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Stephen Colbert and me: How late-night partisan comedy works – until it doesn’t 
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Stephen Colbert and me: How late-night partisan comedy works – until it doesn’t 

Jimmie Dempsey
Last updated: May 22, 2026 7:15 am
Jimmie Dempsey Published May 22, 2026
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Stephen Colbert and I go way back.

I’ve interviewed him many times.

I’ve been on his show, he’s been on my show.

Whether or not you agree with his liberal crusading – and half the country can’t stand it – his final show raised questions about political retribution, a splintered media universe and the crumbling future of late night itself. 

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Putting aside the cosmic conclusions for a moment, I first interviewed Colbert when Comedy Central was giving “The Daily Show” correspondent an eight-week tryout as host of his own show, and he didn’t know if it would last. He was congenial and about as quick-witted as any comedian I’ve seen, possibly matched by Jon Stewart.

While playing a blowhard conservative anchor on “The Colbert Report,” he once took a mild swipe at me. I had reported, factually, on Fox that some Republicans and right-wing media figures were taking shots at Hillary Clinton’s age, 69, and arguing she had a double liability as potentially the first female president.

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Colbert transformed that into MY declaring that Hillary was too old. That was flat-out wrong, but I know how these things go. 

So I made a great show of being offended and hit back with a sarcastic take: “It’s about time someone took on Stephen Colbert. This guy – a fake anchor if ever there was one – has been maligning hard-working journalists for too long. Journalists like me… Well, two can play this game, buddy.” 

(Some of my critics took the shtick a tad too seriously.)

That didn’t stop Colbert from inviting me as a guest when my book “Reality Show” was out. He was friendly and I had a good time. I guess I shouldn’t have been shocked that most of my funny lines were edited out and most of his were kept in.

He was the big star. 

RELATED: COLBERT’S FINAL YEAR MARKED BY ATTACKS ON TRUMP, LIBERAL TALKING POINTS AND CELEBS KISSING HIS RING

Stephen Colbert mocks Trump supporters.

Colbert, 62, raised in South Carolina, is a practicing Catholic and former altar boy who has a form of vertigo and, during one taping, was rushed to the hospital with a ruptured appendix.  

Once leaving Comedy Central, he was signed by CBS’s “Late Show” and landed in third place.

But after hiring producer Chris Licht from “Morning Joe,” Colbert went fully partisan and fervently anti-Trump. He once called Trump “the Antichrist” (adding that he was joking). He shot up to No. 1. 

That was a double-edged sword. Why deliberately alienate half his audience? It was like drinking a magic elixir that contained a slow-acting poison pill.  

Meanwhile, Colbert’s interviews with the likes of Barack Obama and Joe Biden were, shall we say, rather gentle.

The ratings were good enough that CBS suits tried to sign Stephen to a long-term contract.

But last year, Colbert accused the network of accepting “a big fat bribe.” He was referring to CBS paying $16 million to settle a long-shot Trump lawsuit over a deceptively edited “60 Minutes” segment.

This happened to take place as Paramount was waiting for the administration’s approval for its attempted takeover of Warner Bros. Discovery – which, what a surprise, came through a week later.

That’s all it took. Paramount, owned by Trump’s pals Larry and David Ellison, announced the “Late Show” was being canceled. Without so much as consulting with the network’s biggest star or discussing ways to trim his 200-person staff.

Trump exclaimed that “I absolutely love” the move.

This was political retaliation, pure and simple. No one believes the “only for financial reasons” hogwash.

But CBS has turned the long goodbye into a national event, as Colbert has constantly slammed the network. What could the brass do when they’ve already fired him? 

Celebrity guests in the final weeks have included Tom Hanks, Oprah Winfrey, Julia Louis-Dreyfus, Jon Stewart, Steven Spielberg, Bruce Springsteen and founding host David Letterman, who helped him throw furniture off the roof to smash the CBS eye logo. (I thought that was a bit cheesy given Colbert’s goal of an amicable parting.) 

Friendly rivals Jimmy Kimmel and Jimmy Fallon agreed to air reruns last night to shift the spotlight to the curtain call in the Ed Sullivan Theater.

The “Late Show” is being replaced by comedian Byron Allen, who’s vowing to steer clear of politics on his prerecorded show and is actually paying CBS many millions for the airtime. 

And that brings us to the cold hard math. 

Split image shows Jimmy Kimmel and Johnny Carson side by side.

Colbert’s show was losing tens of millions of dollars a year. That’s not sustainable. The 11:35 p.m. shows on CBS, ABC and NBC draw a fraction of the audience compared to the days of Johnny Carson, when you actually had to stay up late to watch his needle-both-sides comedy. 

Colbert and Kimmel each drew over 2.5 million viewers and Fallon 1.3 million last quarter, which is not bad in this environment. But Jay Leno, at the peak of his career, was averaging 5 to 6 million.

Now the main impact of these nighttime shows comes from the brief clips that many watch the next morning.

Do I think late-night shows will be around in five years? Sadly, probably not. The digital age has brought round-the-clock competition for eyeballs, from social media to group chats, from podcasts to Substack. All available in seconds on your phone or watch.

That makes me nostalgic, but I also don’t listen to AM radio anymore or have a Walkman. Technology marches on. 

One thing is sure: Stephen Colbert will have no trouble making ends meet.

Read the full article here

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