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In an interview with New York magazine, Letterman gave his thoughts on the nascent Trump administration, its troubling authoritarian tendencies and whether he felt he was missing out on the target-rich comedy environment right now, an environment in which comedians have an “obligation” to take on the president.
“[C]an you imagine not doing Trump jokes? That would seem bizarre,” said Letterman when asked if it was a responsibility of the late-night hosts to skewer the president. He had high praise for Saturday Night Live‘s often brutal weekly hits at the administration, in particular for Alec Baldwin’s impression of Trump. “Comedy’s one of the ways that we can protect ourselves. Alec Baldwin deserves a Presidential Medal of Freedom. Sadly, he’s not going to get it from this president.”
Letterman said that after 30 years in the business the last thing he wanted to do was watch late-night TV but he had heard good things about Seth Meyers and his successor at The Late Show, Stephen Colbert. On the subject of Jimmy Fallon’s now infamous softball interview with Trump (where he messed up The Donald’s hair), Letterman expressed some sympathy for The Tonight Show host who suffered a backlash for playing it safe, but also said he would have approached things differently. “I don’t want to criticize Jimmy Fallon, but I can only tell you what I would have done in that situation: I would have gone to work on Trump. But the thing about it is, you don’t have to concoct a complicated satirical premise to joke about Donald Trump,” he said.
Needing no prompting, Letterman took aim at the various characters in the Trump administration who have become a staple of late-night jokes including White House advisers Steve Bannon (“the Hunchback of Notre Dame”) and Stephen Miller (“creepy” guy who “fell out of a truck”), press secretary Sean Spicer (“a boob”) and his personal favorite, Trump adviser Kellyanne Conway (“Boy, if this administration decides you need counseling — whoa”).
But it was Trump, or “Trumpy” as Letterman calls him, who would be the chief target. Letterman spoke a little about his long past interviewing the real estate mogul and how he would always take the opportunity to make fun of him. “He was a joke of a wealthy guy. We didn’t take him seriously. He’d sit down, and I would just start making fun of him. He never had any retort. He was big and doughy, and you could beat him up. He seemed to have a good time, and the audience loved it, and that was Donald Trump,” he said, adding that Trump loved the publicity either way.
Letterman said he would love to interview Trump one last time and outlined how he would do it. “I would just start with a list. ‘You did this. You did that. Don’t you feel stupid for having done that, Don? And who’s this goon Steve Bannon, and why do you want a white supremacist as one of your advisers? Come on, Don, we both know you’re lying. Now, stop it.'”
Seemingly enjoying retirement, Letterman also found time to discuss the late-night TV landscape that has vastly changed since he and Jay Leno ran things. He said he would struggle in an era where viral online clips and skits reign supreme and where puff-piece interviews abound. He agreed that the interview had become almost an afterthought and could see that even toward the end of his time. “Well, at some point publicists took over the talk shows,” he said, adding: “They were the people that booked the guests, and they had six or seven guests, so you had to be awfully nice to Guest A if you wanted to get to Guest B or C.”
Letterman also revealed he’s been fielding offers from TV shows, but that one in particular made him too nervous.
“I’m a big fan of Veep, and here’s how nice they were: They asked if I would consider a cameo,” he said of the veteran HBO political comedy. “Holy shit — I got so scared. I thought about it for 24 hours and then I told them, ‘Here’s what would happen: I’m going to do your show. I’m going to worry about it, I’m going to get sick to my stomach, and I’m going to ruin it. I can’t do that to you.'”
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