Tom Penny has amassed a cult following over the years that borders on something of a religion. For those of us who witnessed his maiden voyage assaults -- either on video or firsthand -- back in the early 90s, his Midas touch and supernatural reign over skateboarding are a given of biblical proportions. Tom was like urethane that fell into in a box of clay wheels. Once he landed, skateboarding could never go back. Any questions are null and void. Yet, for the younger readers out there, looking back today and wondering exactly why old men far and wide see God's gift to skateboarding in a soft-spoken, bearded, XXL-clad nomad currently residing in Argentina -- or is that throughout Europe? -- I can understand, or at least pardon, some confusion. As the trite expression goes, I guess you had to be there. The following dudes were.
Describe living in Newport Beach, with a beer sponsor and Tom.
[Laughs] Yeah. Man, basically a month after I met him we were both on TSA and ended up living together. TSA's owner had a house right on the beach with one room available. We both moved into the room with our mattresses on either side of it. I was so psyched. It was the first bed I'd had in like six years or something. From then on we just skated together, partied together, and chilled pretty much every day. He started filming for the etnies video, the TSA video, and Flip, and I was filming for Welcome To Hell (1996). It was rad to just feed off of each other.
What does the kid that's scratching his head and furrowing his brow over why the Penny legend is so big need to understand?
At the time that Tom started on the scene, it was just unimaginable to see the kind of progression he was bringing to the table. Nobody was doing the things he was doing. Not even close. People might look at it now?they might look back and not realize how insane it was. Because these days that stuff is normal in skateboarding. But back then, nobody was kickflipping over ten-stair handrails. That was just something like, "Holy sh-t!" It just blew you away. Like the rail in Huntington?I think it was a twelve-stair at the courthouse across from the skatepark. I remember just being there and seeing him frontside flip over that thing. I couldn't believe he did it. You'd watch him rolling away and it still hadn't registered in your brain.
What about his demeanor?
Yeah. Damn. That was pretty much the craziest part of it all. It was almost like he didn't know he was doing anything special. None of it was conscious. Nothing he's done has been conscious [laughs]. It's just all-natural. His whole life is like that. I remember we'd be at Huntington Park and decide like, "Hey, let's go to Ed [Templeton]'s house." Then on the way to Ed's house we'd pass by these random sets of stairs that were f?king huge. We'd be walking up to them and I don't think he even looked at them first?he'd just roll up and kickflip 'em first try. He'd be rolling away and you'd be like, "Oh sh-t, I better pick my board up and walk down these stairs [laughs]." That was just all the time. Anywhere you went he would just bust something?no cameras, nothing. None of it was ever planned in any way. It was never like, "I'm gonna do this and I'll get this cover and be a superstar." It was just, "Oh, there's an obstacle in front of me and I want to do this down it." Boom. "I'm just doing it."
The TransWorld front blunt cover was forever debated whether he made it or not. It almost didn't matter. It's not like he'd stop trying a trick because he slammed. It was more like he just got bored.
Yeah. For the record, he didn't roll away from that. But that was Penny. I mean, most people were shooting photos of 50-50s or five-0s on that thing. Just to get into a front blunt and slide it that casually was amazing. He just did things or he didn't. He wasn't going to go back and force himself to do something. He just did what he felt. He didn't go back to do the front blunt. He just didn't care.
Was Tom's approach to skateboarding there from the get-go?
Absolutely. He must have been about fourteen when I saw him at Harrow. It was around '91. He was already pretty gnarly and smooth at a real young age. It was definitely baggy-pants, small-wheels days, so he was little bit lost in his clothes. But everybody was already aware of him in the U.K. It might be fair to say that it all kind of came together for him at Radlands '93. There were all sorts of stories even from that where he showed up, did his one run, and left half way through the comp. When he won, they had to call him to get his mum to bring him back to find out he'd won. That was just sort of the way Penny was. He was nonchalant. He sort of didn't realize?I don't think he's ever realized the impact he's had on skateboarding. He never thought about it. Everything was just natural. Were his lines thought out before? Probably to an extent based on what he'd been doing in practice. But none of it was premeditated like, "Right, I'm gonna do this here, then hit the hip, then hit the pyramid." It was just flow.
You were at the chain-to-bank?
I do want to say that was probably the last time I ever filmed. The switch backside flip was probably the absolute last trick I ever filmed. I remember getting back to the office and they were like, "Where are the photos?" and I was just like, "Sh-t." I just knew I was witnessing something special and I thought it just had to have two angles. So just based on how insane that moment was I made a decision to make sure it got documented. It was more important than my job as a photographer. That's how much we knew it meant to skateboarding.
Describe the Earl Warren downhill line. Back tail ender on the rail.
Mind-blowing. F?king mind-blowing.
The beauty in that one to me was that some other guy could have done the same line, as gnarly as it was. But another dude would have been running through the first couple tricks and you'd just see the stress start to kick in like, "Okay, I got the kickflip down the three stairs, now here comes the rail?tense up, get ready." But with Penny it was just in the now. He's just messing with a switch ollie, messing with a switch flip, big switch 180, kickflip the stairs, and then, "Oh, here's a rail. Guess I'll back tail it. Sounds fun."
Yeah, right [laughs]. Like, "Here we go. I'll just let the board do the work."
It's like the combination of his la-de-da composure with the difficulty of the tricks that just baffled me. Have you ever seen another dude that you could put in a similar class?
I don't think there is really. I mean, Chad [Muska] had that going a bit. Jeremy Wray was doing monstrous things, and [Andrew] Reynolds was pushing the limit, but Tom's demeanor was just unique. The other thing with Tom and really all the Flip guys when they came over was that they were absolutely unfazed by contests or demos. That's just what they grew up skating.
In those days he was clearly leaps and bounds ahead of anyone else. But it was that kind of unconscious approach that made it just impossible to comprehend. How do you describe his approach?
Well, the people that knew him knew it was natural. He wasn't trying to be cool and look nonchalant. He really did skate like that naturally. Left to his own devices, that's just the way he rolled. He was insanely innovative, and it just seemed to come from somewhere deep inside him. He single-handedly opened up a whole new realm of street skating that at that time needed to happen. The constant drive that everybody started to have after that almost came from the push he brought to the game. He was a wake-up call to skateboarding, sort of reigniting the flame [Pat] Duffy had lit with his Questionable  part. He made it okay to make an effort again -- it put some balls back into the mix.
Give the story of the Cheech and Chong graphic.
At the time, all the graphics we were doing were very early comic book. Tom loved Cheech and Chong for obvious reasons. He's had a bunch of rad ones that he's brought to Flip. But that one, along with the mushroom board, is probably the most iconic. We winged it at first, then eventually they found out. Cheech Marin was rad enough to continue letting us make the board as long as he got some royalties. So we actually still pay him on a monthly basis. Cheech Marin has been on the Flip payroll since 2000. So you can thank Cheech for that graphic or it would have been long gone. It came out in '96 and is still one of our best-selling boards today. So that's thirteen years strong. Cheers, Cheech.
Tell us about the San Dieguito rail assault [High Five, '95].
Oh man. The switch flip. It's unexplainable. That whole thing is just like the Penny package. It's like a display. Not many people have got kickflip, frontside flip, switch frontside flip, and switch flip all looking exactly the same. It wasn't even really that common to do tricks over handrails at that point. He just killed it.
What about Chicken's pool [High Five, '95]?
Oh man. I have to tell this one [laughs]. I went to Chicken's pool this one time to skate and just thought like, "I want to try and frontside flip where he got the little hip," you know? He did the kickflip back tail and then he just went down and did that kickflip stuck to the wall over that hip. I figured I could frontside flip on a quarterpipe, so I should be able to frontside flip this little hip right? I tried it, and seriously every time the thing would just shoot me out to the flatbottom [laughs]. Like completely out of control. There was just no way I could do it. After that I was just like, "I don't get it." His was just this delicate little thing, just stuck to that wall. Flatground and vert are like the same thing to that dude.
The article is called "The Church Of Tom." Is it fair to call you a disciple?
[Laughs] Hell yes. We got to spread the word, man.
We've Got Apps Too
Get expert analysis, unrivaled access, and the award-winning storytelling only SI can provide — from Peter King, Tom Verducci, Lee Jenkins, Grant Wahl, Andy Staples and more — delivered straight to you, along with up-to-the-minute news and live scores.