‘Jeopardy!’ Fans Reveal What It Was Like Competing Against Ken Jennings

Jeopardy! viewers who have played against Ken Jennings spoke out about what that experience was like. Some contestants also played against him on another game show, The Chase.

Ken Jennings had an amazing 74-day winning streak and participated in 75 episodes. So, that’s 150 different people he would have competed against, as he would have faced two different people each night. His original run was in 2004, and then he went on to compete in numerous tournaments. He racked up $2,520,700 in winnings for regular gameplay, which is the highest ever, according to the Jeopardy! website. Brad Rutter had the highest total of winnings of all time, which includes tournaments. Jennings is currently in second.

“Did anyone here face Ken Jennings? Is there anyone in this sub that went up against Ken Jennings in his original 75-episode run?” a Reddit user wrote.

“I actually went up against him in a team Quiz Bowl event at TCONA* (the Trivia Championships of North America) in….either 2012 or 2013. Interestingly enough, one of my teammates (and a friend) was Adam Villani, who had put up a valiant fight against Ken on Game 61 of his run (he would later end up doing quite well on 500 Questions). My understanding was that Ken roadtripped with his family down to Las Vegas from Salt Lake City to participate. To borrow an aphorism from feudal Japan…we died properly. Ken was a beast – a friendly beast to be sure, but a beast,” one user wrote.

“I played him on Master Minds and I got a question right that he got wrong and they made it into a commercial!” a fan said. Master Minds originally debuted as Best Ever Trivia Show and was renamed in 2020. Jennings was a frequent guest on it.

“No, but I played ‘against’ him on Best Ever Trivia Show, later re-named Master Minds. And I got a question correct that he got wrong,” another Master Minds competitor said. “Could have been scripted for him to miss it but I try not to dwell on that.”

One user said they played against on an unaired episode of The Chase. Someone asked how it was and why it didn’t air. “It was fun. Had a nice interaction with him, and he’s naturally very funny. It wasn’t aired because it was a rehearsal episode before they started taping season 2. So they did everything like a real episode to practice, just nothing counted,” they wrote. However, they said they also played against him on Master Minds.

“I played him in a quiz bowl practice once. He smoked everyone on a tossup on the WWE Intercontinental Title. (I know not what you asked exactly, but I did play him in some form of quizzing, so it’s something!),” said another.

Although no one from Jeopardy! shared their experience, someone suggested that they should do a redemption season for everyone who went up against Ken Jennings. “It’d be really cool to watch,” they said.