Pop, Documented: Tyshawn Jones’ 10 Best Ollies Ever
From a Philly plaza to a Ferrari to Samuel L. Jackson — the two-time Skater of the Year has made a career out of clearing things that shouldn’t be clearable.
Pop, Documented: Tyshawn Jones’ 10 Best Ollies Ever
From a Philly plaza to a Ferrari to Samuel L. Jackson — the two-time Skater of the Year has made a career out of clearing things that shouldn’t be clearable.
Tyshawn Jones has one of the most powerful ollies in the history of skateboarding. That’s not an opinion — it’s a matter of public record, documented across video parts, Thrasher covers, and a Ferrari in a parking lot. But what makes it special isn’t just the height. It’s the ease. Tyshawn does things correctly — the way they’re supposed to be done — while making them look so effortless you’d think he stumbled into them.
That combination of precision and nonchalance is the foundation of everything he does on a board, and the ollie is where it all starts. We’re talking about a guy who turned a Midtown Manhattan subway entrance into a skate spot, who ollied a loading dock in the middle of a line like it was a curb, and who somehow found a way to top all of it by clearing Samuel L. Jackson down a set of stairs.
We went deep on everything else in our cover story on the icon. This one’s just about his ollie — and these ten clips are why it deserves its own conversation.
“Play Dead” (2014)
Ollie Can Into Propped Tile at Muni in Philly
Muni in Philadelphia is one of the most storied spots in street skating, and this clip is a big reason why. Tyshawn ollies over the can, landing easy onto the propped tile kicker— a transfer that demands both precision and serious pop. He claimed the spot by hitting it from the opposite direction, like he never even meant to try in the first place.
“Blessed” (2018)
Ollie Into the 33rd Street 6 Train Entrance, NYC
The 33rd Street subway entrance isn’t a skate spot. It’s a guardrail, a staircase dropping into the street, and a spiked fence on the other end — all of it in the middle of one of the busiest blocks in Manhattan. The clip appeared in “Blessed,” Supreme’s second full-length skate video, which dropped in 2018 and featured Tyshawn in the coveted final part. Getting the trick required as much logistics as it did athleticism: Tyshawn brought a crew of friends to manage the chaos, positioning them around the entrance to hold back the crowd before each attempt. According to a New York Times profile of Jones, when he finally landed it, office workers in the building above had gathered at the windows to watch — and when he rode away clean, the whole floor erupted. The photo landed him on the cover of Thrasher. Only TJ could turn a commuter nightmare into a historic skate clip.
“The General” (2022 / 2023)
Switch Ollie Over the Picnic Table the Long Way
When Tyshawn does a trick, he does it correct. He did this switch over a picnic table the long way and got a Thrasher cover for it. Then Gifted Hater, one of skating’s most notorious online critics, questioned whether it was legit. So Tyshawn did it again, on Instagram, just to settle the debate. The trick is incredible, but the encore is iconic.
“Blessed” (2018)
Ollie Can Into the Courthouse Drop in NYC
The Courthouse is the spot that made Tyshawn famous — it’s where he earned the nickname “The Courthouse Kid,” a moniker he picked up after rattling off a string of tricks at the iconic Foley Square spot that stopped the skate world in its tracks. So it’s fitting that one of his best ollies happened there too. He pops into a can and sends it down the drop with the kind of control that makes a genuinely dangerous trick look routine. Thrasher later ran the photo, which tells you everything about how it landed.
“Blessed” (2018)
Switch Ollie Over a Traffic Barrel at TF West, NYC
TF West — the William F. Passannante Ballfield in Greenwich Village — is a notoriously barren spot: a flat expanse of asphalt with no ledges, no stairs, not even a curb. The trash cans are basically the only obstacles, which is exactly why Tyshawn treats them like a proving ground. This switch ollie over a traffic barrel is deceptively simple-looking — until you remember he’s doing it switch, and that the height he gets is borderline unreasonable.
The Ferrari Ollie (2023)
The setup is exactly what it sounds like: Tyshawn Jones ollied over a Ferrari Monza SP2. But even for someone with his verticle, this one came with a unique kind of pressure. “The Ferrari scared me most because of the price,” he admitted. “I didn’t want to mess it up.” He didn’t. The clip went viral instantly and became one of the most talked-about moments in recent skate history — even if, as he noted in our cover story, it somehow got half the views of a video of him dancing with Tracee Ellis Ross.
Federal Plaza (2024)
Ollie Over the Whole Ledge at Federal Plaza, Chicago
Nick Matthews had already done this one, but when Tyshawn posted it on Instagram with zero fanfare it felt like a completely different trick. No buildup, no big moment — just the clip, dropped casually like it was nothing. The ABD status almost makes it better: Matthews made history, TJ made it look like a Tuesday.
Ollie Four Trash Cans at TF West
Most skaters tip trash cans on their sides to keep the height manageable. Tyshawn leaves them upright. Four in a row, cleared with room to spare. At a spot with nothing to skate, he found a way to make it one of the most memorable clips of his career.
“Kingdom Come” (2022)
Ollie Up the Loading Dock in Line
Watch closely and you’ll catch him rolling over a piece of trash right before he pops — and it barely registers. What follows is an ollie up a loading dock that clears a height most people couldn’t jump standing still, in the middle of a line, without breaking a sweat. And if that wasn’t enough, the very next clip in the part is him jumping a public ping pong table and grinding the middle divider. Back to back. Classic TJ: the setup looks like nothing, the tricks look impossible.
The Ollie Over Samuel L. Jackson (2025)
Yes, really. During a shoot, Tyshawn ollied clean over Samuel L. Jackson as he sat on a set of steps — zero room for error, perfect control, and one of the most surreal clips in recent skate history. The Ferrari was scary because of the price tag, but Tyshawn has since reconsidered which trick carried more risk. “Now that I think about it, Samuel L. Jackson is worth way more than that Ferrari. Damn, I never thought of that. Samuel is worth probably 70 to 80 of those Ferraris, probably more. Shit.” Just another day on the job.
Read our full cover story on the skate icon here, and purchase a copy of Hypebeast Magazine #37: The Architects Issue on HBX.
