Inside Jeopardy! host Ken Jennings’ messiest moments with rival James Holzhauer before game villain won Masters special

JEOPARDY! host Ken Jennings has delivered some seriously shady moments aimed at rival James Holzhauer on Masters – and vice versa, of course.

The pair are known to exchange subtle barbs on the set of the iconic game show and fans love it.

Jeopardy! host Ken Jennings and Masters competitor James Holzhauer have been duking it out for agesCredit: ABC

The game show champs frequently trade barbs and other shady stunts in stageCredit: Getty
Ken, 49, has come face-to-face with James, 38, on the Jeopardy! set plenty of times.

Recently, however, they spent even more time together as the champ-turned-host was pegged to host the Jeopardy! Masters special, which the show veteran appeared on.

The show drew fans in, delivering intense competition, surprise twists, and so much more.

Throughout the competition, Ken threw major shade at James every chance he got.

James, meanwhile, racked up a number of wins on the show and artfully responded to all the jabs thrown his way.

Viewers at home took notice of the back-and-forth banter between them, weighing in on social media and having a good laugh.

While James held his own, Ken has bested him in their war of words more than once.

Here’s a look at some of the messiest moments between Ken and James.

KEEP IT PG

James was slammed over a supposedly inappropriate comment while jabbing at KenCredit: ABC
During an early episode of Jeopardy! Masters, Ken and James faced off in a hilarious and slightly shocking exchange.

As they headed into the second game of the competition, featuring James, Mattea Roach, and Matt Amodio, viewers were treated to a light moment.

James got off to a hot start, building a solid lead against his competitors.

Postdoctoral researcher Matt chose from the category Author’s Pretty Decent Reviews.

The answer read: “The Detroit Free Press said ‘The Mummy’ was ‘vintage’ this novelist; ‘elegantly erotic and full of enchanting terror.'”

Matt incorrectly responded: “What’s Stoker,” before the buzzer rang and host Ken joked: “I also refer to James as ‘elegantly erotic but full of enchanting terror.'”

The contestants and studio audience laughed as Ken then provided the correct response of “Who is Anne Rice.”

Before the show could move on, James quickly quipped back: “Keep it in your pants, Ken.”

Fans took to Twitter to discuss the risqué back-and-forth, with one person writing: “‘Keep it in your pants, Ken,’ is among the top ten phrases I was not expecting to hear on Jeopardy Masters tonight, and no, I don’t know what the other nine are.”

Another tweeted: “Uh… inappropriate…”

While a third person remarked: “Well, that exchange late in the round took Jeopardy Masters close to the ‘TV-G’ line.”

“The game show villain shades Ken again!” one commenter chimed in.

REMATCH TIME?

Ken responded to James’ shady calls for a rematch in an interviewCredit: ABC
James took yet another dig at Ken via a Final Jeopardy message.

During the game, James faced off against Sam Buttrey and Mattea.

Since James completely dominated his fellow competitors, he was able to go into Final Jeopardy stress-free knowing no one would be able to catch up to his score.

James used the question – which asked: Opened in 1909 & less famous than an older neighbor, it connects Brooklyn & Chinatown – to mess with Ken.

James instead answered: “Stop ducking a rematch, Ken,” causing the host to laugh out loud.

“You know how much work I had to go to to get all the way over at this lectern and avoid having to play you again, James?” Ken replied.

James then quipped that he was a victim of autocorrect, hinting that the word “ducking” was actually intended to be something else.

In the wake of the shady comment, Ken sat down with TMZ to share his thoughts.

“I feel like I got away with one last time I had to play that guy,” the 48-year-old said referring to the time he beat James during the show’s Greatest of All Time tournament in 2020.

Ken continued: “He is the best player of his generation and I can’t believe I skated by with a win in my fading decade… I’m getting a little long in the tooth for a Jeopardy champion.”

The longtime TV star then said: “No, ain’t gonna be no rematch… you have to let somebody retire.”

“You can’t keep summoning my unquiet ghost to go play Amy Schneider, she doesn’t need that,” Ken added, referring to the famous Jeopardy! player who won 40 consecutive games in 2021-2022.

MORE LIKE TROLL-ZHAUER

James trolled the Masters tournament and Ken after taking an impressive leadCredit: ABC
Self-described game show villain James trolled Ken and Jeopardy! Masters for having a ranking system despite him being the clear frontrunner.

James found himself in first place after winning five of his six Masters matches and placing several risky all-in Daily Double bets.

The tournament’s leaderboard showed James so ahead that he joked the other stats that would determine the eventual $500,000 grand prize weren’t even necessary.

With only the semi-finals and finals left starting next Monday, he sarcastically tweeted: “Good thing we had those tiebreakers to establish a clear number 1 seed.”

One fan replied: “THE CHAMP IS HERE.”

Another wrote: “Be nice…” though a third write it’s not game over just yet: “Andrew He about to become Andrew HIM when he stomps you and takes the strap, brother.

A fourth wrote: “James, I think you’re great; you make the show exciting to watch; it blows my mind how many things you know. And I know you’re a ‘nice’ guy too.”

And a fifth wrote: “Greatest villain ever!”

However, James then went on to call Masters’ Amy Schneider a “phenomenal human” and Sam Buttrey a formidable foe in a subsequent Twitter post plugging their upcoming projects – and hinting he was breaking character in his caption.

HOW EGG-CITING

On May 24, James celebrated another big Jeopardy! Masters win in an unconventional way.

He cracked an egg over Ken’s head on live TV, shocking viewers.

Toward the end of the game, Ken turned to James and asked: “I wanna hear about your charity raw-egg cracking talent. How is your raw egg cracking?”

Grinning from ear to ear, James explained why he had taken on the bizarre challenge in the first place.

“Yeah so Pat McAfee, a fan of the show and apparently me in particular, sent me a challenge,” he began.

“It was called Crack Cancer. And your thing is, you had to have a video of someone smashing a raw egg over your head.

“So I enlisted my wife to do this, who cackled through the whole thing. And then you’re supposed to kind of pass it on, and I decided I would challenge my opponents from GOAT.”

James continued: “And to this day, none of them have accepted the challenge,” before calling out a particular colleague named Brad.

The video then cuts to Ken and James standing next to one another as Ken said: “Brad’s not here but I am willing to take one for the team here. Are we gonna carry on the raw egg cracking challenge?”

“Three years later but no less sweet!” James announced as he cracked the egg directly onto Ken’s head.

“Great!” Ken blurted out as the studio audience yelped and applauded.

“Do I have a little something here?” Ken joked as he wiped the side of his face with a small towel.

Jeopardy! fans were quick to comment on the video, as one person wrote: “I love this SO much. I am so happy they are friends and help each other out. I knew Ken would be game.”

Another excited fan said: “OMG! THAT WAS AWESOME! I HOPE THE CHALLENGE WAS REWARDING IN SOME SENSE. I REALLY ENJOY WHEN MR. JENNINGS DOES AND SAYS THINGS TOTALLY OUT OF JEOPARDY CHARACTER.”

A third person declared: “@KenJennings is a national treasure,” and a fourth added: “@KenJennings is just amazing.”