Three Strange Nights with Oliver Tree, a Music-Making Meme Machine

As the years passed, however, Mattson watched his old pal fail and rise, and something became clear to him: Much of what Oliver said became true, as if he had developed a supernatural power to will things into existence.

Nearly a decade later, after striking a deal with Atlantic Records, the 25-year-old, who now goes by the stage name "Oliver Tree," got to drive the vehicle of his dreams in his first major video. "All That x Alien Boy," a combination of songs off his first EP, Alien Boy, is a sort of electronic rap ballad hybrid that rapidly shifts tempos and beats, and also features our lead man prancing atop a white horse, speeding through the desert on a pocket rocket, and hoisting a bazooka.

Since 2016, Oliver has been this alien boy—a figure that exists somewhere between an actual musician and an online comedian, a surreal filmmaker and a troll for viral content. An early step was calling up his childhood friend Mattson to be the keyboardist in his band. But there was a condition—Mattson would have to take part in the entire endeavor, in how they would act as artists. Simply put, Oliver Tree would turn himself into a meme, over and over again.

This, he assured me, was only the beginning. He had promptly begun dressing in a multicolored 80s windbreaker, JNCO jeans, and sandals (his feet in socks, of course), the look topped off with a bowl cut. Mattson, meanwhile, would don a long wig, as if he had the hair of a Neanderthal, and, embodying the persona of the fictional "Ronnie G.," serve as Oliver's relatively silent sidekick and foil.

"I'm just trying to be the ugly Justin Bieber," Oliver told me, laughing. The confusion he has been presenting to the world since the start of his transformation actually boils down to a single question: What happens when you're forced to take a joke seriously?

I was sitting in the greenroom right before Oliver Tree opened for Hobo Johnson and the LoveMakers at Brooklyn Steel in the middle of November, surrounded by Oliver's team and internet celebrities I had never heard of. Overall, it was a slightly odd bill; you might recall the folky, nearly slam-poetry headliner from their single "Peach Scone," their backyard love song and NPR Tiny Desk concert entry that went viral earlier this year, and from not much else. They've inspired a legion of very specific types of fans; earlier that night, in the bathroom, I met a man who I presumed had stolen his hat from David Crocket, and who, unprompted, shared that he had run out of gas on his way down from Vermont and hitchhiked about 20 miles to the venue in a snowstorm. This was the general vibe of the audience.

Oliver had been set to perform before Lil Dicky, who canceled his tour at the last minute—which, at least tonally, would have made a lot of sense. He wasn't complaining, though. Actually, he was barely speaking, and was instead sipping tea and resting his voice.

Soon, Oliver and his bandmates had to get changed. In the corner of the space, there was a seemingly bottomless suitcase that might have belonged to a clown, filled to the brim with props, and wigs, and oversize clothes. Mattson and the drummer, Amir Oosman, who also quadruples as the tour manager, driver, and production assistant, put on similar outfits, inspired by their leader's signature style, the mishmashed attire of his childhood, the nostalgic commodities we'd rather just forget. There were those glasses, Oliver told me, he once thought were cool; the pants he always wanted as a teenager; the most ridiculous shoe-sock combo he could conceive; and his mother's ski jacket. Shortly after, he entered the stage riding a scooter, Mattson and Oosman watching, and as he sang, danced with Johnny Bravo–inspired moves, simultaneously dabbed and bowed, and, about halfway through, stripped out of his clothing and revealed, underneath, as if emerging from a cocoon, a Solo Jazz–patterned jumpsuit—the favorite design of online sleuths everywhere, and the one that had been included in LA Weekly's list of the "best (and weirdest) fashion at Coachella 2017."

Though Oliver later promised me the show would be bigger and better during his spring headlining tour Ugly Is Beautiful, which will showcase his forthcoming album of the same name, this rough-draft rendition was like watching a group of teenagers at a high school battle of the bands—except they were good enough to have a song that Apple paid for to be in a prominent commercial.

Oliver Tree is less of a schtick than Weird Al or Blink-182 impersonating N'Sync, because everything is so seamlessly interconnected to his brand, his image. You can't have one thing without the other. It's not a one-off, or a string of one-offs. He's a developing polymath. It's as if he's made a ball of rope, and to start pulling just one of the strings would dismantle the entire shape of what he's trying to accomplish—everything would fall apart. The whole thing is an all-encompassing, calculated effort: his attempts at viral marketing (he has no PR), his eclectic musical interests, his high-production, cinematic, narrative-driven music videos (he writes, produces, and at least co-directs all of them himself). His brand-new one, for the song "Hurt," is reminiscent of a series of Vines, short scenes as Oliver rapidly goes through various stages and scenarios of death—he's placed in a coffin, crucified on a gigantic scooter, captured free-falling from a building.

"I'm leaving a trail of breadcrumbs," Oliver repeatedly told me. He doesn't care, in other words, if people know his past as a more traditional musician, or if they stumble on his tracks after seeing him bathing in a tub of Flamin' Hot Cheetos or dollar bills on Reddit. Or if they're confused. It's something of a chicken or egg situation. It doesn't matter how you got here, so long as you do.

"No one has really placed this living, breathing 90s meme in a serious light," Rogin Losa wrote of Oliver Tree in STATUS magazine earlier this year. "Google won’t be your best friend this time around if you want to know more about him. You’ll only find his redefinition of electro sound or his ironic brand of comedy, though that alone will make you wonder on what came first… the beat or the skits?"

But the context is there—you just need to follow the bread.

What led him here, to Oliver Tree, to a "human meme" screaming at a swarm of Brooklynites, occurred in 2016, when he moved to Los Angeles to study at CalArts. His song with the DJ Whethan, "When I'm Down," went viral that same year, too. But he still wasn't receiving the attention he desired. Though he holds a bachelor's degree, it was, truly, a chance encounter that recalibrated the direction of his life: He briefly moved in with the "suh dudes." (One of them was the comedian Nick Colletti; the other was the American dubstep DJ Tanner Petulla, better known by his stage name Getter.) You might remember them, if you were at all a user of Vine. In 2015, Colletti and Petulla first made a series of six-second clips in which they flash the peace sign and say "suh dude"—a mumbled shorthand for "what's up, dude?"—almost exclusively to each other or at the camera. Along with an eerie, well-received music video he shot with Getter on the same day, it's in a popular Vine of his own that Oliver introduced the character of "Turbo," the somewhat creepy, definitely too-old dude still attending deep house shows, who would go on to achieve his own virality. ("I'm 32 years old," he says in that inaugural video, as he smokes a cigarette and his bowl cut bobs up and down as he walks. "I love to dance, and I sell ecstasy to children at raves.")

"I got millions and millions of views," Oliver told me. "So I kept doing it."

It was the day, too, that Oliver Tree, and his attire, was unknowingly born.

Then, all he did was alter the name. Now, the perceived problem, or perhaps the perverse pleasure, of hanging out with Oliver Tree is that you can't quite conclude if what he's saying is exactly true, even if he insists he's being honest. At first, it's difficult to recognize who he really is, when he's acting and when he's not—or if, really, there's a difference. There are the general, endless questions about if we can or should separate the art from the artist. But what about the man from the meme? Where does the meme end, I kept wondering, and the person begin?

I spent close to three evenings with Oliver, and each time I walked away confident I had figured out everything about him, only to collapse into a paranoid state of bewilderment and despair, second-guessing everything he had told me. His inner circle acts in much the same manner, and his approach appears to rub off on those close to him. Take Steve Zilberman, for instance: The 27-year-old DP who's paid to shoot Oliver's video content with an iPhone couldn't help but slip further into the realm he had already fallen into—he also rocks sandals and socks; he has a large earring dangling over his face; and he's bleach blond, with the remnants of dreadlocks near his neck. (Zilberman informed the group, with no supporting evidence, that if you get dreadlocks, and then shave your head, much of your hair will grow back as dreadlocks.)

At the very least, Oliver's crew is a glimpse into his effect on others—but it doesn't change the fact that he intends to obfuscate. He blurs the line between fantasy and reality, if there's really a line any longer. Imagine him, maybe, as the bastard child of Bowie's Ziggy Stardust, the son who's begging to be seen. Perhaps he has whiffs of Andy Warhol, being accepted into an industry he largely satirically skewers, and of Andy Kaufmann, like when he goes on the comedian Blake Webber's talk show and absurdly sabotages the whole thing at knife point. He has roots with Nathan Fielder, too, and Sacha Baron Cohen.

Scroll through his Instagram (at the moment, he has 323,000 followers), and you'll come across a taste of his satire: him holding a big bag of weed next to his grandma and ripping huge bongs and whipping them at the wall, as well as an array of photoshopped pictures (flying through a ring of fire, sitting in a chair that's far too big with a head that's far too big, looking a bit like Voldemort after a severe car accident). Watch his very real-seeming 16-minute tour mockumentary, which includes the rapper Skizzy Mars discussing the merits of "real art" and Oliver acting like a quick-tempered sociopath, and you might get a better idea. ("Everyone's saying how much they like the video and shit and how good his music is but I'm just sitting here confused as to whether this shit's for real," wrote one comment, upvoted more than 500 times. "Satire in its purest form 👏🏻," said another, upvoted by almost 400.) Then, for fun, visit the rest of his YouTube channel, where, to his 160,000-plus subscribers, he notes that he's a professional scooter rider. (Wikipedia does, too.) In the comment section of a recent clip, "Oliver Tree Scooter Pro," people argue if it's actually him performing the tricks; the video description states that it's a man named Robby Mier. (In fairness to those who fail to notice this—"The funniest part is how you're genuinely good at scooting"—you do have to click "show more" for the rest of the credits to be revealed.)

It's as if Oliver is reverse-engineering the path of the social media star. His career works in contrast to someone like Instagram's Roy Purdy, who is slowly using the notoriety from his high school dancing and pro-level skating videos to build a broad entertainment career (he recently signed with CAA), or Supreme Patty, who is squirting lemon juice in his eyes for professional aspirations, or 6ix9ine, who's online gangster persona turned him (almost) into an actual gangster. Oliver Tree is operating backwards. His music came first. If this is what he has to do to get noticed, to blow up, he's fine with it.

"You'll just have to keep following the crumbs," he said, before he climbed the steps onto the stage and did a 360 on his scooter. I told him I would keep my eyes peeled—even if I didn't know quite what I should be looking for.

Eventually, about halfway through the gig, I leaned over to a security guard standing near the barricade to the pit and asked him, in so many words, what he thought, and if he was aware of what was going on. "I don't know, man," he said, shrugging. "But the kid has some hooks."

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Follow Alex Norcia on Twitter.

All portraits by Michael Marcelle. Follow him on Instagram.

All performance shots by Monet Lucki. Follow her on Instagram.