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The Legend of Tom Penny

Tom Penny is an almost religious figure in skateboarding. You hear about the cult of Tom Penny, talk about his legends. Stories about him appearing out of nowhere, doing something unbelievable, and then disappearing into the ether, never to be seen again for years. You see breathless quotes from other pro skaters talking about how amazing he is. From his style to his demeanor, the way he carries himself both on and off the board, Tom Penny is truly a remarkable pro skater. Let’s take a look at his legacy.

Tom is from England, and started his career in the Radlands contests over there. Although he mostly grew up skating alone or with a small group of friends, his first few appearances were still pretty heavily influenced by what was going on in skateboarding at the time – tech stuff, multiple flips, that kind of thing. But you can see a glimmer of what we would become. There’s some style under there, and some switch and nollie stuff, which was still pretty new. In 1994, Tom got 6th place.

But the next year, in 1995, he won Radlands with a single run.

Skin Phillips said, “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.”

Soon after his win, he moved to the US. He was sponsored by Flip, which had started as Deathbox in the UK. He was also on Etnies, where his first full video part came out in High 5. Let’s take a look at it.

There are a few standout tricks here, like that switch frontside flip over the rail. Doing tricks over handrails was still new, and switch frontside flips were pretty new too. This trick alone could have been an ender.

Also, his switch flip was perfect. Not a lot of people could do them just as well as their regular ones, but Tom could.

Or how about this? The kickflip back tailstall was sick enough, but how about this ultra casual frontside flip over the vert hip? I remember seeing this video part years later and not really being impressed. But that’s because I was new to skating, and he makes it all look so easy that I couldn’t even comprehend the difficulty of doing something like that.

Who can you think of that has the best frontside flips out there? Think about it for a second. Did you say Andrew Reynolds? He actually tried to do that frontside flip at the same spot. Here’s what he says:

“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.”

Look, we’re 20 seconds into his first full video part, and it’s already legendary. His actual ender is a switch frontside flip down this double set. He did a regular frontside flip down it already, and that was good enough to make it to Transworld. A switch one was out of this world.

He also switch frontside flipped Carlsbad. Twice. The first time, he went alone. He had to go back and bring a filmer.

Around the same time, there was in the Industry section in 411, issue 11. Tom only has a few tricks, but just watch this line. Every trick is perfect, or better. His tricks that are a tiny bit sketchy are actually better looking than the perfect ones. Everything is super clean. And watch how he ends it.

A lot of people could probably have done that line. But notice how he keeps his speed going. He just goes with the flow of the downhill spot. He doesn’t push, he doesn’t do a speed check and get ready for the rail or anything. It looks completely unplanned, like he was just kind of messing around and he did it first try. And based on a lot of the stories I’ve read about him, maybe he did.

I’ll share one of those stories with you. There’s no footage from this event itself, but this is from a Transworld article from 2007:

Outside of his ridiculous footage during his early days in The States, one example of the types of urban myths Penny spawned was one that I happened to experience firsthand. In early ’96, West L.A.’s Hot Rod Skateshop had rented a warehouse downtown, built a pretty decent mini ramp, and threw a party to inaugurate/celebrate the whole thing. With jam-packed platforms and anywhere from two to four skaters dropping in at the same time, the session was extremely heated. With his trademark beanie pulled well below eye level, Penny embarked on his run-of-the-mill tranny destruction run, miraculously dodging the likes of Mike Carroll, SAD, and others as he casually cruised the ramp until he was alone. At pretty much that very moment, every light in the warehouse blew a fuse and the entire party was left in pitch black. However, through the darkness, the discernable noise of Tom’s trucks hitting the coping did not stop. For nearly a full minute, until someone found the fuse box by way of a lighter and some luck, Penny kept skating, either unaware, or simply unaffected by the lack of vision on the ramp. Precisely as the lights came back up, a stunned crowd watched in disbelief as Tom was frozen mid-frontside flip, floating over the ramp completely undaunted by either light or dark-sixth sense indeed.

Also in 96, Tom appeared in Transworld’s Uno, with some tricks on this bank spot.

Later, Rob Dyrdek talks about this event. Look it up in Transworld Anthology if you want to hear the original.

So they took Tom to this spot, which is kind of brutal. It’s steep, and it’s just the right length to send you straight to the ground. They thought he’d do his basic stuff, kickflip, frontside flip, and everyone was skating together. But he just didn’t stop, and did a nollie backside flip, going in blind and fakie. After a while, nobody else was skating because they were just watching this guy do everything he wanted within a couple tries. He does a bunch of stuff, then sealed the deal with a switch backside flip.

Crazy. ALSO in 1996, Tom got his first Transworld cover, although this is a little shady. This spot was pretty heavy. You might see a 5-0 on it or something, and here’s Tom with a front blunt. Completely unbelieveable… because it didn’t happen. He never landed it. These days, you wouldn’t really think about publishing a picture of a trick that was never landed, but they did.

But he was always super casual. If he wasn’t feeling it, he wasn’t going to force it. He’d just walk away and go do something else. One thing I kept finding is stories about how he didn’t really care about coverage or anything. He was always skating at video part levels.  Check out this quote from Chad Muska:

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 … 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.”

Tom was one of the biggest skaters in the world at the time, but he suddenly disappeared. Even his disappearance was casual.

But I remember this, even though I started skating a few years later in 2001. It was common to hear about Tom Penny sightings, like he was bigfoot. “Oh, he showed up at my local skatepark, did the biggest nollie flip I’ve ever seen, and then just left.” That kind of thing. Every now and then, pictures or video clips would surface, but you’d never know when they were from, or where they were. Always somewhere in Europe though.

He was completely gone from the public eye, and his sponsors had a hard time keeping track of him.

Like Sole Tech. They wanted to give him a pro model shoe. They asked him over and over for direction on what he wanted the design to be like. But he wasn’t answering. And supposedly, he had been skating around in the same pair of Timbaland boots for a year. Eventually, he sent the boot into to Sole Tech, and they did their sketches based on it. But it wasn’t actually a Timbaland like people thought. It was actually a Columbia hiking boot. The guy has a skate shoe sponsor, or enough money to buy some skate shoes, but he ends up in hiking boots. It just didn’t matter to him.

At one point, he was living right next to a photographer and a public park. He would skate at the park, and sometimes he would invite him, and sometimes he wouldn’t. Apparently he kickflipped the biggest gap there one day, but didn’t bother to invite him. So it just went undocumented.

Theo Hand: “He could have called me to tell me to come down there, and it would have taken me five minutes, and I was bummed that he didn’t, but I was never mad, because when I say spontaneous, I really mean it. “

But why did he leave?

There was always talk about him just being unhappy with the way skateboarding was going in the US. But here’s a quote from Tom himself: “I never really made any decision to leave The States or the spotlight. Right before I left, I was living with (Sean) Sheffey for a couple of weeks and he was like, ‘You’re not coming back.’ I was like, ‘Yeah, I am. I’ll be back in two weeks. I’m just going to the contests and then I’m coming back.’ He was like, ‘No, you’re not coming back.’ I went to all the Euro contests and just ended up in London. I saw all my old friends again and ended up staying there for a while. It just happened.”

Of course. He just wandered over there, and then he just kind of stayed there.

But I want to show you some of the crazy things that happened in Europe. Tom skated transitions and pools, but was never known for vert. But in 1998, he shot this picture: and indy 540 in a half pipe. It ran as an ad in 2000. And it had legit air too, like a full-on vert skater. People had been doing 540s in miniramps and stuff, but this is completely for real.

And according to Transworld, Tom said this was the first and only time he attempted a 540. And he never bothered to call up a filmer, even though he was filming for Menikmati at the time. And he actually made it pretty tough on himself: “I would drink a beer between every try. I think I drank something like eighteen Elephant tall-boy Carlsberg beers before I finally landed it. I manual rolled the flatbottom and manual rolled up the other side. It was pretty crazy.”

Yeah, there was a fair bit of drug and alcohol use around that time, but he says he really cleaned up around 2003.

Here’s another legendary one from the time. This is an unused clip from a line he was filming in 1999 in France. It’s a backside 5-0, backside shove it out. It’s a really low ledge. In fact, I could probably do this trick at this spot. So try to picture how that would look if you did it. Now watch Tom do it.

Transworld wrote a whole article about this invisible shove it. It looks like he was maybe about to go into a tailslide, but then he pulled it back. His feet never look like they leave the board, but somehow, it ends up landing backward. That’s just Tom’s style for you.

Here’s another one. This is Tom in 1998, doing an amazing 360 flip to fakie. Again, no video footage of this one. It was in Copenhagen, at a place called Christiania.

Here’s the story: [Magnus Gyllenberg] There were not many tries, only a few as I remember it. The guy is such a natural it’s insane. That roll in he’s skating is no joke. It’s a gnarly place to do those tricks, and the way he did them it was hard to comprehend. I’m not sure if he even noticed Jesper shooting. Jesper got two great photos—the 360 flip for the éS ad and a frontside flip that I don’t remember if it showed up somewhere. As far as I remember he made a couple of them (360 flips), maybe two or three.

Rumor is, he was mad when the photo ran, because he didn’t know it was taken. Or he might have been there to shoot the frontside flip shot for TSA, and the éS ad was poached. Either way, he was just casually doing these unbelievable 360 flips with no plan or care about it being used for anything.

That makes me think of my skating a few years back. I had a YouTube channel going, and I was always thinking about filming for a ‘part.’ Part of what? Nothing, just clips for YouTube. But it ruined a lot of my sessions. I would force myself to do stuff that was too hard, and fight through it until I finally got one really sketchy. Skating itself got to be really frustrating. Tom wasn’t like that. You could document him skating if you wanted, but he was going to be there doing that same stuff anyway.

Tom started to step back into the public eye around 2000 where he was in Menikmati, one of my favorite videos of all time. He was also in Sorry, Really Sorry and Extremely Sorry.

He moved back to the US with a permanent resident’s visa in 2006.
The parts that he put together in this time were amazing, as were his board sales. His Cheech and Chong graphic sold like crazy, and Flip ended up having to pay Cheech royalties when he found out about it. Geoff Rowley said it was one of their best selling boards for 13 years, as of 2009. But it’s been reissued even more since then.

After a few years in the US, it seems like he ended up back in Europe. You start to see his footage and pictures coming from over there. In 2015, Lucien Clarke mentioned in an interview that Penny isn’t allowed in the US anymore. I don’t know the story there. Maybe his visa got revoked or something? I’m not sure.

In 2014, he was in a video called Albion. It was shot on a VX, but this is actually pretty new.

He’s 37 here, and it looks like a lot of his signature style has kind of faded away over time. Although, because of his cult-like status, people will still argue this is the best looking skating ever filmed. I’ll let you decide.

Last year, he filmed some stuff in Chile. You never really know where he’s going to turn up. And it looks like he’s still rocking boot style skate shoes. His Supra model, which is called the Bandit, looks like this.

He also had a little section in the Supra video Oscar and Friends. At this point, it’s more about cameos than full on video parts. A couple months ago, he did a mini ad for ETN network while in Copenhagen.

So he’s definitely out there and still skating, at 40 years old. Whether or not he’ll ever come back to the US, or if he even cares to, time will tell.

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