Jimmy Kimmel Celebrates 20 Years with More Cheap Shots at Matt Damon — But Damon Shoots Back!

In a sweet moment, he told Chris Martin of Coldplay that they wanted to book a band for that first show that they’d be proud to say they had on 20 years later. In that case, they knocked it out of the park.

“It was a great start guest-wise, and it just went down from there,” he joked about that epic first-night lineup during his opening monologue.

There were callbacks throughout the night to that first show, with Kimmel showing lots of footage from that show, including the entrances of his guests and even a fun segment where he was able to interview himself thanks to digital deepfake technology.

He looked back at when they first met Guillermo before bringing him into the fold — and how far his work accommodations have come from his guard shack to his tequila-stocked dressing room today.

He also shared some of the absolutely brutal critical reactions to his first show, which was called dead-on-arrival and compared to what you find in a baby’s diaper.

“Very few people expected us to make it this far, but we did for two reasons,” Kimmel said in one of several moments he got emotional throughout the night. “Number one, I made a great deal with the devil. My soul is gonna roast. Number two, we have and have had so many great people.”

He went on to list almost all of those people with thanks love and admiration, before reversing course almost entirely for the first of what would be a night-long culmination of 20 years of slams at Matt Damon.

Longtime fans know that Kimmel and Damon have had a mock feud for years and years now, starting when Kimmel randomly apologized to Matt Damon for having to bump him from the show — something he does every night now.

Damon has featured on the show multiples times, as has his BFF Ben Affleck, perhaps peaking in the “I’m F—ing Ben Affleck” and “I’m F—ing Matt Damon” back-and-forth trash songs.

The bit continued into the segment where Kimmel interviewed himself from 20 years ago. After his younger self razzed him for getting old, current Kimmel teased him right back by asking him to guess who was just president a few years back.

“Oh god, not Matt Damon,” said younger Kimmel. “Please tell me Matt Damon isn’t president.” Current Kimmel laughed off the preposterous suggestion, leading his younger self to ask, “Is Matt Damon even still an actor?”

“Was he ever?” current Kimmel responded, leading to the two of them laughing together in unison.

Honestly, this segment was brilliantly conceived and executed, down to younger Kimmel’s dated technology and even the screen resolution of his video footage matching what viewers saw in 2003.

Just like in that first episode, Snoop Dogg came out to co-host alongside Kimmel. Kimmel hilariously reminded the rapper that during his first appearance, he told Kimmel he’d quit smoking marijuana.

“How is that going?” he asked his co-host.

After a beat, Snoop replied, “Well, I guess I’ve relapsed.”

Kimmel then shared Snoop’s 2003 rider in comparison to his 2023 rider, which is the list of his requested amenities for his dressing room. Let’s just say it got so long, Kimmel had to remind him, “You know you’re here for an hour, right?”

George Clooney echoed his first-show appearance, again coming out with some tumblers and booze so they could toast this milestone moment for Kimmel.

He also shared that he’d just gone back and watched that first episode, telling Kimmel, “It’s like a public access show,” to which Kimmel replied, “That’s being generous.”

They reminisced about getting the audience drunk — and the woman in the front row who vomited — before Kimmel circled back to Matt Damon, who recently was among those who honored Clooney at the Kennedy Center.

“You didn’t have anybody else?” asked Kimmel about the decision to invite Damon to be a part of the celebration.

In one of the night’s sweeter moments, that we’re not sure if Kimmel was fully in on or not, Chris Martin of Coldplay came out and told him there just wasn’t time to prepare anything special for the anniversary show.

Instead, he got Kimmel a music box which played the opening bars of “Clocks,” the song they first performed on that very first show.

But it was more than just a callback, as the music box literally did kick off an epic performance of the number, which included an orchestral section, a choir singing in the crowd and ultimately Kimmel and Guillermo joining Coldplay on the roof to finish out the song.

And then, because of course we all knew it was coming, he dropped his apology that there just wasn’t time for Matt Damon, but maybe they’d fit him in sometime in the next 20 years.

What followed was Damon’s reaction, from his dressing room. This was one of the funniest moments in all the years of this feud. If we’re being honest, we’ve watched it multiple times and laughed each and every time.

Below you can check out more celebrity messages for Kimmel’s anniversary from Michelle Obama, Hugh Jackman, Tracy Morgan, Emily Blunt & John Krasinski, Bryan Cranston, Shaquille O’Neal, Huey Lewis, Margot Robbie, Carol Burnett, Oprah Winfrey, Tom Hanks, Kerry Washington, Michael Keaton, Sean Penn, Jennifer Aniston, Julia Louis-Dreyfus, Ben Affleck, and Matt Damon — who thought it was for Jimmy Fallon.