Given his proclivity of constantly trying to keep his employees entertained (and coupled with his juvenile personality), Michael has created a variety of different characters which he uses for both entertainment, and, at times, educational purposes.
- Michael adopts the persona in his improv comedy class, forgoing the opportunity to base his dialogue on the situation in favor of shooting everyone in the room, regardless of their participation in the scene. Sometimes his character's name is Michael Scoon, but the character is otherwise the same.
- Michael adopts the fake name Michael Scarn when posing as a local businessman while investigating the Prince Paper company ("Prince Family Paper").
Prison Mike ("The Convict") wears a purple bandanna over his head, speaking in a caricature of New York English. In his Prison Mike persona, Michael paints an awful, and somewhat fanciful, picture of prison life.
Michael the Magic ("Cocktails") attempts to escape from a straitjacket but fails due to a lost key (actually hidden by Jim).
Caleb Crawdad ("Murder"), a handsome playboy from Savannah.
Mykonos ("The Seminar"), husband of Necropolis (played by Holly Flax) who attends Andy's seminar.
Orville Tootenbacher ("The Search"), a millionaire character that farts popcorn.
Santa Bond ("Secret Santa")