Apocalymon

Apocalymon is the main antagonist of Digimon Adventure.

Personality
Apocalymon has a dark sense of humor despite him being "required" to be miserable; after explaining his plan to the DigiDestined he begins to laugh, but quickly stops himself, commenting that he's "supposed to be depressed". In the Japanese version, however, Apocalymon refers to himself in the plural sense, likely in reference to the Biblical Legion, who claimed to be possessed by a multitude of demons acting as a gestalt. Regardless of how the trait it showed, he's clearly meant to be almost completely insane.

Digimon Adventure
In Now Apocalymon,

In The Fate of Two Worlds,