Steve Olson‘s seen it all. As a skateboarding pioneer who started his career in the empty swimming pools of Los Angeles, he has constantly been on the frontline of the sport, watching it grow and evolve from an underground SoCal subculture to a mass-marketed global phenomenon. 

Already establishing himself as a competitive skater by the age of 16, he was the first vertical skateboard champion. His iconic Santa Cruz Checkerboard model became the first use of full-board graphics. He appeared in the film Thrashin’ as one of the Daggers, and he’s even credited with taking skateboarding into punk rock. The iconic skater is also an artist, translating his uncut and bold attitude into his artwork. He’s best known for his sculpture and mixed media work, and he recently expanded his practice to vibrant abstract canvases.

PRØHBTD chatted with Steve at length about the early beginnings of skateboarding, the sport’s marriage with punk rock, his transition into art and his involvement with the non-profit Learn & Skate.

Let’s start with skateboarding. You practically grew up hand-in-hand with the sport itself.

I did. Probably around 1966 or ’67, my older brother and I got skateboards for Christmas. It was like a toy then, similar to a hula hoop or a yo-yo. After we moved to Southern California, skateboarding had another explosion with a couple of definitive things happening within products, such as the urethane wheel and then precision bearings. I was a surfer, and skateboarding and surfing go hand in hand. I was more of a surfer than a skateboarder, but then luckily I did get into it and kicked some ass!

You sure did! What was it like in this early phase of the sport?

Well, for me, the early stages of skateboarding were not in the ’60s. There were huge companies going on then, but in the ’70s, skateboarding stopped being the stepchild of surfing. It developed its own identity and just grew huge in popularity. Then contests came along, and I was like, “Oh, I can compete with these dudes.” Skateboard parks started to show up in the mid-’70s, and that was mind-blowing. Also, going from clay wheels to urethane wheels was a gigantic step. Then it went from loose ball bearing wheels, which make the wheels turn on the axle of the truck, to precision bearing, and it just advanced to another level. 

Back then, I was into skate parks because it was the closest thing to surfing, really. My older brother worked at a local skate park where we hung out religiously. It inherently just came to me. When I won the first swimming pool contest as a kid, I was like, “Wow, that wasn’t so difficult!” So I just started entering skateboard contests.  

The first professional contest came up. When I was an amateur, I went with a couple of these pro guys to this backyard pool, and I realized, “Oh, I skate as good as these guys if not better.” Not in an egotistical way, just more in a self-realization. I would see all these cats in the magazines, and they were really beyond good. So this company, Santa Cruz, said, “We’re going to make you professional. That means we’re going to pay you.” That was mind-blowing to me. I wasn’t in it for the money, I just had mad love and passion for the sport itself, and I knew how to compete. And compete I could. 

So I went down to this contest with all of the [professional] dudes I’d see in the magazines. It was intimidating at first, but a couple of us younger guys smoked them! I’m still in this weird fog of how it happened. I was actually getting paid to ride my skateboard, which was really cool. And that was that.

What changed when you became a pro?

Money. (Laughs.) No, I’m kidding. It wasn’t that much money. It was more of a feeling, “Wow, so sick!” 

There was a series of four events in the first professional, let’s say, vertical skateboarding contest called the Hester Series. I did well in each one. I always thought that if I could get in the top five, I could win the overall [series] as long as the other guys would maybe blow it. So, a couple of them blew it in the first event, and I was third. I was psyched just to be in the finals.

Then, I went to this other skateboard park, Upland, for the second event, which was the biggest skate park in the world at the time. Scott Dunlap got fourth at the first contest, and I got third, and then I got fourth at the second contest, and he got third. So we tied overall. 

I did aerials, like grabbing the board and flying out of the top of the pool—you had to have that in your arsenal of tricks. So for the next contest up north, I’d learned to do a couple of aerials. I thought, “I’m on point. I can do aerials, and these guys can’t even do all the tricks that I do.” I got a fifth place there.

Going into the last contest at the Big O skate park, which was closest to where I lived with my folks, I thought I just had to get in the top 12, and I’d win the overall thing. So it’s at my park and I’m qualifying first, going into the semifinals, and I’m like, “Yo, I’ve got this.” So I got second in the finals against Steve Alba, and I won overall.

In my crazy little world, I thought that was the best thing ever. I didn’t even have to win a contest, but I won the overall, which was super important. People following it thought it was really amazing, and they started saying, “A new crop is on top.” That’s how I got deep into skateboarding. 

Punk rock also played a big role in your life at the time.

So, at the same time, there was a whole new music thing going on called punk rock and new wave, whatever you want to call it. My older brother was so instrumental. He was also my best friend, and he would keep me in check and make sure I didn’t get out of hand. But I still got out of hand. (Laughs.)

He was into glam rock and Iggy Pop and Lou Reed and so on, and punk rock was just right around the corner. I remember I heard some punk rock at one of the first contests, and I was like, “This is my music. It had the same energy as when we were skateboarding.” I committed to punk rock as well: I cut my hair, I got an earring… I loved the fashion of it. I loved the energy. It was totally new. All the “normals” weren’t into it and thought we were weird. 

Then there was Skateboarder of the Year, through the popular Skateboarder Magazine. I was totally into punk rock, so I pinched a little bit from James Bond, from Sid Vicious, and wore black leather pants and a black shirt with a white dinner jacket and shoes that were way too small but looked really cool. I think I had a black and white polka dotted tie, too. All the other guys were kind of surfer types. 

They started to announce the results, and they’re like, “In tenth place, Joe Blow.” When it got down to the top five, I thought, “Wow, I didn’t even make the top ten. How lame is this?” Then it got down to the top three, and some other guy got third, and then they announced, “And in second isTony Alva,” who had won it the year before. Then the people said, “Yo, you won,” but I didn’t believe it until they said, “And skateboarder of the year is Steve Olson.” 

I was so hammered, but that’s life because I was 17. I went up, and I remember it was like “fuck the establishment” at that point in my life as a kid. I remember people calling for a speech and taking pictures. I was totally psyched out of my mind. I was like, “Wow, this is insane. How is this even happening?” But then I also had to play it off as if I didn’t care. But honestly, I fucking was so, so happy and so stoked. I thought, what would these punk dudes that I looked up to do? So instead of giving a speech, I just started picking my nose and flicking boogers at them and spitting at the camera. Tony Alva got pissed because he was second.

Then the next issue of the magazine said we were terrible representatives of skateboarding: The guy in second place throws his trophy in the trash, and the winner picks his boogers and flicks them at the camera. This is not right when you’re a top professional skateboarder, but we didn’t care. The kids were like, “Yes, we fucking love them that much more. They’re really down for the cause, and they’re not really worried about all this stuff.” And we weren’t at all, but it was funny because it backfired against the industry side of skateboarding.

So you played a big part in bringing punk rock into skateboarding?

Oh, no, no, no, no, I brought it in. That’s for fucking sure. I’m sick of people saying, “Oh yeah, him and da da da.” No, no, no. All those dudes still had long hair. They might have been into it, but they didn’t commit. I committed. I was totally into the fashion part of it as well as the music and the connection between that and skateboarding itself. It was rowdy, and it was new, and skateboarding was relatively new, and it was happening. It was the transition between the two that made them a perfect fit. 

I really like the trophy so much now. I’m so proud of it, and it’s not only because of the trophy and what it represents, but also because of my son. He is now 33 and a really, really amazingly great skateboarder who does his own thing. He moved in with me when he was nine or ten years old, and I used to get him G.I. Joes. I remember, I came home one day, and he had put an army mask on the trophy and made it fucking great. I was like, now I can fucking be prouder than shit of this trophy because of this addition. 

Another thing you’re credited with is introducing the checkerboard pattern, which is now synonymous with skate culture. What’s the story behind it?

Oh, I wham checkerboard! When I was younger, my father worked with decals and adhesives. We would go to races and always see the checkered flag determining who crosses the finish line first. Then there was a little bit of checkerboard in new wave as well. 

Santa Cruz gave me a board with my name on it, but it was a typical screen graphic with their name and my name on it. I thought it was fucking lame, cheap and not going to fly. So I worked with my brother on a graphic. My brother was and still is a really great artist, and I told him to incorporate it, and he did. 

I was stoked out of my mind having my own skateboard with my name on it. I played a role of [pretending to be] cool [about it], but inside my heart, I was so proud of it. So, then it went off. We did two versions. For one, the whole board was checkerboard with a racing stripe and their fucking lame name and then the signature. They went with the one with the big red dot and the whole board. A full screen board hadn’t been done in skateboarding before. 

I had some money, and I could afford to buy some decent shoes. I remember the guy for Vans saying, “Hey Olson, I don’t know why you don’t ride Vans.” I just thought they weren’t my scene, but I asked him if he could make sneakers for me if I bought my own fabric, and he agreed. So I went to the fabric store and bought some checkerboard material. I bought some fake leather—it still looked like leather—and I bought this gold lamé like Elvis’ suit in the ’50s. They made the gold lamé, fine. They made the checkerboard, and I really was hyped on getting the leather sneaker, and they fucking flipped the leather and made it suede instead of leather. I was like, “Of course, they wouldn’t get that. They’re dodos.”

I threw them in the trash, but now I wish I had those fucking sneakers. If I had, people would tell me, “Okay, fine. You did make the first checkerboard sneaker.” Now I don’t have them to prove it. I know someone has a picture of me wearing them. Then later, all of a sudden, fucking Vans have the checkerboard sneaker, and I was like, “That’s cool. Whatever.” 

Let’s talk about Thrashin’. How did you get involved?

Thrashin’ was so amazing! I think the movie’s lame, but it’s super funny and corny and cheesy and whatever. At the time, I became super good friends with David Hackett who’s a skateboarder and a wickedly badass guy. We were at some club listening to some music, and this guy, Alan Sacks, comes up and starts dancing around us. He said, “We’re going to make a film about your lifestyle,” which was kind of annoying. I remember I carried this pink switchblade, and I pulled it out and put it to his throat. He got so nervous saying, “Oh my god! These guys are way crazier than I ever thought.” Then I just put it away and said, “Yo dude, I’m just acting. Relax!” He fucking was like, “Oh my god, I thought you were going to cut me.” Then, he said, “I want you to meet the director, David Winters.”

My friend David and me rolled up to his house in the Hollywood Hills, and we’re assuming the guy is going to be this cool dude. But then some little [guy] pops out in cowboy boots, golfing shorts and a Hawaiian shirt, and we’re like, “Are you fucking kidding me?” We kind of went at him a little bit and said, “You’re making a skateboarding film. You can’t be dressing like this, all right? You’ve got to seriously get your shit together?” 

So they were casting, and a lot of us went in and read for a couple of the main roles. I remember my boy Hackett had been studying acting with Sean Penn and could really act. He was a skilled motherfucker, and he wasn’t really interested in doing something lame or bad. As they were auditioning him for one of the leads, in the middle of his audition, he stopped and said, “You guys are the worst. I’m out of here,” and got up and split. Then the rest of us got on, and we became the Daggers. There was myself and Christian Hasoi, Tony Alva, this guy Munsky, Mondo, Johnny Ray, Masal, Steve Stedham, Jesse Martinez… it was an eclectic group of all different ethnicities in the Daggers. Then there was the ramp locals, which were the good guys, and that was Josh Brolin, Josh Richman, Brett Marx from the Bad News Bears and a couple of other guys. It was so fun! It was one of my favorite things we ever did.

I remember at one point in the film, I did a lot of stunts. I had gone around doing location scouting for the big fucking grand finale race, and I picked all these areas that visually looked cool and gnarly enough or sketchy enough. The first day of the race, we got this place and just said, “This is totally unsafe, and everyone here is going to race each other whether you want them to or not. It’s dangerous, man.” 

A lot of people got fucked up, and I broke my wrist on that day. I remember saying to them, “Who’s going to pay for this because I wouldn’t have broken it if I wasn’t working on your film?” They kind of blew me off. Someone said, “Yo, call SAG,” so I did to make sure I was going to get the hospital bills paid since we weren’t getting paid that much to cover it. I explained everything, and they said, “Well, they’re breaking all these rules, and how much are you getting paid?” I think we were getting 150 bucks or maybe 200, something like that. So they said they would handle my case and take them to court for all of it. I was thinking, “Someone’s actually going to stick up and fight for us?” 

When I came back to the set, the production called me to their trailer and offered me a third of the amount the union said they were going to get [for us]. So I refused to fucking take their little piddly offer and walked out. Then all the Daggers got pay raises and checks, and it was cool.

Since you’ve been constantly on the front line of skateboarding, you saw it grow and evolve. Now that it’s becoming an Olympic sport, how do you compare this phenomenon to when you were the most active?

I’m kind of down with it, but I’ve always hoped for the best and prepped for the worst. I think it would be cool if it’s done right, but I just don’t think the people doing it will do it right. They’re just lames. But it’s cool if some little kid sees it on TV or wherever and then starts skateboarding and finds the groove, and that’s the beautiful thing of it all. I mean, I remember wanting a gold medal. When I was skateboarding, I was like, “I’ll train. I’ll go. I want a gold medal. That would be cool to have.” 

I love these new skateboarding kids. They’re so, so great. And my son is a professional skateboarder so I have a legacy with my son in skateboarding. 

What do you think has changed, and what has stayed the same?

It hasn’t changed, it just progressed. You can’t make a comparison with the skill level of skateboarders now compared to then because it’s not fair to us, the pioneers, because we were breaking down the walls then. They keep breaking down the walls, which makes it that much better. 

But they’re so, so, so good, and the degree of difficulty with which they perform is mind-blowing. I’m so impressed. I’m going to Copenhagen in a couple of days to a paid event, and it’s just so fun to cruise and check out these kids. I’m friends with a lot of them because I think there’s a common thread between us, like “Oh, this guy is an older dude, and he still skateboards and did whatever he did in skateboarding,” which they have no idea of. I’m so excited to go to this next competition with my kid as well. I’m fucking lucky, and he’s lucky. He works hard at what he does. It’s not like he got in because he’s my kid. He fucking can do it. Maybe it’s in his blood. I don’t know. 

Truly, I’m on edge watching them skateboard, which means something cool’s going down. I don’t want to see someone get hurt. They’re pushing it so hard, and it’s just like, “Oh please, don’t slam.” Then they slam, and you think, please don’t be hurt. Okay, they’re a little hurt, but not seriously. But yeah, I dig it.

Art has been a part of your life for two decades or so. How did you transition into doing art for a living and skating for fun?

I skated for fun, and it turned into a profession. I liked art, but my brother was truly a gifted artist and beyond, so I was around it as well. I was going to high school and taking art classes just because I figured, oh, it’s an easy A. Then I would get an F because I wouldn’t do any of the assignments. My brother was the artist, and I was the jock. Not jock, but I was the guy skateboarding and surfing and stuff. But he also surfed and all that. 

I would create art periodically, and I was hanging around with artist friends. One of the first things I made—we were having a little get together at my friend’s house, and a couple of them were serious artists—was an ear out of clay. I painted it like it had moss on it. It looked like it had just dilapidated, like this beautiful decaying ear. I had just seen Blue Velvet where they find an ear at the beginning of the movie. So I wrapped blue velvet around this thing and then mounted it into a golden baroque frame. My friends thought it was cool and asked me what it was called. I was like, “Oh, it’s Do it for Van Gogh.” 

So there were these artist cats from Southern California, from a foundation called Surfrider Foundation. They tried to do fundraisers to clean the ocean. So they gave me a surfboard to do whatever I wanted, which they would later sell to raise funds. I remember I often went to the junkyard here in LA. They had these emblems, and there was this one that said “Futura” with this really dope looking font from Ford. So I wrapped the canvas with this vintage leopard skin, and then I elevated the Balsa Wood surfboard thing. So it was floating above the canvas, and then I mounted the Futura on top of it. One of my friends, this artist guy I love and a dope ass cat, loved it and bought it. 

Then I made a couple more pieces. A woman came by my place and really loved a piece. It was this white fur wrapped around where I mounted an emblem from a 1959 Cadillac. She asked me how much, and I said, “Five grand?” And she’s like, “That’s it?” And I’m thinking, “Oh my god, I’m an idiot.” Either way, she wrote me a check on the spot, and I was so in, thinking, “This game is my game.”

Anyway, that’s how I got into it, hardcore. From that point on, it was done, I was in, I was hooked. It was more like an assemblage than painting or drawing or any of that. I think anything is obtainable. If you are in it and you want it and you have a passion for it, you can learn it. It’s not about selling, it’s actually about producing. If you make a piece of art, you’ve successfully made a piece of art. My friend taught me that.

A few years ago, there was a controversy surrounding one of your pieces.

In maybe 2014, 2015, I was doing a show at a government building through the Santa Barbara Arts Council. It was with this little collective called Love and Guts with some other skateboarders that make art. So I did a piece called Buy Sexual where I took price placards that said “69 99” and wrote over it with “Buy Sexual.” The curator was totally down with it. It’s kind of a social commentary piece, like “sex sells,” but at the same time, there were big things going on with same-sex marriages. I found that to be funny, like, what’s the big deal? If two people love each other and want to get married, that’s great. And then maybe they get divorced. 

They hung my piece front and center, and the fifth district supervisor was so appalled and so offended that he had his assistant remove it from the wall and put it into storage without asking. I’m like, “I don’t really give a fuck, big deal.” So the guy has bad taste. Who cares?

Still, him touching it and removing it from a government building meant he had broken the First Amendment. The people from the arts council were livid, and it became this huge deal over this stupid thing. Another guy even said I was promoting sex trafficking. They were out of their minds, just positioning themselves to be do-gooders to get fucking re-elected again. So they had to go to court to have this piece put back up on the wall. This guy also had a petition for keeping it off the wall, so we did the same to keep it up and had so many signatures that the judge said, “The piece of art goes back on the wall.” They spent thousands of dollars to fight for this stupid thing. What a joke. 

There was a Q&A, and I hoped this guy would show up. I would have loved to explain to him what it’s really about. I was sure by the end of the day he would be my friend and understand it had nothing to do with anything but social commentary. The spineless little bitch didn’t show up, and it went on. Now I have a beautiful fucking story about fighting for the right to freedom of speech.

You recently took up painting. What drew you to the medium?

Yeah I did! I called my old man one day, and he said my mom was sick and in the hospital. I went out there with him, driving them back and forth and hanging out with my mother and making sure my dad was cool. I remember she was always really, really supportive. Then a couple months later, she died.

I thought I’d go insane if I just sat around. So I moved his cars out of the garage, I put up a table and I went down to an art store, bought some art supplies and started painting with rags. The stroke and the lines and how the paint came off the rags were really amazing. I just got into it, and I think I produced probably 400 to 500 of them during that time. I remember taking a couple to my mom. She couldn’t talk because she had a tracheotomy and she wasn’t really there. But I remember her eyes would light up, would get a little wider, and I would just sit there and hold her hand. I didn’t know if she always really knew who I was, but she was always so supportive and said, “Steven, you have very good color sense.”

That’s when I started painting, when my mom got sick, and from not losing my mind. Then I did a bunch of rag pieces and got into the fucking squeegee thing. The way it bleeds and what happens after you’ve spread the paint is really dope. I can work anywhere in the world now and not have to worry about anything but supplies. 

You’re currently an ambassador for Learn & Skate, a non-profit dedicated to bringing skateboard culture and education to developing countries. Tell me something about this collaboration.

I saw this artist from Paris. Someone sent me something of hers, and I started to follow her, which I don’t do often. Then I saw her paint a skateboard, and I saw Learn & Skate, a foundation bringing together skateboarding and art. So I took the initiative and hit up Jean Claude who’s running it: Jean Claude, the secret agent from Toulouse. (Laughs.) 

He said he couldn’t believe it was me, and I told him how interested I was in it and that I was in Paris. I just liked what he was doing and went with my intuition. So I went to Toulouse where they were doing a fundraiser, and I met him. Sometimes you do good things when you follow your intuition.

Jean Claude is just fucking awesome, and I don’t use that word. I was really excited to go down there, thinking he didn’t know what he was getting into dealing with me, but that I could help in many ways. So he asked me, “Will you be my ambassadeur?” and I was like, “Wow. Really? Okay, yeah, on one condition… that you make me a badge that says ambassador.” I’d put it on my suit and wear it to all the meetings. (Laughs.)

I’m so down with his whole program and the foundation. He’s doing it because he wants to. He just feels it. I get it. I mean, I feel it, too. I’m down with Learn & Skate, 100 percent. And it’s not about making it gigantic. We just want to build places for kids. I think we need to have a lot more things like this.

So you’re in Mongolia now building a kids cultural center? 

Yeah, we’re going back in September for the opening. Jean Claude’s there with some artists now. Then we go out, get people behind it to support it and that’s where I can help. Just to be involved with the industry and for all the right reasons. It’s not the only kind of organization in the industry, but the way it combines the learning center, art and skateboarding is really amazing, and Jean Claude does it because he fucking wants to do it, not because there’s some pressure to give back to the community. 

I met a bunch of cats down in Toulouse like skateboarders and a lot of graffiti artists. I don’t know many graffiti artists outside of Los Angeles and New York, but it was such a great scene. I was so all about it. It was just amazing to me. I’m also going to help him do some art with kids in a whole different way than he’s ready for. The kids will love it. I’ve done it in the U.S., and they freak. It’s really more of an introduction to paint than like drawing a fucking [Claude] Monet landscape.

What kind of workshops did you do?

One time I was out on some residency bullshit, and they asked me to talk to some kids at different learning centers and classes. I said I’d do it, say hello, and get into doing something. So I built some stretcher bars and brought paint from the regional art center. There were probably about 20 of them between 6 to 12 years old. I was sitting in one of the chairs, and this little girl sits down next to me and says, “Mr. Steve, I just got to tell you, I love splatter painting.” I was like, “Wow, little girl. We’re going to make a couple of big splatter paintings.”

So I mixed the paint in little dixie cups, and I ran and threw it from about three feet away. The kids were not paying attention, and all of a sudden the fucking paint hits the stretcher bar and makes this crazy sound, which totally fucking stops them in their tracks. Then a little kid throws the paint, and it makes the sound again, and he is exuberant. He is so out of his mind about throwing the paint because he can, and then it just got crazy. We’re painting and painting and painting, and they’re just throwing paint. It’s doing what it’s doing, whatever it is. 

Then I see these kids, and I walk over to them. They’re probably like 15, 16, and way too cool. I was like, “Yo. I get it. It’s lame. It’s not that cool. But let me tell you, I’ll be straight with you, it’s fun. It’s some kind of release when you chuck the paint. So, you can do it or not. I don’t give a fuck. I’m going back with the kids, and they’re way more fun than you guys because you’re not that cool.” And I split. We kept painting, and then I saw them, and they started painting. You could tell they didn’t want to be into it, but they were. We just went crazy and had the best time.

Then I went back and painted with a bunch of schools a year or so later. I painted with little kids, homeless kids. They were the best. They were so grateful just to be able to have the time. And there were special needs adults, too. That was fucking beyond! That was one of the best things I’ve ever done in my entire life. 

I also went to a couple of rock concerts and painted with kids where I just put paint on canvas and then they run through it with their white t-shirts. I did it in Louisiana as well with about 1,500 kids, and it was fucking insane! That’s like the funniest stuff to do.

It sounds fun and rewarding as well!

Oh it is! Totally fun! Kids are way more fun than adults. They’re just real. They’re in the now.

What’s next for you? Any plans you would like to share?

Oh, I have tons of plans! For example, I’m doing a sculpture [this month]. It’s a bicycle guy upside down mounted on a big giant wall⎯one meter by three meters high⎯and it looks like it’s falling over on you. But the structural support and all of that engineering can hold thousands of pounds. It’s going to be sick.

I just like making things, and I’ve been making things forever. I made skateboards when I was in junior high school because we couldn’t afford to buy a $40 skateboard. That cost way too much money. And yeah, you just learn. If you want to do something, you can figure it out.

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