GAME SHOW LEGEND TAKES ON HOLLYWOOD! Jeopardy’s Ken Jennings STUNS Fans With SURPRISE Role In Comedy Sequel Everyone’s Been WAITING For

KEN Jennings from the hit game show Jeopardy! will make a surprise movie debut in a beloved comedy’s sequel.

Seattle-born and raised Ken, 51, can be seen in the trailer for the new Happy Gilmore 2 movie.

Collage of Ken Jennings, Stephen A. Smith, and Nick Cannon.

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Ken Jennings makes a cameo in the new Happy Gilmore 2 movie, with him seen above in the new trailerCredit: Netflix

Adam Sandler as Happy Gilmore holding a golf club on a golf course.

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Happy Gilmore 2 will premiere on Netflix this JulyCredit: © 2025 Netflix, Inc.

Ken Jennings in a scene from a movie.

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Travis Kelce and Bad Bunny also feature in the new movieCredit: Netflix

Ken Jennings in a scene from the movie "Zoolander 2".

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As does Ben StillerCredit: Netflix

Ken Jennings and Adam Sandler in a scene from a movie.

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Bad Bunny has a seemingly prominent role in the movieCredit: Netflix
Adam Sandler will be starring in the beloved sports comedy, which drops onto Netflix on July 25.

And none other than Jeopardy! host will be starring alongside the 50 First Dates star.

Also seen in the trailer and joining the previously announced cast are Travis Kelce, Bad Bunny, Jackie Sandler, Eric André, Margaret Qualley, Martin Herlihy, Tim Herlihy, Nelly Korda, Nancy Lopez, Verne Lundquist, and Jack Giarraputo.

As well as Kevin Nealon, Benny Safdie, John Farley, Kym Whitley, Lavell Crawford, Cam’ron, Eminem, Post Malone, Marcello Hernandez, Dan Patrick, Oliver Hudson, Reggie Bush, Becky Lynch, Nikki Garcia, and Jack Nicklaus.

In the trailer, Jeopardy! host and winner Ken, sports radio host and commentator Stephen, and rapper Cam’ron all make cameos talking about Happy Gilmore.

Taking to Reddit, one eagle-eyed fan spotted Ken and said: “Ken in Happy Gilmore 2??

“Did anyone catch that glimpse of him in the trailer?! I squealed!”

‘WOULD BE HILARIOUS’

Someone then replied with: “I think it will be a super brief cameo.”

A second then said: “I saw this and wondered if he would play the Bob Barker role. Love Ken but I don’t see him faring well in a brawl against Happy.

“But it has to be something related to that storyline, I’m very curious where they go with that.”

Jeopardy! Masters fans make major complaint about player as they say the outcome is always ‘so predictable’

Someone else then responded with: “I think Ken being some kind of MMA savant would be hilarious.”

Ken is known because of his record-breaking, consecutive 74-game winning streak on the game show Jeopardy! when he first appeared on it as a contestant.

He first appeared on Jeopardy! as a contestant on June 2, 2004.

His winning streak then ended that November.

 

Jeopardy! Contestant Rules

 

Passing Jeopardy!’s online Anytime Test is hard enough, but there are also many rules players must follow once they make it to the stage:

The returning champion is always at the leftmost podium and keeps playing until they lose.
Contestants don’t have to say “who is” or “what is” in the first round but must do so in Double Jeopardy! and Final Jeopardy.
Contestants can change their responses as long as Ken Jennings or the judges haven’t made a ruling.
The minimum wager for a Daily Double is $5. The minimum wager for Final Jeopardy! is $0.
Written responses in Final Jeopardy! do not have to be spelled correctly, but they must be phonetically correct (the judges decide this).
If there’s a tie after Final Jeopardy, the tied players enter a bonus clue shootout, and whoever buzzes in first correctly wins.
If all three contestants wager everything in Final Jeopardy! and are incorrect, leaving them with $0, there will be no returning champion (it’s happened before—six times).

He earned over $2.5million and became the highest-earning American game show contestant at the time.

Ken later became a host of the show and has also written several books.

KEN’S LIFE AWAY FROM JEOPARDY!

The Jeopardy! host recently gave his fans a glimpse into his world away from the iconic game show.

Taking to Instagram to share a snap away from Jeopardy!, Ken smiled and beamed beside his son.

“The lucky Mariners earrings might be heading for an 0-1 start,” he captioned the snap.

With his wife, Mindy Boam, Ken shares a son and a daughter.

The couple welcomed their son named Dylan in 2002, and their daughter named Caitlin, in 2006.

In the photo, Ken could be seen beaming beside his son Dylan.

The father and son duo rocked matching baseball jerseys, matching baseball caps and equally wide smiles.

Ken was on the left and snapping the pair’s selfie, while Dylan was on the right as he leaned into his father.

Dylan is in his early twenties and looked ultra cool with his long curly hair grazing his shoulders.

Ken Jennings at the Jeopardy! Masters podium.

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Ken is a contestant-turned-host of Jeopardy!Credit: Getty

Ken Jennings and his son at a baseball game.

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Ken recently headed out with his son DylanCredit: Instagram/whoiskenjennings