Olivia Rodrigo: The Queen of Sad Finds Her Happy Place

It‘s only been 40 hours since Olivia Rodrigo played the biggest show of her life — headlining a music festival she created and organized from the ground up — and the world’s buzziest pop star is already back on the grind.

“It felt like it was my wedding a little bit,” Rodrigo says of her performance in front of 50,000 at her women-led charity festival, Daisy Chain Fields, which took place over a scorching weekend in Irvine’s Great Park.

Now, on an equally hot Monday afternoon at a rehearsal space in the Valley, the pop star — still a bit tired and sunbaked from the event — nurses a tall Philz Coffee, black Ray-Ban Wayfarers shading her eyes.

“Everyone that I ever met in my life was there. My whole family on both sides,” says Rodrigo, an only child born in Temecula, California, to a schoolteacher mother and family therapist father. “I planned it for a year and a half. I was joking about it to Alanis [Morissette], and she looks at me and she says: ‘This is more important than your wedding.’ I was like, ‘Oh, wow,’ and I just suddenly got a wave of nervousness. But, yeah, it was special.”

Rodrigo chalks some of those nerves up to sharing the stage with many of the rock idols who showed up for her, including Stevie Nicks, Sarah McLachlan and Morissette. But for the pop sensation, Daisy Chain was more than a concert and more than a $20 million fundraiser for women-centered nonprofits. The festival marked the culmination of the artist Rodrigo has been transforming into for more than six years. Having delivered her third and most assured album to date, she is now establishing herself as the singular voice of Gen Z — raw, honest and relatable — with all the cultural clout, media scrutiny and potential land mines that come with the mantle.

Many 23-year-olds are heading into their first jobs, maybe moving away from home and starting the next chapter of their lives. Rodrigo has already been working since she was 13 — first as a Disney child star before exploding into a viral pop sensation with 2021’s “Drivers License” — and she tours and records so often that she says, “The blessing and the curse of my job is that I don’t really live anywhere — I’m never in a place longer than two or three months.”

While she spends a large chunk of time in New York, she still considers L.A. home. And so yesterday, she hosted a pool party with some friends to celebrate the festival win — but that brief honeymoon is over. Now it’s back to “Go, go, go, like forever,” as she puts it, turning her attention to the sold-out, 86-date, eight-month-long arena tour that kicks off three weeks from our meeting.

Her latest album — You Seem Pretty Sad for a Girl So in Love — has been an overwhelming commercial hit, one of the biggest of the year. Lead single “Drop Dead” opened at No. 1 on the Billboard Hot 100 in April and has since surpassed half a billion Spotify streams, while the album yielded two more top five singles with “The Cure” and “Stupid Song.” It had the biggest opening sales for a female artist this year (485,000), and it’s been stuck in the top five since its release June 12.

Artistically, it’s also Rodrigo’s most complete work to date. She came into 2023’s Guts just removed from her teens, facing the pressure of besting her debut album, Sour, which is the most streamed album from a female artist in Spotify history. Guts wasn’t quite the same commercial smash as Sour — it went a measly three times platinum to that album’s six — but it affirmed Rodrigo as a career artist who grew only more popular as she established herself as a major live act selling out arenas.

You Seem Pretty Sad also reflects Rodrigo’s ambitions beyond beating album and ticket sales, challenging herself to dig deeper on what she has to say.

“Olivia’s desire to be recognized as a songwriter is very refreshing; it’s unmodern in a way,” says The Cure’s Robert Smith, the first artist to ever feature on one of Rodrigo’s albums, lending his vocals on the You Seem Pretty Sad standout, “What’s Wrong With Me.” Rodrigo calls that song the best on the album.

“It’s not effortless — she spends an awful lot of time getting things right with her music,” Smith says. “But she also gets it right so quickly. It’s bizarre at times. She was in London with me a while back. She played me something she wrote that morning, things that could take 14 years for many writers to get out, and she does it in a morning.”

Beyond catchy hooks and choruses (which certainly help), Rodrigo has struck such a chord on the strength of an old-school confessional songwriting style that offers her fans a unique authenticity and powerful accessibility, putting out vulnerable songs that capture the intense feelings that come with young love and adolescence. Her songs feel urgent and unfiltered; Rodrigo sings about the negative sides of herself, too, whether that’s feelings of jealousy or obsession.

It’s a contrast to the more formulaic, homogeneous tracks the mainstream pop machine can often yield, and certainly to soulless AI slop that’s made headlines in recent years as thousands of those tracks have flooded streaming services.

“I would never use AI in any of my music,” she says. “Absolutely no. Hard line on that. The closest I’d ever got is that once, me and [producer] Dan [Nigro] were like, ‘God, I wonder what ideas ChatGPT would have for an Olivia Rodrigo title,’ and they’re all fucking awful.”

You Seem Pretty Sad lays bare the life and death of Rodrigo’s first adult relationship — in this case, purportedly with English actor Louis Partridge, who inspired Rodrigo’s first love song, “So American,” off the deluxe version of Guts. It starts with the exhilarating butterflies-in-your-stomach phase of finding a new crush (“Drop Dead”), works its way to the honeymoon phase (“Honeybee”), the first signs of trouble (“Purple”), the sobering breakup conversation (“Less”) and even the horrible return to the L.A. dating scene (“Expectations”). “Don’t think my future husband’s at this bar in Silver Lake,” Rodrigo bemoans with her signature cheeky, talky delivery.

Rodrigo didn’t know going in that this is how the album would take shape, and originally she was writing more traditional love songs. The concept changed, though, “when I went through a breakup,” she says with a chuckle.

She decided to make the “pretty sad” latter half of the album, with about two or three more months to finish the record. Along with writing new tracks, she and longtime producer Nigro rewrote and edited other songs to properly fit the new concept, injecting more sadness into the traditional love songs and capturing the “gray area” found in the highs and lows of a relationship.

“What’s Wrong With Me,” for example, was originally about “being in love with this person so much that I’m crazy. Then, post-breakup, you change perspective,” Rodrigo says. “It becomes, ‘Oh, I’m depressed and it’s because this relationship isn’t serving me anymore.’ That was a fun challenge. When you’re young, you just write and write and write. Editing has been something I’ve had to learn to do as I’ve become more of a quote-unquote professional songwriter.”

For an artist whose latest album is driven by a thesis statement about injecting melancholy into love songs, Rodrigo is more hopeful about love than expected. Throughout our interview, between topics, she sneaks in a few questions about my own upcoming wedding: Perhaps most relevantly, what will be our first-dance song?

She has said her own dream wedding song is Modern English’s new wave classic “I Melt With You.” Now she also floats Tom Petty and the Heartbreakers’ “There’s a Break in the Rain [Have Love Will Travel]” so she can complement the more upbeat track with a ballad as well.

I mention my surprise that someone who’s so open about the struggles in their own love life would have so much curiosity about someone else’s wedding.

“Oh yeah, I’m such a lover girl,” she tells me. “I’m very optimistic about love. I can’t wait to get married — one day.”

***

Rodrigo is never more animated than when talking about the music she loves from other artists. She’s still in disbelief about playing with Nicks, McLachlan and Morissette, calling Nicks her hero, heaping praise on McLachlan as the impetus for Daisy Chain’s founding and saying her music would never have been the same if not for Morissette’s Jagged Little Pill.

Morissette, who showed up as a surprise guest at the festival after Karen O had to pull out because of a personal issue, calls Rodrigo “a very unique artist in that her value system shows up in all the choices she makes.”

“Themes of truth-speaking, feminism and humanism, empowered sensitivity and activism permeate her environments in a way that feels mission-full and loving,” Morissette says. “There is a softening in the community around women truly being there for each other. Us women have had good reason to be wary of female safety in a patriarchal world. I can feel it in a handful of us artists that it might actually be safe to lean on each other now. Olivia is at the front of this charge.”

Right now, Rodrigo’s on a PJ Harvey kick and gushes about the all-girl punk rockers Die Spitz, whom she put in the Daisy Chain lineup and who are also one of the tour openers for Rodrigo’s Unraveled Tour. “I was just floored watching their set [at Daisy Chain],” Rodrigo says. “I had chills the entire time. They’re so important.”

Famously an avid Jack White fan, she says she spent an “exorbitant amount of money” to purchase the vintage white Gunne Sax prairie-style dress Meg White wore on the cover of The White Stripes’ Elephant. (According to the Julien’s Auctions site, the dress sold for $25,600.) She actually planned on wearing it during Daisy Chain in August but decided against it because it was “too fucking hot.” “Maybe if I do Daisy Chain in the winter, I can wear it,” she jokes.

Rodrigo’s always been quite open and even overt about her musical influences.

In Smith’s case, his mark is apparent on the record in more ways than one, with Rodrigo referencing his song “Just Like Heaven” on “Drop Dead” and, of course, evoking his band’s name in the song title “The Cure.” (“I was like, ‘Oh thanks, every Google search from now on is going to come up with that,’ ” Smith jokes.)

Championing a mix of singer-songwriters and rock stars who melded her musical DNA — Smith, White, Fiona Apple, Lorde and Bikini Kill and Kathleen Hanna — has also proved savvy, connecting her to a broader set of listeners outside her original core fan base of young pop listeners. And it has allowed her to expand her sonic palette in a way that feels organic, shifting from a heavier bedroom pop influence on Sour to a more overt pop-punk leaning on Guts to new wave on You Seem Pretty Sad.

“She’s really good at it,” Mick Jagger told Billboard earlier this year of Rodrigo’s transformation and her rock performances. “Everyone thought she was a different kind of singer, but there’s quite a few female singers that have made that transition. It’s not a permanent transition necessarily, but the ability to change styles from what you think their original girly pop stuff is — it’s kind of interesting.”

Wearing her musical influences on her sleeve also has had its blowback. Early in her rise, Sour tracks including “Deja Vu” “Good 4 U” and “Brutal” drew comparisons to Taylor Swift’s “Cruel Summer,” Paramore’s “Misery Business” and Elvis Costello’s “Pump It Up.” Rodrigo, who’d called Swift one of her biggest influences, subsequently gave the pop star and her co-writers Jack Antonoff and St. Vincent credit on “Deja Vu,” a move that to this day has the internet speculating why she made the concession and any beef it engendered between the two singers.

Asked about the situation back in May, Rodrigo told The New York Times: “I just try to keep on truckin’. It was so long ago, there’s no use in harping on it.”

After those experiences, she’d have good reason to start quieting down about where she draws her inspiration, but that’s not an option for her. “I love music. I wouldn’t be doing this if I didn’t love music,” Rodrigo says. “I think it’s as simple as that.”

***

Daisy Chain was inspired by Lilith Fair, the late-’90s all-female traveling festival born out of McLachlan’s frustrations over the lack of representation for female artists, and McLachlan was the first person Rodrigo called about her own festival, seeking her blessing. McLachlan was immensely supportive, advising the young pop star, showing up onstage and giving her a matching Lilith necklace they both wore during the show.

“When Lilith Fair was happening 30 years ago, women in America had more rights, had more autonomy over their bodies,” Rodrigo says. “I’ve always felt really protective of my young fans, and when I play a show and I look out into the audience and see young girls with their friends or their moms or their families, I feel such a kinship with them. And if I could be a small part in making the world a safer and better place for them to grow up and live, that’s what I want.”

The week before the festival, Rodrigo dropped her latest single, “Serena Joy,” about as close to a protest song as we’ve seen from a current chart-topping pop act in recent memory. Named after the Phyllis Schlafly-esque Handmaid’s Tale character who championed the misogynistic, fascist regime that would eventually strip her of her own power, “Serena Joy” is a call to action with a stark warning that “if they do it to them, they’ll do it to you.”

“I’ll take it if that’s what you call it,” Rodrigo says when asked if she’d refer to the single as a protest song. She argues, however, that “Serena Joy” isn’t even her first protest song. Instead, she points to Guts opener “All-American Bitch,” her pissed-off anthem on the impossible, contradictory expectations patriarchal society forces upon women.

During live performances, she’ll often tell the crowd to shout during the song’s bridge, channeling all their angst and rage in one long scream. At Daisy Chain, Rodrigo implored the crowd to think of something that “fucking pisses you off — there’s a lot to choose from in this world today.” What followed was about 13 seconds of intense, ear-ringing, cathartic screaming from the crowd of 50,000.

“I always keep my in-ear [monitors] in the whole show so I can hear what I’m doing, and I always make sure to take them out for that part so I can hear the screams,” Rodrigo says. “Every show that I’ve ever done where I did that bit, I always like to take a second to appreciate it.”

The lack of protest songs in today’s music industry has inspired many think pieces exploring what happened and whether it can be attributed to factors like a more general complacency among artists or fear from their record labels. Rodrigo chalks it up more to a writing challenge.

“My honest opinion is that they’re a little bit hard to write without feeling soapboxy,” she says. “You kind of have to be a little sarcastic, otherwise it just sort of feels like kumbaya.”

“Serena Joy’s” first verse has lyrics about “a tower we built” and “painted gold on the walls,” lines many have speculated to be a direct callout of Donald Trump. It wouldn’t be her first time challenging the administration, with Rodrigo calling ICE “barbaric and cruel” after the agency used “All-American Bitch” in ads encouraging immigrants to self-deport. She further told NPR last month that “picking fights with pop stars is a great distraction while they do other awful, awful things.”

When asked whether those specific lyrics were about Trump, she pauses for a moment, then pivots.

“It’s basically a song about complacency,” she says. “It’s about how an attack on one person’s human rights is an attack on all of our human rights. It’s something I’ve been thinking about a lot.”

So does Rodrigo think Daisy Chain Fields was political?

“One hundred percent, yes,” she says. “But I think it’s also about joy. I think the two things can exist at the same time, they kind of have to. … I think young people have lost hope in our leaders and lost hope in each other. I really wanted to galvanize people and be evidence of what can happen when you come together and are part of something and contribute.”

Artists playing into their politics isn’t without risk, as many steer clear to avoid alienating fans or getting embroiled in controversy. A group of NFL owners led by Robert Kraft essentially strong-armed Macklemore off Ed Sheeran’s tour in September over his vocal “Free Palestine” message during his performances. Sheeran, on the other end, faced intense backlash for not standing up for the rapper and avoiding picking a side.

The risk doesn’t seem to faze Rodrigo, at least, who has spoken out about America’s touchiest issues, from abortion rights to the dire situation in Gaza.

“Everyone is welcome to come to Daisy Chain,” Rodrigo says. “But if you don’t agree with the message that we’re sending, then you don’t have to buy a ticket.”

***

Rodrigo’s message of feminine unity wasn’t just cathartic for the thousands of women in attendance at Daisy Chain in August but healing for her, too, in ways she might not have even expected. She says the festival “healed my relationship” with her own complicated feelings about her fame.

“I’ve had all this attention on me since I was 17, and I’ve only ever looked at it like an albatross around my neck,” Rodrigo tells me. “There’s that burden of people taking pictures of you, you can never be private about your life and who you’re dating; all that stuff can feel really negative. But Daisy Chain is a real example to me of how it actually is a real power that you can use for good. I can call Karen O and ask her if she wants to be a part of this festival. I can try and rally all these troops together to raise $20 million for these causes [including Planned Parenthood, the National Women’s Law Center and Baby2Baby] that I really care about. For as many ways as it’s negative, it can also be used for such positive, beautiful things.”

Rodrigo hasn’t had a life fully removed from the public eye for much of her life, starting as a burgeoning Disney star at 13 years old, getting her first starring role opposite her best friend Madison Hu and a pre-manosphere Jake Paul on a three-season run of Bizaardvark back in 2016. She followed that with a starring role in High School Musical: The Musical: The Series. Any remaining semblance of anonymity vanished overnight in January 2021, when she went from Gen Z child actor to international pop star with her first-ever single “Driver’s License.” Sour yielded four more multiplatinum singles, and her star was locked in.

She’s certainly not seeking pity or trying to sell herself as a prisoner in a gilded cage; she’s always quick to point out the charmed life she’s carved out for herself and the privileges that come with it. Still, it’s a challenging paradigm for someone who values her privacy; her career is based around deeply personal, confessional songs, but that’s also the very engine that fuels the constant personal scrutiny she’d like to avoid a bit more.

This summer, for example, she was caught on a few dates with a young New York private equity associate, inspiring news stories about the trendiness of dating finance bros as well as backlash on Stan Twitter, with some going as far as to argue that dating someone in finance sat in opposition to the values Rodrigo purported to stand for.

It’s a lot of discourse for a guy who, as Rodrigo confirms, wasn’t even her boyfriend.

“It’s so hard and kind of sad, especially because relationships are supposed to be something private,” Rodrigo says. “I feel like every time I go on a casual date with a guy, there’s a picture of it on the internet, which feels really invasive. Sometimes you’re out with a guy who’s not your boyfriend, and suddenly the internet’s like, ‘They’re married, blah blah blah.’

“I understand that that’s sort of part of the … you know what? No,” she says, stopping herself. “It actually really sucks, and it feels really invasive. It feels like you’re being stalked and then judged for pictures. Like I said, I’m single, I don’t have a boyfriend, and to be stalked outside of your home and then these pictures are being used as evidence that you’re a bad person, it’s just the craziest thing. But I know who I am, and I know what my values are, and I try to just hold on to it at the end of the day. I wish that I could be 23 years old and experience life normally.”

On that adolescent life, there are plenty of adolescent milestones Rodrigo missed out on as her pop career ballooned just as she reached 18. Arguably the biggest is college. She managed to dip a toe back in 2022, taking a poetry class at USC, an experience that led her to write the Guts track “Lacy.” Thinking about the years ahead, she says she ponders how to make that happen, too.

“I’d love to go back to school. I feel like that’s kind of a misconception that people have, that you have to go when you’re like 19 years old,” Rodrigo says. “But I would love to go and learn in more of a classroom setting. I’d love to sit in a lecture. That’d be really fun. It’s the most basic stuff, but I never had it.”

She’s unsure if she’d pursue a traditional degree or just want to crash a few courses. I point out that Megan Thee Stallion managed to get a degree in health administration a few years ago. Emma Watson also went to grad school, Rodrigo responds, recalling that she was in the Daisy Chain crowd over the weekend.

“It’s funny to think about, though, too, because had I not made ‘Drivers License’ and my career didn’t go the way that it would have, I honestly feel like I would have gone to college and done some sort of nonprofit work.”

Olivia’s education will have to wait. Her fans can’t.

This story appeared in the Oct. 7 issue of The Hollywood Reporter magazine. Click here to subscribe.