100 Interviews

#47. BOBBY PULEO - “A hardcore skateboarder.”

It takes over an hour before Bobby Puleo mentions going to Japan.

Here’s the funny thing about Bobby: he talks very dreamily about skateboarding and then very factually about his own success.

Bobby’s pretty well-known. Googling his name brings up many videos of him doing tricks around New York City and articles about him being a mainstay in the skateboarding community.

Bobby is a slender guy from Clifton, New Jersey in a cushy, black baseball cap-ish hat. His jet black hair hangs stringy and long out the sides and back of the cap and he’s got a full beard too. His facial hair kind of looks like that of an Orthodox Jew. Like Tony, Bobby keeps his cell phone (an older, scratched model) on the table, next to a small beat-up composition notebook. He’s already eating when I arrive, which is a relief because I’m starving and was planning on asking if it was okay to order dinner. At one point he gets up and orders something from the counter, telling me he legit can not resist an apple turnover if he sees one. The cafe displays them right by our table.

I got hooked up with Bobby because he used to work in a restaurant with my friend Jeremy. I know Jeremy because he books the Whiplash stand-up comedy show at Upright Citizen’s Brigade. When he found out about 100 Interviews, he sent me a Facebook message full of suggestions. Bobby was one of them.

Growing up, Bobby spent a lot of time in New York City. He was a diehard Yankees fan growing up and he tells me he lived close enough to the city that he could see the World Trade Center from his house.

“I remember the first time I ever came into the city without my parents,” he says. “I was 16 and I didn’t want my mother to catch me. I was really nervous but I came in to skateboard at Brooklyn Banks. I’d seen it in videos but it was much smaller than I thought it would be.”

Bobby started skateboarding when he was around 8 or 9 years old, in the early ’80s. He had a bicycle and became fascinated with the board graphics at the local skate shop. The bright colors, skulls and other art designs appealed to him. He saw them on the wall and really wanted to own a skateboard.

“Plus, one of my friends went down to the shore and got a skateboard,” he says. “It was a done deal. I had to have one.”

Then, in an act of cruel, but ultimately fortunate fate, when Bobby was 10 years old, his bike was stolen. He was devastated and so his parents bought him a skateboard for Christmas to replace it. He attended demos at the local boys club and fell even more in love.

“It was exhilarating to see people in such control of their boards,” he says. “Skateboarding gives you boundless opportunities to learn anything you put your mind to. You can learn every single second. You’re not bound to the field or the ice rink. The entire city is your canvas.”

Back then, skateboarding wasn’t as mainstream as it is today. There was no Tony Hawk, no Jackass — Bobby says he knew a pre-fame Bam Margera from the Philadelphia scene. (“He was a good kid,” he says.) Skateboarding hadn’t yet been shown on television. Bobby describes it as a “secret club.”

“It was very counter-culture and very few people were skateboarding,” he says. “In my high school, there was one other skateboarder and he was a punk rock, bad sort of kid. Skateboarding was difficult to find on the east coast at first. If you found another skateboarder in the next town over, you were so excited. We were few and far between. It was a language not too many people spoke.”

“The first time I remember seeing skateboarding on TV was Bart Simpson,” I say.

“In Back to the Future, it was a big deal that he was a skateboarder. That was in 1986,” he says.

“And he was a good kid,” I point out. “People usually think of skateboarders as grungy punks.”

“Well, I was exposed to punk rock through skateboarding,” Bobby says. “Thrasher was one of two skateboarding magazines and they always had a section dedicated to music.”

When Bobby was in junior high, and more firmly entrenched in the skateboarding scene, some older skateboarders in his neighborhood took him into Manhattan. At the time, in skateboarding, the older people were responsible for taking on the younger people in sort of “apprentice” roles since there was no other real way for newbies to learn.

“Were there skateboarding cliques?” I ask.

“I mean, there were factions, people from different neighborhoods but no, no, no, everyone was at all different levels,” he says. “I mean, we hated on the goofy kids and there were kids that were really good that we looked up to.”

“When did it start to get more serious for you?”

Bobby tells me in 1990/1991, word started spreading about his skills and he began meeting more people in the skateboarding world. He teamed up with small companies and joined skate shop teams. He had his photo in the other skateboarding magazine, Trans World.

“Some people reject that sort of exposure and that’s never what I aspired to do,” he says. “But a lot of it’s ego. Ego will always factor in. Sometimes money ruins the activity. It has its toxic side.”

We talk about arguably the most famous skateboarder Tony Hawk, who Bobby says deserves his fame. “He’s incredibly talented,” he says. “I don’t agree with bringing skateboarding to corporate sponsors. I think that’s kind of disgusting but whatever, I’m not going to tell people how to live their lives.”

He talks for a bit about making himself into a “product” to sell himself to companies and filming skateboarding videos to showcase his talents to potential sponsors.

“The old guard would say there shouldn’t be that infiltration of this sacred lifestyle. But kids learn about skateboarding on television and people are making money with you know, Mountain Dew as a sponsor. You can make 10 grand a month. But people don’t want to further intoxicate or poison the community with the corporate environment.  There’s nothing wrong with making money. There’s nothing wrong with bringing certain industry into skateboarding if they were with it before it was popular. For example, Vans was a skateboarding sneaker for a long time but then Nike cashed in and Adidas.”

Bobby went out to San Francisco for a while to get sponsored but he quickly moved back to the city. He says it was because he realized that at heart, he was an “east coaster, a certain style of person.” “I couldn’t live there,” he says.

“When did things change for you?,” I ask. “When did you know you were gonna be successful?”

He knows immediately, not hesitating at all in his answer. “My first photo in a magazine. It was the 1992 fall issue of Trans World. It was a trick tip. It was photos of the sequence of a trick I did at Banks. But I’d be embarrassed to do it now.”

“Embarrassed? Why?”

“It’s so old. It’s like a late back foot pressure flip,” he puts two fingers on his phone like legs and shows me what he means, flipping the “board” under his “feet.”

“That looks difficult to me,” I say and it’s true. I think the reason I put a skateboarder on my 100 Interviews list is because to me, it’s always seemed like the most dangerous sport — the sport that makes the least sense to me.

In fourth grade, my best friend Matt and I had attempted skateboarding on his driveway with much failure. He wanted us to work up to being able to use his empty swimming pool as a ramp. I was petrified and could barely even get the board to move the way I wanted, let alone get it to flip in the air. The level of control they have over essentially a plank on wheels just does not compute for me.

“You decide what kind of risks you’re gonna take,” Bobby replies when I explain this to him. “You go based on what you think you can do. If you’re going to hurt yourself, don’t try it or build your way up until you can try it.”

“How long did it take before you were any good though?” I ask and he blinks, telling me he doesn’t understand the question. I repeat: “Like, how long before you weren’t falling or sucking?”

“For me, it was immediately very easy to do,” he shrugs. “I was immediately sort of good at it. Maybe you have to be balanced in a certain way. Not that if you fall, it isn’t fun but it’s fun to be in control. You train your board to obey what your body is telling it, what your brain is coordinating it to do. It’s like dancing.”

I laugh. “I don’t think you can hurt yourself dancing like you can skateboarding.”

“Sure, if you’re doing a particularly hard dance move,” he says, “Sure, why not?”

According to my Googling, skateboarding began in the 1940s when California surfers wanted a way to “surf” on dry land. As of 2002, there were 18.5 million skateboarders in the world, 85 percent of skateboarders were under the age of 18 and 74 percent were male.

“There’s not a lot of ladies in skateboarding,” I note.

“Well, the board mimics the shape of a penis,” he says. I laugh but he’s maintained a straight face.

I furrow my brow, “Are you saying it’s Freudian?”

“Maybe. There’s a lot of ego involved, absolutely,” he says. “You know, there’s not a lot of female hunters or there’s not a lot of female motorcycle riders. I don’t know why.”

During the interview, and perhaps because I just watched it on Netflix Instant, I can’t help but draw comparisons between skateboarding and the street art of Banksy and Shepard Fairey documented in ‘Exit Through the Gift Shop.’ The documentary follows the underground world of graffiti artists. I bring up what I’d been thinking to Bobby and he agrees, saying he feels skateboarding’s equivalent in the art world is graffiti.

“Skateboarders are really good at challenging perceived norms,” he says. “A skateboarder sees a bench and maybe a normal person thinks, ‘I’m going to put my butt on that’ but a skateboarder thinks ‘I’m gonna do a trick.’ I consider it a bit of an art form. It’s really the classic American art form.”

Toward the end of our interview, I mention that there’s a lot of stuff written about Bobby online, that Googling him brought up more results than I thought, but nothing really recent. He tells me this interview and one other are the only ones he’s done in a while, but he’s still making videos with a friend.

“Ask anybody what I’m well known for, they’ll say ‘staying reclusive.’ In a sense, that’s my career as a skateboarder,” he says. “I disappear and pop back up. Some people maintain a visible image but it kept it interesting for me. I like to make things as difficult for myself as possible. I like breaking down whatever I’ve built up. I have a grass roots style. For instance, I don’t have a credit card or a bank account.”

I’m surprised by that, but I can relate. I have a debit card but have been reluctant to get a credit card, even though my parents want me to. I’m worried about “spending” money I don’t physically have.

“Are you one of those people who doesn’t own a lot of stuff?” I ask.

“I own stuff most people would never even think of,” he says. “I do this weird thing where I make collages out of trash. I have lots and lots of crap. My room is almost all garbage but it’s very valuable to me. My interpretation of value is different than other people. Like someone sees a diamond and they’re like, ‘Oh that’s very expensive’ but I see a crushed can and that’s valuable to me. Money is just a belief. It’s just printed cloth and paper. We give it a perception of value.”

Finally, he mentions going to Japan when I ask, “What’s the coolest thing you ever did?”

“I flew to Japan and then wasn’t allowed into the country,” he laughs. “I had to fly right back.”

“What?!”

“I had an expired passport,” he says simply.

I’m astonished. “You didn’t check that before you left?”

He shakes his head.

“Why were you going to Japan?” I ask.

“To skateboard,” he replies nonchalantly.

“Really?”

“I went around the world riding a skateboard,” he says. “It was like a band going on tour.”

“Why didn’t you tell me that?!” I ask. We’ve been talking about his career for an hour and he didn’t bring up traveling at all.

“People don’t really know that about me,” he replies and that’s I guess, sufficient. It’s certainly interesting.

“How long do you think you’ll keep skateboarding?” I ask. After all, it’s been more than two decades already.

“I’ll do it until I physically can’t do it anymore,” he says. “There’s a reward to the physical act of skateboarding. It’s an accomplishment to be constantly learning, not necessarily tricks but to reach a zen point. I do it until I reach a plateau. It goes moment to moment and every day I get a personal sense of satisfaction.”

“Like an addiction,” I say, hoping I’m not being rude with the comparison.

“Yeah,” he says. “Sort of like that.”