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I’m one of those lost souls who falls somewhere between the lands of millennial and Gen Z, both in birth year and in tastes. But in one pop-culture respect, my tendencies slant decidedly toward the latter. That would be the drama surrounding Olivia Rodrigo, her debut album, Sour, and her TV show High School Musical: The Musical: The Series. 
Earlier this year, we all snapped back into the experience of adolescent heartbreak with the release of Rodrigo’s debut single, “Drivers License.” The song offered a collective catharsis for listeners who had just broken up with 2020—the ultimate shitty ex-boyfriend of years. It began breaking streaming records and circulating on TikTok. In turn, it made Rodrigo a household name after she’d already gained some notoriety on the first season of her Disney+ High School Musical series, heretofore referred to as HSMTMTS.
Now Rodrigo has released her first album, Sour, amidst speculation about her personal life. Listening to the record’s 11 lovelorn tracks leads one to wonder who put the sour taste in Rodrigo’s mouth. The general consensus seems to be that the culprit could be Joshua Bassett, Rodrigo’s HSMTMTS costar and onscreen love interest. 
As Vanity Fair’s resident zillenial, I took it upon myself to dig into the ever-expanding Rodrigo universe. After all, the 18-year-old appears to invite listeners to overanalyze in her album’s opening refrain: “I want it to be, like, messy.” Below, you’ll find more than you’ve ever wanted to know about the album, the show, and all of the gossip spilling down Disney’s fake high school hallways.

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