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Interviews

Ken Jennings Watches His Original ‘Jeopardy!’ Interviews: See How He Reacted

Last updated: September 13, 2025 12:10 am
Published: 7 months ago
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What is embarrassing? Ken Jennings sat down to watch all of his Jeopardy! interviews, and he had some strong reactions to some of them. Fans didn’t realize how funny he was.

“Hey, I’m Ken Jennings, and I’m going to be rewatching my interviews from my original Jeopardy! streak. I am genuinely afraid to see what I had to say, but let’s go ahead and do this anyway,” he started the YouTube video.

Appropriately, he started with his first interview. “Aww, look at this young, eyebrowless man,” Jennings said. The first story was about how two drunk teenagers and a truck driver saved him when he was stranded in a Nevada desert after running out of gas. Jennings gave them a shoutout, but didn’t know if they watched Jeopardy!.

For his seventh appearance, Jennings made fun of his shirt. “Look at that shirt,” he chuckled. “It was a bulky shirt.” The then-Jeopardy! player had on a maroon button-down with a gray tie. “I just wanted to wear a lot of big boxy dress shirts. That was my main Jeopardy! dream,” he joked. Jennings shared about a later interview that he borrowed a lot of his brother’s clothes because he was running out of them, and his brother knew he was winning since he was in the audience for the first game.

For his ninth game, Jennings talked about going skydiving with his friend, who basically forced him to go. “Going skydiving is like being on Jeopardy!” the host said. “The brain is just so overwhelmed when you’re out there. What actually took half an hour actually took five minutes.”

Jennings revealed that he lied about a few of his stories. He brought a “good luck charm” with him and claimed it was something he picked up in Japan. However, he was running out of stories and borrowed a small stuffed animal from his sister instead. In another story, the game show contestant lied about liking airline food.

Ken Jennings also joked that he had “killed a man down South,” when asked about his darkest secret, but said he stole the joke from David Letterman. “Maybe I should start asking contestants what their darkest secret is.”

During his last game, Alex Trebek asked Jennings if he had quit his job. He said he hadn’t, but in the interview shared that this was a cursed story because his streak ended that day.

Jennings said that he didn’t quit his job for a couple of years until he got offered to write a book, in which he had to take a leave from his job. “I guess I’m still on leave,” he said.

The host ended the video by saying that the best Jeopardy! story is like a Mad Lib. “Hey, I have two skateboards, but they’re both from Portugal,” he gave an example. “Objectively, that’s a boring story. You wouldn’t try that on a first date, but it’s almost perfect for Jeopardy!”

In August, Jennings revealed he finds the interviews to be the “cringiest part” of the game show. He promised to keep them short.

“Until watching this YouTube video, I don’t think I realized how funny Ken really is,” a Reddit user said.

“Ken is hilarious. I can’t believe they ever considered anyone else for the hosting job. Love him so much,” commented another.

“Now I want to know how many of his interviews were lies out of his near-100 (or more!) appearances lol,” a YouTube user wrote.

Which one of Ken Jennings’ Jeopardy! stories is your favorite? Let us know in the comments.

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