Skateboarding has evolved dramatically since Rodney Mullen laid the groundwork for modern tricks. To celebrate this progression, we’ve compiled a list of 15 of the most groundbreaking skateboard tricks of all time. It’s important to note that “best” is subjective in skateboarding, as it’s not judged by statistics but rather personal preference and impact. These tricks, however, are widely regarded as pivotal moments in the history of skateboarding.
Skateboarder performing a trick with a cityscape in the background
1. Jeremy Wray – Water Tower Ollie (1997)
In 1997, Jeremy Wray elevated the bar for street skating with his daring ollie between two water towers, a feat that landed him on the cover of Thrasher Magazine. After spotting the towers, which were 16 feet apart, he climbed to the top of one, 50 feet high, and after five attempts, he successfully made the jump, setting new standards for skateboarders worldwide.
2. Tony Hawk – The 900 (X-Games 1999)
Tony Hawk, a name synonymous with skateboarding, cemented his legacy at the 1999 X-Games by landing the first-ever 900 on camera. This highly technical trick involves a two-and-a-half backside spin over a coping. Despite practicing it at home, the pressure of performing it live on television was clear on Hawk’s face when he landed this iconic trick.
3. Tony Hawk – The Loop (2001)
Tony Hawk pushed the envelope further by tackling the Loop for MTV’s Jackass. This dangerous, roller-coaster-like stunt had no room for error, and any mistake could have been fatal. After multiple attempts, both Hawk and BMX rider Mat Hoffman completed the full loop, securing another place in history. Hawk’s continued attempts at the loop later resulted in one of the worst slams of his career, showcasing his dedication.
4. Chris Cole – 360 Flip Wallenberg (2003)
The Wallenberg 3 block in San Francisco is a legendary spot in street skateboarding. While not necessarily the most technically challenging trick, Chris Cole’s 360 flip down Wallenberg is iconic due to his sheer determination. It took him 66 attempts of falls and struggles before finally nailing the trick, demonstrating his unwavering passion for skateboarding.
5. Bob Burnquist – The Loop of Death (2003)
Two years after Tony Hawk’s loop, Bob Burnquist, a vert skateboarding legend, took it a step further with the “Loop of Death”. He removed the top part of the loop, creating a gap between the vert sections, and then performed the stunt switch, adding another level of difficulty to this already insane trick.
6. Danny Way – The Great Wall of China (2005)
In 2005, Danny Way, a prominent vert and mega-ramp skater, had the audacious idea to jump over the Great Wall of China. With support from sponsors like Quicksilver and DC Shoes, a $5 million ramp was built on either side of the wall. Despite breaking his ankle on his first attempt, Way returned the next day, after escaping the hospital, and landed a backside 360 with a broken ankle, displaying his resilience.
7. Dave Bachinski – Kickflip El Toro (2006)
El Toro, a famous set of stairs in Lake Forest, California, is known for its challenging terrain. In 2006, Dave Bachinsky landed a kickflip down the 20 stairs, a feat previously thought impossible. This remains one of the most iconic kickflips ever done down such a large set of stairs.
8. Neen Williams – Heelflip Burbank 16 (2011)
Neen Williams, often regarded as the master of the heelflip, is recognized for his unique style and flawless execution. While filming with Baker, he warmed up with a frontside shove-it before landing what is widely considered one of the best-looking heelflips ever executed at the Burbank 16. He caught the board at its peak, achieving a perfect, clean landing.
9. Danny Way – Helicopter Drop-In (2012)
Danny Way once again redefined the boundaries of skateboarding in 2012 with his helicopter drop-in. He jumped out of a helicopter onto a vert ramp. After several scary-looking attempts, he successfully rolled into the 30-foot ramp, further solidifying his legendary status and earning the cover of Transworld Magazine.
10. Tom Schaar – The 1080 (2012)
Thirteen years after Tony Hawk’s 900, Tom Schaar made vert skating history by stomping the first ever 1080, which involves three full 360 spins. What makes this achievement even more impressive is that Schaar was only 12 years old at the time, already having mastered 540s and 720s by age 8.
11. Dane Burman – 50-50 The Municipal Death Rail (2013)
For his video part with Zero, Dane Burman chose a handrail that was considered too dangerous to skate, with a 30-foot drop on the other side. After grinding the rail, he still had to go down a 15-foot drop, cementing his place in history as the only one ever to skate this spot.
12. Aaron “Jaws” Homoki – Ollie Melon Grab Lyon 25 (2015)
The Lyon 25, a gap notorious for its difficulty, had been untouched since Ali Boulala’s injury 18 years earlier. Known as one of the best gap skaters, Aaron “Jaws” Homoki took on this challenge. After a few close tries, he broke his board and tore his ACL, but he returned a year later to successfully land the gap in front of Ali Boulala, making it the biggest ollie gap ever conquered.
13. Chris Joslin – 360 Flip Davis Gap (2015)
In 2015, Chris Joslin, a relatively unknown skater at the time, rose to prominence by performing the hardest tricks at iconic skate spots. Davis Gap, considered an untouchable spot, had only been skated by Jamie Thomas and Corey Duffel. Chris Joslin, however, landed a 360 flip down this gap, securing his place in skateboarding history with the biggest 360 flip ever done.
14. Don “Nuge” Nguyen – Steepest Hill Bomb (2016)
While not a trick in the traditional sense, Nuge’s hill bomb down one of the steepest hills in America is an impressive feat of speed and control. He successfully rode down this street, which was so steep that it would be dangerous to drive down in a car, at 35 mph, avoiding speed wobbles and pebbles.
15. Henry Gartland – 50-50 The Kinker (2018)
Henry Gartland’s trick shows how far skateboarding has come. Grinding an eight-kink handrail was considered impossible. After four sessions, hundreds of tries, and some stitches, Gartland successfully grinded through the entire length of the daunting rail.
These 15 tricks showcase the progression and innovation in skateboarding. For the rest of us, it may be best to stick to learning easy skateboarding tricks, leaving the most daring and difficult feats to the professionals.
