David Letterman’s post-retirement life has been fun to witness. Since leaving The Late Show on May 20, 2015, he’s grown out his beard, hung out at the Indy 500, and generally seemed very happy about no longer being beholden to broadcast television. He’s also been candid: Reflecting on his legacy in an interview with Tom Brokaw for an upcoming episode of Dateline, he spoke openly when asked who should have succeeded him on CBS, saying, “I don’t know why they didn’t give my show to a woman. That would have been fine.”
Letterman didn’t seem to bear any particular ill will for Stephen Colbert, the man who replaced him, though he’s repeatedly noted that he wasn’t consulted on which star should take up the Late Show mantle. But while his new comments reflect a refreshing viewpoint on the overwhelming maleness of late night, they sit uncomfortably alongside his legacy as a host. Letterman was a massive influence on comedy in his 33 years at Late Night and The Late Show, but perhaps the biggest strike on his record was the disproportionate lack of female comedians who appeared on his show over the years.
That issue came up for debate in 2012 when The Late Show’s comedy booker Eddie Brill said he didn’t favor female stand-ups because they were rarely “authentic,” telling The New York Times, “I see a lot of female comics who to please an audience will act like men.” Brill was fired, but the damage was done—he’d been the gatekeeper for The Late Show for 11 years, and in 2011, he let only one woman perform stand-up on the show (out of some 200 episodes).
