10 of the Biggest Game Show Payouts Ever

We’ve seen contestants on game shows go wild over winning a convertible, a house full of furniture or a trip to Europe. All nice prizes, to be sure, but nothing compared to the serious cash that some participants have taken home through the years.

Sometimes, those winnings even extend into the seven figures. While a $1 million payday on a game show is rare, it’s happened on shows that are both legacies — think “Jeopardy!” and others that turned out to be just blips on the television radar. Some of the winners turned out to be household names and figures still celebrated years after their television success.

Read through to learn about some of the 10 biggest game show payouts in history. These dollar figures represent their prize money only on the show listed. Some of these contestants also won thousands more as they tried their luck with other games.

In November 1999, an Internal Revenue Service employee from Connecticut named John Carpenter became the first millionaire on “Who Wants to Be a Millionaire?” He famously used one of lifelines to call his father to tell him he was going to win a million dollars, then told host Regis Philbin without reservation that Richard M. Nixon was the president who had appeared on the TV show “Laugh-In.” He won $250,000 the following May in the Tournament of Champions, giving half of it to charity, but leaving him as a $1.25 million winner.

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Curtis Warren, then an air-traffic controller, won $410,000 on “Greed,” then another $1 million in February 2000 thanks to his knowledge of old television shows. The show was hosted by Chuck Woolery and appeared just one season on FOX.

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The remake of “Twenty-One,” the game show that was proved to be rigged in the 1950s, made U.S. Navy submarine Lt. David Legler a millionaire – a $1.77 millionaire, to be exact. He won the money by playing six games over three days in February 2000. The show was hosted by talk show host Maury Povich and aired on NBC.

Ashlee Register, a registered nurse from Port St. Lucie, Florida, became the highest-winning female game show contestant ever in 2007 when she won $1.79 million on “Duel.” The show, hosted by ESPN personality Mike Greenberg, consisted of just six episodes and 24 contestants when it aired on ABC the week before Christmas.

Edward Toutant became the second “Super Millionaire,” thanks to his persistence. The IBM engineer from Austin, Texas, appeared on “Who Wants to Be a Millionaire?” in January 2001 and lost on the $16,000 question, meaning he walked away with just $1,000. Sure his answer about tomatoes was right and the showrunners were wrong, he submitted his proof and was given a second chance. He was invited back to appear on “Super Millionaire” and won $1.86 million. He passed away from brain cancer in November 2018.

Thanks to his science knowledge, Kevin Olmstead walked away with $2.18 million from “Super Millionaire” — a spinoff of “Who Wants to Be a Millionaire?” – in April 2001. To win the prize, Olmstead, an engineer from Michigan, correctly identified the inventor of the mass-produced helicopter. It was Igor Sikorsky, of course.

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“The Million Second Quiz” was a short-lived, Ryan Seacrest-hosted show that appeared on NBC in September 2013, but it made a lasting mark in game show history. Andrew Kravis was a 25-year-old law school grad from Farmington Hills, Michigan, who won $2.6 million on the show – the highest single payout in game show history. He’s now using his brain power in his role as assistant puzzles and games editor at The New Yorker, according to his LinkedIn bio.

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James Holzhauer, a professional gambler from Las Vegas, won 32 straight games on “Jeopardy!” in 2019. But he didn’t just win games. He dominated them. He holds the top 16 spots for single-game winnings in the show’s history, including the one-day top prize of $131,127, which can be attributed to his aggressive betting strategies on the Daily Double and Final Jeopardy questions.

Ken Jennings, a brainy software engineer from Salt Lake City, make history on “Jeopardy!” when he won a record 74 games in a row, and $2.52 million, in 2004. He added to those earnings through special “Jeopardy!” competitions, including the $1 million he won in the show’s Greatest of All-Time Tournament that aired in January 2020. In all, he has won $4.37 million on the show, still short of Rutter’s record.

Brad Rutter is the highest money winner of all time on one game show, winning $4.93 million on “Jeopardy!” His initial run in 2000 was good but not spectacular. Then a record clerk, he won five straight games and took home $55,102. That was before the show’s rules changed and removed the limits on how many times a contestant can win. Since then, he competed in six tournaments to add to his winnings.

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