10 of The Most Insane Moments in Skateboarding: Skate Legends & Their Jaw-Dropping Stunts

Explore the top 10 breathtaking skateboard stunts. From daring leaps to record-breaking tricks, brace for pure skateboarding insanity.

Ever heard the phrase “riding on the edge”? Well, in skateboarding, it’s more than just an expression; it’s a way of life. And when it comes to the most insane moments in skateboarding, we’re not just talking about everyday thrills and spills but game-changing, jaw-dropping feats that redefine our understanding of what’s possible.

Buckle up, folks, as we take you on a wild ride through skateboarding history, one insane trick at a time. And when we’re done, you’ll certainly exclaim, “No Way! That’s impossible!” But trust me, in the world of skateboarding, “impossible” is a challenge, not a limit. Now, let’s kick, push, and coast through some of skateboarding’s most mind-blowing moments. Ready to drop in?

What are the most insane moments in skateboarding history?

The evolution of skateboarding has been fueled by a series of insane moments, tricks, and feats that many thought were unattainable. These events have not only shaped the course of skateboarding history but also inspired countless others to step on a board and push their limits. Let’s embark on a journey through some of skateboarding’s most gutsy, phenomenal, and simply mind-boggling records ever caught on tape.

Image of a skater doing tricks on a ramp. Source: unsplash
Image of a skater doing tricks on a ramp. Source: unsplash

1. Jeremy Wray’s water tower gap

Jeremy Wray made skateboarding history when he dared to take on a frightening obstacle: a 40-foot-high water tower gap. This stunt remains untamed, with no contenders willing to gamble with their lives. Why does it stay unrivaled? Simple. Executing a larger gap would be a near-certain death sentence.

The remarkable thing about Wray’s stunt isn’t just the fact that he nailed it. It’s the process leading to a successful attempt. Each time he wished to retry, Wray had to clear the gap by running and jumping over it manually.

Moreover, the unnoticed danger was the small rocks on the top of the tower, which had to be swept off to prevent unexpected foot slips or wheel jams. Despite these treacherous circumstances, Wray triumphed, landing solidly and making skateboarding history.

2. Danny Way’s leap over the Great Wall of China

Second on our list is Danny Way’s Great Wall of China jump. When surfers in the 1950s attached rollerblades to boards and carved down hills, little did they know the same object would transcend continents and leap over one of the world’s seven wonders.

“Unlike any conventional stunt, Way’s monumental leap was a dance with the unknown on an unmatched scale.”

Not only was he aiming to fly over one of the most famous landmarks in human history, but he was also attempting to break three World Records simultaneously: the fastest acceleration on a skateboard, the longest distance jumped, and the highest distance jumped from a quarter pipe. Despite suffering a severe ankle injury during practice, Way defied all odds and pain barriers, making the jump the next day.

3. Ali Boulala’s leap of faith attempt at Lyon’s stair

Ali Boulala was captivated by a staircase in Lyon, France. These 25 daunting concrete steps, nestled behind the city’s hotels and eateries, beckoned as an unmet challenge. Who would be brave enough to try such a feat? Ali Boulala’s audacious attempt at these Lyon stairs was highlighted in a mini-documentary by Bayer. The “leap of faith” is used as a metaphor for daring to jump despite the risks, potential pain, and setbacks.

His attempt at Ollie the 21-step monster has captured the imagination of many and written his name into skateboarding history. Ali’s brave crack at the Leap of Faith, though unsuccessful, perfectly encapsulates the free-spirited, no-holds-barred attitude that distinguishes the skateboarding community.

4. Jaws Homoki’s Lyon 25 stair ollie

Just when you thought these stunts couldn’t get any crazier, Aaron ‘Jaws’ Homoki swoops in with an outrageous feat. Homoki’s daredevil league kicked off when he successfully Ollied the Lyon 25, one of the trickiest and steepest staircases in the skateboarding world.

Image of a skater jumping midair on a flight of stairs. Source: unsplash
10 of the most insane moments in skateboarding: skate legends & their jaw-dropping stunts | image of a skater jumping midair on a flight of stairs unsplash | skateboard salad

This monumental jump wasn’t just about the physical challenge; it was also a test of mental resolve. Homoki had to confront the specter of multiple painful and failed attempts. But his sheer determination and unwavering focus saw him conquer the Lyon 25, a feat revered as one of the gnarliest moments in skateboarding history.

5. Chris Cole’ s 360 flip at Wallenberg

The Wallenberg 3 blocks stand as a legendary skateboarding spot in San Francisco, California. Integral to street skateboarding, numerous skilled skateboarders have sought to master it. While Chris’ 360 Flip might not be the most challenging stunt performed there, it encapsulates the essence of skateboarding: unwavering dedication and tenacity.

Chris Cole endured both emotional and physical strain to achieve the 360 flips at Wallenberg. After 66 attempts, facing falls and injuries, he eventually triumphed, showcasing his profound passion.

6. Tony Hawk’s first-ever 900

No list of skateboarding achievements would be complete without Tony Hawk’s jaw-dropping 900 at the 1999 X Games. Even though athletes have since done higher spins, Tony’s initial 900 is still a significant feat that redefined skateboarding.

Hawk’s 900—two and a half spins mid-air—might look smooth on film, but it was the result of relentless practice, numerous falls, and an unyielding belief in himself. His successful 900 showed us the true meaning of perseverance and shifted the world’s perception of what’s achievable on a skateboard.

7. Elissa Streamer—first female skater to feature in Tony Hawk’s Video Game Series

Elissa Steamer, the queen of skateboarding, added a crowning moment to her illustrious career by becoming the first female skateboarder to be featured in the Tony Hawk Pro Skater video game series. This monumental moment wasn’t just a personal triumph for Steamer, but a victory for female skateboarders worldwide.

While Steamer’s virtual accomplishment may not seem insane compared to gravity-defying tricks, its importance is undeniably monumental. The inclusion in the game wasn’t merely about reaching a larger audience or gaining mainstream recognition. It was about breaking social barriers and cementing the place of women in the skateboarding world.

8. Chris Joslin’s 360 flip over the Davis gap

It takes serious guts and a sharp set of skills to attempt flipping a skateboard mid-air while flying across a massive gap. Chris Joslin’s 360-degree flip over the Davis Gap undoubtedly qualifies as a landmark of insanity in the skateboarding world.

The Davis Gap had long been a legendary site for ambitious skaters, with no one succeeding in a three-flip until Joslin came along. Eyeing his board and focusing on the launch, Joslin’s 360 flip was a beautiful blend of fearlessness, precision, and sheer madness.

9. Nyjah Houston’s “til death” part

Nyjah Houston’s “Til Death” part feels like a fever dream of skateboarding’s most extreme tricks. Nyjah’s life-threatening stunts in the film, especially his insane Combination Big Spin, had the skateboarding world holding its collective breath.

Nyjah’s barrage of monster rail tricks, death-defying gaps, and horrendous falls serve as a testament to his near-supernatural skateboarding prowess. Risking spinal injuries on grinding handrails and gaping stair sets, his ‘Til Death” performance is a spectacle of raw skateboarding potential pushed to the limit.

10. Lincoln Ueda’s aerial acrobatics

Finally, we have Lincoln Ueda, the man who looked at the laws of physics and laughed. Known for his aerial acrobatics, Ueda has blown minds and smashed records with his gravity-defying vertical launches. Skating with wild abandon, Ueda has been known to go 20 feet airbound on a vert ramp, spinning and kicking his board under him like a kid defying a bully. His aerial stunts are not just an insane spectacle but also a reminder of the limitless potential that skateboarding holds.

My favorite complete skateboard (at the moment):

Enjoi Whitey Panda Complete Skateboard

10 of the most insane moments in skateboarding: skate legends & their jaw-dropping stunts | 61vn95mf7ql. Ac sl1184 | skateboard salad
My favorite complete skateboard (at the moment):

Enjoi Whitey Panda Complete Skateboard

I had my board stolen a few years ago and was forced to quickly replace it with a complete. I got one with an Enjoi deck and loved it so much that I still buy the Whitey Panda deck each time I need a new deck. This complete with budget-friendly, beginner-friendly parts, but I still swear by it.

My insane skateboarding experience

Alright, let me drop some personal experience here. As a relative novice to the skateboarding scene, attempting even the basic Ollie seemed like a daunting task. The fear of falling was real, but every time I landed a trick (or didn’t), I learned something new about physics, my body motions, and even my own determination.

Once I started ripping around my local park, I couldn’t help but get bitten by the skateboarding bug. Hurting was a given, but the thrill of pushing through barriers and landing tricks I never thought possible is undeniably sick.

In the world of skateboarding, if you can dream it, you can do it. So, ask yourself, “What’s your skateboarding dream?”

If there’s one thing I’ve learned in my skateboarding journey, it’s the potency of patience and perseverance, as evident in our list of insane moments. So to all you aspiring skaters out there: remember, every pro skater was once in your shoes. Or, should I say, on your boards?

Interested in more beginner tales and tips? Check out these helpful tips for new skateboarders that I found really useful in the early days of my skateboarding journey. Skateboarding entails resilience, gumption, and a heck of a lot of heart. So, go ahead, take that board for a spin, take a tumble, then get up, dust off, and drop in. Keep pushing!

Skateboarding progression over the years

Let’s take a look at the progression of skating over the years. This table charts some key moments that have defined skateboarding history and pushed the envelope of ‘impossible.’

YearRemarkable FeatSkater
1963First commercial skateboard(General)
1978First Ollie (flat ground)Alan Gelfand
1986First 720Tony Hawk
1989Natas Kaupas spins 360 on a fire hydrantNatas Kaupas
1999First 900Tony Hawk
2006First 1080Mitchie Brusco
2021First 1260Gui Khury
Skateboarding progression over the years

If you are a visual learner, check out the video below from YouTube.

Frequently Asked Questions (FAQ)

Skateboarding can be a fascinating world to delve into, and naturally, numerous questions strike the minds of both beginners and the uninitiated. Below, I’ve tried to answer some common questions related to the most insane moments in skateboarding history.

Has anyone ever landed a 1260 on a skateboard?

Yes, in 2021, young Brazilian skateboarder Gui Khury made history by successfully landing a 1260. This amazing feat shattered previous records and pushed the limits of what was considered possible in skateboarding.

What was so incredible about Danny Way’s leap over the Great Wall of China?

Danny Way’s jump over the Great Wall of China in 2005 was not only a first of its kind but also an incredible feat because he managed to break three World Records simultaneously. He achieved the fastest acceleration on a skateboard, the longest distance, and the highest distance jumped from a quarter pipe, making this leap a significant milestone in skateboarding history.

Where can I learn more about proper skateboarding techniques?

There are many resources to improve your skateboarding skills, including online tutorials, skateboarding classes, or even practicing at local skate parks. Our guide for new skateboarders can help you get started.

Final thoughts

Skateboarding is a world filled with unprecedented feats, a blend of audacity, creativity, and relentless determination. These insane moments in skateboarding history we’ve walked through make us leap into an awe-inspiring realization of human potential and the sheer joy of defying the unthinkable.

How about you? What’s your favorite skateboarding moment, or is there a trick you dream of mastering? Remember, in skateboarding, the impossible is often the untried. And did I cover everything you wanted to know? Let me know in the comments section below. I read and reply to every comment. Do share this article with a friend, and check out our full blog for more tips and tricks on skateboarding. Thanks for reading, and keep shredding!

Key takeaways

This article covered some of the most insane moments in skateboarding history. Here are some key takeaways:

  • Jeremy Ray’s Water Tower Gap is listed as one of the most dangerous skateboarding feats ever performed.
  • Danny Way made history by jumping over the Great Wall of China and breaking three World Records in one attempt.
  • Aaron ‘Jaws’ Homoki’s legendary Lyon 25 Stair Ollie is widely respected within the skateboarding community.
  • The legendary Tony Hawk performed the first-ever 900 at the 1999 X-Games.
  • Elissa Steamer paved the way for female skateboarders by becoming the first woman to be featured in the Tony Hawk Pro Skater video game series.
  • Skateboarding is more than a sport; it’s an exciting realm showcasing extreme human endurance, creativity, and resilience.

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Steven Portrate
Written by Steven Sadder, Staff Writer

Hey! I'm Steven, a lifelong skater, and proud New Yorker. I’ve been skating since I was a teenager. I may be a bit older now, but I'm not slowing down. Follow me for skating tips and latest gear reviews.

Nick eggert.
Edited by Nick Eggert, Staff 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.

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