Words by Angel Cheng. Photos by Wes Knoll.

Jason Dill is an iconic and inspiring skateboarder, artist, designer… human. We spoke over the phone about his current life. He has given away many of his material possessions and embraced simplicity. After a lifetime of professional skateboarding, he now spends his days making paintings in a shared studio. Like many others, Dill’s skateboarding and lifestyle inspired me as I was growing up. There is a saying within martial arts that I believe suits Dill’s approach: “There are black belts… and then there are black belts.”

DILL — How you doing?

ANGEL — Chilling. How about you?

DILL — Just watching the sun go down, it’s still a hot pink at the bottom. Washing my grocery bag and some towels, you know. Fucking super exciting shit.

ANGEL — I wanted to start by asking you about the minimalistic lifestyle that you’re living. When we went to visit you, you took us through the forest that you walk through on a daily basis. Given your association with hyper-urban environments, I found your nature-inspired paintings to
be a stark contrast. You know what I mean? New York City, Los Angeles. And now your paintings reflect this other side. How did this come to be?

DILL — Well, when I moved from New York back to Los Angeles and tried to recoup my career because I hadn’t skateboarded in about a year, around 2010, I moved right behind Supreme in Fairfax. There was this little duplex. I could throw a tennis ball at Supreme from my place. Turning FA (Fucking Awesome) into a board brand and doing all the work with Supreme at the time, it was super beneficial being that close. It was right before Supreme went super fucking nuts and that whole area got flipped on its head. It was so cool too, getting to spend the time with the kids, meeting Tyler (the Creator) and Thebe (Earl Sweatshirt) when they were really young. Watching that shit explode and being a part of it was really bugged out. Like, you know, I shot fucking photos for Thebe’s first album. It’s on Columbia Records, the same label as Miles Davis. That was a trip and I’m so proud of that. I learned a lot from Thebe.

At 10 in the morning, young Tyler, already doing Odd Future, would come and yell up to my window as I looked from the second floor, like, “Dill! Dill!” I said, “Hey, what’s up.” He’s like, “Can I come talk to you?” And he would just pick my brain about stuff. It was really fucking interesting just to watch him turn into this stratosphere of success. So there was that. At least seven years over there. James (Jebbia) sent me all over the fucking planet for Supreme, doing all the look books and all this stuff. We went to Tokyo two to three times a year for ten to eleven years straight. That was incredible.

But, when you go to Japan that much, your life kind of revolves around when you’re going next at that point. It’s a strange existence. So I’m doing FA and all this and that, and I just got tired of it. I look out my window one day and Kanye West is walking by, and then I look out one night, fucking Nipsey Hussle driving by. It got fucking bonkers over there with all the Supreme lines that started happening. It was just really crazy. I decided I didn’t want to be there. I was getting older, and since about six odd years ago, I moved to a little beach town 80 miles north of Los Angeles called Ventura.

At the same time, my mom needed me. She needed me to help her have a place to live, her and her husband. I said, “Well, then I’m going to move you up to Ventura because it’s cheaper up here. I can’t afford to put you in an apartment in Los Angeles.” Ventura is just a sleepy kind of beach town. It’s cool. It’s different.

Then we’d open the Hollywood store. It was cool to design a store. I never designed anything like that before, and that really worked out. I found myself wanting to be closer to go hang out at the store and get the experience of what it is to be there and see people interact with the environment. So I moved again. I started renting a house in South Pasadena, a super mellow neighborhood north of Los Angeles, and started walking to that wooded area that I took you to. Giant wooded area. Every day. Three months later there was a pandemic, and I would just read and walk every day. I’d already started painting… it was really comfortable to be able to walk to that wooded area and just do my thing.

I have always been fascinate by nature and luckily I was able to travel the world because of professional skateboarding. I like animals and nature and clouds and rain, but then I also love New York City. I didn’t want to leave New York, but honestly I needed to make more money. I was still young enough that I knew I could perform at a high level on a skateboard, but I just wasn’t doing it. I decided to revamp my skateboard career. And it was awesome to do that.

In September of 2022, I left that little house in Pasadena. I went to this town called Astoria in Oregon. It’s the very last little town on the Columbia river in the Northwest. I thought I could buy a house up there and live up there and just commute to where I go around the world, but that place is so strange. It’s epic, but it’s so weird. I started traveling around Washington and Oregon for about a year. Every few months I would come back to Portland and check in with the Adidas guys. But I was mainly just going to small towns, being in nature and snow and walking for miles and miles.

But, yeah, I don’t know, this is a very long answer… With painting, I just get into it and start fooling around with certain colors, then all of a sudden I’ve painted this nature landscape of a valley and a river. I don’t use a projector or photos or anything. I just did the thing and there it is. And it reads as it is, like, wow, that’s beautiful nature. And it came out of my brain. As you saw at the studio, mostly, none of my paintings were finished. Only one of them was finished.

But if I can do that and have the nature laid out and it reads the way it reads, and then I go in and I put a human and animal component into it, and then if I’m satisfied with that, then that painting is done, and that’s where it goes from there. As far as how my paintings will develop later, I don’t know. It’ll be up to me to start painting interior landscapes or different things. But so far, the nature part of the paintings is what’s really driving me. I didn’t paint when I was on the road. You try to paint in a motel room, it’s really difficult. So I’ve been painting that stuff for six months since I’ve been back. I got asked to do a show at a gallery called Naruyama in Tokyo. When I finish the stuff that’s specifically for that, then I’ll have that show, and that’ll be cool.

ANGEL — Does it feel strange? Going from Fairfax, Lower East Side, all this stuff with Supreme and FA opening shops to then making paintings while living a simpler lifestyle?

DILL — Well, so where I stay is where I’m sitting right now. So I’m sitting on the back porch of my friend’s house in a very tiny pool house, which you really can’t even fit a regular car into it. But after I did my sabbatical of traveling around Oregon and Washington, I ended up in Korea and in Japan for three months.

And then I was texting with him in August before coming back in September, and he said, “What are you going to do when you get back?” I said, “I don’t know. I don’t know where I want to live because I don’t particularly like living in Los Angeles, but it works for work, and it works because I paint at my friend’s studio, and it just works for the whole whatever this part of my life that I’m doing right now. And I don’t have fuck off money where I can just fucking live comfortably in New York.” So I asked my friend, “What do you think of me renting your pool house?” He said, “Totally.” And my whole thing is, I just didn’t want to deal with a landlord. I don’t ever want to deal with a landlord again, and I don’t ever want to deal with living above or below anyone ever again.

I’m just too old for that and dealt with it for so long. Of course, I would love to move back to New York, but if I move back to New York, I’m going to pay like $3500 for a place I paid $1000 for in 2009. No way. But if I get Lady Gaga money, then fuck, I’m back there in a heartbeat.

Let’s see how far I take these paintings. I can move back to New York in my fifties.

Working for Supreme all those years, doing FA and working with Adidas, I accumulated so many clothes, and I just decided fuck this. I don’t need all this shit. I don’t want to be super attached to anywhere. I want anywhere that I have some sort of occupancy to be loose and not constrained. And that’s exactly what I have here. I have my little house and I gotta say, it’s like I told you when you were here in California, when it rains at night it feels like I’m in a little cabin, like I’m living outside. Even though I’m in a structure, it just feels… I don’t know. I like it. I don’t wear jewelry and I don’t drive a car. I just got rid of all of my stuff.

ANGEL — It doesn’t seem like you care about owning too many things.

DILL — No, because if it goes away, then you’re sad. I don’t want attachment to anything.

ANGEL — How is it with FA now? Where do you stand with that?

DILL — I’m glad that its been such a nice chunk of my life doing FA in the first place. To have had my career and then have a second career doing that. Its been great for all the ups and downs, but it’s a bitch.

Doing the company is totally a bitch. It really is. I shouldn’t complain at all, but here I am. It is capitalism. We make too much plastic and that bothers me, but it’s just like, fucking… What, are you gonna do better? Like, I don’t know. Stop doing the company? I do think about that, you know, I’m human. I’m gonna be a hypocrite and I’m gonna talk out of two sides of my mouth until I live fucking off-grid in a cabin in Montana. I think that’s what I like about painting so much. Painting is the opposite of AI, it’s the opposite of the Internet, it’s the opposite of television, it’s the opposite of an iPhone, it’s just the opposite. Everything in painting is just the opposite.

Even though it’s super frustrating and largely time consuming, which is a blessing and a curse. It’s frustrating, but when you get something down, you’re like, “Fuck.” And then someone else comes along, they say, “Fuck! You painted that?” Yeah. You get a sense of accomplishment. Putting something into the world that has truth to it.

That’s what I liked about being able to become a professional skateboarder. Skating at a high level and having a good career. I’m really proud of the fact that I’ve smacked my face on the ground. I’ve knocked myself out and broken bones. Now that I’m older, i’m really glad I went through that.

Skateboarding is like boxing. You can’t really fake it. You’re gonna get fucked up and you’re gonna get hit in the face and you’re probably gonna get knocked out. You will probably break something. I did all of that multiple times, and gladly.

Full interview, featured in Issue 7, Living Proof Magazine.