Check Out/Check In: Simon Woodstock



Welcome to our newest online column, the Check Out/Check In, aka the “COCI” as masterminded by our humble Ad Sales Rep/Wilderness Correspondent David Jurusik. The concept, as you probably already guessed is pretty simple. Check in with somebody who has had a “Check Out” in the mag over the last 35 some years. First up, I tracked down the one and only Simon Woodstock. If you haven’t heard of Simon ask your older friend who skated during the late ‘90s. Simon was pretty hard to miss. He was the dude kickflipping a skim board in a clown suit. Here’s what he’s been up to since May 1992. Enjoy the ride.

Intro and Interview: Mackenzie Eisenhour


His Check Out as it ran in our May 1992 issue, Vol. 10, No.5. Photo credits to Lucero but apparently Simon knows better.


ME: Do you remember first seeing your Check Out (May 1992)? That was a while back.

SW: (Laughs.) Yeah. That was a fun era. Back then the “Check Out” was like a big deal. The scene and the media were just a lot smaller. There were maybe a hundred decent street skaters in the world. And if you had a Check Out that was like the one-step coming up. I had already been doing a little bit of writing for the mag. I had written (John) Cardiel’s Check Out.

I scanned your Intro where you had the First Words too with the one-foot photo. I read that when I was a kid. I was a fan.

Oh rad. Yeah, that photo has been buried forever. Awesome. But yeah, I kind of knew mine was coming out. Then let’s be honest, it was pretty indicative of a lot of my career to follow. The photo was pretty rigged (laughs). The photo was actually shot by Mike Ballard, not Lucero. He was kind of on the fence with TransWorld at the time so we just lied and said that Lucero shot it. But later Ballard shot my Pro Spotlight. But for the Check Out we said that Lucero shot them and I think we even had Lucero send it in. I’m not ollieing into the noseslide/tailslide of course (laughs.) I propped myself up there and slid down that way.


Simon’s “Spur of the Moment” Intro from our Sept. 1990 issue. One-foot photo of Simon shot by: O.

I still think it showed the intent though. Sometimes it had to be faked first on a lot of stuff.

Yeah. That was on the cusp back then. That stuff has exploded now with people doing those. But back then we kind of faked it and left people wondering.

How did Salman Agah end up writing it? San Jose connection?

Oh yeah. We skated together all the time. I might have moved to Huntington around that time for a while. But before that, that was sort of our inseparable crew. I’d meet up with Salman (Agah), Jason Adams, Tim Brauch, Shawn Mandoli, and Ed Deverra. That was sort of our core group.

What was your sponsor run from Black Label to Sonic? Was Black Label your first hook-up?

Oh bro. That’s when I had the trifecta. I was on Black Label. I was really trying to get John to turn me pro. He even said that he would but it just didn’t work out. I was still on Spitfire. And then I think I was still on Thunder too. I might have been on Indy. But that was like the promised land as far as sponsors went for ams right then.


Simon’s “Big Business” Black Label ad. TWS, August 1991, Vol.9, No.8.

The Black Label am roster was pretty heavy right then right? Was Gino on and Dill? Cardiel?

Yeah. I was am. Jason Dill was am. Gino was am. Cardiel had just gotten on as a pro. Yeah, it was a sick team.

Did you turn pro for Sonic?

Yeah. John had given me a verbal agreement that I was going to turn pro for Black Label. And I had actually moved down to Huntington Beach to try to facilitate that. Which in hindsight, maybe I should have just stayed where I was at in San Jose. Then no on would have gotten to know me. Anyways, John and I sort of came to a point of mutual disagreement. He was sort of dragging his feet as far as turning me pro and finally he verbalized it. I had marketing ideas and stuff like that for the company but I think Lucero just wanted to be in control.


Early photos of Simon (Poweredge) in the clown suit shot by Mike Ballard in 1989 as published in Big Brother, No. 14, 1994.

When did you sort of transition to the “clown” persona?

It was always sort of there. I had sort of always had both personas. This guy Brian Callahan had actually given me a clown suit that I wore in a Powell Am contest maybe in 1990 or 1991. We shot some photos in it that ran in Poweredge. So I was kind of always doing that stuff.

When did you get your Vans shoe?


From around ’94-’97 you seemed huge in skating. You were all up in every Big Brother and 411. Did you kind of embrace the clown side at some point? I know you’ve also mentioned a lot of it was tied to drugs and alcohol.

Yeah. I would kind of do the “boozy the clown” thing. I don’t know. It was sort of like an Andy Kaufman thing. Like, “Is he for real or is he fake?” At the end of the day, I was pretty conscious of everything that was going on. I had picked up like a street level understanding of marketing at the time so I sort of knew what I was doing mostly. But at the same time I was becoming delusional (laughs.) On drugs, alcohol, and life in the fast lane.


The Wallenberg Big Three ollie on a skim board. Gnarly by any measure. Photo: Vuckovich, TWS Feb. 1994, Vol. 12, No.2.

I always thought ollieing the Wallenberg three on a skim board seemed genuinely gnarly. A lot of the “joke” stuff you did actually seemed to require some skill. How did that go down?

I’m glad you mentioned that one. Here was the thing with that one. You have to put yourself back in that context. People were hardly skating Wallenberg at that point. Gonz had done the ollie grab. They hadn’t even had an informal like 50 dollar to the winner contest yet. But basically, there was the Back to the City contest (1993) in San Francisco and the rumor circulating was that (Kris) Markovich was going to go kickflip Wallenberg. He was telling people like, “I’m gonna do this. If you guys want to come see come watch.” So it wasn’t even like an organized event. I hardly even knew where it was but I caught a ride over with Joey Tershay or somebody and everybody is just standing around. Markovich hasn’t shown up yet so people are all just standing around maybe slappying the bottom curb or whatever. So it was sort of like when you go to a nightclub and nobody is dancing and there’s one guy that’s paid to go out and dance so everyone else starts dancing. I felt like I had to start it off. So I figured maybe I could make it down the three on the skim board. Maybe it would just float down like a wing or something (laughs). I think it took like eight or ten tries. I took some serious hippers. People were telling me to go for the four but I think even I knew better (laughs). Right then Markovich showed up so it worked out perfect. (Ed note: Markovich landed on the first kickflip down Wallenberg that day but didn’t roll away.)


Kickflip sequence from the Back to the City contest in SF prior to the Wallenberg ollie. Footage: Socrates from Big Brother, No. 8, 1994.

I always thought it was gnarly. And skating was sort of in this dark place at the time with little wheels and all these rules. I thought you brought a breath of fresh air just from the fun side of it.

Yeah. Thanks man. I know what you mean but beneath it all there was still a lot of great stuff going on right then. Cardiel was at the height of his game. You had Wade Speyer and Phil Shao. Tim Brauch was always one of my favorites. But then in SF and LA you definitely had the cool cliques. But we all got along too. I would go to the tradeshow and kick it for one minute with Danny Way. We would have our annual Ozzy Osborne vs. Ronnie James Dio debate. Then I would see Kareem (Campbell) and we would talk about marketing or something.

It seemed like you were doing really well for a number of years. Was there a “Rise and Fall” arc? I know people have talked about the legal troubles with Rocco later in the ‘90s.

Yeah. That’s a whole other thing. That was just a non-truth. I pretty much just left on my own.


The “Fishtank Cover,” Big Brother, No. 14, 1994.

Where you back on Sonic after Woodstock skateboards?

I had gotten back on Sonic and they had reissued some models. I had left to do my own thing, and that didn’t really work out, as you know. So I was back on Sonic and they were kind of relying on me to revive the company. I knew that and just signed on for the paycheck more or less. But I had lost all motivation by then. I had wanted to see Hawk do the 900. Word had gotten out that he was probably going to try it at that X-Games (1999). So I drove up there by myself. I was already kind of thinking that I wasn’t doing right by the Sonic guys. I figured they would kick me off. I was already thinking that. Then when I got to the X-Games, it was right by the water in SF and it was just weird man. I had a hard time getting in. I think I paid to get in or somebody snuck me in. Then I couldn’t get the VIP pass. I was like, “Whoa, it’s like I’m not a part of this anymore.” Long story short I snuck back to where the vert ramp was and saw Tony Hawk do the 900, like 15 feet away from me. Everybody runs out on the flat. But for some reason I stayed back. I probably should have run out and hugged him. I was wearing my leaf suit and it would have been cemented in skateboard history (laughs.) But for whatever reason I just stayed back. This meathead guy with a mullet came up to me right about at that exact moment and was just like, “Hey, if you don’t have a wrist band, you don’t belong here.” Normally I would have kicked him in the shins or made Vallely fight him, but instead I just looked back at him and agreed, like, “You know right. You’re right. I don’t belong here.” I got in my car and left and that was pretty much the end of my involvement for many years.


Sonic Skateboards ad from Big Brother, No.14, 1994.

You got sober around then too?

Yeah. It was all in that transition. I had stopped drinking and doing drugs but I was still sort of hanging out in that world. Then I came to faith. God just providentially saved my life. I was going down a pretty bad road at that time. I had burned a lot of bridges. So now I speak to you as a Professor of the philosophy of religion at an undergraduate bible school in Murrieta.

That’s rad. Yeah, last time I talked to you was maybe 10 years ago. We did like a “Skaters and Drugs” article in Skateboarder and I think you were just getting into it.

Oh yeah. Praise God man. I came out of that delusional mindset and it was a long process and I’m relatively clear in my thinking now. I did two undergraduate degrees and then two masters degrees. All essentially in the philosophy of religion. So I do a lot of stuff here. I’m helping with the Library of science and organization. I teach essentially a logic class which I’m teaching tonight. I do missions. I’m getting ready to go back to Uganda, Africa in a little over two weeks. I do missions and outreach. I’ve taught some military chaplains over in that area. We also teach literacy out there.


Another old photo from 1991, as published in Big Brother, Photo: Ballard, No. 14, 1994.

That’s a far path from the Simon Woodstock of my youth.

(laughs.) Yeah. Praise God man. I was actually reading something Theo Hand had written about Lennie Kirk the other day. It’s funny because people are kind of quick to dismiss Lenny’s religious path. It’s a lot different than mine. I did a philosophical type of thing. His path was obviously way different. But the story was that Lennie had gotten a ride from Theo over to the Mission District (in SF) to preach but everybody spoke Spanish. So Theo was bummed anyways that he had driven over there and they left and ended up going back the next day and all of the sudden Lenny was speaking and preaching in fluent Spanish. Theo was like, “What the heck.” So Lenny tells him, “I prayed all night last night that the lord would enable me to speak and preach in Spanish and he did.” (Laughs.) I guess we are both testimonies in our own way.

Well, he’s still in jail. So I don’t know how much of a testimony that is.

Yeah. It’s hard man. I’ve dealt with that a little bit too. If you do certain things, you foul up your brain chemicals. How the firing and synapse in your brain interacts with your soul. It monkeys with your free will and decision-making. It’s tough man. Good luck Lennie.


The infamous “Contract Negotiations” ad. Woodstock Skateboards, circa 1998.

Back to the Rocco stuff, since people always bring it up, from what I understood you had started Woodstock skateboards and it was doing pretty well until you ran the infamous Rocco “Contract Negotiations” ad?

The bottom line on all of that is that I left skateboarding on my own volition. I wasn’t forced out. There was a whole list of companies back then that got into problems. XYZ or Sheep Shoes or whatever else didn’t make it. You just have these secular, hedonistic people in sort of an anything goes capitalistic environment. We’re lucky we didn’t have more casualties than we already do. It’s a dog eat dog, drug eat drug world. But yeah, I had done my own company, and I had done that ad to try and garner some negative attention. I was in communication with Steve (Rocco) almost the entire time. He wasn’t trying to run me out of skateboarding. It was almost like a fatherly thing, because we talked about it. He was like, “I know that people probably think this is a good ad Simon. I’m not mad at you. But you can’t do this. You attacked my brand.”

Dog eat dog like you said. He just had the power to swat your ad down. Even though he had done the same thing to Powell and Vision.

Yeah, he had just gotten sued for fifty grand or something by Disney the week before. I actually ended up befriending his lawyer throughout the process and his lawyer ended up helping me out with some other stuff down the road. It’s one of those things where the public perception of it was totally different from what went on behind the scenes. If people want to be convinced that he ran me out of skateboarding, that’s probably a better story than the real story anyways so they can believe whatever they want.


Bikini slider in San Jose. Photo: Kosick, Big Brother, No.6, 1993.

You also had famous boxing stand offs. I saw you later boxed Sticky Fingaz from Onyx and Mike Muir of Suicidal Tendencies. Was this all media hype or are you genuinely into boxing?

Those were real matches but of course they had this whole promotional side to them too. How we didn’t wind up in prison for racketeering for doing those is incredible. It’s totally illegal to do anything with boxing and charge anybody without going through the proper channels. We didn’t know or care back then so it was what it was. There was talk of me doing one with Mike Youssefpour but at the time he had a physical issue, like his nose was broken or something. So that fell through, then Vallely and I had talked. And it wasn’t like a wuss out thing or anything. I was kind of getting over dealing with MTV and all that stuff by the time Mike was still ready to go at it. He would tell me in a friendly way wherever I saw him, like, “Any time, any place.” In order to fight Mike I would have had to bring my triple A+ game to even have a chance. But that one never happened. I had talked to Brock Little, the big wave surfer who just passed away but that one never happened. We tried to get Henry Rollins but never got a call back.

Did you win most of the ones that happened?

Yeah. I was 3 and 1. 3 wins, 1 loss. This guy Paul McFadden was the only loss, he sings for this band called All Day. It was sort of a Long Beach thing. He’s still around. We actually just talked about it the other day. But he was just a bigger, better fighter that night.


Double truck flipper, Big Brother, No. 14, 1994.

You beat Sticky Fingaz and Mike Muir?

Yeah. I guess I was having better nights with those guys.

Did you train at boxing seriously?

Oh yeah. I was at a gym called the American Kickboxing Academy in San Jose which was small at the time but now they’re pretty well known. Javier Mendez, the owner of the gym trained up Kimball Vasquez and this guy Cung Le. A lot of the modern elite superstar fighters have come out of that gym. But I started out there when it was kind of a hole in the wall.

Do you ever roll around still?

Man, you caught me right at the end of a phase. I started again in 2012. I did some demos over in Ethiopia. Then I kind of caught the bug again. I even started doing some custom board fabrication. We documented a lot of it too. It went to kind of a certain level. I had a thing on the Ride Channel. It got a good amount of views but not a million. Then my good foot started to hurt again worse than my bad foot and I was like, “I’m gonna buy two guitars.” That was my trade off. I’m studying the methodology of Andy James right now—he’s one of the world-renowned shred guitarists. I’m going through his stuff right now. That’s my outlet.


Thanks to Simon for taking the time to talk and for his contributions to skateboarding.

Stay tuned for more COCI’s.




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