Fans may have thought they’d come to know what to expect from a new Olivia Rodrigo album after Sour and Guts established the precedent: four-letter album titles, purple color schemes, lots of ’90s alt and indie rock influences, and melodramatic songs about anxiety and heartbreak. But third album You Seem Pretty Sad for a Girl So in Love, deviates pretty heavily from the proven formula, in everything from its title to its aesthetics to its structuring to its subject matter — while still remaining fairly quintessentially Olivia Rodrigo in its essence.

With this Rollout Report Card episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Billboard staffers Eric Frankenberg and Hannah Dailey as we look at everything surrounding Pretty Sad and the months that have led up to it. We attempt to grade all aspects of the rollout, from the dozens of interviews to the semi-conceptual nature of the album to (of course) her infatuation with The Cure.

Along the way, we answer all the most important questions about Rodrigo’s first album era in three years: Do we actually consider this a concept album? Is Olivia a good music video tour guide? Did she get the ordering right of “Drop Dead” and “The Cure” as the two lead singles? How did Robert Smith get to be such a major part of this album era — and has it actually functioned to get more Olivia Rodrigo fans into The Cure? Is it a quietly big deal for her not to give a f–k about the Met Gala? Does it make lyrical sense to go speeding down the boulevard “without a brake”? And perhaps most importantly: Is this already on its way to being the biggest Olivia Rodrigo album?

Check it out above — along with a YouTube playlist of some of the most important moments from this old-school album campaign, all of which are discussed in the podcast — and subscribe to the Greatest Pop Stars podcast on Apple Music or Spotify (or wherever you get your podcasts) for weekly discussions every Thursday about all things related to pop stardom!

Check out Hannah’s self-titled debut EP on DSPs now.

And as we say in every one of these GPS podcast posts — if you have the time and money to spare, please consider donating to any of these causes in the fight for trans rights:

Transgender Law Center

Trans Lifeline

Destination Tomorrow

Gender-Affirming Care Fundraising on GoFundMe

Human Rights Campaign – In Your Area

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