Oliver Tree Hates Celebrity and Loves Failure

Photo of Oliver Tree from Billboard.

By Kendall Larade

On Jan. 13, Oliver Tree began his month-long “Alone in a Crowd” North American tour. Each show is not just a concert, but a movie, TV show, and play. The show features WWE wrestling, professional scooter stunts, stand up comedy, interpretive belly dancing, and of course, a live string orchestra. 

On Wednesday, Jan. 17, Oliver joined me for a quick Zoom to discuss his new audio-visual experience, Napoleon Dynamite, and why he fails better than most.

This interview has been edited for clarity.

Oliver Tree: Hello!

Kendall: Thank you so much for joining us. 

O: Yeah, thanks for having me. 

K: We’re just going to jump right into it. “Alone In A Crowd” as an album and tour seems to be a culmination of all these different styles you’ve experimented with throughout your career, yet it’s sort of tied together by this strong conceptual throughline. Obviously there’s this absurdist element to all of your work and a new character, Cornelius Cummings, but I’ve noticed themes of loneliness, love, and the idea of celebrity especially in the music videos released alongside “Alone In A Crowd.” What was your vision for this album and tour?

O: Well, for the album I was making something about three years ago that evolved – over the course of three years – maybe eight or nine times. So the album’s changed many many times. It started out a bit darker, it started out a bit more lonely. But then, in the process of making the album, I felt love and I wanted to document that as well. And I had just come out of making “Cowboy Tears,” which was a breakup album, so I didn’t really feel like that was going to be something that I needed to do more – negative and dark stuff. So I was kind of wanting to embrace that [love]. 

But essentially, what happened was, the album is something that was made after the rise of my career on TikTok and I had amassed something like 15 million followers in about a year or two years. And the more successful I became, the more lonely I felt. For me I don’t like that idea; the celebrity idea is a gross thing to me, it’s not something that should be celebrated. It’s very toxic and unhealthy for any human, whether it’s lots of love or lots of hate. It’s a negative thing and ultimately I became more “rapunzel-ed” and more lonely than ever. And as an artist, my job is to speak about what I’m going through and, the truth is, that story isn’t all that relatable, but being lonely is. So I wanted to make something that would connect with people that could be relatable and I tied it to more about the theme of loneliness. I wanted to make an album that reminded people, you know, although you feel alone, we all feel alone; when you’re reminded that everyone is going through that, it’s a little bit less lonely. 

K: Of course, I completely resonate with that. I’ve also noticed you’re very hands-on with all of your projects, whether it’s producing or directing your music videos. Why, for you, is it so important to be as involved as you are in curating your persona as Oliver Tree?

O: I’m a storyteller, so if I’m going out there, whether it’s me singing other peoples’ songs or being in other peoples’ ideas for videos, I’m not really telling my story. As a storyteller that’s the bare basics of what I love to do, tell a story, so whatever means necessary. I feel very strongly that every lyric I write, every melody I write, I have to be telling my authentic story. I don’t want to go out there and sing someone else’s life, that would not make the true, authentic connection, make it feel real to people and it’s the same for the video components. And, really, the music videos are the real reason I keep doing music because the chance to direct them and produce them and write them keeps it exciting for me. 

Music, as it breaks down, is one dimensional, and filmmaking is all things combined, really, as far as art mediums go. So I’m able to put everything I have as a human – my upbringing, being a professional scooter-rider growing up, doing action sports – [into filmmaking]. So I do my own stunts; I choreograph all the movements, the dancing; writing is part of storytelling, as well as understanding psychology; obviously the music component, which is a big part of my life; designing the wardrobe, I design all the costumes. So it’s just everything I’ve ever done all packaged into one thing which is incredibly liberating as an artist. It’s really fun for me, it keeps me excited about the medium of music. 

K: There’s definitely a certain vulnerability to choosing to be yourself as an artist, rather than adhering to the trends. I’ve heard you say that Oliver Tree, the artist, is somewhat of a caricature of yourself. How did you make that decision, to be yourself?

O: For me, creating the personas made it easier for me to be able to put myself out there and be able to create a mask, use my own face as a mask. So, when people judge me – obviously when you put yourself out there publicly you’re going to be completely…people are going to be constantly trying to take down what you do…I don’t know how to say this without swearing. Can I swear?

K: No, sorry. We’re live. 

O: Okay, well, basically, whatever you do as an artist people are going to not always love that. You know? When you’re putting so much of yourself out there and people are constantly judging you it’s a lot of hatred, no matter what. Even people who are the most beloved type of people you can think of, they get so much hatred. People who are the sweetest people that I know that are artists, they still get so much negativity and people wish death upon them. So when people are judging a character it’s a lot easier for you to take that and be like “yeah, well it’s one thing for them to speak that way, but they don’t really know the real person.” Also, you have to keep in mind when you’re developing a persona, it has to be very authentic and very real. So it has to be you, turned up to 11 or 12, otherwise it’s going to be very fake and come off as very phony. There’s this fine line between giving everything you have but also knowing where to kind of set some boundaries to create barriers from your personal life. I kind of tip toe around those lines. 

K: And before you went by Oliver Tree, you were known as Tree or Tree Collaborations?

O: Tree was the project, but Tree Collaborations was an art project surrounding it. So it was a multimedia collective of filmmakers, painters, 3-D artists, and I took that concept and that’s what I made Oliver Tree out of as well. I kind of expanded upon it and just did it a different way that was more tied to identity, because that project, although I was in some of the music videos and stuff, it was less about the face. It’s hard to connect unless you have a human, so instead of making it just about me me me me me I played a character. When you watch a movie you never say: “well why is Napoleon Dynamite in the movie so much?” Well, it’s called Napoleon Dynamite, he’s playing a character! So for me it made it easier to play a character and not feel like it was so egotistical because it’s a persona, you’re playing a character, like a movie.

K: Were you involved with the Ashwood Project on SoundCloud as well?

O: No, that’s just someone collecting all the music I’ve tried to delete off the internet. I did a very good job removing all of it. But, basically, if something’s on the internet, it’s on there forever. So that’s just some people who are fans of the older music and they went through to kind of curate – or keep alive – whatever’s left because I basically demolished everything and took it all off. There’s people who’ve uploaded it onto SoundCloud and are making money off of that music, but I wanted to start fresh with a clean slate. So I just took everything down. Those are people who are just preserving the older projects. 

K: Understood. Initially, you were making music as a DJ, in high school, you opened for Skrillex. And you’re returning to DJ as Doctor Oliver Tree, is that correct?

O: Yeah! And that’s something that I’m actually the most excited about because the live show I’ve been making – that you spoke of at the beginning – that’s been five years in the making. I’ve invested five million dollars into that show. I don’t live anywhere, I don’t own a house, I don’t rent: I put all my money into that show. But the Doctor Oliver Tree thing is really inspiring because I get to start with a clean slate once again and I’ve spent over a year and a half working on that DJ performance. Where are you guys located?

K: Washington DC.

O: Cool. Yeah, so I’m not sure when I’ll be unveiling the Doctor Oliver Tree project out there. But, that being said, I’ve been working so hard on an entire new live show that’s a new project and something that challenges the idea of what DJing can be. It’s bringing art, you know, performance art into DJing. I think to call it DJing is underselling, really, what it is because it’s something that’s much more than that. I think it’s going to push forward the needle on what the idea of DJing and an electronic show like that can be. So I’m very excited about taking a side-step in my career and returning back to DJing after a 13-year hiatus. 

I’m glad I went this other route and really got to express myself as an artist, but it’s fun to come back to something that was my roots in a lot of ways and come with a very fresh perspective – so removed out of the scene and not looking at it like all the people who are really in it. I think there’s a lot of room for improvement and there’s a lot of missing holes in the wall where people haven’t connected dots yet in DJing and dance culture. So I’m very excited to bring some new, fresh air to that scene. 

K: It must be very liberating to be able to make that side-step into DJing. How would you say that your relationship with DJing has changed since you were in high school?

O: For me, I think I’m just thinking much more innovatively and thinking outside the box. I always did that when I was DJing, everything was always planned to the millisecond, so nothing’s changed in that regard; everything’s still planned out to the T and there’s still innovation. I think the production on it is just so much more next level because I’ve had 13 years as a producer, so my skill sets are on a whole other level as well as now I have a lot more funding and a lot more things to work with, resource-wise. So the production value has skyrocketed. Basically the old one was, I describe it as an office building or a large house, and then this version of it is a skyscraper. 

K: Got it. And you even performed in Antarctica? 

O: Yeah that was the first time back after those 13 years. The response was tremendous, it was really, really inspiring. Antarctica was the coolest place I’ve ever been – and I’m coming out of a trip of seven continents in three months, so realistically, it’s a big statement to say that. Last week I was at the Great Wall of China, so I’ve seen so much crazy stuff, but there’s nothing, really, that can compare to the glaciers in Antarctica, the preserved place that was pretty much the last untouched place in the world. It’s mind blowing to see. It’s hard to describe it and put it into words, but it was monumental and very inspiring. 

K: Wow, that’s incredible. Aside from Oliver Tree and Doctor Oliver Tree, you’ve started Alien Boy Records. And it has kind of allowed you to bring in all of these new characters, like Little Ricky and Super Computer, who are working on their own projects. Are these individuals that you discovered or are these from your own imagination? They’re going to be incorporated into your live show, is that correct?

O: So I grew up with Ricky, someone I’ve known for a long time. I just help executively produce these projects, so they’re not my projects, they’re other peoples’. But I have a hand in helping produce and help them be brought to life on the executive side and give them funding and resources as well as bringing them on tour. 

Super Computer opens for me, they’re an electronic duo and I’m very excited about that music. That helps spark my excitement about electronic music again as well, they’re very innovative. They’re thinking outside the box and mixing together lots of different genres. And then Little Ricky, he’s working on a band at the moment, he’s been kind of on a hiatus from releasing stuff. But I’m really excited with what Ricky’s been working on as well. I’ve had a hand in kind of helping behind the scenes, trying to help facilitate his new band and the project he’s working on. It’s been cool working as an executive producer on these projects and helping bring other peoples’ ideas to life. 

K: It gives you yet another angle to build upon this universe that you’ve created. Lastly, do you have any advice for up and coming DJs or independent artists who are trying to curate a persona or build a character like you’ve done?

O: Yeah, ultimately I would say it doesn’t matter what it is, it doesn’t have to be tied to art, it doesn’t matter if you’re in a band or you make sandwiches; do whatever you do because you love to do it. Get super good at it. Don’t do it because there’s the potential of making money or that you think other people are going to give you gratification from enjoying it, you’ve got to do it because you love to do it and you would do it if no one else would be able to experience that whether it’s eating your sandwich or listening to your song. Do it because you love to do it. Be prepared to sleep on couches for years. 

Be prepared to fall on your face about 98% of the time. Be prepared to pull your hair out, be spending sleepless nights dedicated to something. If you really love something, there’s a way to monetize it, but failure is key. Failure is the biggest part of success and I don’t use the term success unless it’s monumental-change-your-life success, which for me has only happened a handful of times. So, for me, everything else has been a failure, and failure, when you approach it that way, is not a negative word anymore, failure is a big part of the success. And, for me, even if I release a song and the song came out, that would be a huge success – just in the context of the 1500 songs I’ve made, you know, I’ve had maybe 80 of them come out – so that’s amazing that it even came out. But the odds of it actually connecting and resonating with it are slim to none and you only get lucky every so often. So, realistically, everything I do is essentially a failure. But my failures are more monumentally successful than most people’s biggest successes. And I’m not gonna say that that’s inherently true, but ultimately some things that are my biggest failures could be considered groundbreaking or maybe will finally be appreciated in five years or 10 years or maybe even after I pass. 

I’ve found that my work takes a while to connect – the artist’s job is to be five years ahead of the curve. So my song “Life Goes On” had success but was eight years old by the time it came out and it was finally able to resonate with people. Sometimes it takes a while for things to connect but don’t give up if it doesn’t work at first, do it because you love it. Do it because you need to do it, not because you think that others will praise you for it because when you get that praise at any point, it’s not going to be what you think it is, it’s not going to fill that empty void in your soul. 

K: Without failure, you definitely couldn’t be as far as you are in your career today. 

O: Yeah and I still haven’t even scratched the surface of what I want to do. So it’s not like I feel like I’m in any place to give too much advice. Because, although I have a massive following and have been able to make art that has resonated in the mainstream, I haven’t even scratched the surface of what I want to do, creatively. I’m still figuring it out just like anybody. 

K: Well thank you, Oliver, for joining us today. I’ll see you next Wednesday on stage! 

Oliver Tree, joined by FIDLAR and Jasiah will be performing at the Anthem, in Washington, DC Wednesday, Jan. 24. Stream Oliver Tree wherever you listen to music.

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