Colbert was joined by his old “Daily Show” boss on his third-to-last show.

Jon Stewart surprises Stephen Colbert with a celebrity guest and a cancellation gift on The Late Show

Colbert was joined by his old "Daily Show" boss on his third-to-last show.

By Raechal Shewfelt

Raechal Shewfelt

Raechal Shewfelt is a writer at **. She has been working at EW since 2024. Her work has previously appeared on Yahoo and in American *Journalism Review* and *The Shreveport Times*.

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and Laura Adamczyk

May 20, 2026 1:19 a.m. ET

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'The Late Show' host Stephen Colbert and guest Jon Stewart during the May 19 episode. Credit:

Scott Kowalchyk/CBS

- *The Daily Show*'s Jon Stewart joined Stephen Colbert on Tuesday's episode of *The Late Show*.

- Stewart and Colbert have been friends and colleagues for nearly 30 years, having first met when Stewart was about to take over as host of *The Daily Show* in 1999.

- Colbert's final episode airs May 21.

Stephen Colbert is going out with a bang.

In the weeks leading up to his forced departure from CBS’s *The Late Show With Stephen Colbert*, the host has 1) Given and/or accepted from multiple guests goodbye kisses, 2) Sheepishly admitted which *Late Show *interviewee he was “wildly attracted to,” and 3) Even partaken in some “wanton destruction of CBS property” with David Letterman.

In something of a full-circle moment on Tuesday, Colbert was joined by his old boss (not *the *Boss, that’s Wednesday night) and very good friend, Jon Stewart.

Colbert asked Stewart what it's like to lose a late-night show.

"It's the best!" Stewart said enthusiastically before his smile quickly faded away, leaving the audience laughing.

Stewart noted that final guest, before *The Jon Stewart Show* on MTV ended in 1995, was Letterman, who told him, "'Don't confuse cancellation with failure.' And I thought that was profound. But then, he said, 'In this case, it is also a failure.'"

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Stewart also brought Colbert a parting gift: a pair of electric-lift recliners that help you stand after a long TV binge.

"Oh, are you gonna enjoy watching *Matlock* in this motherf---er!" Stewart told Colbert. Then he warned that they offered the kind of comfort that make you wonder if you're going to have to use energy to get out of them.

"Stephen, get ready for the ride of your f---ing life," Stewart said, before deciding his recliner gift wasn't enough. "No, no, no. This tribute isn't complete. Stephen. This tribute doesn't represent the joy that you brought to me as my friend and the joy that you brought to this country, as one of its leading entertainers. No, what this moment needs is something so much more."

Then he called out Grammy winner Andra Day, whom Colbert is a fan of. Day belted out her song "Rise Up," while Colbert and Stewart held up their arms together as their chairs simultaneously lifted the two hosts to their feet.

Colbert and Stewart share a long history, having known each other for nearly 30 years. The pair first met in 1999, when Stewart was on deck to host *The Daily Show*, where Colbert had been an anchor for two years under original host Craig Kilborn.

Colbert told ** in 2015 about the pair’s very first meeting, at a press conference announcing that Stewart would become the show’s new host, and *The Daily Show *would therefore become *The Daily Show With Jon Stewart*.

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“So, I heard that there was going to be a press conference that day announcing that Jon was going to be the host,” Colbert told EW. “And I said, ‘Well, wouldn’t *The Daily Show* cover something like this?’ So I left the offices and went over to Comedy Central, and I stood up and said, ‘Stephen Colbert, *The Daily Show*. In what way does this announcement affect my chances of becoming host of *The Daily Show*?’ Jon Stewart turned to the president of the network and said, ‘You told me he wasn’t funny.’”

Colbert remained a *Daily Show* anchor for six more years, honing his satirical Bill O’Reilly-esque persona alongside Stewart’s straight man, as the show became increasingly political.

When Colbert left in 2005, he didn’t go far: He spun off his *Daily Show* character for his own Comedy Central series, *The Colbert Report*, where he'd stay until 2014. The following year, he debuted as host on *The Late Show*.

Colbert and Stewart on 'The Daily Show' in 2004.

CBS announced the decision to cancel *The Late Show *in July 2025 after Colbert criticized parent company Paramount for settling a $16 million lawsuit with Donald Trump. The president had sued the company over a 2024 interview with then-presidential opponent Kamala Harris on CBS’s *60 Minutes*, claiming the interview had been deceptively edited to benefit her campaign. At the time of the settlement, Paramount was preparing for a merger with Skydance Media, which required approval from the Trump administration.

On July 14’s show, Colbert called the settlement a “big fat bribe.” Three days later, he announced that CBS was canceling the show "for financial reasons," according to the network.

The final two episodes of *The Late Show With Stephen Colbert *air Wednesday and Thursday at 11:35 p.m. ET/PT on CBS.

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