The Most Hilarious and Gruesome Parkour Fails

Pole Crotching

One of the most important things to maintain whenever you're doing parkour is momentum. If you have that, it's easy to turn a disaster into something cool. If you don't, the opposite often happens. In this short clip, an aspiring free-runner attempts to nimbly sprint along the tops of some divider poles. He takes the first one just fine, but when the time comes to go for the second, he hesitates - and he who hesitates is lost. And in great groin pain.

Dumpster Faceplant

Dumpsters are popular landing spots for amateur free-runners, as they're usually full of soft trash to soak up your impact. The fact that they could be full of infectious medical waste or live animals doesn't seem to cross their minds very often. Making a roof jump into a dumpster is a common parkour stunt, but this guy didn't seem to realize that the actual dumpster itself is made out of hard, unyielding metal, and his face meets it with a pretty intense noise.

Playground Pants Poop

Parkour is an urban invention, meant to be done in the diverse environments of a city. So what do you do if you don't have access to a bustling metropolis? Head to the playground, as many wanna-be parkour pros do. This suburban chump had a great stunt in mind where he would jump from a pole onto the top of the climbing wall, but his landing didn't quite go as planned, and he put some punctuation on the whole hilarious fail by letting loose a little brown in his undies.

Mailbox Face

One of the toughest things about parkour is the spatial awareness it requires - urban surfaces are typically not as clean and navigable as those in a video game. A great example of this comes from this short clip, where an aspiring free-runner sets up a string of tricks on a wall. He does a halfway decent job landing a wall flip, but when he keeps his head down as he runs forward, he makes a new best friend in the form of a wall-mounted mailbox that knocks him down for the count.

Through The Roof

When you're working on a parkour run, you have to make some assumptions about the environment. In most of the civilized world, you can depend on a certain standard of construction quality. But when this Polish free-runner decided to try a roof jump while on vacation in Egypt, he learned a little something: that roofs there were not built to deal with the possibility of a white dude landing on them. Seriously, that thing looks like it's made out of papier mache.

Underwear Pole Catch

This might be the most embarrassing parkour fail video in this entire list, for a few reasons. First, the stunt that this chubby athlete is trying to do isn't impressive - he's just trying to vault over a pole in a parking lot. But even that simple task is well out of his reach, as his athletic shorts snag on the obstacle and send him flipping to the pavement with his tighty whiteys exposed to his friends - and, by extension, the world.

Triple Flip

Typically, parkour stunts are done solo. But this group in California decided to add a little teamwork to the mix, and the results weren't good. The stunt was simple - three dudes do flips over each other onto the soft beach sand. Unfortunately, the third man to take to the air really misjudged his landing site, and ended up introducing his groin to the back of somebody's head, with hilariously grimy results. I'm sure that poor dude had sand in his gums for days.

Backflip Faceplant

This is one of the most legendary parkour fail videos ever filmed - short, sweet and immeasurably painful. A dudebro in a visor climbs to the top of a candy machine in an alleyway somewhere and launches himself off into a fast-rotating backflip. Unfortunately, he caught the tips of his toes on the opposite alley wall, sending him face-first into the pavement with the sound of cartilage shattering in his face.