Which Pop Star Makes Dildos With Matt Damon in ‘Drive-Away Dolls’?
Here’s a hint: She recently won a Grammy.

Photo Illustration by Luis G. Rendon/The Daily Beast/Focus Features
Here’s a little piece of trivia for you: Which 2024 Grammy winner makes an appearance as a dildo-making hippie in Drive-Away Dolls, director Ethan Coen’s new lesbian road trip movie? The Gaylor fandom would hope it’s Taylor Swift. Billie Eilish is quirky enough to sign up for a movie like this. Maybe all three ladies of Boygenius stepped up to the challenge.
Guess again. It’s not any of them.
(Warning: Spoilers ahead for Drive-Away Dolls.)
It’s Miley Cyrus who makes a kickass cameo in Coen’s bonkers comedy, just weeks after her knockout rendition of award-winning hit “Flowers” at this year’s Grammys. Appearing in a handful of trippy flashback sequences alongside another surprise A-lister, Cyrus proves she’s the kind of dream that can’t be sold.
Cyrus plays Tiffany Plastercaster, who inadvertently sets Jamie (Margaret Qualley) and Marian (Geraldine Viswanathan) off onto a cross-country road trip with a handful of illicit items. When Jamie and Marian offer to drive a car from Philadelphia to Florida, they find some top-secret stuff hiding in the trunk, including Pedro Pascal’s disembodied head and a briefcase full of mismatched dildos.
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Those dildos, we soon find out, once belonged to Tiffany, a hippie who took plaster casts of her lovers’ penises to later transform into reusable dildos. Tiffany appears in dreamlike flashback sequences, sporting eclectic bangles while dancing in front of warping tie-dye backgrounds. Her first appearance is so short that it almost feels like a joke. “Wait—is that Miley Cyrus?” Yes, it is.

Margaret Qualley and Geraldine Viswanathan
Wilson Webb / Working Title / Focus Features
Tiffany comes back for more when we learn why these specific dildos are so precious. Years ago, Tiffany slept with Florida Senator Gary Channel (Matt Damon), who is up for re-election and can’t risk any details emerging from this whirlwind fling. Imagine—the senator’s penis plastered (no pun intended!) over newspapers all over Florida. He’d be a mockery.
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Gary hires a handful of bumbling assassins to retrieve the cast, which was once Tiffany’s, but they fail to find Marian and Jamie in time. Instead, Gary is forced to make a deal with the girls, who have taken a liking to using that particular dildo. Tiffany’s plaster-casting legacy has come a long way.
Marian takes a page out of Tiffany’s book and re-plasters Tiffany’s original creation, making her own version of the dildo, a relic for her and Jamie to share forever. Tiffany’s brilliant work has spread far and wide. Although Cyrus is only present in the film for a few minutes, she has a lasting impact, especially since her role includes a sex scene with Matt Damon. What a random—but fascinating!—duo.
Drive-Away Dolls marks Cyrus’ first screen-acting role in five years. She last appeared on TV as dystopian pop star Ashley O in a 2019 episode of Black Mirror, while her last film was 2012’s So Undercover. This latest appearance is a welcome addition to the MCU—the Miley Cinematic Universe (not to be confused with Marvel, although Cyrus also had a voice-only cameo in Guardians of the Galaxy Vol. 2 in 2017).

Miley Cyrus
John Sciulli/Getty Images/John Sciulli/Getty Images
Between this and her Grammys performance, we need Cyrus back on screen now more than ever. If she can excel as a hippie woman on a quest to make a plaster cast out of Matt Damon’s genitals, she can probably take on any role—the weirder, the better.
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