Ken Jennings Shocks ‘Jeopardy!’ Fans With Unexpected Career News

It looks like Ken Jennings is taking his career from the world of TV all the way to the putting green! Well, sort of.

Ever since Ken first appeared on Jeopardy! back in 2004, fans have seen him make a name for himself as a trivia champion-turned-television host. But as it turns out, he’s more than just a face on the hit quiz show. Among his other accomplishments (like writing a new book that’s set to debut on July 29, 2025), he’s also finding his way into the lexicon of popular movies.

As Jeopardy!‘s official Instagram revealed on June 1, Ken will be making a blink-and-you’ll-miss-it appearance in the upcoming movie Happy Gilmore 2. Sharing the trailer for the Adam Sandler-led sequel to the 1996 film, the project is set to hit on July 25, 2025 on Netflix. And if that’s not enough, the show made sure to let viewers know they have to keep an eye out for Ken’s surprise cameo (wait until the 1:19 minute mark in the trailer) away from the Jeopardy! podium.

“Did you spot the Kenmeo? 😎,” the show cryptically teased in the caption alongside the clip.

Given how Ken isn’t one to venture into acting, fans were absolutely shocked to learn he’d be onscreen during Happy Gilmore 2.

“What is I’m impressed,” one person wrote in the comments. “Loved seeing Ken in the trailer,” another declared. “YAYYY Ken!!! 💜,” a different follower added.

Even though it’s only going to be a quick moment, this is surely something Ken is excited about! What’s more, he’s not the only famous face popping up in a cameo in this movie. Along with Ken, fans can expect to see Travis Kelce, Nikki Garcia, Rory McIlroy, Eminem, Post Malone and plenty more stars appear at one point or another.

But that’s not all. Fans on Reddit also managed to make a surprise game show host connection for Ken, as viewers may remember the late Price Is Right host Bob Barker showed up in the original Happy Gilmore movie.

“Did anyone catch that glimpse of him in the trailer?! I squealed!” one user wrote. “It’s just not Happy Gilmore if he doesn’t get beat up by a game show host,” another joked. “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,” a different follower noted.

No matter who Ken plays, we’re ready to see him tee up on the putting green very soon!