Matt Hensley 1992 – Transworld Skateboarding / Photo: Daniel Harold Sturt

You know what I was thinking the other day? How basketball players are huge pussies. No basketball player has ever said to their friend, “Dude this court is sick, but what if we played basketball on the edge of that huge building!?” Skateboarders, on the other hand, have had this conversation frequently and it’s because of this, that we’re able to continue finding amazing things to skate and document. After many years of photo and video evidence, I have gathered 10 of the greatest moments of skateboarding on roofs, and put them into a nice little list for you to enjoy. So next time you’re sick of skating in front of your apartment building, try skating on top of it instead.

1. Jeremy Wray, 411 (1998)

This is beyond skateboarding. This is like some Evel Knievel deathwish type of shit. Jeremy Wray is a living legend, and if this isn’t reason enough then go back and watch his parts. The man has put in his time on a skateboard and paved the way for gnarly skateboarding to endure since the early 90’s. There’s really nothing more to be said about this ollie other than the fact that in between each try he had to jump to other tower to try it again, which in itself is an incredible feat. Any hungry am’s out there got kickflip? Yeah right…

2. Geoff Rowley’s friend – Jimmy Boyes, Extremely Sorry (2009)

I may be brushing over Rowley’s absolutely insane impossible that he does in this video, but what I want to talk about here is the guest trick, courtesy of Jimmy Boyes. After sneaking onto the Queen Mary (yes, the ocean liner) Jimmy takes the ride down an absolutely absurd death bank, but only after slamming several times before. High speed, very little control, and a completely unideal soft surface to ride on, it’s amazing he never got pitched straight off the side of the roof. But if you’re going to have a guest trick in Geoff Rowley’s part, you’ve got some pretty high standards to meet.

3. Daewon Song, Sneak Preview (2001)

This part has so much gnarly roof skating that standing alone it could be it’s own listicle. The 360 flip noseblunt, the switch crook drop to fakie manual, the list goes on. What I’m focusing on here is the rick flip. The rick flip is easily the most recklessly dangerous trick to be attempted over a roof gap. Beyond the fact that fakie is the hardest form of skateboarding, the rick flip leaves you completely blind, something that I would prefer not to be when skating over a gap with a two story drop beneath it. You’ll notice there’s no plywood put down, I think he tried to make this as hard for himself as possible. Oh did I mention this was just a promo?

4. Ali Boulala, Sorry (2002)

During the golden days of Sorry, Ali was a fucking nutcase. If the Behind The French Fred Scenes don’t illustrate this enough, than maybe we can just break down this one clip from Sorry to make you understand. The kickflip off the roof onto the metal storage unit is as much of a suicide attempt as it is one of the gnarliest clips in his part. Its hard to say just how high the gap is between the roof and the storage unit, but to survive the first gap only to take another drop well over head height seconds after landing the kickflip, it’s hard to really wrap your head around it all. But when you’re gunning for 25 stair ollies and walk around with your “hass” hanging out, I guess it’s all the same to you…

5. Chad Muska, Guilty (2001)

Classic Muska moment right here. In coordination with a classic Muska 360 flip over the Venice roof gap, Muska took a spot formerly used by ledge skaters and made it his own. The ollie from the roof down to the bench is a testament to Muska’s ability to leave all of his fuck’s at home. Just another incredibly gnarly clip courtesy of one of the gnarliest dudes to ever do it. All hail Muska.

6. Tony Ferguson, North Two (2004)

Tony Ferguson being on this list might surprise you, but when you see the clip I’m talking about here it might not seem so strange. Tony Ferguson always struck me as a minimal risk type of skateboarder, but switch inward heelflipping an aluminum roof gap says otherwise about dude’s skating. An incredibly difficult trick on flatground, taking it across a roof gap of any kind, let alone an aluminum roof, is gnarly. I think by this time people had written Tony off as gone with the wind, but this part’s a big ol’ middle finger to anyone that thought he didn’t have it anymore.

7. Tengu Crew, Tengu: God Of Mischief (2014)

The California scene may have pioneered skateboarding on roofs, but it’s the Tengu crew in New York that are keeping it alive today. There seemed to be a hiatus in roof footage for quite some time, gone were the days of gnarly gaps and bench-over-gap set ups. But when Tengu: God of Mischief dropped, it looked like roof skateboarding was still in full effect. Pivot to fakie’s on the edge of buildings, risky grinds 30 stories up, and a wild roll into bank, Tengu introduced the world to East Coast roof skateboarding and it is without a doubt just as fun to watch as our West Coast brethren. And when I say “fun” I actually mean “terrifying.”

8. Clint Walker, Modern Art (2013)

Clint Walker seemed to appear out of nowhere, but since his arrival he’s been nothing but on fire. His Ambiguous Modern Art was an all terrain assault, leaving every spot he skated absolutely destroyed. The nollie heelflip into the bank on a catwalk between two enormous apartment buildings is just a taste of this dude’s unrelenting deathwish via skateboarding. Props to the editor for keeping the clip where Clint’s board flies off the side of the catwalk, perfectly illustrating the certain death Clint would have succumbed to had even the slightest error occurred.

9. Mark Gonzales & John Cardiel, Antihero (1998)

Two legends, one insane spot. Long before Pee Wee and Greco battled it out to claim the legendary Sunset Car Wash as their own, Cardiel and Gonz laid the groundwork for anyone insane enough to try this. I’ve had the pleasure of visiting this spot and I can tell you just running up to the top of the bank is in itself a notable feat. Cardiel’s able to handle the early grab roll-in first try, but Gonz’s attempt ends in a face slide directly into traffic. Let this be a lesson to anyone thinking of hitting this spot in the future: if the Gonz got smoked, you’re probably gonna get smoked too.

10. Aaron “Jaws” Homoki, Instagram Clip (2014)

Is the water in Arizona tainted or something? What is wrong with this kid? It goes without saying but Jaws is out of his goddamned mind. Jaws has had a number of memorable moments skating roofs, but the one I’m referencing here is the mind bending one push drop to a second roof, where he then back 180’s to flat. Was that fun? Were you even scared? Is that what a normal day of skating is for you? “Oh hey Jaws, I got this like roof drop, it’s pretty sick…oh and you might die.” If skateboarding hasn’t killed this dude already, than I don’t know what will. Oh yeah, and in 2014, this was released as an Instagram Clip.

Words: Rob Ridge (@rojosworld)
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