Do we like David Letterman?
Our score: 7 out of 10. Decent record and a clear willingness to stick his neck out, held back by an old trans joke and a workplace past he has since apologised for.
Dave grew up in Indianapolis, went to Ball State, and started out as a local radio host, children's TV presenter and weatherman. He moved to Los Angeles in 1975 to write for sitcoms and became a regular guest host on The Tonight Show in 1978. NBC handed Carson's chair to Jay Leno, so he took his show to CBS, hosted the Late Show there for over two decades, retired in 2015, then came back in 2018 with a Netflix interview series.
The messy chapter is 2009. A CBS producer demanded $2 million to keep personal information about Letterman quiet, and Dave went to the authorities rather than pay. He then told his audience on air that he'd had sex with women on his staff. The producer pleaded guilty to attempted grand larceny and in May 2010 got six months in jail plus 1,000 hours of community service. So he was the target of a crime, but the admission was a very public look at how he'd run his workplace.
That workplace got a harder look from writer Nell Scovell, who alleged in a 2009 Vanity Fair piece that the Late Night writing room was hostile and demeaning for women. In 2019 she says Letterman sat down with her and apologised. She accepted it but didn't think it was a full reckoning. Credit to him for fronting up a decade later, but it counts against him.
On the harm test, the big mark is a January 2010 monologue bit that mocked Amanda Simpson, a trans woman appointed to a Commerce Department role, with the announcer shouting that she “used to be a dude”. The Human Rights Campaign called it “inappropriate and incendiary” and demanded an apology. His spokesman declined to comment and ABC reported no apology. It's one bit from the late-night joke factory, not a campaign, but it's not nothing.
The rest of the ledger points the other way. In 2016 he fronted a National Geographic climate series, Years of Living Dangerously, talking up clean energy. In September 2025 he said ABC's suspension of Jimmy Kimmel was “misery” and called it “managed media”. He also said the presidency ought to be bigger than a guy doing a talk show. I found no conspiracy theories, grievance politics or anti-trans campaigning from him.
The recent fight is over Colbert. In a New York Times interview in May 2026 Letterman said he didn't believe CBS's explanation and said Colbert's show was dumped because of the Skydance deal. CBS replied that it was a purely financial decision. Skydance hadn't responded when Fox reported it. Whichever of them is right, he's making noise on behalf of a mate and a show he no longer owns.