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The Best Jeopardy! Contestants of All Time

Updated November 18, 2019 20.3k votes 6.0k voters 306.5k views14 items

List RulesVote up the Jeopardy! contestants who are the most fun to watch as they win.

Since the first episode of the daily-syndicated version of Jeopardy! in 1984, an incredible number of legendary winners have taken home astronomical amounts of money to cement their status as the best Jeopardy! contestants of all time. What first started as a simple idea in 1964 by Merv Griffin's wife Julann turned into arguably the most widely recognized television trivia game show ever. When you think of the highest-winning contestants, names like Ken Jennings, Eddie Timanus, Brad Rutter, Austin Rogers, and James Holzhauer are just a few of the names you'll think of when discussing the best Jeopardy! contestants of all time.

When most fans think of the best Jeopardy! contestants of all time, they consider the longest winning streaks, most money won, and most entertaining characters. These are the main criteria taken into consideration when putting this list together. These trivia titans amassed their win totals not only through the traditional syndicated show, but also from return appearances on the Tournament of Champions.

Do you remember some of these Jeopardy! greats? Who do you think are the best Jeopardy! contestants of all time? Go ahead and rank them, and when you're done, head on over and vote on the funniest Jeopardy! answers of all time.

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  • 1

    James Holzhauer

     James Holzhauer is listed (or ranked) 1 on the list The Best Jeopardy! Contestants of All Time
    Photo: CBS Television Distribution

    Professional sports gambler James Holzhauer set a new record for single-game winnings on April 9, 2019, with the response "what is quantum leap." His final total set his day's winnings at $110,914, which not only surpassed the 2010 single-day record of $77,000, but is also the same digits as his daughter's birthday (11/09/14).

    A little over a week later, Holzhauer beat his own record single-game winnings by raking in $131,127 in the Jeopardy! episode airing April 17, 2019, in what was also his 10th straight win. In his 14th game on April 23, 2019, Holzhauer passed the $1 million mark. On May 27, he scored his 28th consecutive Jeopardy! win, bringing his total winnings to $2,195,557. When his winning streak ended at 32 games, he had won $2.5 million. After winning the Tournament of Champions on November 15, 2019 his winnings reached $2,712,216, putting his total at third most in the show's history.

    As reported by the Washington Post, each large amount Holzhauer wagered related to an important date in his life, from family birthdates to his wedding anniversary. Holzhauer credited the ability of children's books to engage while informing as his secret to success. 

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  • 2

    Ken Jennings

    Ken Jennings is listed (or ranked) 2 on the list The Best Jeopardy! Contestants of All Time
    Photo: CBS Television Distribution

    Likely the most recognizable Jeopardy! contestant of all time, Jennings ripped off an incredible 74-night winning streak in 2004 that earned him over $2.5 million,  and with tournament winnings at $3,370,700 he reached No. 2 all time. Most of his victories weren't even close, as Jennings became the show's longest-running champion by far. Only one other champion has won more than 20 consecutive games (James Holzhauer at 32).

    Jennings would later finish as the runner-up in Jeopardy!'s Battle of the Decades in 2014 and even competed against IBM's all-knowing computer, Watson. After Jeopardy!, Jennings went on to become a best-selling author.

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  • 3

    Brad Rutter

    Brad Rutter is listed (or ranked) 3 on the list The Best Jeopardy! Contestants of All Time
    Photo: CBS Television Distribution

    Only one being has ever defeated Brad Rutter at Jeopardy!: IBM's Watson. That's it.

    Rutter is the highest-earning Jeopardy! contestant of all time (including tournament winnings), with more than $4.75 million in winnings over the course of his many tournaments. He originally became a contestant in 2001, and went on to dominate in the Tournament of Champions, the Ultimate Tournament of Champions, Million Dollar Masters, and others.

    Through all that, he still never found the formula to defeat good ol' Watson.

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  • 4

    Austin Rogers

    Austin Rogers is listed (or ranked) 4 on the list The Best Jeopardy! Contestants of All Time
    Photo: CBS Television Distribution

    Austin Rogers was the first mainstream Jeopardy! star in a few years, bringing the show back to the limelight while winning $411,000 over his 12-show run in late 2017. Most noteworthy, Rogers owned two of the highest single-game win totals of all time, earning $65,600 and $69,000 on consecutive days on October 2-3, 2017, until James Holzhauer came along.

    It's not quantifiable, but he also might have had the best hair/beard combination in Jeopardy! history.

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