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Driving at High Speeds Missing a Wheel Will Do That To Ya

ouch FAIL mindwarp gifs cars - 8464488192

Target: The Tree

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Via GIFAK Net
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From Downtown!

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Via s8l

Some Days You're the Dog, Some Days You're the Pole

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Via Joanne Casey
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Let's Have a Drunk Mom Ride This Skateboard, What Could Go Wrong?

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Sorry Dad

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Good Try

GIF of a cop trying to stop a skateboarder from grinding the rails but fails to stop him and the cop tumbles down the stairs.
Via Lick Nugo

Life's Greatest Pains

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Via Sarah See Andersen
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Can You Even Touch the Pole After That Burn?

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Created by Unknown

Well I Guess This Seems Like a Good Idea

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Just Take Those Old Records Off The Shelf

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Created by tamaleknight
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No Guts, No Glory

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Via Lonnie Millsap
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Parkour, "Free Running," and Falling Hard

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Madonna Eats It on Stage at the Brit Awards, Does Not Take This as a Sign to Stop Performing

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So Glad We Got These Seats in The Front Ro-OWW

ouch sports FAIL gifs hockey - 8450874368
Created by ToolBee

Slapstick Salon

ouch wtf slaps FAIL gifs - 8451135488
Created by KS_indy