In an intimate interview with New York magazine, the 69-year-old legendary comedian gets candid about everything from politics, late-night TV's changing landscape and life after retirement. Letterman says he watched Jimmy Fallon's infamous Tonight Show interview with President Donald Trump, and that he definitely would have done things differently.
"There is that obligation," he says about comedians and late-night hosts taking on Trump. "We used to have a joke we'd do about booking guests: 'Guess what?' 'What?' 'Neil Armstrong is going to be on the show.' 'Neil Armstrong? That's fantastic.' 'He doesn't want to talk about the moon.'"
"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," he continues. "But the thing about it is, you don't have to concoct a complicated satirical premise to joke about Donald Trump. It's not, 'Two guys walk into a bar …'"
Later, he describes how he would go about interviewing the president.
"I would just start with a list," he muses. "'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.' I think I would be in the position to give him a bit of a scolding and he would have to sit there and take it. Yeah, I would like an hour with Donald Trump; an hour and a half."
Letterman acknowledges that late-night interviews have gotten softer, and says publicists have taken over the talk shows. The famously sarcastic host does, however, have one big regret -- he says he was too hard on Paris Hilton during his famously awkward 2007 interview with her, when he continually pressed her about her experience in jail after she said she didn't want to talk about it.
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"I always felt like, 'We got 500 people in the audience and it’s my responsibility to get a laugh,'" he shares. "Many times, the laugh would come at the expense of the guest. I regret that now, but at the time you think, 'I’ve got to do anything to keep my head above water.'"
"If you had a chance to talk to Paris Hilton in those days, you just kind of want to talk about, 'Well, no, seriously, you were in jail,'" he adds. "But that upset her and she cried and I called her and apologized. I think I bought her a car, too. As the guy operating the machinery sometimes, it was 'You're going a little fast here, pal.' It was easy to overdo it."
Letterman gets candid about the anxiety he felt about his work, and his experience taking anti-depressants.
"A friend of mine, my doctor, said, 'You know, you don't need to kill yourself. It's just TV,'" he recalls. "Then he convinced me to try one of these selective-serotonin-reuptake inhibitors. I resisted it. I thought, 'No, just put me in a state hospital.' But I did try it, and suddenly that wiring had less power than it used to."
"I still have vestiges of it -- I think that's about where you want to be," he adds. "You don't want to be putting your fist through a wall, but I can't imagine going through life not questioning my own worthiness. So, yes, I still have those qualities, but in a lower gear."
Later, he admits to having trouble adjusting to normal, everyday life.
"It's still hard. I have trouble operating the phone," he says. "That's the God’s truth."
"Nobody else seems to have a problem with going to a store!" he also notes, after sharing his overwhelming experience while trying to buy a pair of shoelaces at a shoe warehouse. "You don't want to have painted yourself into some elite position where it's 'Bob, go out and get me some shoelaces.' It makes you feel stupid."
As for what he feels most proud of in his life, Letterman says it's creating jobs.
"I have this conversation with my wife, who is also a schmo. And she will say, 'Thirty years. Think of all of the people you employed,'" he shares. "I thought, 'Yeah, by God, that's good enough.' I was able to give jobs to people. That's an accomplishment."