In The Adventures of Puss in Boots, Puss is challenged by a Riddling Sphinx and manages to get each one even more absurdly wrong than the last, to the point where his answer to the last riddle is a lip popping sound. He then challenges her to come up with a riddle he can solve, but she fails at that.
Sphinx: What is blue and is the sky? Puss: I know this one... Sphinx: It's right in the riddle! I just said it, it's the sky! All you have to do is say "Sky"! Say "Sky"!! Puss: Can I have a hint?
In the episode, "Zoobotnik", Robotnik orders Scratch and Grounder to go downstairs and open the door.
Robotnik: Think you can manage that without falling on your faces? Scratch: No problem. Grounder: Can do. (they proceed to do just that)
On the hero side of the scale, another episode had Sonic become the sheriff of a western town and forced into a gun duel. When training for it, Sonic and Tails find out that Sonic is a poor shot. How bad? He can't shoot the broadside of a barn when he's standing five feet to it.
"The Procrastinators": Gumball and Darwin make a stack of fragile bowls, mugs, and plates, and place them on a table. They then bet on whether anything will break if Darwin pulls the tablecloth out from under it. He then pulls the tablecloth out... causing the building they're in to shatter into a million pieces without damaging the stack at all. In addition, Gumball tries to toss a candy high into the air and land it in his mouth, but he instead knocks a crow into his own mouth while the candy landed in Darwin's.
"The Goons": Gumball is tasked with putting in the only piece in a jigsaw puzzle left, goes nowhere after hours of trying, and gives up.
"The Quest": After twice demonstrating his inability to catch, Gumball fails to not catch an object he's being chased for carrying.
"The Skull": Clayton leans on a sink, knocking it off and spraying water everywhere out of an exposed pipe. He tries to stop it by putting his mouth over the pipe, but that just sends him flying around the room, destroying a bunch of lockers. Then everything catches on fire for no reason.
"The Sidekick": Darwin's inbox is so empty that the page itself is falling apart and bug-infested.
Gumball: What the? Is that cockroach inside your inbox?
"The Tape": Darwin keeps messing up the film's intro. Gumball decides to try it himself and snaps his own neck 180 degrees when he was supposed to turn around.
"The Fridge": A montage of Gumball's accomplishments this week includes jumping off the high dive and getting his shorts pulled off by the board, giving Penny a bouquet of flowers that was full of bees, and his performance for the school band where he had to hit one note on a triangle and missed the instrument entirely.
"The Banana": Banana Joe tries to beat up Darwin and Gumball, but trips and knocks himself out without even touching them.
"The Mothers": Mrs. Banana tries to play the piano and it immediately collapses into a flaming wreckage. Also, one round of the contest is walking over a floor covered in cooking oil without falling over. Mrs. Banana takes one step on it then immediately falls and shatters into pieces like glass.
"The Joy": Miss Simian tries to flip over a table in rage, but it flips exactly 360 degrees, landing it back where it started with no change.
"The Uploads": In a sort of double subversion, Hector is filming an old man tripping with a trashcan and falling over from far above, which isn't that big, but when he turns the camera to him to speak to the viewers it's just in time for an airliner to crash into his neck and knock him down on camera.
Gumball: That's the first of one of those I've seen that was actually epic.
The four times Francine stated "I Told You So" to Stan in American Dad!: Stan somehow crashing a British double-decker bus into the garage, Stan accidentally killing two bungee-jumpers by wrapping the cord around their necks, Stan losing a game of chess to a turkey, and Stan setting the backyard pool on fire — while there was water in it.
And in "Fartbreak Hotel", without Francine, Stan can't even dress himself.
Fu Dog from American Dragon: Jake Long is a magical sentient and talking dog, but the one time he needed to communicate with a normal dog he needed an English/Dog dictionary... And still failed.
In Back at the Barnyard, Pig was so bad at golf, when he had to replace Otis during a game, he managed to wipe out Otis's 300 stroke lead.
This was sometimes zig-zagged in the earliest Ben 10 comics; often, Ben would use the Omnitrix and mistakenly turn himself into an alien other than the one he had wanted. (For instance, in one case he thought the super-strong Fourarms was best for the crisis, but instead he got the super-smart (but physically weak) Grey Matter. Nevertheless, he was usually able to solve the problem with whatever he got.
This tends to be a trend in certain Gene-centric episodes. They start off with him being incredibly enthusiastic about trying something new and then he completely and utterly bombs within five minutes. In one episode, when he's being entrusted with a flour sack baby, he not only drops the first one seconds after getting it, but he then dropped the replacement and the one he stole from another classmate. In the episode where he was on a Little League team, during his very first turn at bat he got so freaked out when someone pitched the ball he purposefully swung his bat three times in a row to strike himself out. The rest of the game went so badly the parents of his teammates consoled their kids by flat out saying it was Gene's fault they lost.
Darkwing Duck once tried to get rid of a fly by using explosives. His house became a mess and the fly survived.
Dexter's Laboratory: The first Dad Cartoon involves Dexter's Dad attempting to clean his car on Saturday, only to break more and more of it as the short goes on, and eventually growing so frustrated by this he just shoves the wrecked car off a cliff in a rage. That's bad enough, but then it's shown that there are dozens of cars down there, implying he's done this every Saturday for MONTHS.
"Invasion of the Dads" is full of this. Mr. Turner causing a flood while trying to fix the plumbing seems reasonable, right? Well, he ended up causing a flood every time he used a monkey wrench, even when there wasnowater involved. It even happened when all he did was open the door.
Want to know how terrible a baseball player Chester is? He once got nine innings worth of outs with one swing.
In "If I'm Dyin' I'm Lying" Peter threatens to go on a hunger strike. Most people could predict he'd fail but nobody could predict how badly he'd fail:
Peter: (after being on a hunger strike for all of five seconds) You gonna eat that stapler?
In "Peter Problems" Peter is promoted to a forklift operator and is eventually fired for negligence. Now stuck at home, he tries to prepare dinner, then ends up putting three raw chickens at the table, and when he realizes his mistake he finds that he somehow put Chris in the oven, put Stewie in the freezer, and decapitated Meg and put her head in the microwave, which then explodes in a splatter of gore. They're all perfectly fine later.
Dr. Zoidberg attempts to fix his beloved slinky, presumably re-coiling it himself (offscreen) after it was all straightened out. Placing it on a staircase made of books, the mangled slinky topples down the books clumsily, and somehow catches fire at the bottom. Dr. Zoidberg bursts into tears.
Nearly everything Zoidberg loves catches fire. For instance, his house which was destroyed by a cigar end, three kilometres underwater.
Zoidberg: My house! It burned down! How could this have happened?! Hermes: That's a very good question. Bender: So that's where I left my cigar. *Takes a puff* Hermes: That just raises further questions!
In the episode "Future Stock", when Mom's children are voting on the Momcorp-Planet Express merger, Ignar has a controller with two buttons, "Yes" and "No." He somehow casts his vote for Pat Buchanan. His excuse: "The ballot was confusing." note If you don't get it, it's a reference to the 2000 presidential election in Florida, which saw an above-average amount of votes in heavily Democratic counties like Palm Beach for Buchanan which Buchanan himself attributed to the confusing nature of the ballot.
In the epic, "absolutely nothing on the line except the shame of defeat" basketball game between Earth and the Harlem Globetrotters planet in "Time Keeps on Slipping", one of the genetically-engineered basketball-playing super mutants accidentally gets splattered. Fry offers to substitute. When asked if he's any good, he says that it doesn't really matter because they're up 35 points with two minutes left in the game, so it's not like he could seriously screw things up. Cue a timeskip where the game is over and somehow the Globetrotters are now ahead 244 to 86.
The sixth season has an episode where Fry is building a machine with Leonardo da Vinci. The blueprints keep rolling back up after being spread out, so Fry gets the idea to tape them to the table. The table snaps in half like a bear trap.
In "A Pharaoh to Remember", a depressed Bender decided to spray paint a blank building wall with a picture of himself and the phrase "Bender lives large and kicks butt." The building is then demolished, changing the picture to a person's behind and the phrase to "Bender licks butt" a la a MAD Magazine fold-in joke page.
In one episode of Garfield and Friends, during a vacation, Jon, Garfield and Odie entered a long tunnel. It took them a whole day to reach the other end. Even Garfield doesn't know how Jon got lost in there.
G.I. Joe: A Real American Hero: In "Cobra's Candidate", a candidate for mayor is exposed by the Joes as a puppet of the evil organization Cobra, who were planning to put their goals into law. As a result, he goes from a commanding lead to losing in a landslide with only two votes out of 2.1 million, both of which turn out to be from Cobra operatives. Not even his own family was willing to vote for him.
Mentioned in the first season finale of G.I. Joe: Renegades when Mindbender's Bio-Viper is destroyed in an experiment he was sure would work.
Destro: I believe the term is EPIC FAIL.
In The Jetsons, George and Jane once left their kids home alone for an extended period of time and Judy tried to serve ice cream. She burned it. She didn't melt the ice cream, she burned it without melting it.
An episode of Johnny Bravo has Johnny entering a cooking contest. He comes in 16th place, in a contest that only had 12 contestants. The cake that he made was made of random junk he pulled out of their pockets.
In the Justice League Unlimited episode "Ultimatum", the Ultimen, an expy duo of the Wonder Twins, tried to defeat AQUAMAN by turning into: A) water, in an attempt at drowning Aquaman; and B) a land-based dinosaur that could barely move in the water, let alone breathe in it. Aquaman's response: "King of the Seas, remember?"
In the ending of the Kim Possible episode where Ron ended up becoming a multi-millionaire (and gaining a personality change to match), Dr. Drakken managed to create a lair with a large laser cannon from the funds he acquired from Ron. He then demonstrates the weapon's abilities by firing it at the moon, deflect on mirrors installed there and start his fiendish Evil Plan. Instead, it returns right back to the source and demolishes his own lair. Shego then tells him that it was a colossal waste of money.
On the other end, Ron also suffered from both this trope and Status Quo Is God; Dr. Drakken was able to steal literally every penny of Ron's ninety-nine-million dollar royalties fortune because...Ron kept all of it in his pants. Somehow.
A King of the Hill episode has Peggy doing the famous "Stick a flower in liquid nitrogen and watch it shatter" experiment, which goes off well...until she drops the flower on the floor and it doesn't break, after which, she tries bashing it against a desk and it still doesn't break. She then throws the rose at the window, which breaks the window but not the rose.
A different episode has Hank, Dale, and Bill being a pit-stop crew while Boomhauer is the racecar driver. Hank and Bill do their jobs, and Hank tells Dale to stand in one spot, not moving, and hold a bucket of sand. Both Bill and Dale somehow get in the backseat. And Dale dropped the sand.
In The Legend of Korra, Bolin is told to bribe the judge for Tonraq's trial and given money to do so. He instead bribes two random people who were not even involved in the trial. Asami lampshades his incompetence in this case.
The Legend of Zelda from The Super Mario Bros. Super Show opened one episode with two pairs of Gannon's troops sneaking into Link's quarters to kill him as he lies in bed reading a book. As soon as they enter, one trips and accidentally fires his crossbow, killing one of his teammates. That teammate fires his crossbow as he's killed and kills another of his teammates. That other teammate does the same and the one he kills does that as well to the one who started the whole debacle. Link's still in bed with his book when the last one falls.
Link: Boy. I'm good.
In The Lion Guard, Kion and the Lion Guard decide to remove the bees in the eland herd's way instead of directing the herd away. Unsurprisingly, they get chased by the bees, but Bunga isn't bothered, happily snacking on bees and honey.
Wile E. Coyote was prone to epic failure, often in humorously spectacular fashion. Some of the more memorable ones included a dose of Chekhov's Faulty Booby-Trap.
None, however, was ever more famous than the catapult in "To Beep or Not to Beep", which fails not once, not twice, but an amazing six times in his latest attempt to flatten the Road Runner with a large boulder. The Coyote, determined to make the catapult a success, but is continually flattened as the catapult fails (and sometimes collapses) in physics-defying ways. When the contraption jams on the sixth try, Wile E. tries like heck to get it unjammed before the arm finally releases the boulder. Wile E. doesn't notice that he's hurtling through the air atop a flying boulder until it's too late, and is crushed against another rock formation, dashed into high-voltage power lines, and sent flying back to the catapult, which throws him to the ground right below the point where the boulder lands. Viewers then see the reason for the epic fail: the manufacturer's nameplate, which reads that the catapult was made by the "Road-Runner Manufacturing Company; Phoenix * Taos * Santa Fe * Flagstaff."
Marvin the Martian does this often too. In "Mad as a Mars Hare", he first tries to zap Bugs with a disintegrator, but winds up disintegrating himself (requiring him to "reintegrate" himself, ranting that "Being disintegrated makes me very angry!"). Then he tries to use a weapon on Bugs that will, in theory, evolve Bugs into a higher form that will make him subservient. Unfortunately, Marvin gets the weapon's setting backwards, turning Bugs into a super-strong Neanderthal rabbit. It ends painfully for Marvin.
Chuck Jones came to define Daffy Duck in these terms, especially by casting him in archetypal 'movie hero' roles, and having him fail spectacularly and worse still, constantly being overshadowed by meek sidekick Porky. Then there's the cartoons where he tries engaging in a battle of wits with Bugs Bunny...
In The Looney Tunes Show episode "To Bowl or Not to Bowl" Daffy is tied with the opposing team in a bowling tournament and is one strike away from winning. He first gets a gutter ball, is given a free turn due to a technicality, then gets another gutter ball. He's so mortified by his embarrassing loss that he stands motionless in the bowling alley all night.
In the The Loud House episode "Changing the Baby", Leni somehow gets trapped in Lily's crib, after entering her room to show her fashion magazines. The image of her trapped in Lily's crib has now become a Memetic Mutation.
It only happens in her imagination, but in the episode "The Ticket Master", Pinkie Pie imagines playing "Pin the Tail on the Pony" at the Grand Galloping Gala, with the result that she somehow pins her own tail on the pony drawing and the paper tail in its place on herself.
Sweetie Belle: Um, I'll just stand over here off to the side and not get in your way, like you said earlier... Rarity:(eye twitch)
In the episode "Over a Barrel", Pinkie Pie's solution to a conflict between a group of Native American-like buffalo and some settlers is to sing an extremely Tastes Like Diabetes song about how they are all the same deep inside and should just get along. Afterwards the two leaders agree—that it was the single worst song they had ever heard, and that they still intend on fighting over the land. The real epic failure comes later: when the buffalo leader has a crisis of conscience, Pinkie figures it would be a good time for a reprise, which causes him to go berserk and lead the buffalo in the charge after all.
Subverted in "A Bird in the Hoof", where Fluttershy starts trying to take care of Princess Celestia's pet bird, which seems to be in awfully bad shape. The bird only keeps getting worse, until it croaks and spontaneously combusts into a pile of ashes right in front of her face—at which point the princess shows up and tells her pet phoenix to stop fooling around.
Rarity: I didn't know you could... burnjuice. [Later, Sweetie Belle presents a bowl full of a bubbling, black liquid.] Rarity: Ugh... Let me guess, applesauce? Sweetie Belle: Nope, toast.
Pinkie Pie's attempts at babysitting the Cakes' twin foals in "Baby Cakes" steadily deteriorate into this. Case in point: Her struggle to put fresh diapers on them ends with her wearing one on her own hindquarters, and the other on her head.
Derpy Hooves's first speaking appearance in "The Last Roundup", appropriately enough, is little more than a rapid succession of these. After she has already done serious damage to the town hall offscreen, nearly electrocuted Rainbow Dash with a thundercloud (and successfully pulled it off on herself), and injured Rainbow by accidentally causing still more damage to the building, the latter exasperatedly orders her to just sit down and do nothing. As soon as she sits, a section of the porch collapses under her weight and she falls through, dragging Rainbow down with her.
In "Spike at Your Service", Spike attempts to do favors for Applejack and turns even the simplest tasks into disasters. One of the best examples is when he is asked to wash a single dish and somehow ends up dismantling Rarity's pipes.
In "Magical Mystery Cure", the mane six (sans Twilight) get their destinies and cutie marks swapped—but the necessary skills to actually perform these new jobs aren't transferred, leading the ponies to fail miserably. Rarity tries to manage the weather, and subjects Ponyville to rain, snow, and sunburn-inducing sunshine all at the same time. Rainbow Dash tries to care for animals and screws up so badly that the animals—even the herbivores—try to cook and eat her. Fluttershy tries to cheer up everybody but only makes them more angry. Pinkie Pie tries to run Sweet Apple Acres and nearly kills all the trees in less than a day. Applejack tries to make dresses and does so badly that she's forced to close up shop in less than a day.
In "Party Pooped", Pinkie Pie goes on a journey to reach Yakyakistan, but at the last moment, the icy edge she's on breaks off, and she ends up sliding all the way back to Sugarcube Corner.
In "Amending Fences", we find out that one of Twilight's old friends, Lemon Hearts, got her head stuck in a flask as a filly.
Until "Crusaders of the Lost Mark," this was the most common ending to the Crusaders' attempts to get their cutie marks. Zip-lining? The carabiners bunch up in the middle and they go into free fall. Taffy making? Scootaloo's tail gets caught in the mixer. Hair care? A filly leaves the shop looking like a rodeo clown.
Knowing Phineas and Ferb have a pet platypus named Perry and seeing Perry fighting "so good" to protect them from Perry the Platyborg didn't ring any bells for him. Perry still needed to put on hisfedora hat for Doof-1 to recognize him.
In school, Doofenshmirtz once lost to a baking soda volcano in a poetry contest.
Rigby: How do you score negative points? How is that even possible?!
In "Benson Be Gone", Benson told Mordecai and Rigby to park Mr. Maellard's limo but ends up crashing it into the park house...on the second floor.
Mordecai: Hey, Benson... remember when I told you I could drive stick? Well, turns out I'm a little rusty.
Richard Scarry's Best Learning Songs Video Ever: After Freddie Fox finishes his song about numbers, he slips on a Banana Peel and grabs onto the curtain, accidentally pulling it down and ruining the stage. This results in him and some of the other kids getting buried under the curtain.
Huckle Cat: Ladies and gentlemen, we're experiencing technical difficulties. Please take a fifteen-minute intermission.
In the Rocko's Modern Life episode "Gutter Balls", Ed Bighead has a flashback to his final frame on a bowling tournament. With the scores tied, he only needs one pin to win, and he deliberately wasted his first roll on a gutter ball. He throws the second ball, but instead of rolling down the lane, it flies off and ricochets all over the place, demolishing the alley. At the end, the only thing left standing are Ed's pins, completely untouched. He could Never Live It Down.
Rocky and Bullwinkle. Early in NBC's run of the show, a live-action Bullwinkle puppet would introduce segments. In one infamous incident, Bullwinkle closed the show by telling the kids at home to remove the turning knobs off their TV sets so they'll be sure to see him next week. NBC received over 20,000 complaints from parents because their children followed Bullwinkle's suggestion, which caused Bullwinkle to advise the kids to glue the knobs back on. The puppet wouldn't be around much longer after that.
In Samurai Jack, Aku at one point sends an entire robot army after Jack, and after one trips, the entire army is destroyed. Aku's expression sells it.
In Scooby-Doo Meets the Boo Brothers, Freako the ghost pokes his head through a keyhole so he can scare Farquaad on the other side of the door. Unfortunately, he gets stuck, so his brothers Shrieko and Meeko try to pull him out. They end up pulling the door off of its hinges and end up plastered against the opposite wall. As Shaggy put it, "Like, you Boo Brothers give failure a bad name." Take in mind that earlier they boasted about their ability to go through walls.
In "Homer the Smithers", Homer has to cook breakfast for Mr. Burns at 4:30 in the morning and is out to make sure it's the best damn breakfast he can provide. He starts off with a shish kebab on a burner, which he doesn't know how to use, and it catches fire. Then he goes to a simple microwave, smashes the window open and sticks in the kebab, and (rather unsurprisingly) it also catches fire. Like a drunken student on a night out in Manchester, he has failed in his kebab quest, and settles for a bowl of cereal, which, as the page image shows, is not only a disaster, but also breaks several scientific laws.
In "Homer Goes to College," he's put in a truck containing a simulator of his work station and somehow causes a meltdown. He later, somehow, does the same with a model proton accelerator in a classroom.
In "Mom and Pop Art," when Homer attempts to build a barbecue, he has several epic failures in short succession. All he manages to build is a chaotic pile of the grill's components (including, somehow, his wristwatch) embedded in a slab of concrete. Angrier than usual, Homer charges the debris with an umbrella like Don Quixote after beating it with a pipe, with about the same measure of success.
Homer: Oh yeah, that's a fine looking barbeque pit. (brings the box down, revealing his crappily made verson) WHY DOESN'T MINE LOOK LIKE THAT?! (screaming in rage) WHY MUST?! EVERYTHING IN LIFE?! BE SO?! HARD?! WHY MUST I FAIL AT EVERY ATTEMPT AT MASONRY?!
A similar incident happens in "Marge Be Not Proud". After Marge doesn't put marshmallows in Bart's hot cocoa because she thought it would make him feel like more of an adult, she then suggests that he do it himself. His attempt results in the marshmallow absorbing every drop of the liquid to form a sort of gelatin, which Bart gloomily eats with a knife and fork. Of course Grandpa views it differently and even asks if he can have a slice of the marshmallow.
In "Days of Wine and D'ohses", Homer crudely creates an alternate gas main in order to allow him to do pyrotechnics with a tiki idol that he got as a result of rummaging through garbage, resulting in a massive gas leak in the kitchen. While ranting to Marge as the tiki idol, he accidentally drops it, causing it to combust, and it is also implied that the house was going to end up destroyed shortly thereafter.
Homer's encounter with the wrecking ball in The Simpsons Movie crosses into this by the end, when it resumes swinging for no apparent reason a couple of seconds after seemingly coming to a stop.
In "Homer's Triple Bypass," the C.O.P.S. parody has Chief Wiggum trying to locate a cattle rustler. He ends up mistaking Reverend Lovejoy's location with the cattle rustler's location next door, despite the obvious hints that they got the wrong house (the next door neighbors had an odd amount of cattle especially for a suburban neighborhood, whereas the house they raided, Lovejoy's, was normal). He also fails to identify the car or even the driver—beyond being "hatless"—despite the driver poking his head out to taunt the cops long enough to have even a ten year old give the specific details.
In the subplot to "Bart the Lover," Homer strives to develop a doghouse for Santa's Little Helper. He manages to complete it, only for this exchange to occur (and it is implied afterwards that he has to contribute to the Swear Jar):
Homer: What do you think? Lisa: How's the dog supposed to get in? Homer: Well, he just goes... (realizes that he forgot to add a door to the doghouse) Doh...!
Frank Grimes attempted to invoke this trope on Homer in "Homer's Enemy" by having him join a nuclear power plant model-creating contest (intended for children) with the intention of having him lose, thus exposing him as a fraud. Homer actually won. But for "Grimey" (as Homer refers to him throughout the episode), the trope is played straight. When his contest scheme fails, Grimes snaps and runs amok through the plant, eventually touching live high-voltage wires that electrocute him on contact.
In "Eight Misbehavin'", Homer's forced to perform in a circus-like show at the zoo. When the show's trained cobras start attacking him, the zookeepers bring out a mongoose to kill the cobras... but the mongoose gets scared by the many number of cobras so it instead joins the cobras in attacking Homer!
Homer: Stupid mongoose! Get the snakes! The snakes!
In "Natural Born Kissers", we learn that when he served in the US Army during World War II, Grandpa Simpson was so terrible at clearing minefields that he was awarded the Iron Cross.
In "My Fair Laddy", after Willie has become a proper gentleman thanks to Lisa, Principal Skinner hires Mr. Largo to be the school's new groundskeeper. When Mr. Largo tries to drive Willie's tractor, he ends up on the school's roof.
In "Bart to the Future", one of the dilemmas President Lisa Simpson's administration has to deal with is that the previous administration's attempts at helping children and keeping them off crime not only didn't turn them off crime, but instead transformed them into implacable supermen capable of doing crime literally all day long.
In "Homer's Phobia", after Bart accidentally breaks the family's gas line, Homer tries to pay the $900 repair bill with money from his retirement fund. Translation: a water cooler tank full of pennies, which he is struggling to carry. Homer barely makes it through his front door before he drops the tank—which promptly buries itself deep in the Earth, leaving a neat hole in the ground.
Homer: Aw, nuts! [looks in the hole] Helloooooo! China? A little help?
In "King-Size Homer", to qualify as "disabled" and work at home, Homer becomes so morbidly obese that he can no longer dial a phone number without assistance.
The fingers you have used to dial are too fat. To obtain a special dialing wand, please mash the keypad with your palm... now.
Then there's the entire point of "Who Shot Mr. Burns?". It turns out that Mr. Burns was shot after he unsuccessfully tried taking candy from a baby (Maggie).
In "Oh Brother Where Art Thou", Homer's up-until-then-long-lost brother Herb asks Homer to help his company design a car for the "average American man". Homer instead designs an $80,000Hummer Dinger that gets Herb laughed straight into bankruptcy. Herb didn't really made things easy on himself by 1) believing Homer, with his immense stupidity, actually could represent an "average American" and 2) Herb decided not to listen when the rest of the research team tried to warn him.
In "Homer to the Max", Homer and Marge are dragged along to a protest where they're chained to redwoods. After Homer declares this to be the worst party he's ever been to, Marge adds it's not as bad as Lenny's New Year's Eve party where he apparently didn't even have a clock for the occasion.
During "Into the Wilderness", Knuckles has trouble starting a fire, and Sonic decides to run laps around it to fix the problem. His shoes catch fire instead. Also, Amy's attempt to put a tent together using a flintstone Sticks left for her also caused the tent to burn to the ground.
Dave the Intern manages this while working at Amy's restaurant:
During a tap contest in "You Got F'd in the A", Butters loses one of his shoes onstage, unleashing Disaster Dominoes that end up destroying the stage and killing eight audience members, traumatizing himnote As Stan later informs him, this was even worse than it seems because a woman killed was pregnant and two family members of victims committed suicide.. After getting over it and entering another contest, this becomes an epic win as the same thing happens, this time killing his opponents (and retraumatizing him).
Squidward's stints as frycook at the Krusty Krab inevitably end this way.
In "Pickles", SpongeBob has to temporarily give up his job as fry cook for reasons irrelevant, Squidward takes over temporarily, and epic fail ensues. The customers cry out "He burnt my Krabby Patty," "He burnt my fries!" and finally: "He burnt my shake!"
When SpongeBob literally played hooky in the episode "Hooky" and left Squidward manning (squidding?) the grill, the results were similarly disastrous:
Customer 1: My sandwich tastes like a fried boot. Customer 2: My sandwich is a fried boot!
During a rehearsal, Squidward instructs his band to repeat a short melody. The brass and wind sections do just fine, but the drums? They blow on their drumsticks and end up accidentally shooting them at Squidward.
Squidward: Too bad that didn't kill me.
Squidward tells the flag-twirlers to speed it up, which then leads to their flags acting like propellers, sending them up hundreds of feet and crash into a blimp, which then explodes, followed by another band member playing Taps (poorly) and Squidward quietly going into the Troubled Fetal Position.
Squidward: Okay, new theory. Maybe we should play so quietly...no one can hear us.
In "Le Big Switch" Krabs exchanges SpongeBob for a French chef from a high quality restaurant during an exchange program in hopes that customer demand for fine expensive food will increase his profits. Things don't go well for SpongeBob in his new surroundings initially since SpongeBob is incapable of cooking anything but Krabby Patties, to the degree where he can't even fry an egg without it instantly transforming into a burger. However his epic fail becomes an epic win when both his boss and his rich clientele both enjoy his Krabby Patties so much they latch onto his ankles begging him not to go back to the Krusty Krab after the exchange ends.
In "Tutor Sauce", when Mr. Krabs tried to teach SpongeBob to drive a boat, he ended up hitting the Krusty Krab every time no matter where he was, even with an arcade game.
In "Mermaid Man and Barnacle Boy V", Mermaid Man, SpongeBob, Patrick, Squidward and Sandy attempt to battle a Terrible Trio formed of Man Ray, The Dirty Bubble and Barnacle Boy, who was Temporarily a Villain. Captain Magma (Squidward) accidentally erupts lava on The Quickster (SpongeBob) causing him to run around in circles, The Elastic Waistband (Patrick) attempts to grab him but fails and ends up with his arms stretched out, Mermaid Man attempts to extinguish The Quickster with a water ball and hits Captain Magma, causing him to turn to ash, and Miss Appear (Sandy) turns invisible only to get hit by a boat and sent falling off the cliff. After the villains survey the aftermath, Mermaid Man falls backward.
Mr. Krabs' attempts at birthday parties for Pearl in "Whale of a Birthday" have apparently all been this, but her 16th birthday is the latest one: the banner is from her baby shower and was crudely edited to say "It's a girl" after he was expecting a boy, the popcorn is stale, the punch bowl is full of dishwater, he dropped the ice sculptor to have Squidward make a sculpture of Pearl out of raw Krabby Patty meat, the cake is made of cardboard and frosting, and he got Squidward to fill in for Boys Who Cry as the musical entertainment.
In the Star vs. the Forces of Evil episode "Lobster Claws", Ludo's minion Beard Deer manages to grab Star and awaits for Lobster Claws to grab Star's wand. Somehow, he completely misses Star and pulls off Beard Deer's left antler.
Star Wars Rebels: In "Through Imperial Eyes", the rebels stage an operation to rescue the Reverse Mole, Kallus, from the Empire as they believe his cover may have been compromised. The thing is, they don't warn him that this is going to happen, and due to some unforeseen circumstances end up indirectly exposing said Reverse Mole's cover to Thrawn.
In a milder example from the episode, Kanan gets himself stunned when he tries to mindtrick Governor Pryce.
Superman: The Animated Series has an episode where Mr. Mxyzptlk tries to harass Superman. He is basically a Physical God, even compared to Supes, but he promises to return home for three months if he ever says or spells his name backwards. This episode consists of Superman as a Screwy Squirrel, constantly fooling Mxy into banishing himself. At one point, his totally hot wife tells him to simply kill Superman before he can say anything. Thus Mxy spends the next 3 months building a killer robot. He marches off, full of vigor. The moment he's gone, she starts counting down from five...too much credit; he's back by three. At the end of the episode, Mxy is tricked into spelling his name TWICE, backwards. In a row. Using heat exhaust from the kryptonite rocket he turned into to chase Superman across Metropolis. Superman goes straight into Smug Super territory as he mocks Mxy before banishing him for good.
One particular instance stands out as severely Epic Fail:
(Superman, as Clark Kent, is shaving himself when Mxy shows up) Mxy: Your three months are up. And this time, you're not gonna cheat me out of my fun! Clark: Oh, it's you again, Mr. Kltpzyxm. Mxy:Not "Kltpzyxm!" Mxyzptlk! Now, the first thing I'm gonna do- Aw, nuts. (poof) (Clark continues shaving.)
Not to mention when he tells Mxy that he'll meet him up on the roof just as soon as he's done proof-reading his latest story. Mxy refuses to let him stall and does so for him ... no points for guessing what all the typos spell out.
In the episode "Deer Taz", when the black bear appears, Taz tries to attack the black bear with his usual attack, but the black bear is way too strong for Taz, and the attack epically fails.
In "Boys Just Wanna Have Fun", in one scene, Hugh, Taz's dad, tries to play a game (using a sponge football) with Taz and Jake, Taz's brother, but as soon as the painting of a woman appears, Hugh ends up running RIGHT INTO THE FLIPPING WALL!
In "Frights of Passage", in one scene, Francis X Bushlad epically fails when he says that he always triumphs, but ends up falling off a waterfall.
In "Hypnotazed", Bull tries to hypnotize Axel into thinking that he is like Taz, but Axel's eyes reflect the beam right back at Bull, causing epic fail to occur.
In the episode "Tazmanian Lullaby", Francis kept on slipping on the same banana peel.
In what is most likely a Shout-Out to the infamous Ulong tribe of Survivor, Team Victory in Total Drama World Tour loses every single elimination challenge and is completely wiped out before the season is even halfway over. The reason is not the unfitting name, but because of the Curse of the Mummified Dog DJ put on himself for his team.
In the very firstTransformers episode, Starscream shoots at the stasis locked Autobots... and revives them. Oops. He goes on to make a long, long career in Epic Fail after that.
In that same opening storyline, Starscream tries to shoot Megatron dead in front of his men. Twice. And fails both times. So pathetic is this attempt at treachery that, both times, Megs can't be bothered to kill him, opting to rub it in his face, land a non-fatal shot, and go about his day.
In the fourth episode, Spike and Bumblebee are spying on the Decepticons and learn that the 'Cons are building a space bridge to Cybertron. While attempting to flee with the information before the Decepticons realize they're there, Bumblebee somehow manages to accidentally throw himself into reverse and accidentally backs off a cliff.
In one episode of Beast Wars, Inferno, having long since suffered from Villain Decay, is told to rush the Maximal's base. So he does. And by "rush", we mean "run in screaming like an idiot, flailing his arms like he's epileptic, and not fire a single shot". The Maximal's reaction is to exchange awkward glances, shrug, and drop a big rock on him.
In one Underdog cartoon, Simon Bar Sinister's plan to Take Over the World involved using a device called the Big Dipper to steal the Earth's water; it could drain the water from lakes, rivers, and even oceans, storing each in a small jar, which he planned to use to starve the world into submission. However, he had a few failures trying to perfect it. The first time, it froze the water solid. The second time, it turned the water into steam (making the fire department think his house was on fire). The third time was the biggest Epic Fail; it did the opposite, flooding his whole house. (His really bad excuse to the police, that it was his leaky faucet, made them suspicious, but they still couldn't arrest him). Unfortunately, his fourth attempt was a success. He may have been evil, but at least he was persistent.