Jeff Winger

Jeff Winger arrives at Greendale Community College a disbarred lawyer, forced to actually earn the degree he faked years ago. Smooth, vain, and allergic to sincerity, he invents a fake study group just to get closer to a woman he likes—and finds himself stuck leading the very misfits he meant to use.

McHale plays Jeff's charm as a defense mechanism, and the show keeps puncturing it until something real leaks through. His rousing speeches start as manipulative reflexes and slowly become genuine leadership, and the joke is that he's often the last person in the room to notice he's changed.