Ryan Sheckler: From Child Prodigy to Skateboarding Legend (And Why Some Skaters Hate Him)

Is Ryan Sheckler the greatest skateboarder of his generation or just another flash in the pan? Dive into the highs and lows of his career, and find out why some skaters love to hate him.

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Ryan Sheckler burst onto the skateboarding scene like a comet. From landing his first kickflip at six years old to becoming the youngest X Games gold medalist at thirteen, his rise was nothing short of phenomenal.

But with fame comes scrutiny, and not everyone is a fan. In this post, we’ll take you through Sheckler’s incredible journey—his early life, his meteoric professional career, his achievements, the controversies, and why some skaters might give him the side-eye.

If you’re a visual learner, check out this video, which explains the life of Ryan (no pun intended) much better than I ever could.

A video titled ‘How Child Fame Ruined Ryan Sheckler’s Life (MTV to Rehab)‘ from the Patrick Cc: YouTube channel.

Key takeaways

  • Ryan Sheckler became the youngest X Games gold medalist at thirteen, marking a meteoric rise in skateboarding.
  • Despite his achievements, he faced criticism from the skateboarding community for being too commercialized and, to be honest, jealousy at his meteoric rise at such a young age.
  • The controversies surrounding him stem from his reality TV show and lying about doing a backside flip on El Toro.
  • His involvement in philanthropy showcases a commitment to giving back to the community.
  • Sheckler’s personal battles, including struggles with alcoholism, highlight his resilience.
  • Launching Sandlot Time Skateboards highlighted his entrepreneurial spirit.

Early life: A skateboarder born to ride

Ever wonder what it takes to become a skateboarding prodigy? For Ryan Sheckler, it started at just 18 months old. Yes, you read that right—barely old enough to walk, and he’s already on a board. Growing up in San Clemente, California, in a surf-and-skate community, skateboarding was in his blood. His dad’s old skateboard became Ryan’s first ride, and by four, he was nailing ollies like it was no big deal. [3]

Ryan sheckler: from child prodigy to skateboarding legend (and why some skaters hate him)is ryan sheckler the greatest skateboarder of his generation or just another flash in the pan? Dive into the highs and lows of his career, and find out why some skaters love to hate him.
Realistic illustration of ryan sheckler.

And get this, Tony Hawk himself showed up at Ryan’s sixth birthday party. Can you imagine that? Tony Hawk at your birthday party.

When the godfather of skateboarding gives you the nod, it’s like getting a golden ticket. It likley validated Ryan’s passion and gave him the confidence to chase his dreams.

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Turning pro at 13: The making of a legend

At 13, most of us were struggling with algebra and wondering if that cute classmate liked us back. Ryan? He was turning pro, encouraged by World Industries. In 2003, he didn’t just dip his toe in the professional world—he cannonballed. First-place finishes at the Gravity Games, Vans Triple Crown, Slam City Jam, and the X Games. And get this: he became the youngest athlete ever to win X Games gold. [1]

Sheckler’s talent didn’t go unnoticed by big brands. He started out with Etnies and Oakley, which are like rites of passage in the skate world. Then he joined Almost Skateboards, only to jump ship in 2007 to Plan B Skateboards—a team he stayed with for 16 years before launching his own brand, Sandlot Times Skateboards, in 2022.

Why leave Plan B after so long? Sometimes, you’ve got to carve your own path. After 16 years, Ryan wanted to create something that reflected his vision and values.

Crushing competitions: The accolades pile up

If there’s a skate competition, chances are Ryan’s won it—or at least come close. Multiple X Games golds, silvers, and bronzes. Dominating the Dew Tour with overall titles in 2006, 2007, 2012, 2013, and 2016. He even claimed first place at Thrasher Magazine’s Bust or Bail in 2008. [3]

The dark side of fame: Life of Ryan and its aftermath

Now, here’s where things get a bit murky. In 2007, Ryan starred in MTV’s “Life of Ryan”. On the surface, it seemed like any skater’s dream—your own TV show! But reality TV isn’t always, well, real. The show took a turn Ryan didn’t expect, focusing on scripted drama and forced relationships. It left him feeling, in his own words, traumatized and disillusioned. [2][3]

Did the show hurt his reputation? In some circles, yes. Some skaters felt he commercialized himself, becoming more of a celebrity than an authentic skater.

Personal battles: Facing demons and finding sobriety

Fame and fortune aren’t all they’re cracked up to be. Ryan faced his own set of challenges, including struggles with alcoholism. With support from his mom and friends like Michael Phelps, he managed to get sober, though he did experience a relapse after four years. [3] Sobriety brought clarity and focus back into his life and career.

Controversies and why some skaters hate him

Alright, let’s address the elephant in the room. Not everyone in the skateboarding community is a fan of Ryan Sheckler. Some think he’s too commercialized that he lost touch with skateboarding’s soul through his TV show and endorsements. Others feel he hasn’t paid his dues like skaters who grinded (pun intended) without the spotlight.

Is the hate justified? Look, skateboarding has always had this underground, counter-culture vibe. When someone becomes as mainstream as Sheckler did, especially through reality TV, purists might feel it’s a betrayal. But at the end of the day, he’s contributed a ton to the sport.

But that’s nothing compared to when he lied about doing a backside flip on El Toro. Skateboarders cannot stand someone who lies about landing a trick. When he did that, his reputation was over. However, he has since admitted it, apologized for the lie, and mentioned that it’s something he has to live with every day.

Business ventures: Beyond the board

Ryan isn’t just a skateboarder; he’s an entrepreneur. Besides launching Sandlot Times Skateboards, he’s invested in ventures like the Palm Springs Surf Club and Ethika. His net worth is estimated at a whopping $100 million. [3]

And you might not know this, but Sheckler isn’t all about the spotlight. In 2008, he founded The Sheckler Foundation, aiming to educate, equip, and empower communities, especially kids and injured action sports athletes. They’ve donated close to $1.2 million to various causes. [1][4]

Is he more businessman than skater now? Depends on who you ask. But diversifying your interests isn’t a crime. If anything, it shows he’s thinking about life beyond skateboarding.

Influence on skateboarding culture

Beyond competitions and endorsements, Ryan Sheckler’s influence on skateboarding culture is significant. He helped bring skateboarding into the mainstream, inspiring a new generation of skaters.

Sheckler has this fearless style combined with technical precision. Clearing a 55-foot gap on Bob Burnquist’s Mega Ramp? (That’s equivalent to jumping over about nine Toyota Corollas lined up bumper to bumper. Let that sink in.) Landing the cover of The Skateboard Mag after conquering the “Costco gap”? Those aren’t just tricks; they’re statements. Check out the Costco gap vid below.

Frequently asked questions (FAQ)

Ryan’s family played a significant role, with his father introducing him to skateboarding and his mother supporting his early ambitions, laying the foundation for his successful career.

The Sheckler Foundation aims to educate, equip, and empower communities, focusing on children and injured athletes, showcasing Ryan’s commitment to giving back.

Yes, Ryan has been featured in several skateboarding video games, including the Tony Hawk’s Pro Skater series, bringing his skills to a digital audience.

Beyond skateboarding, Ryan has invested in projects like the Palm Springs Surf Club and the apparel brand Ethika, expanding his entrepreneurial portfolio.

Final thoughts

Is he a skateboarding prodigy who deserves all the accolades, or a sell-out who lost touch with skateboarding’s soul? He’s a complex figure who achieved incredible success, faced personal demons, gave back to the community, and yes, made some controversial choices.

At the end of the day, skateboarding is about expression, freedom, and pushing the limits—something Ryan Sheckler has exemplified time and time again. Whether you’re a fan or a critic, you can’t deny his skills and contributions to the sport.

Image of jedain.
Written by Jedain Arron, Founder and writer

I'm Jedain, a 30-something-year-old dad rekindling my love for skateboarding. I've been skating since I was 13 back in New York City, took a long break for adulting, and now I'm back on the board.

This blog documents my journey back to the skatepark (creaky joints and all). Follow along as I relearn tricks, reconnect with the skate scene, and share the ups and downs of returning to the sport.

Nick eggert.
Edited by Nick Eggert, Editor

Nick is our staff editor and co-founder. He has a passion for writing, editing, and website development. His expertise lies in shaping content with precision and managing digital spaces with a keen eye for detail. When not working on the site, you can find him sipping Bourbon at the karaoke bar.

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