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Times Somebody Got Way Over Their Skis

Confidence: 10. Execution: ...well.

By Micaela Montaña

Published 1 month ago in Funny

You know that feeling when someone charges in like they’ve got it all figured out and immediately proves they absolutely don’t? That’s this. A glorious collection of moments where confidence took the wheel, and competence… didn’t even make it into the car.


These are the bold, the brash, the blissfully unaware. People who soared into situations fueled by nothing but ego, adrenaline, and a deep misunderstanding of how gravity (or life) works. The kind of moments that start with: “I got this!” and end with: “…do we have insurance?”


Because let’s face it: falling flat is funny. Especially when someone was absolutely certain they were about to crush it. So come on and click. These folks went way over their skis, you're just here to enjoy the wipeout.

  • 1

    Live From the Lion Cage: Tonight’s Special? YOU.

    They’re in a metal box. The lions are ON the box. Who’s really in charge here?

    Live From the Lion Cage: Tonight’s Special? YOU.

  • 2

    The Upside-Down Measuring Human

    He’s upside down. Being held by the pants. He’s also in charge of numbers. Excellent.

    The Upside-Down Measuring Human

  • 3

    Stuntman? No. Just a Boyfriend With No Boundaries.

    He’s standing on her. On a motorcycle. Love is blind. And apparently brainless.

    Stuntman? No. Just a Boyfriend With No Boundaries.

  • 4

    Chaos Everywhere

    She’s the hood ornament now. He’s the Uber driver from doom.

    Chaos Everywhere

  • 5

    Extreme Dad-ing

    Because nothing says safety like strapping a baby to your chest at sea.

    Extreme Dad-ing

  • 6

    Wheelie of Fortune

    They popped a wheelie. Now gravity’s popping them.

    Wheelie of Fortune

  • 7

    Friendship Test: Can I Stand on Your Spine?

    He’s standing on his friend’s shoulders. What could go wrong? Oh, everything.

    Friendship Test: Can I Stand on Your Spine?

  • 8

    Construction Beam Surfing (For Idiots)

    Let’s check if his insurance covers ego.

    Construction Beam Surfing (For Idiots)

  • 9

    Building Your Own Grave, One Shovel at a Time

    He’s inside the pit. The machine is adding dirt. Countdown begins.

    Building Your Own Grave, One Shovel at a Time

  • 10

    Man Enters Wood Chipper And Denies All Safety Training

    Sir, that’s not a doorway. That’s a blender.

    Man Enters Wood Chipper And Denies All Safety Training

  • 11

    Homemade Hazmat: Bag on Head Edition

    He’s cutting metal. With plastic wrapped around his face. Bold choice.

    Homemade Hazmat: Bag on Head Edition

  • 12

    Mobile Ladder, Immobile Logic

    He’s standing on a ladder... in the bed of a moving truck. OSHA just fainted.

    Mobile Ladder, Immobile Logic

  • 13

    Neck-Transportation

    Two men. One ladder. Zero chance this ends well.

    Neck-Transportation

  • 14

    Aaaaand We Have Lift Off (Also, a Lawsuit)

    The raft is airborne. The therapy starts now.

    Aaaaand We Have Lift Off (Also, a Lawsuit)

  • 15

    White Water Flailing

    That raft didn’t flip. It LAUNCHED them into another tax bracket.

    White Water Flailing

  • 16

    Stability Provided by Hope and a Fence from 1962

    When you run out of ladders, and self-respect.

    Stability Provided by Hope and a Fence from 1962

  • 17

    Nothing Says ‘Relaxing Camping’ Like a Lion Nearby

    He’s sitting by the tent. The lion’s eyeing the snacks.

    Nothing Says ‘Relaxing Camping’ Like a Lion Nearby

  • 18

    Camping Tip: Bears Love Marshmallows AND Screaming

    Just two kids and a casual bear. Nature says hello.

    Camping Tip: Bears Love Marshmallows AND Screaming

  • 19

    Ladder Logic from Another Dimension

    This guy looked at IKEA instructions and said: “Hold my broken femur.”

    Ladder Logic from Another Dimension

  • 20

    Chill Date Night, Until a Bump = Broken Collarbone

    She’s on a chair. On a moving bike. On a prayer.

    Chill Date Night, Until a Bump = Broken Collarbone

  • 21

    Carpooling for Pipe Dreamers

    He’s literally hanging on for dear life. On a highway. Behind a moving man.

    Carpooling for Pipe Dreamers

  • 22

    Another Ski Fail Because Snow Hates You

    Different slope. Same regret.

    Another Ski Fail Because Snow Hates You

  • 23

    Ski Trip or Human Slingshot?

    Gravity always wins. Snow just makes it funnier.

    Ski Trip or Human Slingshot?

  • 24

    When Sparks Fly (But It’s Not Romantic)

    He tried to drift. His pants tried to ignite. Perfect date night, really.

    When Sparks Fly (But It’s Not Romantic)

  • 25

    Climbing Toward Lawsuits

    High up with no harness, no helmet, and no sense of self-preservation.

    Climbing Toward Lawsuits

  • 26

    Sawdust & Self-Sabotage

    He’s cutting the branch his ladder is on. Not metaphorically. LITERALLY.

    Sawdust & Self-Sabotage

  • 27

    Stilts + Planks + Ladders = Spine Surgery Incoming

    This guy invented a new yoga pose: the Human Liability.

    Stilts + Planks + Ladders = Spine Surgery Incoming

  • 28

    Trust Fall, HVAC Edition

    One man hangs by his legs. The other man’s arms are the only thing stopping gravity from winning. Zero engineering, 100% faith.

    Trust Fall, HVAC Edition

  • 29

    Sir, You’re the Prize in the Claw Machine Now

    He’s chilling 30 ft up on a crane claw like it’s a hammock. What union allows this?!

    Sir, You’re the Prize in the Claw Machine Now

  • 30

    Architecture by Anxiety

    This setup has more wood than logic. One man. Many planks. Infinite consequences.

    Architecture by Anxiety

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Funny Fail

Tags:

funny funny pictures funny people fail fail photos
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