The commentators' reactions to it make it even funnier.
"Wesson Smith; Right up there with the great masters: Gaugin, Monet..."
"and Ron Jeremy!"
"Indeed, some inspiring skid marking there and we're all tied up at 23."
Many a contestant during many an episode with the rolling rock challenge getting crushed against the wall by the obviously styrofoam rocks, but the bone-crunching sound effects and screaming added in makes it hilarious.
In the very first episode, contestant (Rob Tussin), as he decides to show-off, goes for a backflip... and lands directly on his head, all before he stepped on a stone in Sinkers and Floaters.
Kenny: Oh god, he's still goin'! (Rob does his run and wipes out) Oh, how can he— oh, he must be feeling really stupid!
Vic: I don't think he's feeling anything from the neck down, Ken.
Then there's the interview he gives afterwards. "Did I win?" "I have blood in my stool."
What makes this even funnier is that unlike other wipeouts, we cut to Vic and Kenny in Stunned Silence. They then forget about the contestant's actual performance during the challenge and continue to comment on the backflip gone wrong.
Also note the guy behind them laughing his ass off, the only person in the shot that is expressing any sort of emotion that isn't shock.
What also makes this hilarious is that majority of the interview was given to his son.
Another funny thing about this? Tussin's scream in pain after he hits his head.
Bonus points for it being credited as the #1 Painful Elimination of the Day in the episode.
In the same episode, we have a combination Funny and Awesome with the "Log Drop", where the final contestant keeps nearly falling, only to manage to scramble back up and continue - after doing so 4 times, he manages to actually finish.
Another contestant does something similar (which also was credited as the #1 painful elimination of the episode) in Circle Jerkers Ahoy from the "Novelty Gifts Industry Vs. the Death Industry" episode, after getting excited upon getting the yellow ball, he does a backflip, landing on his head and staying that way for a good five seconds, all before he faced his opponent (even though he faced off against Golden Shower Boy). Poor impulse control mixed with even poorer coordination sure makes for a hilarious cocktail, don't it?
During one challenge in which contestants much run up a hill where giant rocks are hurtling toward them from upslope, with the only shelter populated by gashmen there to keep them out for a challenge, the last contestant for the footwear industry pulls one of them out of his hiding spot, and the second one falls over trying to catch them both. And they all wind up getting crushed, resulting in a chaotic 8 boulder pileup. Now that's carnage!
After the injuries a previous contestant suffered during Boulder Dash, a new safety suit is made and Kenny decides to test it during a Boulder Dash run. He comes out of it with crushed nuts after he ends up "hugging" one of the boulders due to minimal padding in the "groinal-sack region" and stuff dripping out of his ears after a second boulder hits him directly in the head despite the helmet.
On his way to test the suit, Kenny purposely hits his head against the wall to test the helmet.
Kenny: I tested the wall first, it's pretty solid. Vic: Good, thinking Ken.
"For my homies!"
The entirety of the Broadcast version of "Real Monsters vs. Commercial Mascots". If you thought watching everyone wipe out was hilarious, now you get to watch them wipe out in full costume; some of the contestants even try to act in-character in spite of giant boulders rolling their way.
In "Addicts vs. Donors", the last of the addicts in The Dash to Death spontaneously donates his pancreas note actually a prop just broke off in such a way that it looked like something pink was falling out of the man's rear and completes the challenge, scoring a point for both teams.
Also from that episode, the last contestant in Rotating Surfboard Of Death is neither an addict nor a donor, but the guy who runs the sandwich truck that delivers Vic and Kenny's lunch daily, and hilariously, he wins it.
And at the end of the episode, after the addicts defeated the donors, Kenny had a special prize set up for them.
Vic: Well, there's our victorious team of addicts, running through the doors of treasure! Well, what's in the prize bin this week, Kenny? A washer and dryer, some luggage, a new car perhaps? Kenny: Better than that, Vic! I've got two words for ya: "ki-lo!" Vic: "Ki..." (at this point, the contestants have entered a large bin full of a white powder) Kenny! That's not what I think it is, is it?! How could you do that?! THAT'S DESPICABLE!!! Kenny: Oh, don't worry! It's not that, it's powdered milk! C'mon, they're junkies! They don't know the difference!
The Sustained Misunderstanding during Dash to Death in "Adult Entertainment vs. Home Improvement" needs to be seen in full in order to be appreciated:
Captain Tenneal: Who thinks that contempary literature's in shambles and lack the great masters; Shakesphere, Hemingway and Jackie Collins? Show of hands... now! Contestants: (cheers) Captain Tenneal Well, you're wrong; I just published The Captain's autobiography called Well, You're Wrong! by The Captain.
Later, as Door Jam gets underway:
Captain Tenneal: Geeeee-Buy my book!
And later prior to Brass Balls:
Captain Tenneal: I'm going to be manning the gun, shooting the brass ball to our contestants. Now buy my book.
Kenny showing off "upcoming games":
"Beaver Shot", using a clip from a game of Endangering Species.
"Lava Biking", where you bike over hot coals. Kenny tried it and got tenth-degree burns.
"Head Stop", where you try to stop a bucking bronco with your head. You gotta hand it to Kenny, he had the balls and brains to come up with a future Olympic Sport.
"Big Swinging Knockers", a game that's basically a human Newton's Cradle. Kenny got the idea from watching women's volleyball.
"Name That Stain", showing Kenny wearing various messes being swung against a wall. Talk about a brush with Death!
Boulder Dash was based on a Swedish game called Flatternoggin.
Yankin' It was based on the ancient Central American game El Pullo Ropo. The Aztecs used the braided entrails of the giant Yucatan chicken for a rope.
Turtle Gut Check was based on, and I quote, "The beloved bedtime story The Princess And The Cleaver, about the enchanting young stevedore who, with the help of magical sleeping sea turtles, travels to the tiny kingdom of Gazebo and rescues the royal conjoined virgin twins who were forcibly separated by Rusty and Crusty, unlicensed pirate surgeons."
Eat Shitake was originated by hobbits; "It combines the lighthearted frivolity of fungus flying with the horror of drowning!"
Swishbucklers is taken from an drinking game popular among "alternate lifestyle" pirates.
Muddy Runs was based on the Ancient Fluid Druid ceremonial sacrifice "where they believed if they controlled your sewage they controlled your soul." Kenny even commented that "They built Stoolhenge."
"Finger it, created by the ancient Assyrians, combines the dangers of rhythmic dance with the conflict resolution of Roshambo."
Those crazy questions during games of Hand Job (and similar games).
"You've reached your milestone 60th birthday and your children have pitched in to get you the novelty mounted singing bass. How many minutes until you write them out of your will?" Answer: 1.
"How many victims must you have before you are called a serial killer?" Answer: 5. "...what would 4 be?" "Oh, just someone with a bad temper."
"You start with 8 minutes of Pawing, minus a 9-Volt toy, plus 4 hours of football, minus 2 front teeth. equals what?" Answer: Just 1 more unsatisfied wife.
"Take 5 years in a cult, add 5 angry studio execs, plus 3 bogus marraiges, minus 8 minutes bouncing on Oprah's Couch, and you get what?" Answer: A 5ft. action hero.
"You start with 5 cops, killing 3 of them with 9 bullets, and you bribe 6. How many of them were dirty?" Answer: 17.
"Everyone knows that Fake Dog Poo is the #1 best selling Novelity item in the world. How many different kinds of Fake Dog Poo are there?" Answer: 5. "Whodja thought that #2 would be #1?"
"After he cut his ear off, how many times does the phone have to ring before Van Gough realize someone was trying to call?" Answer: 10 rings.
"In each grandstand in a typical NASCAR race, how many fans are sporting a mullet?" Answer: 513.
"How many baton hits are required before it's considered unreasonable force?" Answer: 11.
"You start with 1 good idea, dump 9 friends from the video store, add 8 pop references, and 2 Weinstiens and what do you get?" Answer: Too Powerful to be sued for plagiarism.
"Take 2 days in Daytona, plus 3 drunken college, add one explotive cameraman, and the 9th Circuit court of appeals, and you get what?" Answer: $15,000,000 in profit.
"In Da Vinchi's famous painting of 'The Last Supper', if you look closely how many Apostles ordered the Shrimp Cocktail?" Answer: 7, the other four split a Quesadilla, and Judas had the Nachos.
"How long would a Californa Death row Immate stay on Death Roll before actually being put to death?" Answer: 9 decades.
"How many explorers does it take to wipe out 14,000,000 indigenous people in the Yukatan?" Answer: One Missionary with a Cold Sore.
"On a California freeway, what is the minimum number of bullet holes your car must sustain before the Insurance company considers you a 'High Risk'?" Answer: 5. Kenny's Jetta has 6.
"You're stranded in the Himalayas; it's either starve or milk the mythical Yeti. How many gallons of man milk can you expect?" Answer: 4.
Related: In the Hand Job game in "Hollywood's Jilted Wives vs. Cheating Husbands", the fact that no one finds it odd that one of the Jilted Wives is David Bowie. (What does that say about Angie, the ex in question?)
Kenny swearing in the beginning of "Religious Right Vs Gay Rights".
How Does a Prisoner say "Good Night" to a Cellmate? *Fart Noise*
Tamela Lee's painful fall in Log Drop.
A contestant finding out why his opponent is known as the "Green Teabagger" the hard way, it even Deserved a MXC/Noralco Impact Replay.