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    Olivia Rodrigo’s third record, “You Seem Pretty Sad For a Girl So in Love,” is a 13-song concept album that imagines the arc of a young relationship from desperate yearning, to domestic coupling, to eventual dissolution and heartbreak. It might be Album of the Year. To Wesley Morris, the dating world has only sharpened the 23-year-old’s song craft. Sure, she’s talented and can write a ballad like no other. But musically and lyrically, she’s evolved. She’s both an old soul and very 2026. Which, when compared to other current pop stars like Taylor Swift, Bruno Mars and Ariana Grande, makes her really intriguing. All things considered, Wesley has thoughts. And he could think of no better conversation partner than pop music journalist Caryn Ganz, who profiled Rodrigo in 2023 and has continued to follow her career closely. Read more: https://www.nytimes.com/2026/07/09/podcasts/olivia-rodrigo-makes-heartbreak-pop.html [00:00] Introducing Caryn Ganz [02:20] Olivia Rodrigo: Pop music is about expressing hard feelings [03:49] The cover of “You Seem Pretty Sad for a Girl So in Love” [05:12] “You Seem Pretty Sad for a Girl So in Love” is a concept album [05:38] Discussion of “Stupid Song” [08:41] "Honeybee" and subtle intimacy [12:14] The purposeful ballads on the album [18:28] Why "Expectations" is Caryn’s favorite song on the album [21:28] Musical influences and themes in “Expectations” [23:51] Olivia's chart dominance and comparisons [26:08] The current stagnant music chart sound [30:06] Why Olivia Rodrigo is like Jalen Brunson “Cannonball” is a podcast from The New York Times, with the Pulitzer Prize-winning critic Wesley Morris. Every week, Wesley talks to writers, artists and friends about the culture that moves us — the good, the bad and whatever’s in between. Surprisingly personal and never obvious, new episodes drop on Thursdays. Watch "Cannonball" on YouTube and listen wherever you get your podcasts. Subscribe: https://www.youtube.com/@cannonballpodcast Follow NYTimes: https://www.instagram.com/nytimes Subscribe to NYT Audio: https://bit.ly/3Qz3GZu
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