Ken Jennings, Brad Rutter, and Watson are some of the most famous winners in the history of "Jeopardy," as of 2015. Giant fake checks showing the winnings of Ken and Brad hang in the contestant waiting room for every player to see. Watson is a machine.
Brad has won the most money at $3,385,702. However, Ken is arguably the most famous, although his winnings are slightly less at $3,196,300, because of his unmatched 74-game winning streak. The streak helped him market five books, a board game and numerous media appearances. Watson is the IBM supercomputer that beat both Ken and Brad in a head-to-head match.