Paddywhack

Paddywhack is a minor villain in Darkwing Duck, featured in the episode "The Haunting of Mr. Banana Brain", voiced by the late Phil Hartman.

Darkwing Duck
Paddywhack is a supernatural entity who inhabits a haunted jack-in-the-box. Although he is capable of possessing inanimate objects and imbuing them with his will, he can and will sometimes appear in his true form, which is a very tall, thin duck with long legs and sharp teeth, wearing a black and white leotard with a ruffled collar. Paddywhack feeds off of negative emotions and always exhorts others to "Please play with me!", enticing them to join him in his various acts of mayhem.

At some point, Paddywhack became trapped in his jack-in-the-box which, was unknowingly put on display at a toy exhibit in a St. Canard museum. Quackerjack robbed the exhibit, stealing the box, but ultimately decided it was worthless and threw it aside, thus releasing Paddywhack. The evil spirit possessed Quackerjack's doll, Mr. Banana Brain, and proceeded to run rampant throughout St. Canard, causing mischief.

Paddywhack would trap Quackerjack and Darkwing Duck in his jack-in-the-box world were he tormented them, forcing Darkwing to wear clown outfits with neverending other outfits beneath them if he tries to remove them, and Quackerjack to wear a boring business suit.

Darkwing Duck along with Quackerjack managed to beat them by using positive emotions, literally laughing away his power as he got smaller and smaller until they could trap him in the Jack-in-the-box which Darkwing then threw into the Audubon Bay. However, a large fish swallowed the box, and Paddywhack, escaping once again, possessed the fish.

Darkwing Duck comics
Paddywhack appears in Boom! Studios' Darkwing Duck, at the climax of the "Crisis on Infinite Darkwings" arc, in which he takes advantage of all of Negaduck's rage and hatred. He possessed Negaduck to become a giant hybrid of the two, attempting to cause chaos and misery over St. Canard. He was eventually defeated by Darkwing using the tron splitter on Nega-Paddy-Whatever, and then by the positive feelings from the multiverse of Darkwing's love for Gosalyn, empowering Morgana's positive magic to once again entrap him inside his jack-in-the-box.

Trivia

 * Paddywhack is a parody of Pennywise from Stephen King's IT