In Isaac Asimov's The Caves of Steel, Elijah Baley is investigating a murder and has a robot partner that appears physically identical to the murder victim. He goes to the people who reported the murder, announces his theory that the robot is, in fact, the murder victim, and gives an extended justification. The entire "murder" was a scheme, it was the robot that had been destroyed to produce the "body," and here are the point-by-point reasons why all the supposedly "robotic" actions of his partner actually match perfectly with a human impersonating a robot. All the while, his boss is watching via a teleconference. After the completion of the detailed and rational accusation, said alleged non-robot opens up his sleeve and then calmly opens his arm as well. Elijah faints.
There is an article on Cracked that lists sex self-help books... one of them being what to do if stuff goes wrong. Included? What to do if there are burns, the house is on fire, the authorities are knocking on your door...
The book F in Exams: The Funniest Test Paper Blunders showcases hilarious examples of exam answer fails. Take a look at an excerpt. (Site NSFW due to an odd amount of hentai galleries which are completely unrelated. )
Likewise, Non Campus Mentis, a collection of horrible errors taken from college exams and papers.
There is a cookery book (called, logically, The Something Went Wrong What Do I Do Now Cookery Book) dedicated to correcting various kitchen emergencies. Naturally, it includes a chapter called "Total Failure". One piece of advice therein — if you've tried everything else, if you haven't got enough ingredients for an emergency meal and you have no other recourse, at least make it a memorable failure, one that will be recounted with awe through the generations.
"If you've burned the house down, Mission Accomplished."
In David Eddings' The Belgariad, the character Lelldorin manages to extend an epic fail over the course of several weeks. When he announces that he's going to get back to the main group, his beloved refuses to stay behind. During the departure and trip, he manages to break her father's leg, run his cousin through the leg "just a little bit", punch out all of a priest's teeth, and cause enough assorted mayhem to get a bounty put on his head by the crown. And all of this was without trying. This is also an example of Disaster Dominoes.
He did successfully marry the girl in the process, though! He claims traveling alone with an unwed woman would have caused more trouble, but considering getting married involved punching out said priest's teeth...
In The Mallorean, Garion has to stop a war threatening to engulf the entire kingdom of Arendia. He magically summons a storm that helps him single-handedly stop two charging armies in their tracks, force an old friend to marry the love of his life, and resolve the dispute. He’s very pleased with his hard day’s work. A few chapters later, he finds out that he sparked off blizzards, hurricanes, droughts, and tornados right around the world, and even triggered a new ice age. It took the combined efforts of the Gods themselves and two of the most powerful sorcerers alive over six months to fix it. Needless to say, Garion is banned from touching the weather again for two thousand years.
Codex Alera: The First Aleran Legion, before they have collectively Taken A Level In Badass, are prone to this. The single Knight Ignus is being treated for burn wounds, and while the Knights Aeris can fly up, they aren't very good at getting down again. They wind up getting the nickname "Knights Pisces," since they act more like landed fish than legionnaires.
David Weber's Safehold series features a triumphant example of this. The first book, Off Armageddon Reef, featured the Church of God Awaiting attacking the protagonist kingdom of Charis by creating an alliance of every single other naval power in the world. Unfortunately for them, thanks to Charis' own strong naval tradition coupled with Merlin Athrawes giving the galleon (among other things) to the Charisians, what actually happens is Fail so Epic it takes the Church two and a half books (a good two or three years in-story) to finally recover enough to make any kind of counterattack. That fails hard, too. Though not without a more sizeable cost from Charis' forces. Compounding their failure was the fact that most of the people planning the attack were accustomed to land battles and didn't take into account the realities of the weather, the limitations of the vessels they were using, etc. And one reason it took so long to recover is because they spent a good chunk of that building the wrong ships, as they were building a galley fleet after Charis' victories show how significantly galleons had come to outclass them as warships.
In A Rising Thunder, the Solarian League sends several hundred of their most powerful warships to (they think) effortlessly curb-stomp Manticore after the Manticorans have suffered the twin setbacks of the Battle of Manticore and the Oyster Bay sneak attack, seriously depleting their military resources. Oh, someone gets curb-stomped alright... but it isn't the Manticorans. Or the rest of their Grand Alliance, for that matter.
In the Discworld books, anything created by "Bloody Stupid" Johnson is likely to fall into this to such a degree it crosses over into Achievements in Ignorance. Anyone can create a garden fountain that doesn't work. It took Johnson to create one that creaked for half an hour and then shot a stone cherub a hundred feet into the air. Or crazy paving that committed suicide. A badly designed apartment block is easy. But only Johnson could draw plans so bad the resulting building warps space-time. Despite this his inventions usually work quite well, only at something entirely unrelated to their intended purpose such as the manicure device which makes a very handy automatic potato peeler.
The short story "Wolfie" by Theodore Cogswell is supernatural thriller meets caper gone wrong. A man in New York City goes to a sorcerer for help in murdering his rich cousin. His idea is to take the form of a wolf and rip his cousin's throat out. There is a slip-up at the veterinary hospital he has tricked a wolf blood sample out of; they give him a sample from an old, toothless, mangy poodle named Wolfie by mistake. To make failure even more certain, as a precaution to protect the witch doctor from You Have Failed Me at the hands of his familiar should our Villain Protagonist get cold feet or a Heel Realization, the [the would-be murderer] cannot change back until he has tasted his cousin's arterial blood. In the end, he is put down by the Animal Rescue League.
The backstory for the Wayside School series is that it was supposed to be a single-story building, with 30 classrooms in a row. What was built was a 30-story building, with a classroom on each floor. The builder said he was very sorry. What's more, there is no 19th floor.
Happens multiple times in the McAuslan series, often involving setting something on fire into the bargain.
In Harry Potter and the Deathly Hallows, Crabbe, along with Malfoy and Goyle, corner Harry and his friends in the Room of Requirement. During the battle, he casts Fiend Fyre, an uncontrollable, unquenchable fire that consumes everything in the room... including him and the very magical artifact that Harry had gone in there to destroy.Nice Job Fixing It, Villain.
In A Feast For Crows, the book ends with a very dramatic reveal of a plot to marry Quentyn Martell, a prince of Dorne, to Danaerys Targaryen, overthrow the government, and put her on the throne. Late in A Dance with Dragons, a mysterious stranger arrives in Danaerys' camp, reveals himself to be Quentyn, and promises her love and a throne. She turns him down, although she hints that they can make an alliance or political marriage later. He is so desperate to return home with something to show for his gambit that he tries to abduct two of her dragons. They promptly burn him so horrifically that he dies blind and in agony several days later. Nobody Shoots the Shaggy Dog like GRRM.
Shadow Games, book four of The Black Company, ends with the Company attempting to lay siege to the city of Dejagore. It goes so badly that the next two books deal almost exclusively with the Company picking up the pieces. It even results in the series' first change of narrators, because the original narrator is captured, but presumed dead.