The Biggest ‘Late Show’ Controversies as the Franchise Nears Its End

CBS’s Late Show franchise will end this May after nearly 33 years and more than a few controversies. (And we’re not just talking about the uncomfortable interviews former Late Show host David Letterman had with Madonna, Joaquin Phoenix, and Lindsay Lohan.)

In fact, Stephen Colbert’s Late Show has been lighting up a firestorm of press lately, with some outsiders wondering whether Colbert and his staff are collateral damage in their corporate bosses’ political maneuvering.

Here are the Late Show headlines that weren’t laughing matters — our picks for the franchise’s biggest controversies.

2009: David Letterman makes a controversial joke about Sarah Palin’s daughter

Letterman angered then-Alaska Governor Sarah Palin in June 2009 when he commented on the Palin family visiting New York City and attending a New York Yankees game, joking that Palin’s daughter was “knocked up” by Yankees star Alex Rodriguez in the seventh inning.

The host later claimed he was referring to Palin’s daughter Bristol, who was 18 and a new mother at the time. But Palin’s daughter Willow, then 14, also attended the game, and that’s the daughter to whom Palin thought Letterman was referring, apparently.

“I would like to see him apologize to young women across the country for contributing to that kind of thread that is throughout our culture, that makes it sound like it is OK to talk about young girls in that way, where it’s kind of OK, accepted, and funny to talk about statutory rape,” the politician said on Today at the time, per The Guardian.

Letterman, for his part, said he’d never make that kind of joke about a 14-year-old. “I told a bad joke,” he told Late Show With David Letterman viewers. “I told a joke that was beyond flawed, and my intent is completely meaningless compared to the perception. … I would like to apologize, especially to the two daughters involved, Bristol and Willow, and also to the governor and her family and everybody else who was outraged by the joke. I’m sorry about it, and I’ll try to do better in the future.”

2009: Letterman confesses to workplace affairs

That October, Letterman told Late Show viewers he’d been blackmailed by an individual threatening to release incriminating details about the comedian’s personal life — namely, that he’d had extramarital sex with Late Show employees. And on his show, Letterman admitted that part was true.

“I have had sex with women on my show,” he said on air, as the in-studio audience, for some reason, applauded. “And would it be embarrassing if it were made public? Perhaps it would, perhaps it would, especially for the women.”

Months later, former 48 Hours producer Robert “Joe” Halderman pleaded guilty to attempted grand larceny, confessing to demanding $2 million from Letterman, and he ultimately served four months of a six-month jail sentence, according to CBS News.

Letterman’s confession continued to reverberate in the #MeToo era. “Letterman may not have ever pressured staffers into having sex with him. But that doesn’t necessarily mean his behavior deserves the kind of sweeping, all-is-forgiven pass it received,” Vice’s Drew Schwartz opined in 2019. “Perhaps we didn’t have the tools, in 2009 — the collective vocabulary — to identify why Letterman’s behavior might have been harmful and demeaning to his employees. “

2017: Colbert offends viewers with Trump-Putin joke

In May 2017, after Donald Trump insulted Face the Nation and its then-host John Dickerson, Colbert defended his CBS colleague with a litany of jokes at Trump’s expense on The Late Show. And one wisecrack in particular raised viewers’ hackles: “The only thing your mouth is good for is being Vladimir Putin’s c*** holster,” Colbert told the president.

Soon, the hashtag #FireColbert was trending on social media, with some viewers criticizing Colbert’s joke as homophobic, per Politico. Two days later, Colbert told the Late Show audience that he didn’t regret the offending monologue but did regret “a few words that were cruder than they needed to be.”

He also addressed the anti-gay accusations, saying, “For the record, life is short, and anyone who expresses their love for another person in their own way is, to me, an American hero.”

2025: CBS cancels The Late Show, prompting scrutiny

In July 2025, CBS shocked Hollywood and the viewing public by announcing that it would be ending the Late Show franchise in May 2026. The timing of the announcement was curious, though, considering it came three days after Colbert accused parent corporation Paramount of giving Donald Trump a “big fat bribe” to approve its merger with Skydance. (Paramount had agreed to pay Trump $16 million to settle his lawsuit over a 60 Minutes story.)

CBS claimed the cancellation was “purely a financial decision” and “not related in any way to the show’s performance, content, or other matters happening at Paramount,” but U.S. Senators Elizabeth Warren and Adam B. Schiff said Americans deserved to know whether The Late Show was canceled for political reasons, as The New York Times reported.

2026: The Late Show cancels James Talarico interview, prompting a war of words

In a February 2026 episode, Colbert told viewers that CBS lawyers put the kibosh on a planned interview with Texas State Representative James Talarico that night. The host attributed the interview cancellation to Federal Communications Commission Chair Brendan Carr considering applying equal-time rules to talk shows he found “motivated by partisan purposes.”

CBS then refuted Colbert’s statement, saying the network did not prohibit the talk show from broadcasting the interview with Talarico but instead “provided legal guidance that the broadcast could trigger the FCC equal-time rule for two other candidates, including Rep. Jasmine Crockett, and presented options for how the equal time for other candidates could be fulfilled.”

And then Colbert refuted that statement. “They know damn well that every word of my script last night was approved by CBS lawyers who, for the record, approve every script that goes on the air,” he said.