It's time for the second TV Tropes Halloween Avatar Contest, theme: cute monsters! Details and voting
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Playing Against Type:
crossover fic The Flynns Move to Springfield, casts Lisa, who is normally the heroine/girl-next door The Simpsons/ Phineas and Ferb Love Interest in fanfics as a Jerkass Alpha Bitch whose purpose to the plot is to serve as the Veronica in a Betty and Veronica Love Triangle with Phineas and Isabella.
She was also cast against type as a dark Anti-Hero in Child of Darkness, where she plays the main protagonist, who was turned into a vampire and seeks vengeance for those who did the deed.
The fic Kingdom Hearts Lost Boys and its sequel Broken Heroes has the amazingly peppy and Angst-free Sora as an Anti-Hero Jerk Ass who has become mentally unstable and antisocial thanks to the traumatic event of Ventus-Vanitas destroying the Destiny Islands when he was four. He gets better and worse to varying degrees, and isn't really helped by all of the horrible things that keep happening to him.