3. The Dean
Jim Rashs portrayal of the Dean deserves a special mention. Although it began to get a bit wearing in season four when it was clearly just being used as an already safe popular formula, his cross-dressing, dalmation fetish, crush on Jeff and wordplay with the word Dean were often massive laugh out loud moments. The fact that Jim Rash is a respectable Oscar winner in his own right just makes his outlandish commitment to this role even more fantastic. A personal highlight is in season threes Course Listing Unavailable, when we have a glimpse of him alone in his office singing Come on Eileen, and my hands are so clean, at this moment, I am stapling! Read that in tune and youll understand the pure joy that moment brings.