It should not take a long time to sketch out a basic outline of this story. I think I am an outliner. I do not have to love doing it, I simply have to use my analytical skills to see what should go where. Then use my creativity to make those suggestions concrete. Then use my language skills and persistent focus to actually write the scenes I want. Waiting for inspiration is the mark of an amateur.
Since this is a comedy, the story should have escalating, interlinking twists. Fewer scenes is better, maybe as few as three. The first scene should introduce the main conflict of the story, the second scene should introduce an unforeseen complication, and the third scene should resolve the problem in a humorous way.
The story's theme should be wholesome in order to balance out its crude manners. The characters should be likeable in their own ways, meaning, full of desire, flawed and vulnerable, but also funny to watch. They should interact with one another in interesting ways. Interaction between the characters should be the centerpiece of the story and should contain most of the humor.
The middle twist should redefine the conflict in a way that both generates dramatic tension and brings about heightened drama in the character interactions.
The final resolution should be the logical conclusion and dramatic culmination of everything that has come before. It should come only after the height of dramatic and character tension.
The story should contain no fourth-wall-breaking and no metacomedy. Everything must be played straight.
Now to translate these things into concrete terms.
I need to start with the characters. First I'll characterize each one.
DARK SPARKLE: I have already described her as a misanthropic "goth" masochist. From the picture, her horn is broken, we'll say from some kind of principled, philosophical self-mutilation. We have to assume she's parallel to Twilight Sparkle. Maybe she thinks, "In much wisdom is much grief: and he that increaseth knowledge increaseth sorrow." What could I add to make her a more interesting character? Maybe she treats her friends as if putting up with them is a sentence of punishment which she can by no power escape. A gift to her is a burden, and a favor done out of goodwill is the same as a knife in the back. But she's resigned to it all. Spike calls her "Dee".
RAINBOW FLASH: Why not Rainbow Gash or Rainbow Slash? Anyway, Rainbow Dash is the most powerful personality in the show, so Rainbow Flash should be likewise. Heh, I suppose she could be a sexual pervert, if I keep the humor tasteful. From the picture, she has bat-wings. Maybe she could be a man-hungry freak of nature. Though Slaughtershy's batwings make that less compelling.
SCARITY'S cutie mark is a blood diamond. It has to be. It would be funny if she were not even evil, just cursed by misfortune to be off-putting to others, and lonely as a result.
APPLEHACK: I suppose she could be a communist revolutionary / aspiring novelist.
SLAUGHTERSHY: Has batwings, like Rainbow Flash, and her cutie mark is a bat. I think this one I can't really get away from. She has to be murderous, but since she's "shy" about it, I think she should always be trying to kill others on the sly instead of outright. Also she ought to be comically inept at it, like in Flutterrape stories. Why a bat cutie mark? A bat was the first living thing she killed with her own hooves.
PAINKEY PIE: Her cutie mark is a skull that looks oddly like a comb. And she has really bad hair. That's not much to work with. It would be boring to have TWO murderous, sadistic characters in the same story. But "bad hair Pinkie Pie" is too stupid. Maybe obsession could be her thing. She sees her hair as looking awful even when it's not.
Hey, maybe this could turn out to be a Power Ponies story. Eh, they aren't really villainous though, they just need counseling. Depression, nymphomania, paranoia, sociopathy, social rejection, obsession? This could actually turn out pretty heartwarming.
I think they should try to assassinate Princess Celestia and then, when they meet her, they just end up breaking down crying in a big emotional heap and the benevolent, gracious Princess helps them change their lives.
First things first. What are the obvious sources of threads of humor for this story?
Let's start in terms of interpersonal relationships.
SLAUGHTERSHY should make mental notes of every slightest offense, and seethe indetectably behind a collected facade. First it will be funny if someone says something that isn't really offensive to her, but she still clearly starts devising ways to murder them. Then it will be funny if her failed attempts at revenge actually come in play later, after you've already forgotten about it. Third it will be funny and fitting if one or more of these attempts actually affects the plot in a significant way. Does Angel Bunny accompany her? Not usually. That's an interesting question: the place of the ponies' pets in general. Maybe the pets would be out of place and I should omit them. Except that Slaughtershy should keep a veritable zoo of wildlife in cages in her backyard.
SCARITY is very lonely and only hangs out with the rest of them because they are the only ponies who will have her. She talks about insignificant things like a normal person trying to make conversation and feel like she has friends. She's overbearing. She overlooks her friends' flaws aggressively and is the first one to put herself on the line defending them. It would be funny if she stood up for SLAUGHTERSHY even after nearly being killed by her.
APPLEHACK contributes Marxist class analysis to the conversation, regardless of whether it is appropriate at the time. Is she really a failed novelist? If so, one possible angle is to make her a sort of parody of fanfiction authors. But I do not really want to write any metacomedy. Let me consider: why should she be a novelist? Merely to make the "hack" in her name work out? I admit that's a suitable enough reason, but it raises the question of what role her writing will play in the story. She could be sensitive about it, or paranoid, so that if someone reads her work she could be embarrassed. Or conversely, which is more probable, she could be fiercely proud of her work, convinced it is genius. But I do not see in that case how the fact that she is a writer could actually contribute anything to the plot. Maybe she could want to go on an adventure to get plot ideas. But presumably the revolution itself will be against the monarchy. Killing the Princess would be the logical first step. So her being a writer still contributes nothing. But maybe it sort of shapes her ambition, maybe she wants to be the intellect behind the establishment of the new world order and her prophetic novel will provide the guidance necessary.
PAINKEY PIE is difficult to figure out. The comb and hair thing is all I've got to go on. Maybe she could have a sadistic, dominating skull comb as her companion, and she has an unhealthy relationship with it. If so, then the only remaining question is how to distinguish her unhealthy relationship from the unhealthy friendship of SCARITY. But maybe that's not such a big problem that I need to worry about it right now.
RAINBOW FLASH is a sex fiend compensating for horrible self-esteem. What else can I give her to make her more interesting? Her cutie mark is some kind of storm cloud creating horrible weather. Maybe she could fart rainbows, blizzards and lightning. If I've established that she's a sex fiend ashamed of herself, then most of what she does should be oriented toward boosting her low self-esteem. She wants to matter and be strong, but she isn't. Per Carl's suggestion, Rainbow Flash can be an out-of-work night guard fired for sleeping around on the job. Maybe this could also explain her ability to fart weather--she's got some kind of implant or something.
SPIKE is the straight man, but a loyal companion of Dark Sparkle. He is just Spike from the show.
Now I realize I have overlooked figuring out what these ponies do for a living.
RAINBOW FLASH is already established to be an out of work night guard. Maybe she takes freelance bodyguard jobs, or works as a bouncer at a nightclub.
PAINKEY PIE does whatever her magical comb tells her to, and occasionally it leads her to food and other necessities of life.
But look, I think I have gone ahead and saved the real characterization for this part. So now I need to revisit the idea of how to draw humor out of these characters.
SLAUGHTERSHY I have already covered in sufficient detail. Make her take offense at something completely inoffensive, then seek revenge for it in a comical, underhanded way and fail (in a way that makes you believe she might still succeed in the future), and make her do so more than once, and make one of the attempts have a significant impact on the plot. She agrees to take part in the assassination because of the murder it will entail.
APPLEHACK should believe herself a genius, mistakenly, and seek to usher in the revolution. She takes part in the revolution because she is a communist seeking the violent overthrow of the monarchy, and further is convinced she will be the brains behind the new world order as it picks itself up from the ashes.
DARK SPARKLE hates the sun because she hates life. Eliminating the sun will mean the end of all life and thus all suffering. But she is somehow the only person who understands that. What threads of humor arise from her character? First, people ignore her attitude for some reason, so that every conversation in which she takes part has a certain lack of correspondence between speech and response. This is a source of constant, low-level gags. Pertaining to that, it would be funny if DARK SPARKLE were outright insulting to SLAUGHTERSHY in a consistent way but with no negative repercussions. Juxtaposing this with slight or perceived insults from others should be funny.
RAINBOW FLASH might be the hardest character to integrate at this point. Sexual promiscuity is not exactly something that comes into play a large percentage of your life, especially if you are on an assassination mission. Either way it would probably be funnier if she is not overt or aggressive about it, but fails at trying to be covert.
The birds and grasshoppers of Ponyville heralded the morning as the freshly blooming sun cheerfully limned the horizon in the promise of another golden day. The wind was smiling, and the scents of spring danced through the gossiping city trees and across the limpid, cool, fertile rivers that whispered the secrets of the faraway lands from which they flowed.
From within her treehouse bedroom, lit with a magical black candle, Dark Sparkle set down her quill and poetry journal, bound in black leather, and scowled at the budding day from behind her scarlet-tinted window.
She gave a low groan, then spoke. “Spike, the sun is coming up. The implacable inquisitor who sustains all life in the depthless agony of existence. Burn me again before I go to sleep.”
