Dave Madden
Dave Madden made Jeopardy! history by setting a record of playing in 19 games in a row, which brought him the title of second longest streak at the time, earning $403,400 total. Madden is an art historian and a trivia buff in general. He’s founded and serves as executive director of the International History Bee and Bowl as well as the National Science Bee, and the International Geography Bee.
Dave Madden
Dana Venator
Dana Venator may not be at the top of the list of highest earners, but she is certainly a fan favorite. She competed on the very first Teen Tournament in 1987. Even Alex Trebek greatly enjoyed her presence on the show due to her quirky personality and funny anecdotes. She shared that she’s played the bagpipes in the woods once and also purchased bathrooms from the hotel she was staying at during her time on the show!
Dana Venator
