The 14 Most Successful Contestants in American Game Show History
Watson may be able to beat Ken Jennings, but it will never know love. Then again, neither will we. Yeah, we’d rather be Watson.14 John Carpenter: $1,250,000
In 1999, Carpenter became the first person in the entire Who Wants to Be a Millionaire franchise to be like: um, I do. He tacked on another $250,000 in the champions edition.
13 Curtis Warren: $1,546,988
Warren absolutely blew it in a 1986 Jeopardy! appearance, walking away with nothing but moths in his wallet. But he came back in a major way, winning over $100k on Sale of the Century that same year, then about $1.5 million on the one-season Fox show Greed in 1999. He also won a cool 700 of Ben Stein’s monies on Win Ben Stein's Money in 1998.
12 Ike Barinholtz: $1,635,000
The actor and comedian has found a lucrative second career in the past five years as a game show ringer (although he’s given all of it to charity). He won $125,000 on Millionaire in 2020, followed by $1,000,000 on Celebrity Jeopardy! in 2023. He and his dad won another million on Millionaire in 2024.
11 David Legler: $1,765,000
Legler got all his dough from one game, Twenty-One, although it was spread over six appearances. He’s the biggest winner in the history of that show.
10 Ashlee Register: $1,795,000
Her single appearance on Duel makes Register the highest-earning contestant who only ever played one game, and the first woman to break the $1 million glass ceiling.
9 Amy Schneider: $1,864,800
Her 40 consecutive Jeopardy! wins is second only to Jennings, racking up over $1 million. She collected the rest on various tournaments of champions and Jeopardy! Masters appearances.
8 Ed Toutant: $1,871,401
He was knocked out of a Millionaire episode with just $1,000 in his pocket, but the question that got him was later found to be flawed. He was invited back and redeemed himself to the tune of $1.86 million (at the time, there was a “progressive jackpot” that grew as contestants were knocked out).
7 Matt Amodio: $1,879,601
Like Amy Schneider, Amodio made his near millions on various Jeopardy! games, the bulk of which came from his 37-consecutive-episode stint, which was nicknamed the Amodio Rodeo.
6 Kevin Olmstead: $2,205,901
He got most of his winnings from that same progressive Millionaire jackpot in 2001, and held the title of winningest contestant in history for two years.
5 Andrew Kravis: $2,656,550
He kicked off his career as a loser in the 2002 Jeopardy! Teen Tournament, but redeemed himself in The Million Second Quiz in 2013. He initially won about $300,000, then hit a $2 million jackpot. Next, producers upped the prize to an even $2,600,000 as a marketing stunt to break Jennings’ record.
4 James Holzhauer: $3,772,549
Early in his game show career, Holzhauer won $58k on The Chase, and later came up $58k short of Jenning’s regular-season Jeopardy! record during his 33-episode run. No matter — he became a fan and producer favorite, making lucrative appearances on various Jeopardy! games, even getting a cool $250k just for appearing on the “Greatest of All Time” tournament.
3 Brad Rutter: $5,153,436
He’s officially the winningest Jeopardy! contestant, with all but $100k of his winnings coming from one five-day stint and 17 tournament appearances. Until 2020, he’d never lost to a (human) opponent.
2 Ken Jennings: $5,296,214
Jennings’ 75-episode Jeopardy! run is still the record-holder, but he’s also racked up notable wins on Are You Smarter Than a 5th Grader?, Grand Slam, Who Wants to Be a Millionaire, Wheel of Fortune and 1 vs. 100. More notable still, he was knocked out of 500 Questions with zero dollars after a paltry four questions.
1 David Genat: $5,800,000
Just this past March, Genat skyrocketed past Jennings when he cut a great deal during Deal or No Deal Island. The final two briefcases were worth $75 and over $12 million, and he accepted a deal of $5.8 million — he learned afterward that he had the $75 briefcase in his possession. His game show career is merely sandwiched between appearances on Australian Survivor, where he’s already won $500,000.
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