Kirk Gleason

Kirk is a fixture of Stars Hollow, forever between jobs and always mid-scheme, whether he's running a business, entering a dance marathon, or explaining some new venture to anyone who'll listen. He's odd, humorless about his own oddness, easily wounded, and treated by the town with a fondness that outpaces his actual usefulness.

The show could have made him a one-joke weirdo, but Sean Gunn plays every scheme with total sincerity, so the comedy comes from Kirk's total lack of self-awareness rather than mockery. He never winks at the audience, which is exactly why the town's affection for him feels earned instead of ironic.