Matt Damon brings drama to Jimmy Kimmel’s episode

Damon arrives, Kimmel shocked on Millionaire

The season premiere of Who Wants to Be a Millionaire kicked off with a twist when Ken Jennings brought Matt Damon as his surprise partner. Jimmy Kimmel, the host, was completely caught off guard by Damon’s arrival.

The audience erupted with laughter as Damon walked onstage, reviving his famous feud with Kimmel. Jennings and Damon formed a trivia team, leaving Kimmel feeling betrayed.

The unexpected team-up created a spark and immediately turned the game show into a comedy-packed event.

Kimmel calls out Jennings over betrayal

After teaming with Damon, Jennings faced Kimmel’s fury. Kimmel jokingly attacked Jennings for joining forces with his longtime rival. Their banter became part of the entertainment, turning trivia questions into a roast session.

Kimmel mocked Damon’s beard and teased Jennings for helping him. Jennings asked why he was being insulted, and Kimmel said it was because he brought Damon. The playful hostility made the show feel more like a sketch than a quiz.

Kimmel throws insults at Damon

During the game, Kimmel fired a series of jabs at Damon. He questioned Damon’s intelligence and hinted that Affleck probably did all the work when they co-wrote movies. When Damon said he hadn’t seen the Minecraft movie, Kimmel quipped that “the good people” had already watched it.

He then compared Damon to a “homeless wizard,” taking another dig at his beard. These remarks added a comic edge to the competition and delighted viewers.

Damon and Jennings dominate game

Despite Kimmel’s jokes, Damon and Jennings played a strong game. They climbed the prize ladder confidently and answered questions with ease. Their chemistry made them a solid team.

They reached the $250,000 question before the clock ran out. Their total winnings will benefit the charity Water.org. Because the episode ended before they finished, they’ll return in the next one. This means Kimmel has to face Damon once again on his stage.

Carey and Tyler open the episode

Before Damon appeared, the episode began with Drew Carey and Aisha Tyler playing as a team. They shared a funny connection, having both hosted Whose Line Is It Anyway?

Tyler said they felt like siblings and wore reading glasses to prove the point. The pair had fun with the questions and supported each other well. They performed smoothly until they hit a tough music question worth $64,000 that ended their winning streak.

Wrong guess costs Carey and Tyler

The $64,000 question asked which diva had 11 #1 Billboard hits: Britney Spears, Tina Turner, Celine Dion, or Whitney Houston. Carey thought it was Houston, but Tyler followed the audience and picked Spears.

That answer was incorrect, ending their run. Even so, they walked away with $32,000 for their charities: International Rescue Committee and La Maida Project. After they exited the stage, Jennings joined Kimmel, which led to the surprise involving Matt Damon.

Kimmel teases Jennings onstage

When Jennings joined Kimmel after Carey and Tyler’s game, Kimmel joked about a past conversation where Jennings said Millionaire was harder than Jeopardy!. Kimmel used the moment to boost his ego.

But with Damon arriving next, the tone changed fast. Kimmel’s playful teasing grew into comic frustration. The trio’s interactions made the episode feel less like a quiz show and more like a mini late-night comedy special featuring celebrities.

Fake feud started back in 2005

The feud between Kimmel and Damon started as a random joke in 2005. During a bad episode of Jimmy Kimmel Live!, Kimmel ended by saying, “Apologies to Matt Damon, we ran out of time.”

Damon wasn’t even scheduled to appear. Kimmel made the joke to entertain his producer, and it became a recurring sign-off. Damon and Kimmel hadn’t even met yet. But the throwaway joke caught on and soon became one of the show’s most famous running gags.

Damon’s first show visit goes wrong

Damon’s first appearance on Jimmy Kimmel Live! came in 2006. Kimmel gave a dramatic introduction, but as soon as Damon sat down, Kimmel ended the show again. Damon stormed off, pretending to be furious.

Fans believed the fight was real. The act was so convincing that it confused viewers. That moment helped the gag evolve into a full-on “feud” that both Damon and Kimmel kept alive in future sketches and celebrity bits.

Sarah Silverman enters the Joke

In 2008, Sarah Silverman joined the feud. She made a video with Damon called “I’m [bleeping] Matt Damon” as a prank for Kimmel’s 40th birthday. The raunchy song caught everyone by surprise.

Silverman’s video added fuel to the feud. Damon looked victorious for once, flipping the joke around. The video became a viral moment that kept fans entertained while continuing the rivalry in unexpected new ways.

Damon hijacks Kimmel’s show

In 2013, Damon got his biggest revenge. He tied Kimmel up with duct tape and hosted Jimmy Kimmel Live! himself. Damon interviewed guests and joked freely, with Kimmel stuck backstage.

This moment showed how far they would take the gag. Damon flipped the script completely and stole the spotlight. It became one of the most memorable episodes and proved their “feud” was Hollywood’s favorite running joke.

Damon uses costumes and cameos

Damon crashed the show again in 2017 dressed as Tom Brady after the Super Bowl. He walked onstage in full Patriots gear, pretending to be the football star before revealing his identity.

He also joined Kimmel in fake couples counseling and once hacked into the show during Chris Hemsworth’s interview. Each prank kept the feud going strong and let fans enjoy Damon’s clever ways of sneaking into the spotlight.

Celebrities join the ongoing gag

Other stars joined the feud, too. Ben Affleck smuggled Damon onto the show in a large coat in 2016. Kimmel pretended to be surprised and quickly had Damon pushed offstage again.

In another sketch, Kimmel hired Brad Pitt and George Clooney to “take care” of Damon. They joked they’d do it for free and made fun of Damon’s movie, We Bought a Zoo. Their help added star power to the feud.

Kimmel takes it outside the studio

In 2019, Kimmel brought Tom Brady to Damon’s house. Brady threw a football through Damon’s window. Damon ran outside, angry, and Kimmel acted like he didn’t know Damon lived there.

That same year, Kimmel joked that Damon was banned from his Las Vegas comedy club. He said local police were on alert to stop Damon from entering. These gags kept the fake rivalry hilarious and unpredictable.

Awards shows fuel the fire

Kimmel even joked at the Oscars. In 2017, he said he didn’t want Damon to win anything and blamed him for the 2017 envelope mix-up. Damon later clapped back on red carpets.

At the premiere of Air, Damon called Kimmel a “terrible human being” and shouted Kimmel’s catchphrase: “We ran out of time!” Kimmel, playing along, acted like he didn’t recognize him. The feud stayed alive and well.

In other news, Jimmy Kimmel roasted Elon Musk over Tesla vandalism and stock collapse. Check it out.

Next episode continues the rivalry

Back on Millionaire, Jennings and Damon’s win means they’ll return next week. Kimmel must deal with another episode featuring Damon right next to him. The audience will get more drama and laughs.

From surprise visits to footballs through windows, this fake feud has lasted nearly 20 years. It all began with one joke and became a classic Hollywood tradition. And with Damon not leaving just yet, Kimmel’s troubles aren’t over.

Jimmy slammed CBS publicly right after Colbert’s cancellation was announced in July. Check out his reaction.

What was your favorite moment from the feud? Drop your thoughts below!

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This slideshow was made with AI assistance and human editing.