Matt Damon teams up with Ken Jennings to face old nemesis Jimmy Kimmel on ‘Millionaire’
Matt Damon and Ken Jennings Join Forces to Face Off Against Old Nemesis Jimmy Kimmel on ‘Who Wants to Be a Millionaire’
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In one of the most unexpected and star-studded television crossovers of the year, Hollywood A-lister Matt Damon and Jeopardy! legend Ken Jennings have officially teamed up—for a showdown with none other than Damon’s long-time frenemy, Jimmy Kimmel, on a special celebrity edition of ‘Who Wants to Be a Millionaire.’ The announcement, made during a surprise joint appearance on Jimmy Kimmel Live, instantly sent shockwaves across both Hollywood and trivia circles alike.
While Who Wants to Be a Millionaire is no stranger to celebrity contestants, this particular episode has already been dubbed “the most anticipated game show event of the decade” by fans on social media. The stakes are high, the drama is guaranteed, and the bitter-sweet rivalry between Damon and Kimmel is about to reach a whole new level—this time, with money on the line and trivia as the battlefield.
The Longest Running Fake Feud in Hollywood
To appreciate the weight of this showdown, we have to go back nearly 20 years to the origin of the iconic Damon-Kimmel “feud.” What began as a running joke on Jimmy Kimmel Live!—with Kimmel constantly “apologizing” to Matt Damon for bumping him at the end of episodes—quickly turned into a hilarious, long-standing bit that audiences grew to love. Damon played along, frequently “storming off” sets, crashing shows, or appearing in skits mocking their faux rivalry.
The two even went viral in 2008 with the infamous “I’m Fing Matt Damon” music video, featuring Damon and Kimmel’s then-girlfriend Sarah Silverman. That was followed by Kimmel’s revenge song “I’m Fing Ben Affleck,” pulling in half of Hollywood. It was comedy gold—and for fans, the dynamic between these two has been one of late-night TV’s most enduring gags.
But now, the feud steps into a whole new arena.
From Red Carpet to Hot Seat
The upcoming Millionaire episode will pit Matt Damon and Ken Jennings, an unstoppable trivia force, against Jimmy Kimmel, who is not only the long-time host of Jimmy Kimmel Live! but also previously served as host of Who Wants to Be a Millionaire during its primetime revival. That’s right—Kimmel will be back in the hot seat instead of behind the host’s podium, making this a full-circle moment for the late-night star.
The idea came from a charity brainstorming session, according to insiders at ABC. All proceeds from the special will go to causes chosen by the celebrity contestants: Damon and Jennings will play for Water.org, the clean water initiative Damon co-founded, while Kimmel is supporting Children’s Hospital Los Angeles.
Ken Jennings: The Ultimate Secret Weapon
While Matt Damon is beloved for his charm and humor, he’s also made it clear that he’s coming in to win. So who better to partner with than Ken Jennings, the undisputed GOAT of trivia?
Jennings, who holds the record for longest winning streak in Jeopardy! history and currently serves as the show’s full-time host, brings a level of knowledge and calm under pressure that few, if any, can match. While he’s used to answering the questions, not asking them, sources say Jennings is thrilled about the chance to team up with Damon and try his hand at a different trivia format.
“I’ve battled computers, champions, and daily doubles,” Jennings joked. “But going up against Jimmy Kimmel? That might be my toughest opponent yet—he’s got jokes and strategy.”
The duo has reportedly been training together over Zoom, running mock questions, and trading pop culture references. Damon’s strength lies in history, film, and politics, while Jennings brings encyclopedic knowledge of science, literature, and obscure facts from virtually every discipline. Together, they could be an unstoppable force.
Kimmel’s Return to the Hot Seat
Jimmy Kimmel is no stranger to the game. As former host of Millionaire, he’s read through thousands of questions, seen players rise and fall, and understands better than anyone the pressure that builds with each increasing dollar amount.
But will that experience help or hinder him?
“Knowing the answers is one thing,” Kimmel quipped during the announcement. “But sitting in that chair, staring into the lights, hearing the music ramp up… trust me, it’s a whole different beast. I might crack by the $8,000 question.”
He’s joked that if Damon and Jennings beat him, he’ll “ban them from his show for life,” but most viewers suspect that’s just another bit of their comedy rivalry. The truth is, Kimmel has deep admiration for both men—and the camaraderie is expected to be just as entertaining as the trivia.
Celebrity Trivia with Real Stakes
Unlike standard game show episodes, this one promises a hybrid of light-hearted comedy and serious competition. Each pair will be playing cooperatively, with the goal of reaching the elusive $1 million question, and potentially winning the full prize for their chosen charities.
There’s also a twist: Kimmel will not be playing solo. While his partner has not yet been officially announced, rumors suggest it could be his longtime sidekick and comic relief fixture, Guillermo Rodriguez—which, if true, would turn the trivia battle into even more of a comedy spectacle.
ABC executives are calling it “a once-in-a-generation TV event,” with viewership expected to surge. The network has already teased a few moments from the pre-taped episode, including Damon whispering to Jennings, “Don’t let him psych us out,” and Jennings laughing, “This isn’t Jeopardy!—I don’t even get a buzzer!”
A Cultural Moment That’s Bigger Than Trivia
This showdown is more than a game. It’s a cultural moment: a celebration of brainpower, humor, celebrity, and friendship disguised as fake animosity. In an age of streaming, chaos, and social media fights, it’s refreshing to see three famous men come together for a purpose that blends wit, cause, and entertainment in a positive, uplifting way.
There’s no question that the trivia will be challenging and the banter electric. But at the heart of this special is a reminder that beneath the jokes, the fake feuds, and the on-camera personas, these men share a mutual respect and a desire to do good.
Will Jennings and Damon climb to the million-dollar question? Will Kimmel hold his own—or crumble under the pressure of the very game he once hosted? One thing’s certain: fans will be tuning in, tweeting every moment, and waiting for the next punchline—or gasp-worthy blunder.
Final Answer?
Whether you’re Team Kimmel or Team Damon-Jennings, one thing is clear: this isn’t just another celebrity game show. It’s trivia meets showbiz history, with a healthy dash of comedy and competition. And with three of the sharpest minds in entertainment going head-to-head, we’re all in for an unforgettable ride.
Mark your calendars, charge your buzzers, and brush up on random facts—you won’t want to miss this.