A major part of the problem with writing humor is that humor is very subjective; what one reader sees as hilarious, another will view as stupid. Thus, no matter how good a humor writer you are, you always have the disadvantage that many readers will think your stuff is dumb. While this caveat applies to all writing, it is more pronounced with humor and satire.
A mistake I see in many short stories, and one that occasionally I'm prone to make, is a failure to tip off the reader early on that the story is humorous. The author has to let the reader know this at the beginning of the story. If the story starts off with a serious tone and then changes to a humorous one, the reader will get confused and many of them will get annoyed. Just as annoying is a story that starts off humorous and then bogs down with a serious plot problem. This happens frequently with movies. They start off hysterically funny and then degenerate into a more serious tone that has only a few smiles in the second half of the movie.
Character and plots
One of the ways I produce humor is through the characters and the plot. The humor is produced by characters who have a mental flaw, one that prevents them from reacting the way normal people would react in a crisis. The more bizarre the flaw, the more potential humor it can produce. If the reaction of a normal character would be to flee a situation, the comic character will stick around, curious about what will happen.
This flaw has to be deeply ingrained into the character's psyche and be ready to go when the situation warrants. It can't be something that occurs haphazardly.
In Chasing Dreams, a novella in Tales From Gundarland one of the major characters, Zarro, is a vigilant who is determined to free his town from perceived (by him) evil influences. His flaw is that he never asks the citizens if they wish to be freed from these influences and he is stunned at the end when the citizens threaten to riot if he doesn't stop his vigilante activities.
In Falstaff's Big Gamble, a Shakespearean spoof, one of the main characters, Hamlet, has such a flaw. Here is my version of Hamlet's famous siloque:
Hamlet paused, gazed at the multitudinous stars, sighed and continued his pacing. A breeze brought the smells of the harbor: salt water and rotting fish guts. At last, he stopped, thrust one hand to the sky and declaimed, "To bee or not to bee?" He stroked his chin. "Whether 'tis nobler to buy honey from the peasant farmer in the market and thus provide him sustenance and income to support his brood of brats, possibly keeping him from rebelling over high taxes... or to grow my own honey thus gaining coins to assert my independence from my noble family and the sordid court? Hmm."
He paced some more, still troubled by his vexing question. Nothing less than his future depended upon the answer. Because his uncle, and now stepfather, Clodio, had usurped his right to rule the kingdom, he needed a profession and an income.
Hamlet's passion for bees continues and shapes and influences his character though out the novel.
Most of the classic humorous characters have an obsession. This obsession leads the character to react in ways that normal (un-obsessed) people would never consider attempting because it is dangerous or life-threatening. As an example of this type of obsession, consider the Pink Panther series of movies. Inspector Clouseau believes he is the greatest detective in the world. That is his obsession. This obsession and the radically different opinions of his supervisor is what makes the comedy work. As the world's greatest detective, Clouseau can't conceive that anything he does is wrong, no matter how bizarre. That is another source of humor.
Similarly, the trick that changes a bigot into a comedic character is that the character doesn't see his obsession (bigotry) so he comes across as a buffoon rather than a bigot:
Archie Bunker for instance
Inexperienced writers often think that humor can replace one of the basic elements of a story: a protagonist and an antagonist contending over a plot problem. This is always a fatal mistake.
As an example of how inexperienced writers attempt to write humor, consider this story I critiqued recently. The scifi story had many characters, all of them under-developed with none of them assuming the role of protagonist. The antagonists were a vague group of Mars colonists and the so-called plot consisted of a series of loosely connected events with huge logical gaps in between the events ( like pulling a nuclear device of thin air and developing a tractor beam out of spare parts on the spur of the moment (by a florist)
The attempt at humor consisted of these disconnected rudiments combined with dialog filled with non-sequiturs and factitious comments. The obvious problem here is that the story contained none of the required elements such as protagonist, antagonist and a plot. The writer assumed no one would notice the omissions because of his jokes.
Humor doesn't come from mocking a character's disabilities or deformities. A reader will see this as cruelty, not humor or comedy. Humor comes from oddball behavior caused by bizarre inner characteristics in one or more of the story's characters, not through their physical appearances.
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