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Wednesday, July 16, 2008
Updated: August 8, 12:16 PM ET
JUST ANOTHER LONELY MILLIONAIRE SKATEBOARDER

By Allison Glock

It's 10 in the morning and cherubic skateboarding pro Ryan Sheckler is sitting at a large conference table watching a PowerPoint presentation scored with "inspirational" techno music. The 18-year-old is flanked by entrepreneur (and Apprentice Season 4 contestant) Josh Shaw and Steve Astephen, his agent. Sheckler eyes the skin-care promo with strained interest. This is his third meeting in as many hours, and he will have at least five more before the day ends. As Shaw runs through his shtick, Sheckler nods and says, "Yeah, yeah, uh-huh," as if a string were being pulled.

His hair is buzz-cut, and in his ears glitter diamond studs that frame his round face and Bambi-wide eyes. His watch, the size of a tricycle wheel and rimmed with more diamonds, is a gift from Nixon, one of his sponsors. Bedazzled, short (his bio lists him at a generous 5'8") and boyishly handsome, Sheckler looks like a cross between Chris and Charlie Brown. Shaw tries to fan his interest by trotting out products, and Sheckler obligingly sniffs the lotions and lip balms.

"A signature ChapStick would be so sweet," he says to no one in particular.

Encouraged, Shaw leans forward. "So," he says, "how do you feel about flavors?"

Not much later, Sheckler is in a hired car, headed to his next appearance, lip balm deal still to be finalized. He's in New York for two days in May, and marketing executives for his sponsors—Etnies, Volcom, Red Bull, Oakley and Panasonic, among others—want him to drop by stores to meet and greet. Also on the day's docket: an appearance on Run's House and a Kanye West concert he'd rather not attend.

"When I met him, I told him I was a big fan," says Sheckler. "And he said, 'Of course you are.' " He rolls his eyes and slouches into his seat. Astephen, the pied piper of action sports, asks him if he's up for "the thing at the place later on."

"Whatever you need, man," Sheckler answers. "It's part of the gig."

He is unlike any street skater in history. One, because he is preternaturally gifted, able to ride with uncommon grace and with the consistency of a dart pro. And two, because he's happy selling out. He plans to start a clothing company. A gear company. Do movies. "You know what I really want?" he asks earnestly. "My own cologne."

Sheckler's willingness to acknowledge his Hollywood-size ambition in a sport that pretends it doesn't have any sets him apart. From other riders. From (male) spectators at contests. From anyone who objects to his fame and fortune and resents the fact that while most skaters earn thousands—pros with a signature board or shoe make healthy six-figure incomes—Sheckler earns millions. "I get 'Sellout' a lot," he says.

"The real skate rats, they don't want to see Panasonic have anything to do with skating," says pro street skater Jereme Rogers. "Personally, I think skateboarding is harder than throwing a basketball into a hoop, so I'm all for it growing up and being taken seriously. Ryan is helping do that, and he gets hated on the hardest." SHECKLER IS UNLIKE ANY STREET SKATER IN HISTORY. ONE, BECAUSE HE IS PRETERNATURALLY GIFTED. TWO, BECAUSE HE'S HAPPY SELLING OUT.

In 2003, at 13, Sheckler began skating for prize money, becoming the youngest skater ever to turn pro. The same year, World Industries released a Sheckler pro model board. Since then, Sheckler has dominated street skating, racking up wins at the Slam City Jam, Vans Triple Crown, Gravity Games and X Games. He's the undefeated three-time winner of the park event on the AST Dew Tour. "I won the first contest I ever entered, when I was 6," he says. "People were like, Who does this kid think he is? Even back then, people were giving me s—."

Trash-talking is part of skate culture. Even so, Sheckler has received more than his share. "For some reason," says his mother, Gretchen, "hating on Ryan seems to be the cool thing to do." Never more than lately, as his hit MTV show, Life of Ryan (filming its third season), has turned the former niche celebrity into a bona fide pop culture touchstone, revealing the oft-shirtless skater as a young man interested in far more than mastering tricks. The show pulls healthy ratings, easily winning its time slot in the coveted 12-to-24 demographic. As a result, sponsors beyond the usual skate companies have begun circling the Sheckler brand. Film scripts arrive on a regular basis, including, Sheckler says, one based on Avril Lavigne's song "Sk8er Boi." So, too, TV development deals. To the real world, Sheckler is a hot guy who happens to skate. But to the skate world, he's Paris Hilton on wheels.

"His show adds a lot to his problems," says Rogers. "It's like a skateboarding Laguna Beach. He cries on TV. They latch onto that."

"People knock on him pretty hard," says Andy Macdonald, who became the first vert skater to net a drink sponsor, when he signed with SoBe nine years ago—and was harassed as soon as the sticker went on his helmet. "The people hassling Ryan need some perspective. We started doing this because we wanted to make our own rules. And now this core group wants us to conform."

Haters loathe Sheckler for taking street mainstream, for turning something mutinous into something your mother would love. Also, because he gets more play than Tiger's putter. "He's on teenybop magazines," says Rogers. "He has a fan base of girls. That's a first for skateboarders." At events, Sheckler's supporters are obvious: the young, pretty ones who pack the stands, squeal with delight at deafening decibels while he rides, then leave after they see him change his shirt. "Ryan is the first legitimate teenage heartthrob in our industry," says Macdonald. "People who watch him aren't skateboarding fans, they're Ryan Sheckler fans."

Which suits Sheckler just fine.

"I'm going to capitalize on everything I can," he says unapologetically. And though he may wince when someone yells "Douche bag!" as they pass his autograph line, it's a rejection he registers for about as long as it takes him to roll up the window of his CLK63 AMG Black Series Benz.

"Every time somebody calls me out or tries to start something, it's motivation," he says cheerfully. "I want to give them more reasons not to like me."


Sheckler's first fight happened when he was 15 and 115 pounds. An older, much larger football player thought Sheckler was after his girl ("I wasn't") and suggested they meet in a parking lot. They wrestled for a bit—Sheckler was on his school's team—then went their separate ways, amid much red-faced bluster from the football star. "It was the first time I realized that people, seriously, have no brains," Sheckler says.

It wasn't the last. Since he's become a TV personality, strangers throw themselves at him. Girls grab at his clothes. Nipples are flashed. (Not just his.) Tough guys want to prove themselves by talking smack and pushing his buttons. Sheckler brushes it all off; he says he's trying to keep his eyes on the prize. And for the most part, it's working. After reinjuring his right elbow days before the event, Sheckler came in fourth at the July 13 Maloof Money Cup. (Paul Rodriguez took the top spot —and the $100,000 purse, the richest in skate history.) But he'll take aim again when he skates in street and superpark at the X Games in August. He's hired a personal trainer and says he tries to swim or bike every day to get into what he calls "contest mode." Sheckler takes skating seriously, not just because he loves to ride but also because he's smart enough to know that skating is the goose that laid the golden egg, that without it he'd be just another pretty California boy with ripped abs and prematurely acquired tattoos. "People think this life was just handed to me. But I started from ground zero like everybody else. I have been doing tricks since I was 6 years old. I was focused and determined from that long ago. That's why I am where I am."

Sheckler's resolve is legendary. He was on a board at 18 months, doing ollies at 4. He could kickflip before he could read. By 8, he had two sponsors (Etnies and Volcom). When asked if stage-parenting ever came into play, the Shecklers demur, even though their son's show captured choice scenes of Mom and Dad pushing Ryan to heartbreaking limits. (The two decided to divorce last year, a private event that played out during the filming of Life of Ryan.) "I worked 18 hours a day so that we had the money to facilitate Ryan's hectic amateur traveling schedule," says father Randy. "Many parents come and thank me for raising Ryan the way I did. Quite frankly, I'm at total peace with it."

Sheckler says he is too. He credits his parents with making him "mentally strong," a child who didn't cry when his arm had to be reset at age 6 (after he failed to clear a picnic table on a jump), an adolescent whose doctors said he should be x-rayed every six months because he never complained when a bone broke, a 16-year-old who skated in the Dew Tour with second-degree burns on his foot (from stepping on a hot hibachi) to keep himself in the hunt for the title. "That's what it takes to be a champion," Sheckler says, voice rising. "My mantra? Never give up." He takes a breath, twirling his pinkie ring around his index finger. "I don't think a lot of people think like me." He is proving as much even now. Despite his gammy elbow, Sheckler intends to skate a full contest season brace-free and will deal with the consequences (and probable surgery) later.

For now, Sheckler is managed by his mother, a situation he calls difficult. "I miss that just-Mom relationship. I could never fire her, though. It would kill her," he quips, alluding to the future that all child stars face when they outgrow their momagers. The transition is something neither party wants to talk about. "When he talks to me as his manager, he calls me Gretchen," says his mother. "Without even thinking, I respond. It's second nature now."

Sheckler turned 18 last December, a milestone he celebrated by moving out of his family's palatial San Clemente house and into his own place, a three-story Mediterranean in a nearby gated community. The 5,000-square-foot house has ocean views and a tiered-seating home theater. "My mom said I couldn't leave home until I was 18," Sheckler says. "So the day of my birthday I put an offer on a house." He says the move has made him feel "so old—like 25."

Sheckler goes on, his words tumbling over one another like a litter of puppies. He talks about his best friend, Casey, and his family trips to Hawaii and how The Goonies is his favorite movie, "for real," and how the other day his brother Shane, 16, got in a fight because some jerk-off was bad-mouthing Ryan. "Run's House is my favorite TV show," he says. "Ever since he made fun of my tattoo." Sheckler is referring to his back tattoo, a mammoth, shoulder-to-shoulder rendering of his surname in Old English script. He has other tattoos, the newest being the word Fear on his right forearm and God on his left. "I travel with the Bible," he says, completely serious. "I get so consumed in my life. That's why I got those. To remind myself this is God's plan."


Sheckler is eating a breakfast of biscuits and gravy, scrambled eggs on the side. Here, in the W Hotel's dining room by New York City's Union Square, no one recognizes him—unlike yesterday, when, while walking down the street after his business meetings finished, a gaggle of high school girls clocked him. "I saw him first!" one shouted, rushing to snap a picture with her phone. "I got swarmed," he recalls, laughing.

Sheckler twists his hips a bit in his seat, then pops his neck. Although only 18, his body is tweaked. His ankles ache every night. His elbows appear to be hiding Ping-Pong balls under the skin. "My whole body hurts pretty bad every day," he says. It's not just his body. His brain has been spinning out of control, thoughts colliding and overlapping like waves. "I have ADD. It was diagnosed in 2007. My mom didn't believe I had it, so we went to the doctor. I don't take Ritalin or anything. I just roll with it."

But there are days he gets unbearably manic, dizzy, irritable. He longs for it all to stop, to be still. On those days, Sheckler gets into his Mercedes and drives as fast as he can ("I like speed") into the open landscape. Sometimes he checks into a hotel alone—no phone, no TV—and just sits in the room until he can breathe again. "I just go away. I need time to be quiet. It just happens. It makes me an a—hole to be with, I guess." "HIS SHOW ADDS A LOT TO HIS PROBLEMS," SAYS FELLOW PRO SKATER JEREME ROGERS. "HE CRIES ON TV. HIS FANS ARE GIRLS."

He sighs. "It's not like depression or anything. I just deal with so much bulls— all day. I can feel overwhelmed. But then again, I never want it to stop." Sheckler offers a world-weary look. "I'm a normal kid with an extraordinary life," he says with a weak shrug. Then he smirks. Even he can't swallow that one. He knows the truth. That he is exceptional. That most kids can't make two-story drops on a rolling piece of pressed wood. That most kids don't party with rap stars or get their pictures in the tabloids or travel the world in private jets or have TV shows named after them.

He knows, too, the price of that life. That he is growing up fast and is expected to be a man, to be marketable, to be a product, to live as if he were a normal kid when he so clearly isn't, to—most critically—capture all of the contrived reality on camera for YouTube and MTV, so that we can watch while his life of Ryan unfolds, watch him cry and fall and suffer, then decide for ourselves who he is and what his life means.

"I may just be telling myself that 'normal' stuff to make myself feel better," he says, dropping his fork to his plate with a clank. A short while later, Sheckler climbs into a waiting car and opens a can of Skoal. "My only addiction," he says, tucking a wad into his lower lip. "I started doing it about six months ago. I don't know why." He says he doesn't do any other drugs but does drink a little now and then. As it turns out, he drank the previous night until 3 a.m., hitting the clubs and dance floors of New York City, making out with America's Next Top Model winner CariDee English, a woman nearly five years his senior. "She kept tugging at my hair. It was like, What is that about? She wasn't so great with the conversation, either," he says. "She wants to fly out to a contest. Whatever."

The car inches slowly through the city streets, and Sheckler, hungover but sociable, is imagining his bright future, something he has done since he was 7. "Ten years from now, I'll be relaxing on my yacht."

He laughs.

"Nah. I'll still be doing the same thing, you know. I'll still be skating, doing my business things, doing everything I want to do. Clothing line. Acting. Only with more downtime."

There is no downtime on the current schedule.

"This is my job. I love my job. My job is fun," he says, almost robotically, looking out the window, his reflection bouncing back at him in the glare of the glass. He grabs an empty water bottle and spits as the car drives past the Brooklyn Bridge.

"How high do you suppose that is?" he asks. "That would be one good jump."

He was told that Travis Pastrana jumped off a bridge for fun recently and knocked himself unconscious. Nearly died.

"Dumbass," says Sheckler. Then, after a pause, "Did anybody film it?"