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Time I uploaded an OC I wrote quite a lot of lore for, and one that plays a large role in my own internal headcanon: Mirthful; the Demon of Laughter.
 
In case you’re wondering, no he’s not actually a demon. Though some do believe he might have been possessed by one, he was simply a particularly infamous character back in his time and one that travellers would dread to be caught by on the open road. It would take the Pillars of Equestria to bring him down, and even then his legacy lived on a millennium past his own death. Both in the form of his own branch of magic, known as “Gigglemancy”, and the disciples he left behind to continue his work as a proud tradition, passed down the generations.
 
My main inspiration for Mirthful (apart from the fact that jesters look great and that I wanted to make a tickle-magic based character) is that I wanted to take the “Evil Clown” archetype in a different direction. Most examples in media are just sadistic creeps that torture or murder people because they find it funny, an overplayed trope and one that doesn’t really fit into the world of MLP.
 
I wanted to make a variant of that archetype that would work within the more light-hearted nature of the show. If Mirthful looks rather silly and non-threatening, that’s by design. I wanted him to still recognisable as a silly clown, but one that believes he has a higher purpose then himself. An end goal that he strives to attain by any means necessary, and it’s those four key words that serve as the root of his villainous behaviour. I believe the term for this kind of villain is a Well-Intentioned Extremist.
 
When drawing Mirthful, the main rule is that he should look and act goofy and fun, not threatening and sadistic. Even after losing his marbles, he still sees himself as a jester and his mission in life is to make ponies laugh, to make everypony laugh. He does this mostly by tickling them against their will, but hey…it works~
 
I’ll upload the story in parts on each picture.  
Part Two: A Royal Fool
With his talent discovered, and realising that he was already considered beneath contempt, Queen Majesty realised that the court needed a new fool to entertain her, the current one was getting on in years and she was rehashing old jokes. And so, when he came of age, Mirthful became the Jester of Princess Majesty’s Royal Court.
For a while, all was well. He was most amusing and talented, not simply as a comedian, but as a singer, acrobat, juggler, performance actor, dancer…even some scandalous rumours about burlesque shows in private parties hosted by the Queen herself. All unsubstantiated of course.
When Mirthful’s appointment was decided, his liege had ordered some of Unicornia’s finest to train and hone his skills over the proceeding decade. But beyond that, he had a natural charm, a charismatic and jovial aura around him. Not matter how bad the Queen’s day was, her Jester always found a way to bring a smile to her otherwise perpetually scowling face. In fact, it became wisdom around the court that any day in which not even he could make Queen Majesty smile, meant a dark and terrible tragedy had befallen the land.
But over the years, despite his ability to radiate a seemingly endless font of cheer, Mirthful could not help but feel a creeping sense of hopeless despair. The world before Equestria was one of unceasing instability and mutual disdain between tribes, every month the political situation sounded more and more dire and the common folk would always suffer the worst. To a pony whose entire existence was predicated on bringing joy to others, the always dour scowls on the faces of those around, the smiles that would never stick longer then it took to pass him by…
His talent was to bring cheer and joy, to make ponies laugh. He felt hollow. A failure.
 
Rest of the story is in the alternative version uploads, please let me know what you think.

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