Oliver Tree on Being Musics Biggest Troll, His Country Reinvention and Imminent Retirement

A cartoon character by design, Oliver Tree’s comical image and mastery of over-the-top gimmickry can be a double-edged sword. Simultaneously a living, breathing meme and a genre-fusing sonic adventurer of the highest caliber, this is an artist who artfully combined alt-rock, pop and electronica on 2020’s “Ugly Is Beautiful” — while going viral for performing on stilts and riding the world’s biggest scooter. Instead of returning to that wacky musical well, the 28-year-old reinvents himself as a country star on his sophomore album, mixing pathos with pristine hooks on “Cowboy Tears” (out today).

Tree’s change of direction is a result of spending six months of the pandemic at his grandparents’ ranch in Northern California. He didn’t intend to write a new record, but inspiration took hold. “My grandfather was a cowboy, his grandfather was a cowboy,” Tree tells Variety. “It’s just something that’s part of my lineage.” Even so, the resulting album was a shock to both the artist and his fanbase: “I never would have guessed that I’d make a country album, and I think my fans feel the same way.”

Like many a twangy opus, “Cowboy Tears” is about a breakup. However, Tree is more interested in detailing the rollercoaster of emotions that accompanies one rather than airing dirty laundry. “In America, boys are told to suck it up,” he says. “The album is simply about embracing crying.” That’s particularly apparent on lead single and tone-setter “Cowboys Don’t Cry,” which seemingly references his ex-girlfriend, alt-pop artist Melanie Martinez. “Everything I write is pure fact,” Tree says. “When I play these songs, it’s essential that they are true stories.”

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Like in the five stages of grief, denial and depression capture the first aftershocks of a breakup via “Cowboys Don’t Cry.” The healing process starts to kick in on “Doormat,” which is about “recognizing you’ve been walked all over,” while “Villain” chronicles the epiphany that your ex is experiencing the same gamut of emotions — only, to them, you’re the antagonist and not the slighted hero. Tree is even self-aware enough to know he’s bound to do it all over again. “I wrote one of the songs when I was 17 and recorded it at 27,” he says. “A decade later and I’m still dealing with the exact same shit.”

While heartache is the overarching theme, the album’s scope is deceptively ambitious. “There are some really big ideas,” notes the artist. “I studied Pink Floyd and they say a great album covers a wide span of themes. On ‘Cowboy Tears,’ you have songs about money, time, religion, and addiction.”

However, matters of the heart are never too far from the surface. “It’s true that the concept of the heartbroken cowboy underpins the album,” he confesses.

One song that links “Cowboy Tears” with “Ugly Is Beautiful” is the outsider anthem “Freaks And Geeks,” which functions as a sequel of sorts to “Alien Boy.“ Says Tree: “At my shows you’ve got the grandma with the pink bowl cut, you’ve got the frat bro, you have a bunch of queer kids, you have furries.” His goal, now and then, is to create a community of nonconformists: “I want people to congregate and not feel so alone, everyone can relate with being an outcast at some point in their life.”

Broadening his sonic horizons meant waving goodbye to his alter-ego. “The whole outfit was limiting my potential, but it was my own doing,” Tree says. Atlantic Records initially questioned his bowl cut and flared jeans, but the Santa Cruz native told them to “fuck off.” Ironically, the public fell in love with his outlandish shtick just as he was beginning to tire of it. “The final video I shot with that look was ‘Life Goes On’ and it changed my life,” Tree says. The song went top 10 at alternative radio, and ranks as his first entry on the Billboard Hot 100.

Reinventing himself after that commercial breakthrough was scary. “When I hinted at the change, my own fanbase turned on me,” Tree says dramatically. “They said, ‘Keep your country record, we don’t want to hear it.’ People were up in arms.” To make the segue smoother, he incorporated familiar elements such as his knack for outrageous visuals. The video for “Cowboys Don’t Cry,” for example, finds the mullet-sporting artist on the back of a mechanical bull/quad-bike with Bella Thorne.

Tree’s willingness to experiment wildly with sound and aesthetics comes from his own tunnel vision. “I don’t use the internet,” he says. “I’m not on TikTok. I’m not on Instagram.” It should be noted that Oliver Tree, the character, is very much an online personality and does have accounts on all of those platforms. His point is that he makes music, first and foremost, for himself. “I’m my own biggest fan,” he says. “I don’t have Spotify, I don’t have Apple music. The only music I listened to for the last two years was ‘Cowboy Tears.’”

To his surprise, fans came around to the new sound. “It’s crazy for me as an artist to be able to flip someone’s perspective,” he says. It’s exactly what Tree has been doing, in one way or another, for his entire career. Whether it’s winning over haters, one good song at a time, or ignoring genre altogether on “Ugly Is Beautiful,” his eclecticism helped prepare listeners for his country adventure.

It’s a detour, it turns out, that very nearly didn’t happen. Tree was going to retire after “Ugly Is Beautiful,” but now intends to hang up his fringed jacket when this era ends. “’Cowboy Tears’ is my last album,” the JNCO jeans-enthusiast says plainly. “I want to focus on making feature films.” Tree adds says he’s already written two scripts — one that’s family-appropriate, the other “hardcore, NC-17” material. “If ‘Life Goes On’ wasn’t so successful, I probably would be making one of the films right now.”

Tree wonders aloud if “Cowboy Tears” is an attempt at self-sabotage. “Who knows? Maybe that’s the reason why I picked country — so I never have to make another album,” he says. It’s hard to ascertain the genuineness of his disdain for the music business. “I’ve been trying to make my music flop from the beginning,” Tree says adamantly. “Why do you think I look this way? If I tried to look good, I would’ve been a hell of a lot more successful. If I wasn’t so annoying, I’d be a superstar. But instead I’m on the Z-List. I’m riding down with the real low bottom of the barrel stuff because I’m on my way out.”

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Reinaldo Massengill

Update: 2024-08-15

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