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Olivia Rodrigo Trades Heartbreak for Happiness on the Hollywood Reporter’s Music Issue Cover

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Olivia Rodrigo built her career on heartbreak. Her debut album ‘Sour’ turned teenage sadness into a global phenomenon, topping the UK albums chart and winning Grammys for best pop vocal album and best new artist in 2022, before ‘Guts’ followed with more anger, angst, and confession.

This year, though, the singer has been telling a different story. Her third album, ‘You Seem Pretty Sad for a Girl So in Love’, arrived on June 12 through Geffen Records, and Rodrigo has described it as a record about her first adult relationship.

That shift is the focus of her latest magazine cover. Rodrigo fronts the October 7 Music Issue of The Hollywood Reporter under the cover line “Pop’s queen of sad finds her happy place,” with dreamy new portraits shot by photographer Emma Summerton.

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The images were photographed on August 21 at The Ebell of Los Angeles. In one shot, Rodrigo lies on a faded floral carpet in a delicate embellished slip dress trimmed with soft white feathers. Another series frames her through a weathered window, in a white feathered top, with her dark hair loose around her face.

The muted colors and worn textures give the photos a nostalgic, almost cinematic feel. The shoot quickly caught fans’ attention online. Many praised the photos as some of the most striking images of Rodrigo’s current era.

The cover line reflects how Rodrigo has talked about the new album. She has said she wanted to prove to herself that she didn’t have to be miserable to write a song she liked. She has also explained that the record is mostly chronological, following events in the order they happened in her life, which she said was a first for her.

Longtime collaborator Dan Nigro returned as producer. The album produced 3 singles: ‘Drop Dead’ in April, ‘The Cure’ in May, and ‘Stupid Song’ in July. Rodrigo first performed ‘Drop Dead’ live during a surprise appearance at Addison Rae’s Coachella set.

Rodrigo leads an issue that also features RAYE, Don Toliver, Slayyyter and Universal Music Group chief Lucian Grainge. The magazine is also looking ahead to awards season. In its Grammy predictions, THR suggested that the album of the year race could come down to “the two Olivias,” Rodrigo and Olivia Dean.

That puts Rodrigo’s new chapter right in the middle of one of the year’s biggest awards conversations. The cover arrives in the middle of Rodrigo’s biggest touring run yet. The 65-date Unraveled Tour began on September 25 and runs through May 2, 2027, across North America and Europe.

The tour includes 4-night stands at Brooklyn’s Barclays Center, Los Angeles’ Intuit Dome and London’s The O2. Opening acts include Wolf Alice, The Last Dinner Party, Grace Ives, Die Spitz and Devon Again.

Rodrigo has also been active off the stage. Her inaugural Daisy Chain Fields festival raised $20 million for women’s rights in August, after Melinda French Gates doubled the donation total.

This week, she also spoke out on Instagram against institutions that fail to hold abusers accountable, adding her voice to criticism surrounding a lawsuit involving Cornell University. Between the tour, her activism, and awards buzz, Rodrigo’s happy era is shaping up to be her busiest yet.

Which Olivia Rodrigo era do you prefer?

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