The Most Surprising Celebrity Jeopardy! Champions

Andy Richter is best known for being the host's sidekick on Late Night with Conan O'Brien and Conan. In Jeopardy! lore, however, Richter is a bit of a legend unto himself. In his first appearance in 1999, he crushed the competition. "I've always called you Mr. Knowledge behind your back," O'Brien told him after his first victory, adding, "You know about stuff that no one has to know about." Richter agreed: "Boy, I've cornered the market on crap knowledge." At the time, the comic held the third-highest score in Celebrity Jeopardy!, a record he would absolutely destroy the next time he took the stage.

In 2009, Richter competed against actor Dana Delaney and journalist Wolf Blitzer during the quarterfinals of the Million Dollar Celebrity Invitational. When the game was done, the Jeopardy! prodigy had $68,000, nearly three times his score from the first game and by far the highest of all time for celebrities. Unfortunately, we never got to see what Richter could do in the semifinals as he was replaced by Isaac Mizrahi due to a scheduling conflict. "I have a lot of incredibly shallow knowledge about a lot of things," he said in a humble interview with The A.V. Club, adding, "Being that great on Jeopardy! doesn't necessarily mean you're smart, it just means that you have a lot of, like, little post-it notes of bullsh*t floating around in your head."

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