Jeopardy! Legend Ken Jennings Joins Who Wants To Be A Millionaire? as Contestant—Teamed Up with Matt Damon

Ken Jennings, the Seattle-born trivia maestro who became a household name with his record-breaking Jeopardy! streak, is making a surprising leap from longtime host to contestant—on a rival game show no less.

ABC’s Who Wants To Be A Millionaire? announced today that Jennings will appear this season as a contestant paired with none other than Hollywood A-lister Matt Damon. The season premiere is set for July 23, promising fans a star-studded lineup full of unexpected pairings.

“It’s going to be a season to remember!” the show teased on Instagram, accompanied by a graphic revealing the celebrity teams.

From Contestant to Host — and Back Again

Jennings’ journey on Jeopardy! is the stuff of trivia legend. In 2004, he stunned the nation with a jaw-dropping 74-game winning streak, racking up over $2.5 million and setting the record for highest-earning American game show contestant—a mark that stood for years.

His deep knowledge and affable charm eventually led to a hosting gig, cementing his place as the face of Jeopardy! for a new generation.

Now, Jennings is stepping out from behind the podium to try his luck on another iconic game show, rubbing shoulders with Damon, whose film credits include Good Will Hunting and the Bourne series.

One fan on social media quipped: “Pretty sure Ken Jennings doesn’t even need a partner, so score for Matt Damon.”

Expanding His Entertainment Footprint

Jennings’ foray onto Who Wants To Be A Millionaire? adds to his growing presence in pop culture. Recently, he was spotted in the trailer for Happy Gilmore 2, making a cameo alongside comedian and sports commentator Stephen and rapper Cam’ron.

The upcoming sports comedy sequel, starring Adam Sandler, is slated for a July 25 Netflix release. Jennings’ brief glimpse in the trailer delighted longtime fans who eagerly took to Reddit and Twitter to share their excitement.

The Ever-Expanding Jeopardy! Universe

Since its original launch in 1964, Jeopardy! has evolved with multiple spin-offs and special tournaments. The show now features events like Jeopardy! Masters, Celebrity Jeopardy!, and the streaming-exclusive Pop Culture Jeopardy, hosted by Colin Jost.

Jennings has been at the center of this universe, both as a champion and as the host guiding the game into new formats and generations.

What’s Next for Ken Jennings?

With his unique blend of quick wit, encyclopedic knowledge, and growing Hollywood presence, Ken Jennings continues to surprise and delight audiences.

Whether he’ll dominate Who Wants To Be A Millionaire? like he did Jeopardy! remains to be seen—but one thing is certain: Ken Jennings is not done making headlines.