The Five Biggest Money Winners In American Game Show History

By on August 12, 2015 in ArticlesHow Much Does

Did you have a favorite game show growing up? Maybe when you stayed home sick from school, you watched "The Price Is Right." Or perhaps you thought you'd try your luck on "Wheel of Fortune," or start answering everything as a question with "Jeopardy!"

Whatever your favorite show was, chances are the winning contestant walked away with a nice tidy sum of money. Some contestants are luckier than others, though, and came out of the studio with an incredibly big haul. Here are the people who have won the most money on American game shows.

#5 Ed Toutant – $1,871,401

Though he won $11,401 in a lone victory on "Jeopardy!" the majority of Toutant's winnings also came from the accumulating jackpot period of "Who Wants To Be A Millionaire?" though his experience was a bit more stressful. He appeared on the show and reached the $16,000, which asked: "Scientists in England recently genetically altered what vegetable so it glows when it needs water?" Toutant asked the audience and agreed with the majority, who said "tomato," rationalizing that an underground plant like potatoes and carrots wouldn't need to be lit up. But "potato" turned out to be the right answer.

Toutant wasn't having that, though, and did some research after he got back home. The glowing potato actually came from Scotland, not England. What's more, Toutant found an Oxford professor who sent a journal article to Toutant, detailing his work with glowing tomato plants. Toutant wrote the show a "concise, friendly letter," and about six weeks later, received a phone call. "Millionaire" not only wanted him back on, but they would let him play for the $1.86 million he was going for at the time, even though the jackpot had been reset after Olmstead won it.

Toutant returned to the show, used two lifelines on his new $16,000 question, but still managed to reach the final question with a 50:50 in hand. His million (and change) dollar question? "During WWII, U.S. Soldiers used the first commercial aerosol cans to hold what?" Toutant used the 50:50 to narrow the choices down to antiseptic and insecticide. Toutant chose the latter, and took home his big winnings.

After the show, Toutant remained working for IBM in Austin, Texas. He still participates in pub quizzes, and picked up quite a bit of "Millionaire" paraphernalia from eBay during and after his run, including a life size cardboard cut-out of Regis, a CD with all 76 of the shows musical cues on it, or a keychain with Regis asking the show's famous catch phrase: "Is that your final answer?"

We just hope Toutant didn't blow too much of his winnings on that one.

#4 Kevin Olmstead – $2,207,000

Olmstead won $2,180,000 on "Who Wants To Be A Millionaire?" back in 2001. At the time, it was both the record for biggest winner in American television as well as the biggest winner on a U.S. primetime game show. Those records have since been broken by Jennings and Kravis, respectively.

How did Olmstead nab more than a million bucks on the show? He happened to be lucky enough to play during the "accumulating jackpot" period – anytime someone appeared on the show and didn't win a million dollars, the jackpot increased by $10,000. By the time Olmstead appeared, the jackpot was at its absurd number, and he walked away as the biggest winner in the show's history. That record still stands.

Olmstead also added another $27,000 to his bank after appearing on Jeopardy.

#3 Andrew Kravis – $2,656,550

Kravis earned nearly all of his winnings on the short-lived show "The Million Second Quiz." The show, which was played 24 hours a day, lasted for about 11 and a half days, or one million seconds. One contestant sat in a "money chair" and would accumulate winnings based on fending off challengers to the chair. The four highest-earning contestants moved on to the final round; Kravis was one of those four, winning $326,346 in the main competition. He then earned another $273,654 in the championship round, plus the $2,000,000 grand prize.

This was actually Kravis's final appearance on a game show. Prior to "The Million Second Quiz," he reached the semifinals of the "Jeopardy!" Teen Tournament, winning $5,000 at age 13. He won $50,050 dollars on "Wheel of Fortune," and a modest $1,000 on "Who Wants To Be A Millionaire?" Today, he co-hosts events and writes quiz questions for TriviaNYC, New York's longest-running trivia event company. Kravis writes a free weekly crossword puzzle, as well, and his crosswords have appeared in a number of publications, like The New York Times and The Los Angeles Times.

#2 Ken Jennings – $4,123,414.29

Jennings holds the record for the longest winning streak in "Jeopardy!" history, having won 74 games in a row in 2004. During that original run, he won $2,522,700. Most of his other performances have been in matches that also featured Rutter. Jennings finished in second place in the Ultimate Tournament of Champions, $300,000 in the 2011 IBM Challenge ($150,000 of which he donated to charity), and $100,000 for finishing in second place in the Battle of the Decades.

Even his wrong Final Jeopardy! answer proved to be beneficial. When Jennings finally lost in his 75th straight appearance on the show, he incorrectly answered "What is FedEx?" to the clue: "Most of this firm's 70,000 seasonal white-collar employees work only four months a year." The correct answer was H&R Block, and the company reached out to Jennings after he was eliminated, offering him free tax planning and financial services for the rest of his life. The company estimated Jennings would owe about $1.04 million in taxes on his winnings.

Jennings has also appeared on the game show "1 vs. 100," where he won $714.29 as a member of the "Mob" after incorrectly guessing the color of the number 1 space on a roulette wheel (it's red, if you're scoring at home). He won $100,000 on "Grand Slam," and reclaimed his title from Rutter as the leader in career winnings (though, as we mentioned, Rutter has since returned to the top spot) by winning $500,000 on "Are You Smarter Than a 5th Grader?" In 2014, Jennings appeared on "Who Wants To Be A Millionaire?" and won $100,000.

After his success on "Jeopardy!", Jennings authored a book that looked at his experience on the show and delved into American trivia history and culture. He's since written several other books, mostly focused on trivia, as well, though one is about maps and geography, and another is an examination of myths, tales and warnings that get passed down from generation to generation. He currently lives in Seattle, and writes and edits questions for the National Academic Quiz Tournaments, a quiz bowl organization.

Jeopardy Productions via Getty Images

Jeopardy Productions via Getty Images

#1 Brad Rutter – $4,555,102

Rutter, born on January 31, 1978, is the biggest all-time winner in game show history. He's always had a penchant for quizzes, participating in the Quiz Bowl in high school (where he was named to the National Academic Championship Hall of Fame) and hosting a local broadcast show called InQuizitive through 2007.

Rutter earned most of his game show money from "Jeopardy!" His first appearance was in 2000; at the time, winners could only remain on for five days. Rutter's initial winnings were $55,102, plus two Chevy Camaros. As a five-day champion, Rutter was invited to the 2001 Tournament of Champions, which he won, picking up an additional $100,000. The following year, he participated in the Million Dollar Masters tournament, winning $1,000,000 and becoming the biggest winner in "Jeopardy!" history.

He didn't stop there, though. In 2005, Rutter returned for the Ultimate Tournament of Champions, securing the grand prize of $2,100,000. Along with Ken Jennings, he participated against IBM's Watson supercomputer, and won $200,000, donating half to charity. Since this was technically an exhibition event, it doesn't count in Rutter's career standings, so he remains undefeated in 19 career appearances on the show. However, the money won counts towards his career total.

He did lose his "biggest winner" title to Ken Jennings in 2008, but last year Rutter reclaimed the #1 spot with a victory on the "Jeopardy!" Battle of the Decades match. He won another million dollars to bring his total to where it sits today. Recently, Rutter moved to Los Angeles to pursue a career in acting. His current project is serving as executive producer and actor on a show called "Discount Fitness," which is in post-production.

Articles Written by Joey Held
If there's a story anywhere in the world of music, sports, or entertainment, Joey wants to tell it. He's been freelancing since 2010, and prior to that, he attended the University of Miami, where he double majored in broadcast journalism and sport administration. A Chicago native, Joey currently resides in Austin, TX. Follow him on Twitter and Google+ and always feel free to suggest a song for his next karaoke performance.
Did we make a mistake?
Submit a correction suggestion and help us fix it!
Submit a Correction