12. Celebrity Jeopardy
Air Date: 1/23/99
Starring: Norm MacDonald, Will Ferrell, Jimmy Fallon, Darrell Hammond
If you were to add up all of the scores from the contestants on "Celebrity Jeopardy," you'd be lucky to break zero. With categories like "Colors That End in 'Urple" and "Your Ass or a Hole in the Ground," it's amazing how far cast members went in depicting celebrity stupidity. Of course, no one really cared about how smart (or dumb) those participating in this sketch were.
In the end, it was all about one thing and one thing only: Alex Trebek (Will Ferrell) vs. Sean Connery (Darrell Hammond). No matter how much he tried to ignore Connery's constant barrage of jokes about his mother, Alex Trebek could never win. If only real Jeopardy were this entertaining.