Darrell Hammon as Sean Connery

Memorable Quote: "I'll take the Penis Mightier for $500"

We don't know why we love to watch Trebeck suffer, he's a nice guy. But watching Connery one-up him on celebrity Jeopardy, where everybody's an idiot, is so satisfying. It was crazy to watch Connery spin even the most innocent of clues into a "your mom" joke, and Hammon's spot-on impression always sent everyone over the edge.