5 Most Memorable Jeopardy Contestants

Since the show has been on the air for so long, Jeopardy! has had countless contestants come through the ranks. The most memorable ones have been the ones that have racked up win after win, while also having a personality to boot. These contestants are able to display their personality more often since they get a daily interview with the host, with some of the more successful contestants running out of things to talk about.

Throughout the history of Jeopardy! there are certain contestants that fans still think about to this day. Here are our picks for the five most memorable Jeopardy! contestants that had the most significant impact on the popular game show.

James Holzhauer

Many people incorrectly assume that Las Vegas resident James Holzhauer had the longest winning streak due to the massive amount of money that he won. However, he actually ranks fourth in consecutive games won with 32, but the way he dominated was unforgettable. In 2019, Holzhauer went on a tear, and the professional gambler would typically lay it all on the line in Double Jeopardy and Final Jeopardy.

Holzhauer would end up taking every single one of the top 10 spots in the single-game winnings record books and was able to get into six figures on six different occasions. His highest one-day total on Jeopardy! Was an astonishing $131,127, which he accomplished on April 17, 2019, and his total winnings on the show ended up at just under $3 million, good for third place all-time.

Ken Jennings

You can’t tell the story of Jeopardy! without mentioning Ken Jennings, who holds a record that will likely never be broken. In 2004, Jennings went on an insane win streak that caught the world’s attention, and it reached 74 games. No other person in Jeopardy! history has won more than 40 games, showing just how untouchable the record is.

Jennings also has the record for highest winnings in non-tournament play, with a whopping $2,520,700, putting him just ahead of Holzhauer. Jennings, of course, would take part in several tournaments after his insane 74-game run and eventually was named as one of the hosts of Jeopardy! following Alex Trebek’s death.

Austin Rogers

Austin Rogers isn’t in the top 10 in terms of games or money won, but he has a special place in the hearts of Jeopardy! fans around the world. Rogers is a bartender from New York City, and before Holzhauer came along, he had multiple entries in the top ten in terms of most money won in a single game.

Rogers was able to showcase his personality and quickly became a favorite for Alex Trebek. His reactions to getting answers wrong or right were must-see television, and he would end up winning $445,000 thanks to winning a dozen shows.

Brad Rutter

Nobody has been able to take advantage of the tournament structure of Jeopardy! quite like Lancaster, Pennsylvania native Brad Rutter, who earned his spot in the show’s list of all-time greats before there was a cap on the number of games you could win. Rutter won all five of his appearances in the regular season and then won all five tournaments that he took part in.

Rutter was unstoppable, and no human could beat him, with IBM’s artificial intelligence machine Watson being the first to defeat Rutter. Over the course of his Jeopardy! career, Rutter would make $5,053,436, which is number one of all time.

Amy Schneider

In 2022, it looked like Ken Jennings’ amazing streak might come into, well, jeopardy. That’s because engineering manager Amy Schneider from Oakland went on a long streak of 40 games and made headlines as the first transgender person to make the Tournament of Champions. Schneider’s 40 games was good enough to become second all-time, passing Matt Amodio’s 38 games the previous year.

Overall, Schneider ranks fourth in terms of money won from regular season games and overall with tournaments included. She pulled in $1,382,800 throughout her regular season wins. “I didn’t want to make too much about being trans, at least in the context of the show,” Schneider said. “I am a trans woman, and I’m proud of that fact, but I’m a lot of other things, too.”

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