Ken Jennings is switching game shows—and teaming up with a surprising Hollywood A-list star
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Veronica E.
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Ken Jennings is making a surprising move this summer—and it’s not on Jeopardy!.
The beloved trivia champ and host is stepping away from his usual role to appear on a different, long-running game show.
And he won’t be doing it alone.
His unexpected teammate is a household name, but not someone you'd expect to see on a quiz show!
Let’s just say this duo is already turning heads—and the episode hasn’t even aired yet.

A game show crossover we didn’t see coming
For long-time fans who’ve followed Ken’s remarkable journey—from his 74-game Jeopardy! winning streak in 2004 to his current role as host—his upcoming appearance on Who Wants to Be a Millionaire marks a major moment in game show history.
The news was shared on the show’s official social media page, teasing: “It’s going to be a season to remember! Don’t miss #WhoWantsToBeAMillionaire, premiering July 23rd on ABC and streaming on Hulu.”
Among the celebrity pairings revealed, one duo stood out right away: Ken Jennings and actor Matt Damon.
One fan summed it up best: “Pretty sure Ken Jennings doesn’t even need a partner, so score for Matt Damon.”
With Ken’s trivia expertise and Matt’s quick wit, this unexpected team might just be the one to watch!
Also read: Ken Jennings' shocking off-camera reaction to Ryan Seacrest replacing Pat Sajak!
Ken Jennings: from Jeopardy! royalty to Millionaire rookie
Ken Jennings first appeared on Jeopardy! in June 2004, where he went on to win 74 consecutive games—the longest winning streak in the show’s history.
He took home more than $2.5 million and became a household name almost overnight.
In the years since, he’s become a central figure in the Jeopardy! universe—not just as a player, but also as a guest host and now the show’s permanent host.
He’s written several books, made countless TV appearances, and helped usher in a new era of trivia culture.
Now, he’s taking on an entirely different format, showing once again that true champions never stop playing.
Also read: Ken Jennings takes a playful jab at Ryan Seacrest—Here’s what happened!
Jeopardy!’s growing legacy—and Ken’s place in it
Jeopardy! has been an American television staple since 1964, evolving over time to include tournaments like the Tournament of Champions, Jeopardy! Masters, and the new Pop Culture Jeopardy! debuting on Amazon Prime.
What started as a straightforward trivia game has transformed into a competitive landscape, complete with leagues, formats, and superstar contestants.
And through all of it, Ken Jennings remains one of the franchise’s most recognizable and trusted faces.
His move to Who Wants To Be A Millionaire? may feel unexpected, but it’s also a reminder: even trivia’s biggest names are game for a challenge.
Also read: Ken Jennings just dropped a bomb on “Jeopardy!” with this obscene word–Fans can't believe he said it!
Wait—Ken’s also in Happy Gilmore 2?
If Ken’s appearance on Millionaire wasn’t enough pop culture buzz for one season, fans also spotted him in the newly released trailer for Happy Gilmore 2, the sequel to the beloved Adam Sandler golf comedy.
While no official details about his role have been released, fans are already speculating—will Ken make a surprise cameo à la Bob Barker?
Or is it just a fun blink-and-you-miss-it moment?
Either way, it’s clear Ken Jennings is enjoying his moment in the spotlight.
Source: Facebook / Who Wants To Be A Millionaire
Also read: Jeopardy! contestant’s unexpected slip—what really happened behind the scenes?
Why this crossover has fans talking
For many viewers, both Jeopardy! and Millionaire shaped the golden age of American quiz shows.
Seeing Ken Jennings cross over is more than a novelty—it’s a nostalgic, feel-good reminder of how trivia connects us all.
Add in a Hollywood A-lister like Matt Damon, and you’ve got something special.
Ken’s charm, intelligence, and genuine enthusiasm have made him a trusted presence in millions of homes.
Whether he’s delivering clues, writing books, or teaming up for charity trivia, fans appreciate that he never phones it in—even if “Phone a Friend” is a lifeline in the game.
How Millionaire works—just in case you forgot
Who Wants To Be A Millionaire? features contestants answering increasingly difficult multiple-choice questions to climb a ladder of cash prizes, with the top prize set at $1 million.
Along the way, players can use classic lifelines like Phone a Friend, Ask the Audience, and 50:50.
In the celebrity edition, two-person teams play together for charity.
With Ken and Matt at the helm, this might be the most competitive (and entertaining) pairing yet.
Will they make it to the final question? Or will Matt defer to Ken for the heavy lifting?
Either way, it’s bound to be a fan favorite!
Read next: You won’t believe which classic game show topped the charts—and what’s not working with Ryan Seacrest’s show!
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Are you excited to watch Ken Jennings and Matt Damon take on the Millionaire money ladder? What’s your all-time favorite Ken Jennings moment? And if you could pair up any two celebrities on your favorite game show, who would they be?
Let us know in the comments! Whether you’re a die-hard Jeopardy! fan, a trivia buff, or just tuning in for the fun of it, this is one crossover we can all get behind!
The beloved trivia champ and host is stepping away from his usual role to appear on a different, long-running game show.
And he won’t be doing it alone.
His unexpected teammate is a household name, but not someone you'd expect to see on a quiz show!
Let’s just say this duo is already turning heads—and the episode hasn’t even aired yet.

Ken Jennings, longtime Jeopardy! champion and current host, is stepping into the spotlight once again—this time on a brand-new game show stage. Image Source: YouTube / Jeopardy!.
A game show crossover we didn’t see coming
For long-time fans who’ve followed Ken’s remarkable journey—from his 74-game Jeopardy! winning streak in 2004 to his current role as host—his upcoming appearance on Who Wants to Be a Millionaire marks a major moment in game show history.
The news was shared on the show’s official social media page, teasing: “It’s going to be a season to remember! Don’t miss #WhoWantsToBeAMillionaire, premiering July 23rd on ABC and streaming on Hulu.”
Among the celebrity pairings revealed, one duo stood out right away: Ken Jennings and actor Matt Damon.
One fan summed it up best: “Pretty sure Ken Jennings doesn’t even need a partner, so score for Matt Damon.”
With Ken’s trivia expertise and Matt’s quick wit, this unexpected team might just be the one to watch!
Also read: Ken Jennings' shocking off-camera reaction to Ryan Seacrest replacing Pat Sajak!
Ken Jennings: from Jeopardy! royalty to Millionaire rookie
Ken Jennings first appeared on Jeopardy! in June 2004, where he went on to win 74 consecutive games—the longest winning streak in the show’s history.
He took home more than $2.5 million and became a household name almost overnight.
In the years since, he’s become a central figure in the Jeopardy! universe—not just as a player, but also as a guest host and now the show’s permanent host.
He’s written several books, made countless TV appearances, and helped usher in a new era of trivia culture.
Now, he’s taking on an entirely different format, showing once again that true champions never stop playing.
Also read: Ken Jennings takes a playful jab at Ryan Seacrest—Here’s what happened!
Jeopardy!’s growing legacy—and Ken’s place in it
Jeopardy! has been an American television staple since 1964, evolving over time to include tournaments like the Tournament of Champions, Jeopardy! Masters, and the new Pop Culture Jeopardy! debuting on Amazon Prime.
What started as a straightforward trivia game has transformed into a competitive landscape, complete with leagues, formats, and superstar contestants.
And through all of it, Ken Jennings remains one of the franchise’s most recognizable and trusted faces.
His move to Who Wants To Be A Millionaire? may feel unexpected, but it’s also a reminder: even trivia’s biggest names are game for a challenge.
Also read: Ken Jennings just dropped a bomb on “Jeopardy!” with this obscene word–Fans can't believe he said it!
Wait—Ken’s also in Happy Gilmore 2?
If Ken’s appearance on Millionaire wasn’t enough pop culture buzz for one season, fans also spotted him in the newly released trailer for Happy Gilmore 2, the sequel to the beloved Adam Sandler golf comedy.
While no official details about his role have been released, fans are already speculating—will Ken make a surprise cameo à la Bob Barker?
Or is it just a fun blink-and-you-miss-it moment?
Either way, it’s clear Ken Jennings is enjoying his moment in the spotlight.
Source: Facebook / Who Wants To Be A Millionaire
Also read: Jeopardy! contestant’s unexpected slip—what really happened behind the scenes?
Why this crossover has fans talking
For many viewers, both Jeopardy! and Millionaire shaped the golden age of American quiz shows.
Seeing Ken Jennings cross over is more than a novelty—it’s a nostalgic, feel-good reminder of how trivia connects us all.
Add in a Hollywood A-lister like Matt Damon, and you’ve got something special.
Ken’s charm, intelligence, and genuine enthusiasm have made him a trusted presence in millions of homes.
Whether he’s delivering clues, writing books, or teaming up for charity trivia, fans appreciate that he never phones it in—even if “Phone a Friend” is a lifeline in the game.
How Millionaire works—just in case you forgot
Who Wants To Be A Millionaire? features contestants answering increasingly difficult multiple-choice questions to climb a ladder of cash prizes, with the top prize set at $1 million.
Along the way, players can use classic lifelines like Phone a Friend, Ask the Audience, and 50:50.
In the celebrity edition, two-person teams play together for charity.
With Ken and Matt at the helm, this might be the most competitive (and entertaining) pairing yet.
Will they make it to the final question? Or will Matt defer to Ken for the heavy lifting?
Either way, it’s bound to be a fan favorite!
Read next: You won’t believe which classic game show topped the charts—and what’s not working with Ryan Seacrest’s show!
Key Takeaways
- Jeopardy! host Ken Jennings will appear as a contestant on rival game show Who Wants To Be A Millionaire? later this year, teamed up with Hollywood star Matt Damon.
- The new season of Who Wants To Be A Millionaire?—featuring celebrity pairings like Ken and Matt—is set to premiere on July 23 on ABC and will also be available to stream on Hulu.
- Ken Jennings first rose to fame with a record-breaking 74-game winning streak on Jeopardy! in 2004, later becoming the show’s host and authoring several books on trivia.
- In addition to his game show appearances, Jennings will also make a cameo in the upcoming Happy Gilmore 2, as spotted by fans in the movie’s trailer.
Are you excited to watch Ken Jennings and Matt Damon take on the Millionaire money ladder? What’s your all-time favorite Ken Jennings moment? And if you could pair up any two celebrities on your favorite game show, who would they be?
Let us know in the comments! Whether you’re a die-hard Jeopardy! fan, a trivia buff, or just tuning in for the fun of it, this is one crossover we can all get behind!