Ken Jennings reveals whether 'Who Wants to Be a Millionaire?' was harder to win or 'Jeopardy'
Jennings recently won a million dollars on Who Wants To Be A Millionaire with Matt Damon.
Aug. 16 2025, Published 8:45 a.m. ET
"Jeopardy!" host Ken Jennings has not just been a phenomenal contestant on his show before, but he has added another feather to his cap by winning on "Who Wants to Be A Millionaire." Alongside Matt Damon, he ended up winning the million bucks for Damon’s charity, Water.org. After the show was over, Jennings was asked which game show was harder to win.
The host impressed again with a diplomatic answer, stating that there were elements of gameplay in both that were tougher than the other. “Jeopardy!” covers a lot of topics, but one can choose to avoid a topic that they are not comfortable with, while that is not the case with “Who Wants To Be A Millionaire.”
“I guess you could say that we won the million, so clearly, it’s not a Jeopardy!-like crucible, and that’s true. Jeopardy! probably, objectively, has a lot of things that are harder about it, but the thing about Millionaire is that it’s like you have to swing at every pitch. You cannot let a ball go by and say, ‘That’s not my pitch.’ You can’t miss a question. And you always are so aware of that. It’s like you’re teetering over an Indiana Jones death pit, because the next question could be it at any point,” he said, according to a TV Insider report.
Thankfully, Jennings had a good teammate in Damon, who was no slouch. The pair easily cleared a lot of the questions in the beginning. The trouble came in the $500,000 question and the $1 million question. But by that time, they had not used a single lifeline and could get all the help they needed to win the money. That is exactly what they did. Another interesting dynamic that Jennings commented on after the show was that of Damon and host Jimmy Kimmel.
The two have had an on-screen rivalry of sorts for many years now, and it seeps into whatever programming they have been a part of together. Even on “Who Wants To Be A Millionaire,” that rivalry was evident. Jennings claimed to have loved it. “I’d seen them do that on TV so many times, and loved it, but for some reason, I had forgotten it was just gonna go on in person while I was trying to win on a game show,” he said.
“So I tried to get 15 questions right, and I’m very worried and stressed about this. And then these two are doing a Friar Club roast, which was great. It actually ended up kind of taking off the pressure, because I started really enjoying seeing it up close. They’re both super funny.” Ultimately, they all had fun, and it was a good watch for fans as well.
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