Oliver Tree Works Hard, Plays Hard and Cries Hard

Oliver Tree
Oliver Tree Photo by Jimmy Fontaine, courtesy of The Oriel Co.
Oliver Tree, the enigmatic musician with a flair for creating memorable visuals for the genre-bending songs in his oeuvre, has a novel approach for meeting people these days.

“To be the dumbest guy in the room, to be the poorest guy in the room is really the perspective for me,” Tree said. “Because the second that you’re the richest and the smartest guy, you’re not in the right room. So, that’s been a big thing for me, challenging myself and only really letting in people into my life that are really inspiring and motivating to me because I already have enough close friends and people from the beginning who have stuck around with me.

“I don’t need new friends. But, when I do bring them in they’re only people who are legends and push me and inspire me and show me what’s possible and make me think that what I’m doing is embarrassing really and on a small microlevel. It’s been very motivating.”

Few would qualify what Tree is doing as embarrassing or small. In the last five years, he’s amassed a global following thanks to catchy tunes and social media savvy. Videos for his songs have hundreds of millions of hits and his latest album, Cowboy Tears, charted in Billboard’s Top 10 listings for both alternative and rock albums. A mystery man with an extreme sports background who changes personas to fit the needs of the music he’s making, it’s no surprise that he describes his live show as “a shitty Broadway musical” or “a high school play on steroids.” Tree brings the live set to 713 Music Hall Friday, March 25.

Ahead of the show, we talked with Tree by phone and posed the old music writer’s go-to question with a Tree-like twist. Not whether he hears the music or lyrics first, but if he's ever created a song after first  imagining its video.

“For me, typically it starts with the song because I’ve made a thousand songs in my life at least, probably well over that, and you never really know what song is really going to be good enough to make a video out of, so it’s a lot of work to make a video idea,” he said. “I’m a very visual person. When I’m writing lyrics, I’m seeing things in my head but I usually would never write the video until after the song is really developed. And, a lot of times the visuals I see in my head are just way too expensive.

“For this album, I wrote 32 different music videos and I only have the budget to really make four. There’s a chance I might make two more of them or one more but at this point I’ve capped out and had a whole battle with my label and they’re like, ‘No more money! Blah, blah, blah,’ and I was like, ‘Alright. You guys need to tell me when you want a video because I’m not going to beg you guys for money to do this.’”

“Realistically, to answer your question, the song will come first. I’m a very visual person so I’m seeing as I’m writing what that looks like in my head, but the videos really come later ‘cause I can’t afford to make what I really see in my head,” he said. “It would cost, you know, if I made all 32 videos, I would have probably spent upwards of $40 million, something like that.”

The frequently bizarre videos allow listeners to get in tune with the lyrics which is critical. Despite his gonzo approach, Tree's lyrics are artful. Like many other artists who created during the pandemic’s lockdown, Tree wrote songs about loss and grief. But, the tracks from Cowboy Tears take a decided look at loss, grief and the male ego. In a day and age where incels exist, where some men shout down the “Me Too” movement, with male lawmakers legislating women’s body politics, it’s maybe not reading too much importance into this music and how it implores men to get in touch with their emotions.

“I’m an emotional guy. I cry quite often. I cry typically from just seeing things that are moving, less than just being sad, because I live a crazy-ass life and just seeing how my art and the things I do can impact people is a very moving experience, when done right,” Tree shared. “For me it was an interesting dichotomy of pulling in the tough guy – the cowboy is really symbolic for the toughest cookie – and really just setting up that contrast. The most exciting thing that I’ve been able to explore hard is juxtaposition, pulling things that don’t really go together and finding a way to make them connect.”

“It was an emotional period. I lost a close friend that passed away and I lost partners, went through different relationships and different things. It was a very emotional time. I dealt with trying to get sober, I’ve become sober during the process of the record,” he said. “I went through so many different iterations and self-evolutions. For me it was a big message just trying to teach guys – and really everyone – that it’s okay to cry and it’s important to cry and let it out instead of holding it in and letting it out in a violent spurt.”

click to enlarge Cowboy Tears jumped to the top of Billboard's charts on its February 2022 release - ALBUM COVER ART
Cowboy Tears jumped to the top of Billboard's charts on its February 2022 release
Album cover art

Speaking of "violence," we note a current beef Tree is having with YouTube personality turned boxer, Logan Paul.

“Oh yeah, I hate that guy. I hate him,” Tree seethed. Real seething or not, who can tell with Oliver Tree? There’s a sense of intrigue to much of what he does. He’s talked about an impending wrestling career so this could all be a bit of theater. In any case, Paul has called Tree’s music “for babies,” to which Tree replies, “That’s insane and I can’t believe he went that far. He’s like a big baby himself so I think maybe it was a more introspective statement coming from him because he looks like a baby.”

We both agree Paul could benefit from a deeper listening of songs like the TikTok-fueled megahit “On and On” or the new single “Swing & A Miss,” because they poignantly cover ground almost philosophical in scope. We ask if Tree has an interest in classical thinkers like Kant and Nietzsche. If you surf around the ‘Net enough you’ll learn Tree pursued a business degree in college, not necessarily the type to fall in with ponderers of human existence and experience.

“The truth is I don’t have a whole lot of influence right now in my life. I don’t listen to music, I don’t really look up to anybody, I see everyone on an equal playing field so it’s been interesting because I don’t really have anyone that I look up to or anyone that has really been very influential to me and I don’t know if that’s a good thing or a bad thing – but I will say ignorance is bliss and it’s nice to try to just kind of live in your own world.

“I think it is important to pull from different mediums over to music,” he added. “I love philosophy, I love psychology, I love seeing what makes people tick and I love seeing what makes someone motivated to do something.”

Tree admits work is his motivation. He’s recently reached back to his action sports roots to build the world’s biggest scooter (nearly 14-feet tall and 10-feet long!) and teamed with Arizona Iced Tea last year to learn motorcycle stunts. He’s got nearly two dozen documentaries filmed in places like Egypt, India and Thailand awaiting release. He spent the pandemic creating new music and writing two feature films. Beginning production on one of the movies is his next move, he said, noting - as he did after the release of his breakthrough album, 2020’s Ugly is Beautiful - that he’ll soon retire from music to devote time to filmmaking.

“I would definitely say my parents. Workaholics,” he said of the basis for his work ethic. “On the weekends, when I was a kid, they would make me work every weekend at the house – painting, cleaning the garage, doing anything that they were working on. They were always project-oriented, always doing a lot of different things. They took a house that couldn’t even be lived in, that had holes in the floor, and they built it into a very beautiful place and added a story on and did so much beautifying to their personal space. It was constantly an evolution.

“I always thought about it and I thought, you know, that’s amazing. It’s kind of selfish. I’d like to take my time and give it towards something that people can hopefully get more inspiration from than just your own living space. For me, I always kind of made that a goal, to take that work ethic and apply it to something that was more beneficial to a lot more people. And, I love my parents, not to throw shade on them, but that was something I’d always think about.

“But really, they installed that work ethic,” he continued. “You know, I have a very addictive-type personality and I’ve dealt with drug addiction and I talk about that in the record. The truth is, I got sober during the course of making the album and when you have an addictive personality it’s not about necessarily ending addiction as much as it is learning to be addicted to things that are less detrimental and more beneficial to others and not gonna hurt you.

“I’ve always been a workaholic, this is not a new thing, but when I got sober I was able to take it to the next level,” he said. “It’s definitely ramped up my time and being able to work, if you’re not constantly going out to smoke a spliff every fucking 20 minutes, that saves you a lot of time.”

Tree said he likes to date in his downtime. He enjoys travel. He tries “living life big and saying yes to things” because, he adds, ““If you don’t live you don’t have anything to make new art about.” His time is currently focused on the live shows. Tree said this is the best time to take in everything his live show offers.

“Before it was pretty painful for me to do, when I was playing for smaller rooms. You know, when you’re playing for 500 kids or a thousand kids and you’re making social media content that’s reaching millions of people the same day, it’s just like, ‘What the hell am I doing?’” he noted. “This tour, moving into those four- and 5,000-cap rooms and feeling the energy, it’s been very inspiring. This tour is the first one that I’ve really felt has really been motivating me to want to play shows.

“So, this will be the final tour. This will be the final chapter. If people wanna see this show this will be the time to see it because we will not be coming back,” Tree promised. “But, I will say the show itself, there is something for everyone there. It’s a mixture of everything from performance art, extreme stunts, scooter stunts, there’s some WWF wrestling in there, we’ve got everything from comedy to storytelling to essentially what I would describe as a shitty Broadway musical, or you could call it a high school play on steroids. Even belly dancing, you know, I do some belly dance moves. We really have a diverse show.

“As far as the music goes it’s everything from a pop show to a rock show to a dance show to a hip-hop show to a country show. We’ve got something for everyone. And the show, the way it’s come together, and the fact that I write every melody and every lyric, things that I’m speaking from my truth and from my heart, and the biggest impact is felt that way. The fact that I produce on all these records makes it cohesive no matter what I choose to do so we have a very diverse, eclectic show, we have something for everyone,” he said. “It’s been really motivating seeing that in real time, seeing people come together trying to celebrate life. There’s even motivational speaking mixed in with it all and some really heartfelt messages. Very highbrow stuff, very low brow stuff and I like to call it 'unibrow.'”

Oliver Tree, Friday, March 25, 2022 at 713 Music Hall in POST Houston, 401 Franklin. With Sueco and 347aiden. Doors at 6:30 p.m. and music at 8 p.m. for this all ages event. $39.50-$45.
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Jesse’s been writing for the Houston Press since 2013. His work has appeared elsewhere, notably on the desk of the English teacher of his high school girlfriend, Tish. The teacher recognized Jesse’s writing and gave Tish a failing grade for the essay. Tish and Jesse celebrated their 33rd anniversary as a couple in October.