Photo Credit: Parker Day


Interview by Mia Anderson


I was honored to speak with artist Oliver Tree before his two shows in Boston last Friday. Oliver Tree has amassed over 16 million followers on TikTok and Instagram and is known for his musical talent as well as his out-of-the-box character work. Tree is embarking on a tour that pushes the definition of what a typical artist concert looks like. While speaking with Tree, he described his show as a combination of a concert, TV show, movie, and Broadway play all in one. Along with performing at MGM Music Hall, Tree is debuting a new DJ set and audio/ visual experience, titled Dr. Oliver Tree, right after his performance in Fenway. 


Mia Anderson:

I’d like to start off by congratulating you on recently starting your tour. I know today you play MGM Music Hall in Fenway. My first question is what does a normal day-of-concert look like for you?


Oliver Tree:

Well, today’s actually a really unique day because I’m playing two concerts in one day and I’ve never done that before. So I’ll be playing at the MGM for a concert with my band and that shows a mixture of a movie, TV show, a Broadway play, as well as obviously a concert. It has stand-up comedy, motivational speaking, WWE wrestling, karate as well as some scooter stunts. So that’s kind of 360 entertainment and on days for those shows, I typically will go to a sound check at some point. I’ll typically do some interviews, some radio stuff. I’ll typically prepare, getting ready for the show, writing my notes, because every single show I give a speech where I make it very, very centered around my experience with each city.

So I kind of write jokes and things like that to make it a special show for each city, but then tonight is a very unique show because then I go directly from this show to the next show. Which is at the Grand. It’ll be the debut of my new project Doctor Oliver Tree, which is my DJ project. But to call it DJing is underplaying what it is. I think it’s really exciting. This project is something I worked on for a year and a half and It’s a mixture of an audio-visual experience centered around nostalgia. So all my favorite moments from not only music, but also cinema. I just chopped up to oblivion every single thing.

So in the audio mix, I have over 689 different audio layers that have been chopped up and blended together. It’s a sound collage mixed with all the things that have inspired me as an artist and as a human, and then visually speaking, it’s a mixture of a multimedia show that mixes together my favorite moments in cinema and my favorite moments that I’ve directed in music videos. Last week I was wearing a mocap suit, which are the suits with the white dots, and I have a 3D version of myself as a surgeon and I’m actually singing some of the songs on screen while doing choreographed dance that matches, so a mix of performance art and a lot of different layers to it. I’m very excited because I think it’s gonna push and challenge the idea of what DJing can be.

Today, I go to the venue where I’m doing my rehearsal for the band and I’ll be working on the DJ set, chopping up stuff, figuring out everything, making sure all the visuals are fully finished, and preparing and practicing the DJ mix. Then I’ll go do a sound check and then I’ll go to the next venue and do another sound check, and then I’ll go back to the other, play a show and then I’ll go to another venue, play the other show and then hop on the bus and drive to Philly and play. 


Mia Anderson:

Yeah, that sounds really busy and that’s super exciting that you’re debuting that show here in Boston. Is there any part of either your normal show or this new DJ show that you are the proudest of or most excited for people to see and react to?


Oliver Tree:

Yeah, I think for the live concert with the band, for me, that’s such a labor of love. And it’s something that is taking the idea of a concert and expanding upon it. You never really recreate the wheel, but I think I’m doing something really outside the box with that show.

I wrote a 40-page screenplay for my concert, which I think is pretty much outside the box typically and mixing together everything I’ve done in my entire life. Essentially in that show, It’s so much of everything, the whole entire we call it the Oliverse, the Oliver Tree universe, where it pretty much ties the dots between all the characters, all the music, and videos, and turns it into a feature film that you get to see the lead actor and director of it on stage performing.

I think there’s something really crazy about it where the audience comes to watch me and I’m at moments, obviously, I’m performing for the bulk of the show, but there are moments where I’m sitting on the couch watching the character that I’m dressed as on stage and he’s inside the screen watching himself in his house watching music videos of himself and then that character in the music videos at times is even watching himself into another layer. So there’s like 5 layers deep of media, so things like that I’m super proud of.

There’s a big statement on commercialism and trolling the audience a lot. There are some crazy moments where I really get the audience to turn on me and boom me and that turns into the hero’s journey and taking people on a pretty wild ride through emotions. I think both shows take people through a wide array of emotions and you can laugh and you can cry and you can dance and be moved and inspired and I think that there is something for everyone.

Sonically speaking, both these sets cover as much different diversity of music as I possibly can cover and basically, each show is between an hour and a half to two hours long. For my normal concert with the band, we have a string ensemble so there’s a four-piece, so we have from classical music to rock music to pop music, to dance music, to electronic music, to hip hop music, to folk music and country. So wide array, and then the DJ sets covers. Over the last 30 years of all different stuff, including rock, including dance, including drum and bass, and house music and techno, and hip hop, and pretty much covers all the music I grew up listening to. So I’m really excited about debuting that tonight. 


Mia Anderson:

That’s awesome. You just kind of mentioned this briefly about all the different character work that you do and I know that you’re known for these characters and being outside of the box in the industry, which is really cool. Could you explain a little bit more about your character work and maybe what inspires these characters?


Oliver Tree:

Yeah. So the cool thing about the first show that I’m playing with the band is that I have three different outfit changes, three different wig changes, three totally different looks, which I’ve designed all of them, and each character is true to my own life. I think we have a lot of versions of ourselves within us. The version that you show up to the classroom. Might be different than the one you show up to.

When you go to a party, the version of you that shows up for Christmas might be different than the version of you that shows up on a date. You know it. It all depends on, you know if it’s a business meeting or you’re hanging out. Things are very different energy-wise, kind of the way we present ourselves. So for me, I embrace the different versions of myself that exist and I kind of have just explored whatever I could find within myself and try to keep it as true and authentic to myself.

So like the first character from the first album, Ugly is Beautiful, the character’s name is Turbo and he’s centered around my childhood. The haircut I had, the bulk cut, I had my whole life and was too scared to get another haircut, the ski jacket I used to wear skiing when I was a kid that I stole from my parent’s closet, the JNCO jeans, the absurdly large pants, which I always wanted those pants, the socks, and sandals, which is the shoe combo that I thought was the most ridiculous. The little red glasses that made me feel cool. Sort of, all the things in my life that kind of were the most ridiculous kind of crazy. When I packaged it together, it felt kind of like it was the first iteration of the project. So it’s kind of like the child version of it.

Then the second album Cowboy Tears, explored my interpretation of country, even though I don’t like country music. I decided to make a country album and there’s a heartbreak album that explored kind of my roots. My grandfather was a cowboy. My grandparents had a ranch, so I go there every summer and my grandfather’s father was a cowboy and his father was a cowboy, and it was just part of the lineage of my roots. So I kind of got in touch with that.

With this new album, I’ve been designing a lot of fashion and doing a lot of just exploring the fashion realm. I made a character Cornelius Cummings and he’s exploring fashion as a designer, and the cool thing is each album has these really big themes. The first album is teaching people how to learn how to love themselves and be able to embrace their flaws and learn to be able to recognize what makes us so unique. In the second album, I explored kind of this sadness and this heartbreak and teaching people, you know the cowboy is the toughest type of person, and saying it’s okay for guys to cry. It’s okay for everyone to cry. It’s important for us to cry instead of letting it out in anger or in other ways.

The third album, Alone in the Crowd, I explored loneliness and after amassing 15,000,000 TikTok followers over the course of a few years, I’ve felt more lonely, more isolated, and more Rapunzel than ever and it’s not really that relatable, but I think you know, as an artist, my job is to create things that connect with people and is relatable. So really what I was experiencing with loneliness, and that’s a very relatable thing. So I explored that and just kind of created an album as a reminder that although we all feel lonely, when you look around and everyone else is lonely, it makes you feel a little bit less alone when you remind yourself of that. 


Mia Anderson:

Yeah. I feel like you have a pretty hands-on experience with a lot of your art and your music. You’ve even talked about filming aspects, mixing music, and singing your songs as just a few of the parts you are involved with. What is your process for coming up with music or new songs?


Oliver Tree:

So it’s always different. Every song I make there’s never one specific way that It goes down but, you know, it basically just starts with playing the instrument part and sometimes there’s a better instrumentalist in the room, but sometimes it’s me. This album, I’m really proud of, ‘cause I played 80% of the instruments, so guitar, piano, bass, and synthesizers. I produced some of the drum beats by myself as well, but you know, sometimes it’s more fun to just be hanging with your buddies. And if my friend’s a crazy piano player, I’ll let him jam out on the piano. If it’s someone who’s a great drum beat maker, then I’ll just play the piano or play guitar. So it it varies time to time, but always kind of starts with some kind of instrumental.

And then, you know, once you have some chord progression then seeing and searching for a melody, and sometimes that’s more calculated and it’s written out and sometimes it’s fully improvised and just really seeing what comes out of me, what I’m feeling that day. But in general, the theme that I notice is that. No matter how bummed I’m feeling, no matter how much negative energy I have going into the studio that day, I harness it into positive energy and I go from maybe being super bummed to then feeling super excited, jumping around, dancing, and feeling super inspired. So it’s a very cool thing to harness your negative energy. The positive energy that you can share with others. 


Mia Anderson:

If you could pitch yourself or your sound to a new audience, what would you say?


Oliver Tree:

Sonically speaking for me, I think a lot of my sound is centered around nostalgia and pulling from the past. I think I’ve explored kind of a melancholy expression where I have maybe a darker lyricism mixed with a more upbeat production around it. My whole project is centered around juxtaposition, my music’s very serious, but my image is as ridiculous as it gets.

So for me, it’s about exploring. Kind of mixing together things that shouldn’t go together and at the core. I think that’s where there’s the only real room for some new ideas because there are only so many chord progressions. There are only so many lyrics that rhyme well, rhyming patterns and words. The English Dictionary, it’s kind of limited, so I mix together things that shouldn’t go together.

This is kind of at the roots of where I find the most inspiration to do something fresh, and that is not just in the music side, but the filmmaking aspect where I direct and write and produce all my music videos, and it’s about storytelling and using whatever means necessary to tell a story. 


Mia Anderson:

You do have some pretty amazing and iconic music videos. Could you further explain your process of making these music videos and how you came up with those ideas?


Oliver Tree:

Yeah, so I will just write tons and tons of ideas and then essentially it comes down to finance. There’s a lot of stuff I can’t afford to do. There’s a lot of stuff that just isn’t practical, and it’s a lot about killing your darlings. But the cool thing about the last album I made is that I went to Serbia for three months and I filmed a series so that they played together as a short film which is really cool because it ties in all this stuff I had already written the live show. I kind of reverse-engineered it and wrote it in the context of the show I was already building as basically a feature film.

So I think what differentiates them is that since I do direct them, write them, design all the wardrobe, and I do my own stunts, there’s a huge version of everything I’ve done as a human from storytelling like the acting and the humor. There’s so much of everything I’ve ever done and I’ve kind of neatly packaged it into a box where I put a bow on it and present it to people. Music videos are kind of what keep me excited about making music, the process is usually just writing thousands of ideas and then kind of figuring out what’s the craziest ideas.

Then I have to come down to Earth once I start meeting with the financiers and people helping produce it, and okay, this is how much money I have to work with. I got to spread it through all these ideas and trim these ones out, but a lot of it has to do with writing down ideas and then taking them and putting them into a story and connecting the dots. Then basically, I make these meme pictures, which are like super crude. I make Photoshops on my phone of every single image and kind of how each shot should look so if I’m inventing a new vehicle, like for example I invented the bulk quad which is like a four-wheeled mechanical bull that you can ride around and things like that don’t exist. So I have to kind of create memes to present my ideas, as an inventor, if you will. 


Mia Anderson:

Yeah, I was gonna say you seem like a really big inventor like, jack of all trades, which is really, really cool. 


Oliver Tree:

Yeah, I’m not necessarily good at anything, but I think it’s when you can kind of express everything you’ve done and put together everything that you’ve done as a human, then no moment was a wasted time and you can use it to share something that makes it much more unique. I grew up being a professional scooter rider and it’s like, well, where does that fit in with music that’s so random? But for example, I figured out ways to tie that in so that it became something that made me more unique and stand out, like how I built the world’s biggest scooter in the Guinness World Record.

Not only did I build it, but I crashed it as well and I got arrested for driving it through traffic in Los Angeles about 3 and a half months ago. You know things like that where I can bring it in and tie it to a marketing campaign to get people to listen to the album or whatever it is, so it’s been something where I just figure out creative ways to make everything an art piece, especially the marketing, because that’s like 80% of it. So if I’m not expressing myself and feel like it’s creative, even when I have to market something, I’m not going to feel like my time is spent well doing it because my job is to create so all the marketing, all the promotion, which is kind of energy and time suck. I found ways to be able to turn it into performance art.

I just was on TV in Toronto and just trolling the biggest TV station in the entire country in Canada. Just using the opportunity of the traditional marketing campaign of promotion, but instead, I kind of flip it on its head and was telling crazy elaborate stories and stuff that, you know, the reality and the real things I do are equally as crazy. So it’s hard to tell what’s what sometimes but it’s all performance art for me. 


Mia Anderson:

Yeah, I feel like it brings in a sense of authenticity that these marketing parts are actually from parts of yourself. My final question, since this is for my college radio and there are so many young minds out there to influence, what advice might you give to anyone who wants to pursue music or art?


Oliver Tree:

It doesn’t have to be music. It doesn’t have to be arts. It could be anything. I think the key to being able to find success in your field, whatever that field may be, is to just be prepared to fall on your face most of the time. I think that’s probably 95% of what I do. Be prepared to just go get your hands dirty, you just do it. Don’t think you need to wait for the opportunity to come to you. You have to create the opportunity yourself. It’s a lot of trials and tribulations and sometimes you don’t know where the line is till you cross it.

The reality is that you should find something that you love doing so much that you are happy doing that without a single other person being able to experience it besides yourself. If you really love it, you will do it. For years upon years, you’re probably gonna spend 10 years just sleeping on couches like I did. You’re probably gonna have just one monument of failure after another, but if you really love doing it, you will do that no matter what you would do for the sake of doing it because you love to do it so much and those are the things where you’re going to really accelerate at. Those are the things you’re going to be able to make a very successful career out of because you will do that no matter what and you will do whatever it takes to make that work.

The second you’re doing something because you think it will bring you wealth or that you think other people will like it, that’s the second you’re going against the grain of your natural trajectory. You have to follow the core of your gut. You need to get good at trusting your core and your gut and try to feel where things are going and where you should naturally put that energy because so much of what I do is just centered around the feet, and in the gut, and knowing when to be able to trust myself and when to be able to know when to trust other people.

If I listened to people and listened to what everyone told me, there would be no Oliver tree, and there would certainly be no two concerts back-to-back tonight. People are always saying we think you should make it simpler. Oh, maybe people don’t want to see a movie when they go to see a concert, but you have to just think outside the box. Dare to be different and just most importantly, go out there, get your hands dirty and fall on your face time after time, and be prepared for that.

Remember that failure is a huge part of success and failure should not be a negative term. Failure is a positive term. For me, failure is most things I do and it’s not a negative thing. Our failures were remembered by our real successes. Unless someone was truly hurt by our failures, the reality is that most of it just goes under the radar. 


Mia Anderson:

That’s really good advice. It definitely feels like I’m working through some of that ideology right now. But thank you for joining me today. 


Oliver Tree:

Thanks for having me, appreciate you.