Spoilers for Matt Damon and Ken Jennings run on Who Wants to Be a Millionaire are ahead!
Well, they did it. Ken Jennings and Matt Damon won Who Wants to Be a Millionaire; however, I can’t say I’m shocked. As these episodes aired on the 2025 TV schedule, I fully expected Jeopardy’s host and Jimmy Kimmel’s faux nemesis to win, and they did. However, when asked about the challenges of playing on this game show, the Jeopardy legend didn’t mince his words as he said it felt like “teetering over an Indiana Jones death pit.”
The A-list actor and one of Jeopardy’s biggest winners became the third team of celebrities to win the million dollars. However, it wasn’t all easy work. They had to use their lifelines – Jennings brilliantly called out of its traps last week, by the way – and they had to talk through their options. It wasn’t a total walk in the park, and the Jeopardy! host opened up about that while comparing the game show he hosts with the one he just won, telling TV Insider:
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 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. So it’s tense out there. I think Matt felt it too.
I totally get what Jennings is saying. On the surface, since Jeopardy! is not multiple choice, it seems objectively harder. Also, you don’t play for a single amount of money; you keep playing until you lose, so it can require a different kind of endurance.
However, Millionaire has higher short-term stakes. If you miss a question, you don’t just lose money, you’re out for good. So, there’s no room for error, whereas on Jeopardy! you can miss a question or two, you just need to make sure you’re not in the red before the final round.
So, on Millionaire, you do have to take bigger swings, and I agree that it can feel like “you’re teetering over an Indiana Jones death pit.” Thankfully, though, Jennings had someone he could talk his proverbial swings out with, much to Jimmy Kimmel’s hilarious chagrin.
To that point, much like how Matt Damon complimented his partner’s intelligence, Jennings spoke highly of the Good Will Hunting star. He said that having a partner on the show really did make it better, explaining:
Absolutely easier with a partner. It turned out to be easier that Jimmy knew the one we didn’t know. We had a lot of good Millionaire luck.
Well, teamwork, luck and experience playing some of the best game shows certainly paid off big time, as Jennings and Damon ultimately won the million for the actor’s charity water.org.
Meanwhile, we got a good show out of it, too. The episodes, which you can now stream both with a Hulu subscription, were wickedly entertaining. We got to see Jimmy Kimmel and Matt Damon’s rivalry on full blast, we got to witness the actor and Jennings kick butt at trivia, and in the end, we got to see them win a bunch of money that’s going to a great cause. So, it was a win-win all around, even though it made the Jeopardy! icon feel like he was “teetering over an Indiana Jones death pit” at times.
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