Ken Jennings, best known for being the first contestant to take full advantage of Jeopardy! canning their five-game limit. During his initial run, he won 74 games and amassed $2,522,700 in winnings. He also won $900,000 in three subsequent tournaments (the Ultimate Tournament of Champions, the IBM Challenge and the Battle of the Decades) along with $500,000 on Are You Smarter than a 5th Grader?, $100,000 on Grand Slam, another $100,000 on Who Wants to Be a Millionaire? and $714.29 as a mob member on 1 vs. 100. His grand total: $4,123,414.29, making him the second biggest winner in American game show history.
Andrew Kravis surpassing Ken Jennings for most winnings on an original game show run when he won $2,600,000 on Million Second Quiz. In addition to his winnings from Jeopardy!, Wheel of Fortune and Millionaire, he is the third-highest winner with $2,656,550.
Mark Lewinald winning $177,600 on Tic-Tac-Dough, including $50,000 on the Tournament of Champions. He also was a four-time champion on Jeopardy!, cashing in with $43,700 and an extra $1,000 on that show's Tournament of Champions. Mark also won $24,156 early on Press Your Luck and also competed on The Challengers.
Kevin Olmstead becoming the biggest winner in the history of Millionaire, taking a Progressive Jackpot of $2,180,000, along with a previous win of $27,000 on Jeopardy!
Brad Rutter is the all-time leader in American game show winnings, nearly all of it from Jeopardy!. He won $55,102 in his initial five days on the show and has won every tournament he took part in, except for the IBM challenge. In addition to the $4,455,102 he won on his Jeopardy! appearances, he also won $100,000 on Million Dollar Mind Game
Ed Toutant also won a a Progressive Jackpot on Millionaire; he won $1,860,000 on that show along with $11,401 on Jeopardy!.
Curtis Warren winning the Winner's Board lot on Sale of the Century: $136,288 in all, $69,600 of it cash. He later went onto to win $1,410,000 on Greed's Million Dollar Moment. He also won $700 on Win Ben Stein's Money.
