations” remix music video, which dropped on Oct. 15, showed Rodrigo and Roan on a series of different ’80s and ’90s-inspired celebrity game shows, like Wheel Of Fortune and Family Feud. Their outfits, nails, accessories, all of it was on point. And while they were playing their game shows, they had a few famous friends make some cameos. The host of the game show was a character named Johnny Johnson, played by David Byrne from the band Talking Heads. Also making a quick appearance was Dan Nigro, Rodrigo’s co-songwriter and producer.
This “expectations” music video is the fourth MV for You Seem Pretty Sad For A Girl So In Love, after “Drop Dead,” “The Cure,” and “Stupid Song.” And Roan hasn’t released a video since her single “The Subway” back in July 2025, where she wore a comically long wig and gallivanted around New York City, chasing a mysterious figure.
Rodrigo announced the new song and video on Tuesday, Oct. 13 with an Instagram post of her and Roan. In the photo, the two are sitting in a yellow car with the licence plate “XPECT8NS.” They’re both wearing strapless dresses with tutus — a-la Carrie Bradshaw from Sex and the City — and bows in their hair. Rodrigo also posted a video to her TikTok where the pair grab hands to a Heated Rivalry audio, labeling Rodrigo as “Canada’s Shane Hollander” and Roan as “Russia’s Ilya Rozanov.”
The “Drivers License” and “HOT TO GO!” singers have worked together many times before — with Roan even appearing in the film version of Rodrigo’s Guts tour for a performance they did together. Plus, she opened for both Rodrigo’s Sour and Guts tours in 2022 and 2024, respectively, and most recently performed at her inaugural Daisy Chain Fields Festival in August 2026. So while this is the first Rodrigo and Roan have officially released a song or video together, it feels like a long time coming. And now that they’ve opened the door to collabing in the studio, all I want is “more and more and more and more and more.”