Olivia Rodrigo: The Queen of Sad Finds Her Happy Place

She's spent years turning heartbreak into hits — and wrestling with the fame that followed. But Olivia Rodrigo has finally found her happy place.

In The Hollywood Reporter's October 2026 cover story, the 23-year-old pop star reflects on a year that has seen her release a chart-topping third album, announce a massive global tour, and pull off something no one of her generation had attempted before: a feminist music festival that raised $20 million for women's charities.

From "Drivers License" to Daisy Chain Fields

Rodrigo's rise was almost overnight. At 17, "Drivers License" made her a household name, breaking streaming records and launching her debut album Sour to seven Grammy nominations and three wins. But the years that followed were complicated — the pressure of sudden fame, the scrutiny of her every move, and the inevitable comparisons that come with being young, female, and wildly successful.

Daisy Chain Fields, held in August at Irvine's Great Park, was her answer to all of it. Inspired by Sarah McLachlan's Lilith Fair, the all-women festival featured Chappell Roan, Doechii, Bikini Kill, and Stevie Nicks — a lineup that spanned generations and genres.

"At the time of Lilith Fair, women were told that they couldn't lead a festival," Rodrigo said. "And those women proved everyone wrong."

She raised $10 million, which Melinda French Gates matched to reach $20 million for organizations including Planned Parenthood and the Center for Reproductive Rights. Performing in front of 50,000 people, she told THR it "felt like it was my wedding a little bit."

The Album and the Tour

Rodrigo's third album, you seem pretty sad for a girl so in love, arrived in June and became her third consecutive No. 1 on the Billboard 200, moving 485,000 units in its first week — the biggest opening of her career. Lead single "drop dead" made history, making her the first artist to have the lead singles from her first three albums debut at No. 1 on the Hot 100.

"The Unraveled Tour" kicks off September 25 in Hartford and runs through May 2027, with 65 dates across North America, Europe, and the UK, including four-night stands in Los Angeles, Brooklyn, and London.

Finding Peace in the Noise

For an artist whose early image was defined by sadness and raw vulnerability, Rodrigo now speaks with a sense of control and purpose. Her latest single, "Serena Joy," takes its name from the Handmaid's Tale character and serves as a stark warning about the erosion of women's rights. She acknowledges it's "as close to a protest song as we've seen from a current chart-topping pop act."

But she also knows when to let the crowd scream for her — and when to take out her in-ear monitors to hear it.

"I always make sure to take them out for that part," she says of the cathartic screaming moment in "All-American Bitch." "Every show that I've ever done where I did that bit, I always like to take a second to appreciate it."