License to Thrive: Olivia Rodrigo Zooms Ahead After 2021’s Biggest Breakout Hit

All of this is happening quickly for Rodrigo, in large part because her official debut single — the midtempo breakup ballad “drivers license” — was the kind of runaway hit that demands to be capitalized on. The brilliantly detailed tearjerker struck an immediate chord with listeners everywhere and went viral on TikTok as Internet speculation about its real-life inspirations added fuel to the fire. By the end of its first weekend, it was already the biggest new smash of 2021, breaking Spotify records for daily plays both nationally and globally. It then debuted atop the Billboard Hot 100, where it spent eight weeks at No. 1 — unprecedented for an artist with only a couple of TV soundtrack credits to her name. Rodrigo went from promising Disney starlet to bona fide pop star almost overnight.

One viral hit is no guarantee of continued stardom, however, especially in the age of TikTok, when listeners often get attached to a song without bonding with the artist behind it. Rodrigo has already departed from the playbook of past Disney stars — unlike Miley Cyrus, Demi Lovato and Selena Gomez, she skipped a stint at Disney-owned Hollywood Records and went straight to a major label. But the path to artistic independence is not clear-cut, especially when the sheer phenomenon of her success (spawning fan theories, think pieces and parodies in short order) could very easily drown out the art itself.

Despite the challenges ahead of Rodrigo, no one around her seems particularly worried about her coming down with senioritis. Her work ethic is already the stuff of legend, both on the set of High School Musical: The Musical: The Series and at her label. “I honestly don’t think she sleeps,” says Nicole Bilzerian, executive vp at Geffen. “She sets the bar for us. We definitely have to rise to the occasion and work as hard, if not harder, to make all of this happen.”

That focus and ambition also inform her songwriting — which, despite her list of accomplishments, remains both her primary artistic calling card and her top career priority. “She’s never satisfied,” says Dan Nigro, her Sour producer and co-writer. “With Olivia and I’s dynamic, there’s a constant, like, ‘What if we tried this? What if we changed all the pianos out and made them guitars? What if we rewrote the lyrics?’ No song feels like it’s done.”

Rodrigo’s team is betting that she has the presence, the talent and the fortitude to use “drivers license” as a springboard to greater things — and come into her own as a singer-songwriter in the classic sense. “It’s the music, and that’s what people are connecting to, but I think that people believe in her,” says John Janick, chairman/CEO of Interscope Geffen A&M (IGA). “She’s the real deal. And that’s why she’s going to be a global superstar who’s going to be around for a long time. Because she gets it — but she also has the drive and wants to win.”

Over the course of our conversation, Rodrigo raves about her infatuation with all sorts of musical subjects: vinyl records, the Grammy Awards, Jack White, Taylor Swift’s recently released Fearless (Taylor’s Version). But while she may have many obsessions, she’s perhaps most obsessed with, well, being obsessed.

“I am just obsessed with all types of music,” she says, even though she can’t help but give an eye roll at her own overexuberance. “You know how somebody’s like, ‘Oh, what kind of music do you listen to?’ And they’re like, ‘I like all music!’ And you’re like, ‘OK, that gives me nothing.’ But I truly am!”

Rodrigo’s inextinguishable excitement for music is one of the most striking things about her. Along with certain wardrobe choices (like the Twilight: Eclipse shirt she wears during our Zoom call) and a habit of responding to questions that catch her off guard with a gleeful but slightly anxious giggle, it’s a reminder that the wise-beyond-her-years songwriter is still a teenager.

“She’s a young adult now, but I remember being struck and moved by how ordinary the conversations were [between her and her castmates] in between takes,” says Tim Federle, creator and showrunner for High School Musical: The Musical: The Series. “All the insecurities and all of the self-doubts and all of the dreams that every kid out there has, Olivia has and had them too. And she happened to strike gold where her dreams met a perfect intersection of her abilities.”

Rodrigo inherited her earliest musical obsessions from her parents: Jennifer, who is German and Irish, and Christopher, from whom Rodrigo gets her Filipino heritage. (Rodrigo calls the recent wave of violence against Asian Americans in the United States “heartbreaking,” adding that “we all need to keep speaking out against these injustices in the world.”) Growing up in Temecula, Calif., she would go record shopping with her mom, a third-grade teacher. Although Rodrigo describes her mother as “the sweetest woman ever,” Jennifer gravitated toward metal, punk and ’90s alternative rock. Those influences, mixed with Rodrigo’s fondness for Lorde’s emotionally layered pop anthems and the vivid storytelling of country music, began to influence her own songs, which she started writing as a tween.

Her first chance to write professionally came on High School Musical: The Musical: The Series, where she was cast by Federle, who wasn’t aware of her songwriting abilities. Federle realized he needed a song for Rodrigo’s character at the end of a mid-first-season episode. He found out about the diaristic original songs Rodrigo was posting on Instagram and asked her to try writing it herself.

“I sent Olivia this email, being like, ‘I think Nini needs a song, and I think you should be the person who tries to write it,’ ” says Federle. “And I remember three days later, Olivia was sort of sheepishly like, ‘I’ve got a little something, do you mind if I show you?’ ”

That “little something” was “All I Want,” a piano ballad about being repeatedly let down by significant others, which blew Federle away, and landed in episode four of the first season. Though the song was one of many featured in that season — and far from the showiest or most prominently placed — it was the one that became a hit on TikTok, crossing over to the Hot 100 in early 2020. “I didn’t even have TikTok at the time. I was like, ‘What’s this thing? Why are people making stuff that’s [just a few seconds] long?’ ” Rodrigo says with a laugh. “But that song is how Interscope found me.”

“You just knew right away — her personality, her vision, her talent as a songwriter and as a singer,” says Janick of his first meeting with Rodrigo. “She had all of the pieces that we look for in an artist. We knew right away that we wanted to sign her.”

Still, it took six months, as Rodrigo was being courted by multiple other majors at the time. “It has always been important for Olivia as a songwriter and artist to be able to separate herself from the characters she has played on TV,” says manager Kristen Smith. “When the time came to look at labels, we were lucky enough that we had created the freedom for her to be able to meet with different potential partners who would be the best fit for Olivia.”

An industry source tells Billboard that Rodrigo’s camp proposed to at least one company that it pay roughly $10 million to sign her, but Janick ended up signing her to Geffen for closer to $2 million, the source says; neither Geffen nor Rodrigo’s reps commented on the terms of the agreement.

In the end, Rodrigo says Geffen had the right pitch for her. “All the other major labels were like, ‘Oh, you could be a star,’ ” she recalls. “And I remember going into Interscope for the first time and [Janick] telling me, ‘We love your songwriting. We think you’re a great songwriter, and that’s the most important thing to us.’ And I remember being like, ‘Oh, OK, this is where I’m supposed to be.’ ”

Janick saw Rodrigo as a potential new face of the resurgent Geffen — once home to iconic ’80s and ’90s artists like Aerosmith, Guns N’ Roses and Nirvana — which officially relaunched in 2017 as part of the IGA family. The label’s rap-heavy roster now boasts streaming stars Lil Durk and Rod Wave, but few pop singer-songwriters, and no one with a hit the size of “drivers license.” “As we rebuild it, it’s hyperfocused on her and turning her into a global act,” says Janick. “[She’s one of] those artists who move culture and are going to be career artists.”

So far, Rodrigo says she’s very happy with the fit. “I really just trust and value their input,” she says of the team at Geffen. “I’ve done a good job of surrounding myself with people who are really honest with me and can help me make my music instead of just being like, ‘Yeah, you’re perfect!’ Because I hate that. Like, that’s my least favorite thing in the whole world.”

In early April, Rodrigo posted a snapshot of a parking ticket she had recently received from the city of Los Angeles to her Instagram story: “damn this driving s–t isnt all fun and games,” read the quippy caption. “I parked on street cleaning day,” she explains a few weeks later, still incredulous at her own naiveté. “I remember being like, ‘Huh, nobody’s parked on this street. Oh, well!’ So stupid.”

Writing one of the most popular songs of all time on the subject of driving tends to mean you’ll forever be associated with motor vehicles. For her part, Rodrigo’s fine with her pop cultural place behind the wheel — some young fans even write to her asking for advice about their own driver’s tests. “Driving in the car is like my favorite thing — any time I’m stressed out, I just get in the car and drive around aimlessly and listen to music or something,” she says. (She says a few car companies have reached out about using the song in commercials, though no such licensing deals have been struck to date.)

Though Geffen announced her signing only three days before the song’s release, Rodrigo first played them “drivers license” last August. The label was immediately taken with it. “When ‘drivers license’ came in, we were like, ‘Whoa, we got one here!’ ” says Sam Riback, co-head of A&R at IGA. “Obviously we didn’t know the level of bigness, but we knew it’d do well.” Rodrigo, however, says she was convinced of the song’s power when she played it for her father in — where else — the car: “I could just see the tears under his sunglasses — and I like, never see my dad cry, ever. I was like, ‘Oh, OK, maybe I did something here.’ ”

Seeing people react to her music in person is still a novelty. Apart from a lone TV performance on The Tonight Show Starring Jimmy Fallon, Rodrigo experienced her debut smash mostly through stat updates and celebrity co-signs viewed on her phone — she was ensconced in Utah, under strict COVID-19 protocols, while filming the second season of High School Musical: The Musical: The Series. “While everything was happening, I was literally doing the same thing [as always],” she says. “Going to set, doing my statistics homework and then going to sleep.”

“Drivers license” wasn’t a song that needed much of a promotional boost from Rodrigo. It received countless covers and reinterpretations, both through scores of amateur musicians on TikTok and more established artists like pop-punk social media star Jxdn. Saturday Night Live even dedicated an entire skit to the song — on Rodrigo’s 18th birthday, no less — with a bar full of male cast members discussing the song’s lyrics and belting along to its towering bridge. “It was really crazy to see [how much] it started to impact culture,” says Matt Morris, part of Geffen’s A&R team. “People where I’m from were talking about it — people reaching out to me that I hadn’t talked to in 10 years.”

The song was also inescapable in the headlines. Fan theories quickly circulated that it was written about Rodrigo’s rumored relationship and breakup with co-star Joshua Bassett and his supposed new flame, fellow singer-actress Sabrina Carpenter. Rodrigo never commented publicly on the matter — “to me, that’s really the least important part of the song,” she told Billboard in January. But subsequent single releases from Bassett (“Lie Lie Lie”) and Carpenter (“Skin”) appeared to come at least partly in response to Rodrigo’s song, turning the “drivers license” love triangle into one of the biggest entertainment stories of early 2021.

That buzz was hardly quashed by Rodrigo’s follow-up single in April, the wistful but seething “deja vu,” which appeared to be a thematic continuation of her breakout hit — down to Rodrigo’s disappointed sighs in the second verse about her ex’s new girl: “another actress.” Returning to that subject matter was not necessarily a safe choice: It further churned the gossip mill and risks typecasting her as, in her words, “the heartbreak girl.”

There’s much more where that came from on Sour, which has no shortage of additional heartbreak on its 11 tracks. “At first I was like, ‘I don’t want to do this. I don’t want to be pigeonholed,’ ” says Rodrigo. She even tried to balance out Sour with some sweeter-skewing love songs. In the end, though, it wasn’t worth fighting inspiration. “I’m a songwriter who writes from a place of authenticity and truth,” she says. “And truthfully, love and happiness and everything weren’t feelings that I was feeling at the time. And what’s the point of putting out a record if it isn’t something that you feel is important to say to people?”

If listeners got déjà vu of their own from Rodrigo’s second single, they certainly didn’t mind: It debuted at No. 8 on the Hot 100, making her the first artist ever to debut both of her first two official singles in the top 10. “When you have a monster song, sometimes it takes up all the oxygen for your second release,” says Riback. “In this case, ‘deja vu’ has held up fantastic.”

Lee L’Heureux, executive vp and GM at Geffen, feels confident that the rumors and tabloid fodder around Rodrigo’s early songs won’t be a big part of their legacy. “It’s the songs that are really resonating with people,” he says. “Any other sort of story that somebody wants to make of it, that’s not what people will be talking about down the line.”

Besides, any notions that Rodrigo has already shown all she has to offer won’t last more than 12 seconds into Sour. That’s when album opener “brutal” swiftly transitions from a fluttery string intro to a stomping, distorted-guitar crunch — an homage to her mother’s ’90s alternative favorites and a bold opening statement that, of course, Rodrigo says she’s “obsessed” with, too. The song’s pivot comes by request of Rodrigo herself, who is first heard on the album giving instructions in the studio: “I want it to be, like, messy.”

Those instructions were for Dan Nigro, who got his start in the 2000s indie rock band As Tall as Lions before becoming a go-to collaborator for left-field pop artists like Carly Rae Jepsen and Conan Gray. Though he co-wrote and produced all but one song on Sour, he describes their early sessions as bumpy but promising. “We both knew that there was something really special there,” says Nigro. “I feel like it took about two to three months — a couple of days a week of us getting together. We did a real deep dive into exploring the sonic palette of every song we were working on before we kind of decided on, ‘Oh, this is how it should be.’ ”

Originally, Geffen planned for Rodrigo to release an EP. Instead, unsatisfied with the scope of the shorter project, she focused on making a full album that was “truly reflective of what I can do.” (It’s also good business sense: Plenty of viral-breakout artists have taken their time working up to an album only to lose the momentum.) Rodrigo, in fact, can do quite a lot: Sour includes ballads, folky torch songs and sung-rapped freakouts. One song starts off like a menacing Billie Eilish creeper, then explodes into an early-Paramore-style rave-up. For an artist whose early praise often focused on comparisons to other acts, Sour is exceptional at subverting listener expectations.

As with other close writer-producer partnerships in recent years — Eilish and FINNEAS, Lorde and Jack Antonoff — the album works because the songs are so gut-punching. A lyrical detail like Rodrigo decrying her ex and his new flame “watching reruns of Glee, being annoying, singing in harmony” (in “deja vu”) hits not only because the image is so specific, but also because she and Nigro cleverly double her vocals on the last three words so she’s “in harmony” with herself.

The album has plenty of drama for fans to nibble on, but what Rodrigo really excels at with these songs is building her own pop universe — something Taylor Swift, her songwriting idol, would be proud of. Swift has, in fact, said as much publicly on Instagram, where she offered “drivers license” a valuable early co-sign, and in a handwritten letter to Rodrigo.

“I don’t want to divulge too much because it’s really sweet and personal,” says Rodrigo of the note. “But she talks a lot about how, I think, you make your own luck in the world. And when you do kind things to others, good things come your way…” She trails off, worried that she’s not doing the writing justice. “I don’t know, she put it so eloquently, and when I say it now… it’s not as cool.”

In February, Rodrigo spent her 18th birthday in L.A., hanging out on the beach and getting her Tarot cards read in Malibu with her best friend. “The Tarot card lady predicted some good things happening in my life,” says Rodrigo, laughing at the timing. “She was talking about, like, success and celebration. She might’ve saw the Billboard charts that day or something.”

With just two singles, Rodrigo has pulled off the kind of four-quadrant approval very few artists can achieve in 2021 — dominating not just streaming but also the airwaves, topping Billboard’s Radio Songs chart and crossing over to a half dozen formats. In order to capture as big an audience as possible, Geffen is taking a long-term approach to promoting Sour. “We’re really looking at: ‘What does it look like for Olivia for the next 12 to 18 months?’ ” says Janick.

That means more music videos and singles, her own Saturday Night Live appearance on May 15 and, when it’s safe, Rodrigo’s first headlining tour — her first time playing her own songs anywhere, for anyone besides her mom. (She got her first vaccine dose the day before her Billboard cover shoot: “So if I look tired as hell, that’s probably why.”) But her team wants her to take some time off first. “Booking a vacation is really important,” says Smith. “We’re making sure we’re taking into account all aspects of her as a human being, not just as an artist.”

Rodrigo is already dreaming about her future beyond Sour. She’s still making music in the studio, but what she’s most looking forward to is collaborating with other artists, particularly as a writer. “The second the album cycle for this is over and I’m not traveling, that’s the one thing that I want to do so bad,” she says. “I always said that I wanted to do that: Maybe when I was, like, 30 or something and I had kids — I’d stop making music and just write for other people. Because I just love songwriting. I love songwriting more than putting out songs.”

There are few artists operating at her level who are fantasizing about slinking back into the writing credits. But Rodrigo seems a little ambivalent about the glare of imminent stardom.

“To a certain degree, having really commercially successful music means that lots of people are really affected by your music and really like it, and that’s awesome in and of itself,” she says. “If my music becomes really commercially successful, that’s incredible, and that means I did a good job. But some of my favorite artists are not commercially successful, and that doesn’t mean that they’re any less amazing.

“The answer is I don’t know,” she concludes, sounding at peace with not having all the answers. “But I’m really just truly enjoying myself, and I love that I get to do this for a living. And it’s super cool that people want to listen.” Maybe they’ll get a little obsessed themselves.

This story originally appeared in the May 15, 2021, issue of Billboard.