15 Biggest Game Show Winners of All Time and How Much They Won

Since the 1950s, a time when the television set had become a prominent feature in every household, game shows have been a regular source of entertainment for people around the world. Viewers tune in to not just get a chance to find answers to some of the most intriguing questions but also watch potential game show winners contesting for the prize money deal with the pressure of knowing that one wrong answer can end their dream of winning big.

The huge sums of money that are made available to be won attract people from all works of life to participate in these shows, which makes it an even more intriguing view. Here is a list of game show winners who have been able to take home record amounts of money from participating in some of your favorite shows.

1. Brad Rutter

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Total Winnings: $4,888,436
Game Show(s): Jeopardy! and Million Dollar Mind Game

The biggest game show winner in history is Lancaster, Pennsylvania native, Brad Rutter, who has never lost a Jeopardy! match against a human opponent, although he has at some point in time trailed another player.

Rutter’s total earnings come from a combination of his winnings from two different game shows; Jeopardy! and the Million Dollar Mind Game. He appeared in the latter show in 2011, winning $100,000, a portion of the $600,000 prize money that was split between six contestants. He appeared on Jeopardy! in 2001, 2002, 2005, and 2019, where his collective earnings from the Alex Trebek-hosted show total to $4,788,436.

2. Ken Jennings

Ken Jennings
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Total Winnings: $4,223,414
Game Show(s): Jeopardy!, Are You Smarter than a 5th Grader?, Grand Slam, and Who Wants to Be a Millionaire

Ken Jennings is a computer scientist and author who has over the years provided good competition for Brad Rutter as the two have gone head to head on multiple occasions for the title of highest earner from Jeopardy. While the Edmonds, Washington native has fallen short of that title, he holds the record for the longest winning streak on Jeopardy!, and the record for the highest average correct responses per game in the history of the game show.

In addition to Jennings’ exploits on Jeopardy, where his total winnings are placed at $3,522,700, he has also contested on other game shows like Are You Smarter than a 5th Grader? ($500,000), Grand Slam ($100,000), Who Wants to Be a Millionaire ($100,000), and 1 vs. 100 ($714.29).

3. Andrew Kravis

Andrew Kravis
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Total Winnings: $2,656,550
Game Show: The Million Second Quiz, Wheel of Fortune, Jeopardy!, and Who Wants to Be a Millionaire

The Million Second Quiz was a short-lived game show that was dubbed the Olympics of Quiz shows. While the show failed to garner a following to ensure it remains on the air, it did manage to create a millionaire out of the then 25-year-old Columbia law school graduate, Andrew Kravis, who took home an incredible $2,600,000 in total, after spending 250 hours on the show.

Other game shows in which Kravis has participated and won some money from include Wheel of Fortune ($50,550), Jeopardy! ($5,000), Who Wants to Be a Millionaire ($1,000).

4. James Holzhauer

Game Show Winners
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Total Winnings: $2,522,549
Game Show: Jeopardy! and The Chase

The third entrant in the biggest game show winners list is a professional Las Vegas gambler named James Holzhauer. Like those that come in above him, the Naperville, Illinois native made this list as a result of his winnings from Jeopardy!, where he enjoyed a 32-game winning streak and set multiple single-game records for winnings.

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His total earnings from Jeopardy! are reported to be $2,464,216. Other game shows in which he has appeared in include The Chase in 2014 where he won $58,333.33 and 500 Questions where he left empty-handed.

5. Kevin Olmstead

Kevin Olmstead
Kevin Olmstead on Who Wants to Be a Millionaire? (image source)

Total Winnings: $2,207,000
Game Show: Who Wants to Be a Millionaire? and Jeopardy!

Kelvin Olmstead is the first contestant on this list to have gained his primary winnings from the Who Wants to Be a Millionaire? game show. The Ann Arbor, Michigan native, who works as an environmental engineer, won $2.18 million from the show to become the biggest game show winner in history at the time. He held that title for about three years before his winnings were surpassed by those of Jennings.

6. Ed Toutant

Ed Toutant
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Total Winnings: $1,871,401
Game Show: Who Wants to Be a Millionaire? and Jeopardy!

It is well known that questions in a game show are usually created with technicalities that would direct the contestant towards the wrong answer. This seemed to be the case for Ed Toutant who failed a question when he first appeared on Who Wants to Be a Millionaire, however, he was later recalled to the show after it was revealed that the question was flawed.

Following his return, the IBM employee was able to carry on from where he left off as he went ahead to answer the remaining questions to win a jackpot of $1.86 million.

7. Ashlee Register

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Total Winnings: $1,795,000
Game Show: Duel

Duel is another short-lived game show that was able to create a millionaire out of one of its contestants, Ashlee Register. The registered nurse from Florida happens to be the first female on this list of game show winners and the only one to appear high on the list as a result of her winnings from one game show. She won $75,000 plus an accumulating jackpot of $1,720,000.

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8. David Legler

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Total Winnings: $1,765,000
Game Show: Twenty-One

Twenty-One, a reboot of a 50s game show of the same name that was notorious for being rigged, is another short-lived game show that was hosted by Maury Povich and aired for a five-month period in 2000. During its time on air, naval submarine lieutenant David Legler was able to beat the odds to amass winnings of $1,765,000 in an unbeaten run that lasted for six episodes.

9. Curtis Warren

Win Ben Stein's Money
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Total Winnings: $1,546,988
Game Show: Greed, Sale of the Century, and Win Ben Stein’s Money

Once upon a time, Curtis Warren, like a few others that appear on this list, was once the biggest game show winner in history thanks to his winnings from Fox’s Greed. Warren won $410,000 from the show in late 1999 to earn an invite as one of four big winners invited back to the show in early 2000 for the Million Dollar Moment. It was at this time that he was able to win a then-record $1,000,000 prize to bolstered his winnings from the show.

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Other shows he appeared in and won something include Sale of the Century ($136,288) and Win Ben Stein’s Money ($700).

10. John Carpenter

Game Show Winners
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Total Winnings: $1,250,000
Game Show: Who Wants To Be A Millionaire

In a time when no game show contestant had been able to win the whole prize money and only one other person had made it to the penultimate $500,000 question on Who Wants to Be a Millionaire?, IRS agent John Carpenter shocked the world as he seamlessly went through all the shows questions without using any lifeline to become the show’s first million-dollar winner.

Following that appearance, Carpenter returned to the show to participate in its champions edition where he went on to win $250,000 to take his total earnings to $1,250,000.

11. Adam Rose

The Price Is Right, biggest Game Show Winners
The Price Is Right game show (image source)

Total Winnings: $1,153,908
Game Show: The Price Is Right

As many people who watch game shows hope to achieve, Adam Rose’s fortune changed when he got the chance to appear on The Price Is Right. The California teacher, who earned about $11 an hour from his job, was able to become not just one of the biggest game show winners, but the biggest winner in The Price Is Right history as he won $153,903 in cash and prizes and then a cash bonus of $1 million from the episode.

12. Michelle Loewenstein

Michelle Loewenstein
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Total Winnings: $1,026,800
Game Show: Wheel of Fortune

Another contestant to make this list that was the first person to win a million dollars from a particular game show is Michelle Loewenstein, who took home $1,026,800 from the long-running Wheel of Fortune. The Malibu resident, who notably said she had been an ardent fan of the show as she would often yell out answers while watching it with her family, had just returned from her honeymoon when she got a chance to participate, an opportunity she grabbed with both hands to become a millionaire.

13. Kathy Cox

biggest Game Show Winners
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Total Winnings: $1,000,000
Game Show: Are You Smarter Than a 5th Grader?

Kathy Cox, a superintendent of public schools in the U.S state of Georgia, is the second person behind Jennings on this list to have earned big from Nickolodeon’s Are You Smarter than a 5th Grader?. Cox, however, beats Jennings as the number one earner from the show as she notably took home $1,000,000 to become the first million-dollar winner from the show.

Read Also: Top 10 Video Games That Changed Gaming Industry

14. George Smoot

George Smoot
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Total Winnings: $1,000,000
Game Show: Are You Smarter Than a 5th Grader?

To think of it, having an astrophysicist, cosmologist, and Nobel laureate contest on Are You Smarter than a 5th Grader? is not fair to other contestants. As you would imagine, George Smoot answered all the questions on the show correctly to become the second person to win the one-million-dollar prize.

15. Robert Essig

Robert Essig,biggest Game Show Winners
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Total Winnings: $1,000,000
Game Show: Who Wants to Be a Super Millionaire

In this ABC network spin-off of Who Wants to Be a Millionaire, contestants are given the opportunity to potentially win $10,000,000. Unfortunately, no one seemed to be able to get close to the ultimate cash prize as the highest amount won on the show is  $1,000,000 by Ashtabula, Ohio native, Robert Essig.


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