“It’s like you’re thrown out of a speeding truck,” David Letterman, the stand-up and late-night comedy legend, says as we sit down at the Bedford Post Inn in Bedford, New York, about an hour outside of Manhattan, to record an episode of The Hollywood Reporter‘s Awards Chatter podcast, and I ask him what it was like to wake up on May 21, 2015, and, for the first time in 33 years, not have to stress about hosting a talk show. Letterman, of course, hosted Late Night With David Letterman on NBC from 1982 through 1993 and The Late Show With David Letterman on CBS from 1993 until May 20, 2015. “In a way, it was a relief, because you didn’t have the pressure of a daily show,” explains the 72-year-old, who rarely grants interviews. “On the other hand, you didn’t have the pressure of a daily show.”
Nobody in the history of television has hosted more episodes of late-night TV than Letterman’s 6,080, and when he stepped away and was succeeded by Stephen Colbert, few thought they would see much of him on their TV again, as had been the case with Letterman’s hero, Johnny Carson, after Carson’s retirement. But a little more than two years later, Letterman decided to dip his toe back into the water by hosting My Next Guest Needs No Introduction, a longform interview show on Netflix, and he found that he loved it. The first season featured smart, revealing and, yes, funny interviews with Barack Obama, George Clooney, Malala Yousafzai, Jay-Z, Tina Fey and Howard Stern, and was nominated for the Emmy for best informational series or special. Kanye West, Ellen DeGeneres, Tiffany Haddish, Lewis Hamilton and Melinda Gates are his guests on the second season, which dropped May 31 and is the favorite to win that aforementioned Emmy this year.
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Born in Indianapolis, Indiana, the middle child and only son of a flower shop owner and a homemaker, Letterman grew up rather aimlessly. He was not a great student and had no particularly hobby or passion — until, that is, sophomore year of high school, when he took an elective speech class. “It was the only thing in my life I had done up to that point, academically or under the guise or heading of schooling, that came easy to me,” he says. “Talking about myself? That was easy.” He pondered what sort of a career might allow him to continue to do this, despite his innate shyness and insecurity over his appearance, and settled on one in radio.
Letterman went off to Indiana’s Ball State University, got married at 21 and, through a friend, landed his first job in showbiz: as a summer announcer for Indianapolis’ ABC television affiliate. After graduating, he remained with that station for a while, and then moved to another in Minneapolis, doing his best to inject humor into even weather-related and kid-targeted programming. He ultimately left for a job in radio, and then a year later, in 1975, decided to relocate to Los Angeles.
Letterman told friends that he wanted to write for a sitcom, having already penned several spec scripts, but what he really wanted to do, in spite of himself, was what the guests on late-night TV did: stand-up comedy. “I was petrified with anxiety, and in those days I drank, and drank heavily,” he admits. “When I made the decision [to move to Los Angeles], I could only live with the decision when I was drunk; during the day when I was sober, I was scared silly.” When one of his spec scripts landed him a West Coast agent, it gave him the confidence to give L.A. a try.
Though Letterman had never previously attempted stand-up, he ventured, on his first Monday night in L.A., to Mitzi Shore‘s The Comedy Store, the name of which he knew from comedians’ introductions on late-night TV, and participated in its open-mic night. He wasn’t yet great, but he was good enough to earn a return invite as an emcee, and then later as a performer. And he relished getting to spend time there with other up-and-coming stand-ups, including Robin Williams and one Jay Leno. “When we were there, maybe there were people as good as Jay, but there was nobody better than Jay,” he says. “It seemed like he had figured out his personality onstage, figured out his attitude onstage, figured out an infinite variety of topics that he could make funny. He didn’t necessarily rely on jokes; it was a lot of attitude, a lot of hyperbole, a lot of sarcasm. It just seemed effortless.” The two became good friends.
Letterman, like many fellow stand-ups, split his time between developing five good minutes of material with which he might one day get to audition for NBC’s The Tonight Show, the most iconic of the late-night shows, and taking jobs where he could find them writing and/or acting for others — in his case, writing jokes for everyone from Good Times‘ Jimmie Walker to Bob Hope, and playing a small part on a Mary Tyler Moore variety show. It was thanks to the latter gig that, in November 1978, he got his first invitation to perform stand-up on The Tonight Show — and, even more thrillingly, to stick around afterwards for an on-air chat with Carson. “You knew one thing for certain,” Letterman says. “When you went through that curtain, your life was going to either get better or get worse — in five minutes, one or the other would happen. And luckily for me, it got better.”
Carson took a liking to his fellow Midwesterner — “He was very nice to me,” Letterman emphasizes — and, before long, Letterman was invited to guest host when Carson was unavailable, something that made him a star in the highly contained, pre-cable comedy world. “It [the show] was a king-making machine,” he says of the show, and, as a result of his increased profile, in 1980, he was hired by NBC to host a 90-minute morning show. He hired his then-girlfriend, the comedienne Merrill Markoe, to be his head writer, and together they built a show unlike any other that had existed in that time slot, with bizarre segments like “Stupid Pet Tricks” (which he would carry with him to subsequent shows). The show won a Daytime Emmy, but its ratings were terrible out of the gate and never recovered; it was canceled after just four months, and Letterman was sure he had blown his shot.
“When the show went off the air, I went back to drinking,” he says, noting that he also smoked a lot of marijuana at the time. But then he caught a break: Grant Tinker, Mary Tyler Moore’s husband who had hired Letterman to appear on his wife’s variety show, became the head of NBC, and wanted someone to replace Tom Snyder, the host of the struggling Tomorrow Show, at 12:30 a.m. Letterman got the job, and on Feb. 1, 1982, Late Night With David Letterman began following Carson’s Tonight Show. There was a catch: Carson also owned Late Night, and insisted on “many prohibitions,” as Letterman calls them, to distinguish his show from Letterman’s, which were communicated to Letterman by Carson’s “lieutenant” Dave Tebet. Among them, Late Night was not to have a monologue, a sidekick to the host, an orchestra or A-list guests.
Letterman, under director Hal Gurnee, turned these limitations into assets, crafting a late-night show unlike any other, with outside-the-box segments (e.g. “Viewer Mail” and “Top 10 List”) and eccentric guests (e.g. Harvey Pekar and Andy Kaufman), which appealed to younger viewers. For more than a decade, Letterman, as the host of that show, was widely regarded as Carson’s heir-apparent, not least by Carson himself. But at a certain point, things went awry. Tebet and Henry Bushkin, another Carson advisor, asked Letterman if he would be willing to host The Tonight Show a few nights a week while Carson hosted the other nights, presumably grooming Letterman to eventually take over full-time. Letterman says he was thrilled with the idea, but asked if Carson had approved of it, and when he learned that Carson had not yet been consulted, he asked the men to return once Carson had. They never did.
In the meantime, Leno was made The Tonight Show‘s regular guest host and, when Carson retired in 1993, it was Leno, not Letterman, who was hired as his successor, sparking what became known as “the late-night wars.” There was a widespread perception that Letterman had been wronged not just by NBC, but by Leno — but what did Leno do, apart from accept a job offered to him? Even after all these years, Letterman wants to hold his cards close to the vest. “I will say, without specifics, there are ways friends behave in competitive situations in life, and there are ways people behave who are not your friends,” he volunteers cryptically. “And that’s all I’m going to say about this.”
Soon thereafter, Letterman, obviously disgruntled and unwilling to follow Leno, got out of his NBC contract and signed a rich deal to host The Late Show for rival CBS. which was happy to have buzzy programming at 11:35 p.m. to go up against The Tonight Show. For the first year-plus, Letterman did indeed beat Leno in the ratings — “and then it slipped away, and stayed slipped away,” Letterman laments. (While Leno forever after beat Letterman in the ratings, Letterman retained a cool factor among people in the comedy world that Leno lost, not least from the way he was perceived to have handled the situation with Letterman and then, years later, with Conan O’Brien.)
Letterman’s new show, while retaining the same sort of eccentric and ornery nature as Late Night, featured more A-list guests. Regulars included Madonna, Cher — and New York real estate mogul Donald Trump, who was Letterman’s guest more than 30 times between the two shows. “More than 30?” Letterman says in disbelief. “Wow! You’re welcome, America.” Turning serious, he says of the president, “I think he just liked being on TV. I had no sense that he was the soulless bastard that he’s turned into.” Letterman continues, “Everybody says, ‘Oh, wouldn’t you like to talk to Donald Trump [today]?’ And I would. I would just like to say, ‘Don, it’s Dave. Remember me? I want to talk to the real Donald Trump.’ Because I now don’t know which is the real Donald Trump, and if the Donald Trump that I was talking to [back then] was the real Donald Trump, how do you get to be the guy he is now? Politics notwithstanding — let’s just say everything is great and he’s done a great job, but he still behaves the way he behaves — who behaves like that?!” Letterman emphasizes, “He used to be kind of like the boob of New York that pretended to be wealthy, or we thought was wealthy, and now he’s just a psychotic. Is that putting too fine a point on it?” He adds, “I don’t even care if it’s recorded, I would just like to talk to the guy, because, as I said before, he knows me, I know him, what the hell went wrong?!”
Letterman remained Late Show‘s host for 22 years, the last few of which he didn’t always look like he wanted to be there. Part of this may have been a misunderstanding, he explains: “I think I inherited [from his late mother, Dorothy Mengering] some of that resting — what is it called? Resting bitch face. God rest her soul. And it was only later that I kind of realized, ‘Maybe I ought to be a little happier to be here.'” But part of it may have been the result of a scandal that became public in 2009 — the same year he married longtime girlfriend Regina Lasko, with whom he had already had a son, Harry, in 2003 — in which he was extorted over evidence that he had engaged in extramarital relationships with female employees, conduct for which he apologized on the air. “Since then, honest to God, I realize that there have been so many mistakes in my life, and so much good fortune in my life, that I really have to concentrate on being a better person,” he says solemnly.
On top of all of that, there was the rise of political comedy, in the form of Jon Stewart‘s The Daily Show and Colbert’s The Colbert Report, and of new late-night hosts who specialized in crafting segments that would go viral online, which was increasingly important as younger viewers cut the cord. “I didn’t know how to do that,” Letterman admits. “Sure, I’ll sing and dance, but I just didn’t know how to do it.” Eventually, Letterman realized the time had come to move on. “I didn’t want to be the old guy,” he says. “And then Jay announced that he was leaving, and I looked around and I thought, ‘Holy crap, I’m going to be the old guy.'” He adds, “I probably stayed too long. There are other things to do, other things that are important. You know, I was old, for God’s sakes. Nobody wants to see an old guy doing that every night.”
Letterman’s final Late Show aired on May 20, 2015, and then he was gone, at least from daily life in the public eye. Paparazzi photos occasionally emerged of him with a giant beard, which mystified many, but he explains, rather logically: After having to shave every day for 33 years, he hated it. Now, he says, “I don’t have to shave, and thank God for that,” adding, “I’m afraid to see what might be under there now. I think I’m doing the world a favor.”
By the time Letterman showed up on Netflix in early 2018, he seemed a person much happier and more at peace with himself. “I have enjoyed this,” he says of the new show. “For me, it’s been great because we can talk to these [famous] people. They’re so interesting, superficially. And then, beneath that, the facets that create the outer layer of the human being — that’s where you get lost, that’s where you get your work in [as an interview]. And, you know, the great thing is they’re all smarter than I am.”
Letterman insists that he doesn’t miss doing a late-night show, and usually doesn’t stay up late enough to watch those who do — although he has formed general impressions of those who now walk in his old shoes. Colbert? “He’s fantastic. He has taken that show and harnessed the political energy of the country and done a great job.” Jimmy Fallon? “Jimmy is doing something else, but doing a great job at it.” Jimmy Kimmel? “Kimmel is Mr. Everyman. I’m very fond of Jimmy, been on his show a couple of times. I like him. He’s genuine, and he knows when to make a point of things that are not right in this country.” James Corden? “I see him singing and dancing and stuff, and God bless him.” Seth Meyers? “Also a smart kid, and I’ve been on his show, and he does a very nice job. I think he’s right where you want to be. These are troubled times, and I think he is navigating them nicely intellectually.” Trevor Noah? “He does a great job, and also he wrote a book that became a textbook. You may have noticed, I haven’t done that.” Samantha Bee? “She is one of those people that not only has a television show, but through the television show and how she conducts herself has become an activist, and you have to admire that.” O’Brien? “How can you not like Conan O’Brien? The longest-running current late-night host, and a very smart and very funny guy. I love Conan.”
The person who makes him laugh the most, though? “My son. Without question.”