Jon Stewart roasts CBS and Trump as Colbert’s Late Show is about to end

Stephen Colbert’s final week on The Late Show has not been a quiet television goodbye. It has been crowded, emotional and unusually pointed, with famous guests using the CBS stage to celebrate Colbert while also questioning why the show is ending at all.

The final episode airs tonight, May 21, on CBS. Jon Stewart has appeared during this final week, alongside Steven Spielberg and David Byrne, while Bruce Springsteen appeared separately.

CBS has said the cancellation is financial, but the timing has kept skepticism alive because the decision followed Colbert’s criticism of Paramount’s settlement with Donald Trump and came as Paramount was navigating its Skydance deal.

Had expected more time

In April, weeks before his final broadcast, Colbert discussed the cancellation with The New York Times.

He said the decision surprised him because CBS had encouraged him in 2023 to consider a contract of up to five years, and he ultimately signed for three.

The host did not accuse CBS of misleading him. He acknowledged that broadcast television has become harder to monetize in the streaming and YouTube era.

Still, he said he understood why viewers found the timing suspicious, especially after Paramount settled Trump’s lawsuit over 60 Minutes.

To him, both things could be true: The business model may be under real strain, and the timing could still raise fair questions.

Kept returning to CBS

Jon Stewart came out joking about Colbert fixing his suit backstage, saying Colbert had noticed from across the room that he had buttoned it wrong.

He used the story to describe Colbert as a careful friend who protects people even in small moments.

The conversation soon moved to CBS. Stewart joked that the network had found a strange strategy: End The Late Show, weaken the evening news and cut down 60 Minutes.

“They’re tanking for a draft pick,” Stewart said.

Colbert did not turn the moment into a speech. He said he was enjoying the chance to be with friends, the audience, the band and his staff during the final run.

Stewart then asked how Colbert had stayed graceful through it. Colbert answered that he had learned how to work under pressure from Stewart.

Letterman’s advice came back

When the two discussed cancellations, Stewart remembered his own experience losing a late-night show. He said David Letterman had been his final guest and gave him advice afterward.

“Do not confuse cancellation with failure,” Stewart recalled.

Then Stewart added that Letterman immediately joked that in his case, cancellation was also failure.

Stewart praised Colbert’s staff for helping him with strange bits over the years. He remembered asking for a hidden room, a moving bookcase and alpacas for a sketch, and said the team somehow made it happen.

Politics stayed close to the surface

Colbert has said he did not originally plan for The Late Show to become so topical. In the New York Times interview, he explained that CBS initially discouraged him from leaning too hard into news and politics. His own instinct was also to avoid the country’s increasingly ugly public argument.

That changed during the 2016 campaign. Colbert leaned into political comedy, especially criticism of Trump, and the show found its voice.

He has rejected the idea that this made the program simply partisan. His argument is that comedians naturally resist authoritarian behavior, and that powerful figures do not like being laughed at.

Stewart made a similar point during his visit. He said Colbert’s show should not be reduced to opposition to Trump. To Stewart, the program was also about joy, craft, friendship and the nightly work of making something alive in front of an audience.

Springsteen made the criticism blunt

Bruce Springsteen, appearing separately on the show, made the political argument more direct. According to Pitchfork, he defended Colbert and criticized CBS and Paramount leadership from Colbert’s own stage.

Springsteen said Colbert had lost his show because America has “a president who can’t take a joke.” He also accused powerful media figures of accommodating political pressure instead of defending basic creative freedom.

His remarks gave the farewell week a sharper edge. Guests were not simply saying goodbye to a host.

They were also asking what happens when corporate caution, political pressure and entertainment all collide.

The finale still waits

Colbert’s final week has become more than a nostalgia tour. Stewart brought friendship and ridicule. Springsteen brought open political anger. Colbert, for his part, has tried to balance gratitude with skepticism, saying he would rather end his CBS years thankful than furious.

He has also admitted that he does not know exactly what comes next. He is working on a script connected to a new Lord of the Rings film and has spoken about loving live audiences, interviews, podcasts and comedy.

But the show has taken up most of his mind for years, and he has said he will need time before deciding his next move.

For now, the last chapter is still being written. The final broadcast comes tonight, after a week in which Colbert’s friends made one thing plain:

Whatever CBS calls the decision, the people around him are not treating the end of The Late Show as a quiet business adjustment.

Sources: The Late Show with Stephen Colbert / CBS; The New York Times; Pitchfork.

This article is made and published by Kenneth Glad, who may have used AI in the preparation