Skateboarding
Skateboarding
Top Ryan Sheckler moments: A tribute to a skateboarding icon
His “Rolling Away” documentary takes a deep dive into these complexities and shares new insights into the making of this skating legend.
In the skateboarding community, Ryan Sheckler is known as an all-star. His young start, rise to TV fame, and excellence on the board have all contributed to his massive impact on skateboarding history. Sheckler impresses spectators and fellow athletes alike with his performance, along with his transparency about what it takes to reach pro status. In Sheckler's documentary “Rolling Away,” he admits that his commitment to skateboarding has led him to take countless risks — and plenty of falls.
Ryan Sheckler Ollie over a rail in Riverside
© Tim Aguilar
“Why would a professional skateboarder continuously want to smash themselves to pieces to skate a bigger rail [or] a bigger gap…?” he asks the camera. He answered his own question with ease: “Somebody’s gotta do it.”
Ultimately, Sheckler’s risks have paid off, and he remains one of the most iconic skateboarders of all time. Below are some top Ryan Sheckler moments as we celebrate his most memorable achievements throughout his career.
01
Ryan Sheckler's early success and rising star
Inspired by his father Randy Schekler’s skateboarding career, Ryan Sheckler’s interest in skateboarding began at two years old. While he started small in his hometown of San Clemente, California, he quickly garnered national attention — including sponsorships from Etnies and Oakley — at the age of 7. Six years later, Sheckler became the youngest-ever X Games gold medalist at the time, winning Skateboard Park in 2003.
Ryan Sheckler performs a backside heelflip in Escondido in 2007
© Jody Morris / Red Bull Content Pool
From there, Sheckler’s fame skyrocketed. From 2007 to 2009, he starred in his own MTV reality show, "Life of Ryan," which gave the public a glimpse into his life. With the help of this show, Sheckler transformed from a young skateboarding sensation into a borderline household name in the 2000s.
02
Top Ryan Shecker moments: iconic tricks
Throughout his career, Sheckler has had plenty of standout runs — all featuring unforgettable tricks. One of the hardest to forget is his gold-winning performance in 2010’s X Games 16. During this memorable run, Sheckler flawlessly landed several jumps over two long, high staircases. The roar of the crowd as he landed these tricks is a telling accompaniment to these stunts.
Later, on a 2019 episode of the MTV show "Ridiculousness," viewers got to see footage of an especially daring Sheckler trick. The show’s host, Rob Dyrdek — another skater turned reality TV star — called the trick “the gnarliest kickflip that the world has ever seen.” Sheckler estimated that the jump was over a roughly 15-foot fence.
Ryan Sheckler skating in the streets of Taiwan
© Kenji Haruta / Red Bull Content Pool
Sheckler’s show-stopping tricks didn’t stop after the 2010s. For the 2020 X Games Real Street Best Trick, he managed an impressive fence jump that the skateboarding community still can’t stop talking about. After gaining momentum in the adjacent bowl, Sheckler was able to get over the tall, wire fence, executing a near-360 turn while at it. In 2021, jaws dropped again when Sheckler completed an epic tail drop over a bridge in Taiwan — among moving vehicles on either side of him. This stunt was featured in Red Bull’s "YOU GOOD?" segment.
Sheckler’s impressive catalog of tricks highlights his mastery of technical skating skills, as well as his ambition and courage in the park. They cement Sheckler’s skateboarding excellence and his lasting impact on modern skate culture. His discipline and patience also continue to inspire aspiring skateboarders to aim for greatness, even if they don’t immediately succeed.
03
Overcoming adversity and personal growth
7 min
Ryan Sheckler: LIFER
After three years and multiple injuries, skateboarder Ryan Sheckler releases his best video part to date.
With a career this successful, Sheckler naturally faced some roadblocks along the way. In the wake of young fame, Sheckler began to struggle with addiction. In 2016, he entered rehab, and, after a relapse in 2020, he pledged to be completely sober. Throughout these experiences, Sheckler was entirely transparent with his fans, as well as the general public, about his upward battle. Today, Sheckler believes that becoming sober was the best decision he’s made in his life.
Sheckler has also faced challenges with his physical health. After all, to achieve his level of excellence, Sheckler has taken many risks on the board, and some have led to serious injuries. From a broken vertebra to a torn ACL, he’s spent countless months in recovery, but his outlook has nevertheless remained positive. In fact, he has said that the healing time has allowed him to become spiritually, physically, and mentally stronger.
Ryan Sheckler poses for a portrait in Durham, NC
© Zorah Olivia / Red Bull Content Pool
Ultimately, Sheckler’s challenges have empowered him to pay his success forward. Today, the Sheckler Foundation supports skateboarders of all ages, especially those who are facing injury or otherwise in need. His success in the face of his personal and professional struggles has given him a powerful perspective on skateboarding. Marked by determination and resilience, both his attitude and accomplishments make him a powerful role model in the skating world.
04
Legacy and influence
Whether sweeping up wins in the X Games or empowering the next generation of skateboarders, Sheckler’s enduring legacy can’t be overstated. He continues to influence the world of skateboarding with his legendary tricks and his impressive come-up story. Sheckler has made his mark on both the present and future skating scenes as a mentor and inspiration to young skateboarders. His social media presence illustrates that he remains humble and fiercely devoted to both the sport and his fans, even amid his stardom.
47 min
Rolling Away
Get an in-depth look at Ryan Sheckler’s three-year journey to complete a career-defining video part.
Ryan Sheckler is more than a professional skater — his path to fame and excellence is complex and worthy of praise. His “Rolling Away” documentary takes a deep dive into these complexities and shares new insights into the making of this skating legend. Skaters, other athletes, and enthusiastic spectators alike can learn a lot from his moving success story.
