Michael George Dupée
Michael George Dupée won an impressive total of $203,901 in his appearances on the show, which included winning the 1996 Tournament of Champions, making him the 4th biggest winner of the time. After his impressive wins, he later went on to release a book entitled How to Get on Jeopardy! and Win! It seems that he definitely is an expert on this matter!
Watson
This Jeopardy! champion is a bit different from the rest on this list, as Watson is not even human! The IBM robot competed against the top Jeopardy! contestants in a battle of machine versus human. Watson initially won $77,147 in two special exhibition games, and later beat the top champions, winning the grand prize of $1 million. Luckily, IBM donated the prize to the World Vision and World Community Grid non-profit organizations.