Written by Mat Weir
For Oliver Tree life is all about dreaming big.
And why shouldn’t it be? Afterall at 28 years old the Santa Cruz native pop star has appeared on late-night shows like Last Call With Carson Daily, The Late Show With Stephen Colbert and Jimmy Kimmel Live! He’s performed for thousands of people at festivals across the country such as Coachella, Outside Lands, Lollapalooza and the Electric Daisy Carnival. He holds the world record for riding the largest kick scooter and his video for the single, “Hurt” is the 34th most expensive music video ever made at 
$1,000,000. It’s a feat he pulled off by tricking his record label, all of which can be seen in the behind-the-scenes documentary on YouTube.
With only four EPs and two full-length albums under his belt–or bowl cut in Tree’s case–his music has hit an international level with platinum hits (like “Alien Boy”) and recently collaborated with Russian rave group, Little Big. He pulls in 15.9 million listeners on Spotify every month, 3.33 million YoutTube subscribers and 241,000 Twitter fans. His 2021 single, “LIfe Goes On,” hit the Billboard Top 40 list and spawned a plethora of fan memes, several different music videos and a remix featuring Trippie Redd, Ski Mask the Slump God with cameos by the Island Boys and Getter.
“They were even playing it on the radio in Morocco,” he recalls from a recent trip to the Middle East. “It’s amazing that it’s transcended on such a global scale.”
But lately, the dreamer has been wondering what’s next for his boundary defying career.
“When you’ve played for 30,000 people and have platinum hits, it’s no longer a dream but a reality,” he says matter-of-factly. Don’t get it twisted, it’s not a brag. Just the reality of years of hard work and zen-like focus.
“So as someone who is a dreamer, I have to have my next dream mapped out.”
Oliver Tree started making music as a child and got his first big break in high school, when he opened for electronic producer Skrillex. By the time he was 20 he was signed to a major label and released his first EP, Demons, featuring a version of Radiohead’s 
“Karma Police,” blessed by Radiohead frontman, Thom Yorke.
“I was trying to be a super serious artist but nobody took me seriously,” he remembers.
The change came in 2016 when he was featured in the video for the single “Forget It,” a collaborative effort with close friend and producer, Getter. It was Tree’s first time appearing in a video and he wanted to stand out, so he grew out a goatee and gave himself a bowl cut.
“It was a decision to basically develop my own ugly Justin Bieber, an unconventional pop star,” says Tree. “When I got to the video shoot, even Getter, my longtime friend who I’ve known and worked with since high school, didn’t recognize me.”
As promo for the video the two decided to shoot short, internet videos through the Vine app. For those of you too young–or too old–to remember Vine was basicallu the 2010’s version of Tik Tok. Surprisingly, or not in retrospect, those videos all received over 1 million views on the first day.
“I thought, ‘This is insane! Why did those get over a million views but I can’t even get 100,000 plays?’ But everything I posted with this character kept getting a million views,” he recalls. “I wondered how I can use this character to pull people to my music, so I made him the lead singer of my band.”
And thus, Olive Tree was born.
Originally named Turbo, the Oliver Tree character wears giant, JNCO jeans, a pink and purple windbreaker–or sometimes an outfit
fashioned after the 1990’s blue and purple Dixie cup design–a bowl cut and rides around on a kick scooter. He’s the anti-pop star. The weird kid in class who wants to be loved but from a distance. Socially awkward and always working on the next big thing that, most likely, isn’t popular. It’s a character and look that he was able to commodify into an internet sensation with videos, music and tons of memes.
“I think to be a true artist you have to be five to ten years ahead of the curve,” he says. Take “Life Goes On” for example. He originally wrote it with Getter in 2014, a full seven years before it became a hit.
“You’ve got to do things outside the box and not do what everyone else is doing. Sometimes that can turn people off and that’s ok. In order to push culture forward, you have to push the envelope and take chances.”
So where does Tree go from here? Retirement, of course.
“This new album I’ve been making, Cowboy Tears, will be my last,” he says.
Ok, granted this is something he has said before, most notably surrounding his previous album, 2020’s Ugly is Beautiful. However–this time–Tree says he’s serious and wants to focus on the other aspects of his artistic dream. Writing, for example. A lifelong writer, Tree recently dropped a 120 page graphic novel in 2021 called Oliver Tree vs. Little Ricky Alien Boys, which he 
collaborated on with friend and illustrator, Orpheus Collar.
“I want to branch out into as many different avenues as I can,” he explains. “I’ve been exploring a lot of different types of art outside of music.”
It’s a fact not missed on anyone paying attention to his career.
Tree has written and directed all of his videos and even some for other artists, like Lil Yachty. During the 2020 lockdown, while other artists were busy live streaming from home, Tree kept his head down and buried himself in writing.
“I wrote a few different screenplays that I’m in the process of pitching to producers in hopes of making them feature films,” he declares. “I’ve also been making documentaries of my travels around the world. Everything from behind-the-scenes video shoots to tours, living in Russia for four months while working with Little Big, and more.”
Over the last five years he’s directed 17 documentaries released under his Alien Boy Films production company. It’s a collaborative effort with his friends, saying if they all weren’t working together, he would never be able to see them.
“Making art is a religion, it’s a sacrifice,” Tree explains. “It cannot be done without a team. When I was in Santa Cruz I tried to do it all alone, but without a team I was nothing. Collaboration is key. Art is so much bigger than one person.”
And while his dreams might be big, they’re born from simply wanting to inspire everyone around him and the world. It’s one of the reasons why since his humble days at Harbor High, Oliver Tree has collaborated with neighborhood friend, Casey Mattson. Mattson continues to play keys for Tree on tour, along with UC Santa Cruz Alumni, Amir Oosman, keeping Tree firmly grounded in his roots.
“Anybody can do this and, if you don’t, someone else will, like the guy down the street,” he explains. “In this case, me and the guy down the street did it and I think that’s beautiful.”
It’s this inspiration that led him, Oosman and Mattson to perform a free show at the Rio last December. Audience members were encouraged to make a monetary or canned food donation at the door and proceeds went to the Homeless Garden Project and Second Harvest Food Bank of Santa Cruz County, respectively. It’s an idea that came to Tree while visiting home last summer and seeing the rows of unhoused individuals camping along the San Lorenzo River and in the Benchlands.
“We want to make an impact. I want to inspire the world. Anyone can do this, it’s just a matter of getting your hands dirty and dedicating your life to the craft.”
The concert raised 1,038.5 pounds of food for Second Harvest, which generated 1,271 meals for the community. An additional $110 was raised for the food bank as well.
“It was a lovely event and so incredibly generous,” Second Harvest Food Bank Chief Development Officer, Suzanne Willis, explains in an email.
But before he decides to set music on the sidelines, Tree is currently gearing up to release his new album and launch the subsequent–final–tour.
In true Oliver Tree fashion, Cowboy Tears an outside-the-box project, one he calls a “country album for people who don’t like country.” The first single, “Cowboy’s Don’t Cry” just dropped two weeks ago and already has over 12 million views on YouTube. In it he introduces a new character, swapping his patented bowl cut and JNCOs for a blonde mullet and fringed cowboy suit. It’s 
centered around the classic, American cowboy image but with Tree’s signature twist.
“I had to ask, ‘How do I make my version of that? How do I make an absurdist cowboy? How do I make an emo cowboy?’” he ponders. “At the core is the concept that ‘cowboys don’t cry.” But, really, tough guys can cry. Everyone should cry. It’s a healthy part of getting through things and processing life. Otherwise they’ll bottle those emotions up and take them out through violence and aggression.”
Cowboy Tears comes out February 18th and he takes it to the stage on February 22 at the Warfield in San Francisco.
Here are the videos from the Rio Show:
