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'Jeopardy' host Ken Jennings makes playful but risky joke that most fans didn’t see coming

While he has a spotless track record on screen, Jennings loves to have fun behind the scenes.
PUBLISHED AUG 18, 2025
Screenshot showing Ken Jennings' reaction after making the joke (Cover image source: YouTube/Jeopardy!)
Screenshot showing Ken Jennings' reaction after making the joke (Cover image source: YouTube/Jeopardy!)

"Jeopardy!" is usually all about history and pop culture trivia, but the show has had its controversial and awkward moments. Ken Jennings has maintained a good record when it comes to on-screen slip-ups and apologized for a sexist clue on the show. However, the b-roll of the show holds many secrets, some of which were recently released on social media. During a break, the crew released a blooper tape on YouTube, sharing the fun moments where Jennings slipped up. In one of those, the record-holding champion even slid in a "that's what she said" joke on the family-friendly game show.

Screenshot showing Jennings laughing at his own joke (Image source: YouTube/Jeopardy!)
Screenshot showing Jennings laughing at his own joke (Image source: YouTube/Jeopardy!)

The clips showed how jittery the host is, especially with smooth transitions and some difficult words. It also showed just how witty and unafraid the host is to crack a joke. In a clip, Jennings read a clue that included the phrase, “How big do you wanna go?” and he couldn't hold back from saying, “That’s what she said.” As the crowd started laughing, Jennings tried to salvage the situation by immediately admitting, “That doesn’t even make sense.” He then went on to laugh at his own joke as the producers reset the scene for the host to do it all over again.

Screenshot showing Ken Jennings' reaction after making the joke (Cover image source: YouTube/Jeopardy!)
Screenshot showing Ken Jennings' reaction after making the joke (Image source: YouTube/Jeopardy!)

It turns out the former champion also jumped around a tall contestant to be in the same frame. "I'm sorry. Tall people love tall people jokes," he said as he walked away.

Screenshot showing Jennings hopping beside a tall contestant (Image source: YouTube/Jeopardy!)
Screenshot showing Jennings hopping beside a tall contestant (Image source: YouTube/Jeopardy!)

Later on, Jennings even struggled to go into a commercial as he kept missing the mark. "I promise we're going to get to this commercial, you guys. This is going to happen," he joked. The video included a clip of Jennings taking a question from the audience as well, where a fan asked, “Do you ever finish a particular episode and at the end you realize, ‘Boy, this contestant doesn’t know s**t’?” 

Screenshot showing Jennings taking a question from the audience (Image source: YouTube/Jeopardy!)
Screenshot showing Jennings taking a question from the audience (Image source: YouTube/Jeopardy!)

Instead of answering the question directly, Jennings replied with another reference to make a joke out of himself. “I do remember, I lost to this lovely woman from Ventura named Nancy Zerg, who knew Final Jeopardy when I did not. And, you know what she thought? She was like, ‘That guy doesn’t know s**t,'" Jennings quipped.

This wasn't the first time that "Jeopardy!" shared the candid side of its host. In another blooper clip shared by the show, Jennings cursed on the family-friendly show! Previously, during the Tournament of Champions, Jennings was hosting a special exhibition game featuring three of its top champions, Amy Schneider, Matt Amodio, and Mattea Roach.

While the game was going smoothly, Jennings was stumped by a clue where he had to present a correlation between the numbers in the Numbers, Please category and the winning streaks of former champions, including Jennings. “I don’t know if you noticed, but the numbers in that category are 40, 23, 38, and 74, which is larger than all of them," Jennings said, bragging about his 74-game winning streak. But what he didn't realise was that he gave away an extra clue in the process.

When someone off-camera signalled him to stop, the host blurted out, "Oh s**t!”, making a grimacing face. 



 

He then requested the contestants to do it all over again, but it was too late a Amodio took advantage of the extra clue and answered the question in no time to win cash.

More on Market Realist:

'Jeopardy' host Ken Jennings reveals the most cringeworthy part of his job, and we totally get why

'Jeopardy' host Ken Jennings names two shows where he can achieve another 74-game winning streak

'Jeopardy' host Ken Jennings and Matt Damon win $1 million prize on 'Who Wants to be a Millionaire'

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