Matt Damon crashes Jimmy Kimmel’s Who Wants to Be a Millionaire and wins big after years-long feud

Who Wants to Be a Millionaire returned with its new season on July 30, 2025, and kicked off with a surprise appearance that reignited a long-running late-night rivalry.

Matt Damon, known for being the frequent punchline in Jimmy Kimmel’s ongoing “feud,” finally joined the show’s host as a contestant, much to Kimmel’s shock.

Damon was paired with Jeopardy! champion Ken Jennings for the special celebrity edition, and together they competed to win money for Damon’s Water.org charity.

“This dude is the Michael Jordan of trivia,” Damon said about Jennings, crediting him as the ultimate teammate during the intense game.

The episode quickly became both a high-stakes quiz and a platform for playful jabs between Damon and Kimmel. As Damon told him at the start,

“I finally made it on your show,” referring to Kimmel’s long-standing gag of “banning” Damon from Jimmy Kimmel Live!.

Despite the jokes, the episode mainly showed how well Damon and Jennings worked together as a team. They stayed focused and used good strategy to answer each question.

The episode mixed fun, teamwork, and a good cause, and ended with a big win. Damon and Jennings reached the $1 million prize, which surprised both the audience and Kimmel.

Damon surprises Kimmel in opening moments of Who Wants to Be a Millionaire

 

 

 

 

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This episode of Who Wants to Be a Millionaire opened with Kimmel expecting a routine game but being visibly surprised when Matt Damon walked out to join him and Ken Jennings.

The unexpected entrance was Damon’s cheeky way of breaking the “ban” Kimmel had maintained for years on his late-night show. Damon pointed out that he has finally made it on Kimmel’s show, referring to their long-running fake feud.

Kimmel reacted with surprise and sarcasm, asking Who Wants to Be a Millionaire producers, “Is this really happening?” The serious tone quickly turned light as the two began joking with each other.

It was the first time Damon appeared as a guest while Kimmel was hosting.

Jennings, playing the mediator between the two, remained focused on the game.

“I just want to win some money for a good cause,” he said.

Throughout the segment, Kimmel teased both players while Jennings carefully explained their thought process.

The segment was built on a blend of surprise, humor, and charity. Damon’s entry flipped the usual dynamic between him and Kimmel, offering a fresh take on their decade-long bit. The moment also set the tone for a competitive and cooperative game ahead.

Jennings and Damon navigate tough questions to reach $1 million on Who Wants to Be a Millionaire

As the game progressed in Who Wants to Be a Millionaire, the questions increased in difficulty. Jennings often took the lead on logic and recall, while Damon relied on instincts and occasional guesses.

Their toughest moment came with a science question involving Bill Nye.

“A lot of the answers looked plausible. We’d never heard that fact about Bill Nye,” Jennings later explained.

He added that Kimmel’s input helped steer them in the right direction, even if unintentionally.

Damon frequently leaned on Jennings’ expertise, calling him “the Michael Jordan of trivia.” The duo made use of all available lifelines but remained calm under pressure.

As the million-dollar question approached, both players took their time and debated options. When they finally locked in the answer, Kimmel revealed the result with dramatic flair, confirming they had won the top prize.

The win brought applause and a moment of surprise for both contestants and Kimmel. Damon expressed gratitude and praised Jennings again:

“I could never have done this without him.”

The episode ended on a celebratory note, with the full $1 million prize going toward Damon’s Water.org charity.

Stay tuned for more updates.