The years that follow are predictably manic. There are magazine covers, lucrative endorsement deals, a successful reality show, an appearance on Scooby Doo and addiction battles – all of which we'll cover later.
Now 29 years old, Sheckler has stepped out of the limelight to recalibrate a bit, focusing less on the celebrity lifestyle and more on what got him to where he is: skateboarding. Living a stone's throw from the San Clemente beach where he grew up in California, he's in good spirits. "Being home is such a blessing for me," he beams over Skype. "Life has been pretty hectic so far, so being home now is like a holiday – that's why I've never really moved."
In fairness, "pretty hectic" is putting it lightly. After the X-Games, living a normal life became increasingly difficult, very fast. As his brother Shane tells it: "Big companies started to pursue him and TV channels wanted to book him for interviews. You could tell something crazy was about to happen."
Pretty soon, Ryan was skating with professionals he'd looked up to his whole life, as well as competing against them.
"I was suddenly just in the mix with these dudes I'd looked up to when I was a kid," he says. "I would feel so nervous I'd think I was about to cry. But I realised that I loved that feeling of fighting through to find my composure to plan my runs. That year, I just felt unstoppable."
Going on tour presented a new set of problems. Skateboarding road trips are notoriously chaotic – not the kind of place you'd usually find a 13-year-old boy. This is perhaps best exemplified on Thrasher and VICE's show King of the Road, where Ryan's appearance when he was 14 has gone down in history.
Though his skateboarding out-shined the professionals ten years his senior, it was his make-out scene with an older woman that stood out. "I think she was 12 years older than me," he laughs. "But all of my friends were there hyping me up and I felt like one of the guys. It sounds stupid when I say it out loud, but I was a kid and was with my idols. It was a crazy time."
His boyish good looks coupled with a friendly demeanour and cheery attitude turned him into a teenage heartthrob – something MTV were more than happy to capitalise on when they offered him his own reality TV show. Life of Ryan followed the teenage skateboarder as he went about his daily life: parties, skating contests, making out with girls and arguments with the family. Think Viva la Bam meets Keeping Up with the Kardashians, featuring the hottest skateboarder in the country.
The show was a success, spanning three seasons and pushing Sheckler's already rising star even higher. Suddenly he was much more than just a big name in skateboarding; he was a household star. Ryan's long-time manager Steve Astephen draws similarities to a young Justin Bieber.
"Honestly, it was like Bieber-fever before Bieber-fever," he says. "Over 2,000 teenage girls would turn up for autograph signings, malls would be shut down regularly. It was like the Beatles had come to town. We were once shut down in a Chillies restaurant in Orange County and the SWAT came."
"It seemed like everywhere we went, people wanted a picture with him, says his brother, Shane. "When we'd go to contests, there would be hundreds of people waiting to meet him. It was crazy."
Inevitably, the party lifestyle shown on Life of Ryan eventually caught up with him. Alcohol went from being a fun addition to a house party to a daily necessity. After years of heavy drinking, it came to a tipping point at the age of 25, when drinking began to consume Ryan's life.
"My life had been 100mph since I was seven," he sighs. "I didn't really know how to drink, or how much to drink, or any boundaries. I bought a house when I was 18 and I was the only kid in school to have one, so we partied. It just felt normal. When I was 25 it hit hard, because I realised that my passion for skateboarding was withering away because all I wanted to do was party and get drunk. It was so empty."
The only answer was rehab, which Ryan decided himself was the right thing to do.
"I broke down and told my friends and family that I needed to go," he says. "I'm blessed to have an amazing team around me. I finished an international trip and checked straight in. Now, I'm four years sober and I wouldn't trade it for anything in the world – it was the best thing I've ever done. Life is so much clearer now."
With a fresh outlook, Ryan is now able to focus on skateboarding without the distractions. He embraced Christianity and devoted himself to becoming a solid role model across all aspects of his life. As a public figure, he's been touring the US with his charity, The Sheckler Foundation, donating $10,000 grants to underprivileged communities across the country. As a skateboarder, he's back entering top level contests, representing Etnies at the X-Games in Minneapolis.
As we finish up, there’s one last question I need to ask: what really happened at the El Toro stair set?
Some background: El Toro is a set of stairs in a Californian high school which has become one of the most iconic spots in skateboarding. Its size means that only a handful of tricks have ever been landed down the stairs, so when someone lands something new, it's big news. A few years ago, during an interview with the late Thrasher editor Jake Phelps, Ryan claimed he had backside flipped it. If this was true, it was arguably one of the more impressive tricks ever landed on a skateboard. It would set a new benchmark in street skateboarding.
After years of being asked where the footage was, Sheckler admitted – in the above video – that he'd done the one thing you never do in skateboarding: lie about landing a trick. It ended up defining a large part of his career. "It's turned into the biggest life experience I've ever had to deal with," he sighs. "I was a young kid and I looked up to Jake, and I didn't want to disappoint him. He poked me with the question, and in my mind, because I'd just backside flipped a 17-stair, I felt that I’d be able to add on three more stairs and it's the same thing."
"Skateboarders still harass me everywhere I go about it," he continues. "I don't feel like skaters should be hating on each other. I owned up to it, I apologised for it. It showed me the power of what one lie can do, though. I haven't told a lie since!"