Dana Venator
Although, she didn’t win as much as other contestants, fans always name Dana in the list of most memorable contestants. She was very quirky and even Trebek seemed enamored with her. Back in 1987, she competed in the very first Teen Tournament and won $15,000. However, she returned again for the Teen Reunion Tournament. Anyway, many loved her stories like how she played bagpipes in the woods or buying the bathrobes from the hotel she was staying at while filming Jeopardy! What a character!
Arthur Chu
Jeopardy! fans remember Chu from the unusual playing style of jumping between categories instead of going in sequential order. In his first game, he won $37,000 alone! Then, after an 11 game streak, he lost in March 2014. He went home with $298,200, but also later won $100,000 for earning second place in the Tournament of Champions. Now, he writes for The Daily Beast and Salon on things like sexism in nerd culture and racism.