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The 10 Richest Game Show Winners Of All Time

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The 10 Richest Game Show Winners Of All Time

Game shows were a popular broadcasting staple long before the 21st century wave of reality TV took off. Throughout the years, the record for the largest total winnings by various game show contestants has changed more times than many of us can count. These shows have changed a lot over the years and as the shows have gotten bigger and better, the prizes have as well, making several winners millionaires in the process.

The longest-held record was set by Teddy Nadler who, in 1957, won $264,000 because he reportedly used his photographic memory to memorize an entire encyclopedia. We can only imagine what someone like that could make on today’s game show circuit.

But we have our fair share of Teddy Nadlers today; those game show contestants who manage to win big against the odds. One of the most notoriously difficult shows to get on and win big at has to be Jeopardy! It’s a show many of us are familiar with, and for good reason. It’s full of random, tricky trivia questions and fans are often stunned by those who manage to correctly answer so many different – and difficult – questions consecutively. Jeopardy! features everything from classical music to calculus to Biblical names on the game board, yet there are some contestants who seem able to whip through it all without even stalling.

Some have won big on Jeopardy! but many of the major winners on our list won big on other, more obscure shows. In fact, it would appear that several of these folks could almost make a living simply by traveling the game show circuit. Every lucky winner on our top ten has managed to make more money than most of us could even dream of making in a lifetime, much less in just a few hours.

10. “Boston” Rob Mariano – $1,345,910

Boston Rob

“Boston” Rob Mariano has appeared on Survivor four different times, finally winning Survivor: Redemption Island where he took home the $1,000,000 prize. But his winnings aren’t just from Survivor. He’s also appeared in The Amazing Race alongside fellow Survivor contestant and wife, Amber Brkich. They came in 7th place. He met Amber while on Survivor, and they have two daughters together.

Rob holds a Bachelor of Arts degree in psychology, which he earned at Boston University. He’s also an avid baseball fan, and was well known for wearing the cap of his favorite team, The Boston Red Sox, while competing on Survivor.

9. Curtis Warren – $1,546,988

Curtis Warren

Curtis Warren made the rounds at a few different games shows, amassing his wealth in a variety of ways. Most of the money came from his appearance on the show Greed, where he walked away with $1.4 million. He’s also appeared on Sale of the Century and Win Ben Stein’s Money, bringing in less on both of those shows, but still adding to his overall wealth.

8. David Legler – $1,765,000

David Legler

David Legler was 29 years old when he won over $1 million on the game show, Twenty-One. Legler has an undergraduate degree in engineering and was working toward an M.B.A while serving as a recruiter for the Great Lakes Naval Training Center in Chicago.

Twenty-One was a classic game show revived for the 21st century, and at the time, Legler was the biggest game show winner of all time, winning six games in three episodes in 2000. This wasn’t the first game show Legler attempted to get on TV. He’d also auditioned for Who Wants To Be A Millionaire? several times, but never managed to get a callback. Legler also tried out for College Jeopardy! as an undergraduate but didn’t make it on the show.

7. Ashlee Register – $1,795,000

Ashlee Register admits that she had one thing going for her in Duel, and that was her sweet appearance. After all, in a game where you have to outbluff your opponents, many people base their instincts on how a person looks. Ashlee proved that sometimes looks can be deceiving. While she’s a nurse with a nice bedside manner, she admits to having a tough side that her competitors didn’t pick up on.

One other secret they kept from the competition until later in the game was that she holds a B.S. in Microbiology. Many people probably don’t realize that nursing is an intellectual degree, meaning that they greatly underestimated her until that point.

All of this led her to take home the grand prize, and walk away as one of the biggest game show winners in history.

6. Ed Toutant – $1,871,401

Ed toutant

Ed Toutant’s road to winning wasn’t easy. In fact, he was originally eliminated from Who Wants To Be A Millionaire? by supposedly answering a question incorrectly. However, Toutant went home and did his research. What he found was the question he answered incorrectly was not only flawed, but that in the end, he was actually right. After letting producers know what he’d found, they invited him back on. At the time he was on the original show, they had a special promotion where each time the show ended without someone winning the million dollar grand prize, an additional $10,000 would be added to the pot. Between the time he was eliminated and when they invited him back on, another contestant had won the jackpot. However, the show decided to give the same offer to him and Ed managed to win it… Taking home the big prize.

He also won some money on Jeopardy! proving that to some people, trivia is more than just a hobby; it’s a way of life.

5. Sandra Diaz-Twine – $2,000,000

Sandra Diaz-Twine managed to outlast everyone on Survivor not just once, but twice. In fact, Diaz-Twine was the first person to ever win the reality show two different times. Sandra Diaz-Twine originally won Survivor: Pearl Islands, and later came back as a villain in Survivor: Heroes vs. Villains where she managed to beat out Russell Hantz and Parvati Shallow for the grand prize.

Sandra was originally considered by many to be a weak player due to her lack of physical strength and her inability to swim, but she proved to be cunning and resourceful. The mother of two teenagers lives in North Carolina with her husband. Before Survivor, she worked as a senior office associate with the Army and Air Force Exchange Services. Prior to that, she served as a chemical repair specialist in the Army.

Upon being cast as a villain, Sandra has said that she knew she needed to be the nicest on the tribe to make it. And that proved to be her advantage, allowing her to make it to the end with someone as abrasive as Hantz.

4. Kevin Olmstead – $2,207,000

Kevin Olmstead

Kevin Olmstead held the record for the highest total winnings on a game show for three and a half years. Olmstead made it all the way to the Jackpot round of Who Wants To Be A Millionaire? and answered the question correctly to win a total of $2.18 million. He also won some money on Jeopardy! back in the 1990s.

Olmstead is said to still work for the same environmental engineering firm he worked for before appearing on the show, and he joined Toastmasters because he received so many requests to speak at game show conventions. He’s said to have spent his fortune on a condo and a minivan (because it’s more practical than a sports car in Michigan, especially during the harsh winters).

3. Andrew Kravis – $2,656,550

One of the biggest prizes in game show history went to Andrew Kravis. While he’s only number three on the list for highest winnings of all time, he does hold the distinction of winning the biggest prize on any one game show. The bulk of his winnings came from The Million Second Quiz after he beat out 19-year old Brandon Saunders. The Million Second Quiz took place over 11 days, 13 hours, 46 minutes and 40 seconds and allowed a group of contestants to compete for up to $2 million. Kravis and 2nd place contestant Saunders claimed to have become best friends during their time spent on the show.

Kravis is an LGBT rights advocate and a Columbia Law School grad. He’s a public interest lawyer who’s started a fellowship with Lambda Legal, the nation’s largest legal organization working for LGBT civil rights.

2. Brad Rutter – $3,470,102

Brad Rutter

When you ask people who won the most money on Jeopardy!, usually the answer that comes to mind is Ken Jennings. But actually, that honor goes to Brad Rutter. Rutter, a 36-year old aspiring actor from L.A. only took home $55,000 on the first day. However, he won the bulk of his cash from the Million Dollar Masters Tournament and the Ultimate Tournament of Champions. This total could rise too, since he’s been invited back to the Battle of the Decades Tournament and is already a quarter-finalist for the tournament having won his first competition. Rutter has never lost to a human, only a supercomputer named Watson on Jeopardy’s IBM Challenge. His original win streak ended due to a rule Jeopardy! had in place at the time that forced a winner to “retire” after five straight wins. Who knows how much farther he could have gone had that rule been lifted at the time?

Brad is a self-described “slacker” who dropped out of college to work at a record store before appearing on Jeopardy! He’s been on a couple of other game shows now as well, and his official occupation is listed as actor/tv show host/game show contestant.

1. Ken Jennings – $3,623,414

Ken-Jennings

Ken Jennings is a computer scientist from Washington who is noted for holding the record for the longest winning streak on the popular quiz show, Jeopardy! In 2004, Jennings won a whopping 74 games (in a row) before he was defeated by Nancy Zerg on his 75th appearance.

Jennings came back for the Jeopardy! Ultimate Tournament of Champions where he won $500,000 and the IBM Challenge where he won $300,000 (half of which was donated to charity). However, not all of his winnings were amassed on Jeopardy! alone. Jennings also competed on the show, Are You Smarter Than a 5th Grader? (where he took home $500,000), Grand Slam ($100,000), and 1 vs. 100 ($714.29). Jennings wrote about his game show experiences while exploring the history of American trivia in his book Brainiac: Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs.

Ken Jennings has been invited back for the Battle of the Decades Tournament, so he could go on to win even more money. Along with Rutter, he was also beaten by the supercomputer named Watson during the IBM Challenge.

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