When we got word from the Flip Team Manager that Tom Penny might possibly be down to do an interview, we sort of blew off the idea as a pipe dream. Through his extensive career, Tom Penny has not only been notoriously elusive on all kinds of levels, his legendary status and nomadic whereabouts have led to the creation of an almost mythical being. Sure we hoped like hell that it would go down, but we certainly didn’t believe it would or could ever happen.

Well, it did. With the help of the Flip crew, we got some questions to Tom, who came through and answered everything from a location that’s still uncertain to us.

Sit back, kick up your feet and absorb the words of one of skateboardings all-time greats…Tom Penny.

You lived in the states, France, London, Argentina. Why have you stayed in Barcelona? I’ve traveled all over the world and love all the places I’ve been to, but Barcelona and Cali are definitely two of my favorites. I’ve been going to Barcelona since I was 13 and always loved chilling and skating there. All the locals have always been really nice to me plus you got the sun, the beach, the skatespots, the nightlife…everything you need to have a good time. Cali too…you got the good weather, the skate spots the beach, the perfect lifestyle. Everything you need. Cali and Barcelona are definitely two of the best places I’ve traveled to. If I was going to get a crib, those would probably be my destinations. In Cali, probably LA and Barcelona…pretty much anywhere central except the Baghdad, Beirut hooker area.

You and guys like Gino Iannucci, have long been considered some of skateboarding’s most elusive and highly sought after skaters. Was it a conscious decision of yours to remain underground for so many years? I love Gino’s skating and always had mad respect for him as a person. And it’s an honor to be considered an underground skater on that level. I think it’s like Wu Tang’ overground, but yet underground at the same time. Out there in the videos and magazines but not so much [so that] it gets played out.

Have you ever felt pressure to get coverage from your sponsors? As long as I am skating they are happy. And I’m pretty much always skating, so it’s cool.

A lot of skaters have noted your Kickflips and Frontside Flips as some of the best in the business. Which skaters have a Kickflip and Frontside Flip that you really respect? It seems like everybody can do those these days, but I remember Kareem Campbell doing probably the best flatground Kickflip ever over one of those metal drum barrels standing up in a line, which included him checking his pager for a message halfway through, which was super dope. Then you got Jeremy Wray and Andrew Reynolds. They both do perfect Kickflips and Frontside flips. Kareem didn’t really do that many Frontside Flips but he had one of the illest Switch Frontside Flips out.

A lot of kids out there don’t know that you can skate vert. How did you start skating vert? When was the last time you rolled around a vert ramp? In Oxford where I grew up, we had a mini ramp complex with a 4-foot section, 6-foot section with a spine, then the 9-foot section…all built by hand by my friend Doug. The 9-foot section sort of went to vert so we would try to skate that like a vert ramp. Last time I had a vert session I tried to Fakie 360 Flip into a ridiculously big roll in. I knocked myself out and woke up at my apartment about an hour later with blood all over my eye not knowing what happened or how I got home.

Do you feel pressure to keep up with the younger skaters these days? Nah man, I don’t even look at it like that. I love skating and appreciate all the different aspects of skating. From little kids just starting, seeing them roll around and learning tricks for the first time…Then the newer generation doing all their crazy ledge trick combinations and the older generation, just seeing them carve around, smiling and having a good time. Skateboarding for life.

Growing up who were some of the skaters you looked up to? When I was young there wasn’t a million pros. There was probably only about 20, and I looked up to all of them, not only because I was mad small, but because you had to be seriously good to be a professional skater back then. I think if you had an award for best all-around skater of all time, it would have to go to Danny Way. Not just because he’s one my favorites, but because it’s pretty much just a fact.

Who are some skaters you’re particularly hyped on today? Out of all the new ones, I like Felipe Gustavo. He’s got tricks in, tricks out for days. My friend Jamal from Jamaica, Barcelona, he’s super dope. He just got on Sk8mafia and was out in the states killing it. I just met Lil’ Louie Lopez this summer and he’s ill. Kickflip Back Lip Frontside 270 out over the box in Hamburg. Yeah Louie, you the man! But I think out of all the new skaters I’m going to have to say Keelan Dadd. I met him this summer on a Supra tour and got to travel with him and see him skate. I’d seen him in Da Playground clip, but when you see him skate in person he really does skate that good everyday. It’s not just camera tricks. The last trick in his clip, he does a Nosegrind Nollie Hard Flip, then I see him skate in London and he do it first go. It seemed like he got better and better every demo. By the time we got to Copenhagen he was unstoppable. Plus I never seen anyone rock a pair of Bob Marley shorts that good. Come to think of it, I don’t think I ever seen any one wear Bob Marley shorts.

What are some of your favorite memories of the Huntington Beach and Huntington Beach Skatepark? Probably the Friday night sessions when they had the lights on for the football game and the park would be lit up. Everyone would go down there to chill and smoke and skate and drink and pick up girls or whatever they might be doing Friday nights. Everybody was there, Chad Muska, Sean Sheffey, the Ghetto Child crew, Skip Pronier, Ed Templeton, Pat Channita, Steve Black, Jamie Hart, Jose Cerda, Quy Nguyen, Alex Moul, Jeremy Wray, Jason Dill, Clyde Singleton, Ronnie Creager,  Angel Cabada, Mike Judd, the OG Flip crew Andy Scott, Rune Glifberg, Geoff Rowley and myself, plus a list of endless others that I can’t remember. Damn, that’s a trip down memory lane right there.

When you got to the states, did your perspective of “California” skateboarding change? I remember the first time I went to California. Not even 1 minute out of LAX airport and already seeing the first handrail Rodney Mullen ever boardslid. I was like, ‘Wooaaahhh the first street we drove down and we already seen a spot? That’s crazy’! Then we drive a couple more blocks and we see another spot. By the time we got to Huntington I’d seen more spots in one hour than I had seen my whole life growing up skating in England.

You were one of the first people I’ve ever seen that skated both regular and switch so naturally. Did you make an effort to skate both ways with equal ability? I think it came fairly naturally to me, but I still had to go through the learning process like anyone else. From the Nollies just bouncing off the cracks or drains in the pavement not hitting the nose, just bouncing off the wheels to doing the real Nollies, hitting the nose, then the Nollie Flips, Switch Flips, etc.

Supposedly your mushroom board graphic sold like crazy? What did you do with some of those hefty royalty checks? Yeah, I heard that was one of the best selling graphics of all time. Most of the money I saved from skating I spent on traveling, eating good, chilling with my friends and enjoying life!

Thanks for checking the interview, take care and have fun skating. Peace.

All Photos by ARTOFOTO. Peace Sign Photo by Ewan Bowman.

Get Tom’s board and more from Flip here.