A clown-like Arch-Demon sealed away in a jack-in-the-box, his chaotic insanity has made him one of the more dreaded entities in the known multiverse. He was born out of the misery felt by the first humans from cruel pranks pulled on them by their compatriots. Although his chaos magic power made him almost nigh-unstoppable, the High Council was able to defeat him by sealing him away in the jack-in-the-box forged by Hermes. Through manipulations by the other Friends, the Jack-in-the-box was transferred across different hands before winding up for display in a toy museum just waiting for the chance to break loose again.

During a robbery and subsequent battle with Darkwing Duck, Quackerjack inadvertedly released Paddywhack from his prison and wound up getting manipulated by the Arch-Demon, possessing his puppet Mr. Banana Brain at the time, into causing chaos so as to feed on the misery felt by victims of the pranks in the process. He was eventually defeated by Darkwing Duck, but ended up possessing a fish so as to continue his manipulations deep within St. Canard Bay. Paddywhack soon revealed himself months later to put his plan into effect and wound up merging himself with Negaduck to be able to wreak massive chaos across the city. He was finally destroyed by Darkwing using his love for Gosalyn as a catalyst for Morgana McCawber to unleash a light magic spell to defeat the fused aberration once and for all.

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