Olivia Rodrigo, ‘Sour,’ and Her ‘High School Musical’ Drama, Explained

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.

First things first: Who is Olivia Rodrigo?

Rodrigo is an 18-year-old singer and actor who got her start on the Disney Channel series Bizaardvark before parlaying her three-season stint into a gig on Disney+. The streaming platform’s meta follow-up to the original High School Musical trilogy premiered in November 2019, and became a showcase for Rodrigo’s songwriting skills. “All I Want,” an original song by Rodrigo for the show—her character Nini ”writes” in the first season’s fourth episode—led to her real-life record deal with Interscope, Rodrigo told Billboard.  

In between the show’s first and second season, Rodrigo shot to world recognition with her debut single, “Drivers License.” Her first album, Sour, was released on Friday, May 21.

What sets Rodrigo apart from other Disney darlings?

First of all, she cusses. Rodrigo let expletives fly in all three of her first singles—a milestone that eluded the Selenas, Demis, and Mileys of the world until they had at least left their respective Disney shows. Secondly, her music has resonated on a larger scale and than that of most stars plucked from the House of Mouse. Some have even anointed her the next Taylor Swift, an artist Rodrigo has frequently cited as her musical hero. When her song was nestled at number three on the iTunes chart beneath two of Swift’s Evermore tracks, Swift let Rodrigo know the feeling was mutual: “I say that’s my baby and I’m really proud,” Swift wrote on Instagram.

Rodrigo has spoken about her choice to curse in all three of her first songs as an artist. “People always ask me, ‘Oh, did you say ‘fuck’ in ‘Drivers License’ to show that you aren’t just a Disney star?’” she explained in an interview with NYLON. “It’s cool that people might think that, but I’m just making music that I love and that I feel passionate about. It’s who I am. I have a dirty mouth. It was what felt natural and good to me, and people resonated with that.” Rodrigo added, “If I am ushering in a new generation of pop stars that aren’t afraid to speak their mind, that’s so cool. I’m just doing my thing, though.”

So she’s responsible for the song I sing in the shower to mask my tears?

Yes, she is. After its January debut, “Drivers License” broke records, earning 76.1 million U.S. streams, according to Billboard, and inspiring the #DriversLicenseChallenge on TikTok. The song was also featured on Saturday Night Live on Rodrigo’s 18th birthday, leading to her own turn as musical guest on the May 15 episode alongside host Keegan-Michael Key.

In subsequent months, Rodrigo also released her two follow-up singles, “Deja Vu” and “Good 4 U.” After the debut of “Deja Vu,” Rodrigo became the first artist to have her first two proper singles debut inside Billboard Hot 100’s Top 10.

So who hurt Olivia, and why won’t they go driving with her?

Shortly after “Drivers License” was unleashed upon the world, speculation began swirling that Rodrigo was singing about her HSMTMTS costar and onscreen love interest, Joshua Bassett. Though their relationship was never confirmed, the pair were rumored to be dating behind the scenes—that is, until Rodrigo posted a TikTok in August 2020 captioned, “And that’s on failed relationships.” The video also featured “All I Want,” the original Rodrigo song that her character Nini sings to his character, Ricky.

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