The Curious Case of Clairo

One day, when Claire Cottrill was 13 (which was not a terribly long time ago), she gazed into the glowing green dot atop her MacBook and recorded herself covering a Maroon 5 song. Even though she’d always loved singing, this was the first time she’d ever done something so official, and she spent the better part of an anxious day deciding whether she should even share the video with anybody else. “It took me hours to figure out if I wanted to post it on Facebook or not to even tell my friends that I’d made it,” she recalled several years later in an interview with Rookie. “I was so nervous about it! I just closed my eyes and did it, and then I closed my computer and tried not to think about it.”

For the next few years, while attending a Boston-area high school, Cottrill uploaded modest covers and snippets of songs she’d written herself to websites like Bandcamp and SoundCloud. Her musical heroes were the wry indie songwriter Frankie Cosmos, the velvet-voiced crooner Norah Jones, and, eventually, the DIY rap collective Brockhampton. YouTube, in particular, became “a secret space” for Cottrill and her music. This might seem paradoxical, given that it was the platform by which she made her videos visible to the public, but few enough people watched them that her YouTube channel felt like a semi-private diary. And anyway she didn’t talk much about it with her friends, so she could cultivate a persona a little different from the one she had at school. Then, one day last summer, something unexpected happened. One of her videos went viral.

Cottrill—who releases her music under the name Clairo—says she wrote and recorded the song “Pretty Girl” in about two hours; filming the video took even less time. “I woke up, it was like a terrible day,” she said in a Fader interview last year. “My hair was disgusting, my skin was so gross, I didn’t even take off my makeup from the night before. It was just a terrible day for me to look in the mirror. I had nothing to wear; it was bad. I decided it was the perfect day for me to make the music video, and to portray that I don’t need those things to make myself who I am.” That aesthetic echoed the song’s message; “Pretty Girl” (a catchy but decidedly homemade pop song centered around a chintzy drum machine, simple keyboard riff, and Cottrill’s dreamy vocals) is about someone who loses her identity in a relationship because she’s trying too hard to please the other person. “I could be a pretty girl,” Clairo sings in a tuneful, knowing deadpan, “shut up when you want me to.”

In the video, Cottrill has an undeniable everygirl charisma: She grins, does goofy dances, croons to a plastic toy. All the while, she keeps her earbuds in as though she doesn’t want the other people in her house to hear what she’s doing. “Pretty Girl” is an ode to teenage boredom, to having nothing better to do with your afternoon than make up a song and star in your own DIY music video. (After all, nearly every laptop comes equipped with one of those green dots, as though it’s just waiting for you to realize your own star potential.) The whole thing has a strange, palpable digital-era intimacy that makes the viewer feel in on a secret. Which is not exactly true anymore—“Pretty Girl” has now been viewed more than 17 million times.

“I didn’t expect any of my videos to blow up like ‘Pretty Girl’ did,” Cottrill said in an interview shortly after it did just that. In the coming months, she’d be profiled by Pitchfork and The Fader, ink a 12-song deal with the latter publication’s record label, and sign on with Chance the Rapper’s manager. To the large majority of her fans, Clairo’s rise was the quintessential anyone-can-do-it success story of the viral era. But a vocal minority took to blogs and Reddit threads to wonder, after digging into her family history, whether it was in fact a more old-fashioned and familiar story than anyone else was letting on.

It has been a rough year for North Brooklyn music venues sponsored by performatively edgy corporations. At the end of this summer—following a final run of shows headlined by the likes of Jaden Smith, Pennywise, and Interpol—the Vans-funded Greenpoint concert space and skate park House of Vans will permanently close its doors. The Patch, Sour Patch Kids’ much-scrutinized Brooklyn “crash pad” for touring bands, no longer seems to be operational. And earlier this year, with little fanfare or explanation, Converse’s Williamsburg space and recording studio Rubber Tracks quietly packed it in. Converse-music.com, at which bands could previously apply for opportunities to record for free at the state-of-the-art Rubber Tracks studio, is now a dead, tumbleweed-y URL that, for some reason, redirects to a local politician’s website.

I bring all of this up because Clairo’s father, Geoff Cottrill, formerly the chief marketing officer at Converse, was one of the executives behind Rubber Tracks. “We’ve seen what the music industry has done to help build and grow our brand around the world,” he said in a 2011 profile in American Songwriter magazine shortly before the launch of the studio (and around the time a 13-year-old Clairo would use much more modest tools to upload her Maroon 5 cover). “This isn’t about building a studio and then seeing return on investment. … We’re coming at it from the perspective that we need to just let go of the brand and provide people the opportunity.” But he did make sure to add: “At some point in history, a lot of people within the music and artistic community adopted the Chuck Taylor as their expression of individuality and independence.”

Once someone on Reddit realized Geoff Cottrill was Clairo’s father, armchair skepticism began to ping around the internet. “Although I enjoy her music and I think she is an inspiring, aspiring, talented, and gifted songwriter I do not understand how her connections to the music industry hasn’t been mentioned in a SINGLE interview,” went one widely shared post. Others have called her an “industry plant,” alleging that her homespun, “indie” ethos was just a marketing ploy engineered by her dad and his cronies. All the while, Clairo got ever more popular. Though it doesn’t have quite the same charm as “Pretty Girl,” her follow-up video, “Flaming Hot Cheetos,” has racked up more than 3 million views. Even if she was an “industry plant,” her fans didn’t seem to think it mattered.

Something you hear a lot these days is that there’s no longer such a thing as “selling out,” or at least that younger generations have different standards than, say, the people who got mad when the Beatles’ “Revolution” was used in a 1987 Nike commercial. Streaming companies and declining physical sales have made it nearly impossible to make a decent wage as a musician or a “creative” of any kind. And the economy that today’s young people will inherit is essentially a decaying amusement park made of carcinogenic garbage, so, the argument goes—why not get money by any means necessary? “There are endless ways to sell your soul on YouTube,” the writer and podcaster Gaby Dunn wrote in an op-ed a few years ago. “The fact is if you choose not to do any of it, you lose out.”

And yet, it’s easy to see how this perfectly understandable way of thinking can easily be exploited by corporations and then bleed into all sorts of delusions, conflicts of interest, and blurred ethical lines. We are, after all, living in the era of Brands Saying Bae. It can be difficult to tell the difference between well-intentioned patronage and corporate brainwashing, between “lifestyle marketing” and, well, life. But we should also never underestimate the industry-grade strength of teens’ innate bullshit detectors.

I do believe that after “Pretty Girl” hit, Clairo likely had an easier time getting meetings with labels and management companies because her dad was well-connected and knew exactly who she should be talking to. But to believe that Geoff Cottrill was the mastermind behind “Pretty Girl” and that a dad-aged ad executive who also used to work for Starbucks’ Hear Music campaign knew exactly how to engineer a fool-proof viral video (“Just sing into this webcam when your hair’s real greasy. Everyone will love it.”) is to give the Olds, and maybe even the advertising industry, more credit than they deserve. The controversy surrounding Clairo’s ad executive father and his industry connections would have likely raised more eyebrows had she been a Gen X–er … but also it is impossible to imagine Clairo’s success in a Gen X world, so vital is the internet to her appeal. And I deeply believe that the appeal is genuine because there are parts of it that even I am too washed to understand.

On a sticky Monday night in late July, the Bowery Ballroom was sold out, but its downstairs bar was almost completely empty. Clairo’s first big headlining gig in New York was a 16-plus show, and almost everyone there who met the legal drinking age was chaperoning a child from a close but socially respectful distance. Across the room from me, a teenage boy in a Rick and Morty T-shirt sat at the bar drinking a Coke next to a man who I assumed to be his father. The bartender had so little to do that he obliged to take a picture of them on the son’s iPhone. Another boy with a safety-pin earring asked to take a photo with someone he seemed to recognize from YouTube, thanked the person obligingly but with a surprising amount of poise, and then turned away from his friends for a moment to upload the picture to Instagram. Feeling idle, old, and not knowing what else to do with myself, I Slacked my editor, “I feel like my evening is being directed by Bo Burnham.”

The show had sold out weeks in advance, and the crowd was overwhelmingly and giddily teenage, even if the girl they’d gathered to see would be a teenager for only another month or so. On the cusp of her 20th birthday, Cottrill recently finished her freshman year at Syracuse University. Speaking of her double life as a college student and an internet pop star, Cottrill has said she feels “like I’m Hannah Montana sometimes.”

After a mood-setting opening set from the minimalist indie-funk crooner Garren Sean (“YES, DADDY!” one fan shrieked approvingly between songs), Clairo emerged onto a stage with a gigantic mirror as its backdrop. Backed by a guitarist, bassist, drummer, and her own sticker-encrusted laptop, she opened with “B.O.M.D.,” her sunny collaboration with PC Music producer Danny L Harle. “YOU’RE SO PRETTY!” a boy shouted between songs. It felt like an odd compliment given the message of “Pretty Girl,” but everyone roared in agreement so loudly that Clairo’s own response couldn’t be heard.

Both live and on the record, Clairo has a solid voice—it’s sweet, but alive with a husky texture. And yet she does not yet seem as comfortable on a stage as she does in the glow of her laptop. While singing, she mostly paced languidly back and forth and back again, occasionally busting out some of the endearingly awkward dance moves from her music videos. In the middle of the set, she picked up a guitar and played some of her older, more indie-rock leaning songs, and although she looked more comfortable in these moments, the audience wasn’t quite so engaged. Clairo seemed happiest when, during her more popular songs, she’d extend the microphone to the audience—who seemed in some sense to be on stage with her in the spangled glow of the giant mirror—and let them scream out every word. It was then that she’d flash that irrepressible grin I recognized from the “Pretty Girl” video.

That’s the challenge Clairo will have going forward: What initially made her so endearing was that she did not seem like the sort of person who could (or would ever have to) command a stage in front of hundreds (or, when she opened for Dua Lipa earlier this year, thousands) of people. She was shy, mumbly, awkward—the kind of girl who would upload something from the heart and then immediately shut her laptop in embarrassment. The gig itself—a sold-out “showcase” for a hot new pop star—felt a tad old-fashioned, or even beside the point. Is catapulting someone like Clairo from her bedroom to a generic spotlit stage the best way to show off what makes her unique? Probably not.

And yet, even when her stage presence was less than transfixing, the kids around me screamed their heads off, so psyched were they to be seeing their YouTube hero IRL. An advertising executive would have killed to have known how to engineer something like this, I thought to myself. As millennials gradually cede their young-person market share to the members of Gen Z, it’s a bit of a relief that most advertisers are still uncertain how to market things to this curious new generation of digital natives. (Kendall Jenner playing a Pepsi-fueled activist will not suffice.) The masterminds behind things like shoe-sponsored event spaces and “Sour Patch Kids: The House” will likely find themselves returning to the drawing board. But Clairo, through a bit of savvy and also a lot of accidental luck, has tapped into something incredibly pure and resonant. Maybe there were dollar signs in the eyes of some people watching from the VIP balcony area that night. But from the cheap seats, it was all heart-eye emoji.