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.”
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:
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.