I'll take hilarious Jeopardy! FAILs for $800, Alex. Jeopardy! is known for a being a little bit dry when compared to other game shows, but that doesn't mean it can't be hysterically funny from time to time. The funniest Jeopardy! answers almost always involve something dirty or clever, like Ken Jennings' famous "Immoral Pleasure Seeker" question that went viral in the early days of YouTube. Some of these are stupid Jeopardy! answers, but no matter how silly these contestants look, you can bet they are all fairly intelligent if they were able to get onto the show to compete.
Perhaps one of the funniest parts about these answers is the way Alex Trebek reacts to them. Sometimes he laughs at you, while other times he will just solemnly and quickly say no and move on (see the age of consent question). We even got IBM's Watson in on the fun here, so sit back and get ready to laugh at these hilarious Jeopardy! moments.