Sometimes, OK, all the time, David Letterman, who used to host his very own television program, is asked whether he still wishes he were on TV. Back then, he could do almost anything he wanted in front of millions of viewers: chat with a president, toss a wheel of runny brie off a building, even mock his once mortal frenemy Jay Leno.
He must miss it terribly.
“Not for a second,” Letterman says before delivering a lengthy analogy about a prison sentence that references beatings, food poisoning and a knife fight.
You sit there waiting for the punchline, the twist, the resolution and then, at a certain point, realize it’s not coming. Wait. Mr. Letterman, are you saying hosting a late-night talk show is hard time?
“They are exactly the same,” he says.
The David Letterman who will receive the Mark Twain Prize for American Humor this month looks different from the guy you remember from television. He’s got a bushy white beard everybody makes a big to-do about — stop asking, folks, they will BURY me in it, he says. But that voice and octave-jumping cackle is hard to mistake for anyone but the man who hosted NBC’s “Late Night” and CBS’ “Late Show,” a stretch that ran from 1982 until 2015.
At 70, he remains a masterful storyteller, infinitely curious and as quick with a quip as Kyrie Irving’s first step to the hoop. What’s gone is the nightly entertainment race that ruled his life for 33 years. There was a time, even he’ll admit, when he cared about nothing more than that TV show. Today, as he tries to keep up with his boy Harry, 13, that former life baffles him. That brooding guy on television, he’ll shrug, was “a different man.”
“It was ‘The Late Night Wars,’ oh ‘Jay’s winning, nobody likes me, and everybody likes Jay,’ ” he says. “Now I think, what was that? Who’s at war here? There’s no war anymore. And I think, why was I in the war?”
It’s a Wednesday afternoon and Letterman has driven from his home in New York to visit the Mark Twain House in Hartford, Connecticut. This is textbook Dave. When he realized he would be receiving the Twain Prize, Letterman didn’t feel proud, he felt guilty, and on multiple levels. First, he’s sadly deficient in the study of Samuel Clemens.
“All I really knew about Mark Twain was Tom Sawyer, Huck Finn, trying to get through his autobiography and then I read a book of his letters, and I’m currently reading ‘The Innocents Abroad,’ ” he says, referring to the 685-page travel book.
If failing to measure up to Twain isn’t enough, Letterman notes the other 19 recipients of the prize, including Neil Simon, Tina Fey and Bill Murray.
“There’s one gaping sinkhole on that list at No. 20,” says Letterman. “And it’s me.”
That’s a good one. The prize is meant to recognize those who have had an “impact on American society in ways similar to” Clemens. During his tenure, Letterman invented an entirely new language for television, one steeped in irreverence, edge and sarcasm but fortified, particularly as he grew older, by his presence as a trusted, calming voice. He may have made his name by throwing himself against a Velcro wall or with the show’s “Monkey-Cam” — yes, a camera strapped to a live chimp — but after the World Trade Center attack, it was Letterman who returned to the air with a somber eight-minute monologue that displayed both a steady hand and a comforting vulnerability.
Jimmy Kimmel, a lifelong fan who, as a teenager, had a “L8 Nite” license plate installed on his Isuzu, admits he thought of Letterman recently when he spoke out, passionately, on his show about health-care protections and gun control.
“You reach a point in your career where you feel like you’ve done enough silly stuff and you realize, thanks to Dave, that it’s OK to be serious sometimes,” says Kimmel.
His comedy career, unofficially, began in Indianapolis, where Letterman grew up.
Steve Brown, a lifelong friend, remembers sitting around one day after school when Letterman, then just 13, saw a listing in the want ads of the local newspaper. A guy was selling propane tanks. Letterman picked up the phone.
“This guy had a large quantity, I don’t know, maybe 50 of them,” says Brown. “So Dave gets the guy on the line and he put him on for 15 minutes and had the guy convinced that he was from the naval department and they were interested in buying all of these and they were going on a miniature submarine project, that they were going to equip them as weapons. He got to the point where he was actually trying to negotiate a price with the guy.”
Harry Joseph Letterman, his father, introduced him to Jack Benny’s radio show. He also introduced him to the concept of the tortured performer. Harry owned a flower shop. To this day, Letterman isn’t sure why because his father seemed happiest when he was playing organ, which he could do for hours, or putting on an impromptu show, even at church functions.
“He would throw in jokes, he would have props,” says Letterman. “He would turn something dull into something silly. While he liked flowers and liked growing them and arranging them, it is not where he wanted to be.”
In 1975, two years after his father’s fatal heart attack, Letterman decided to take his leap. He quit his gig as a weatherman on a local TV station and drove out to Los Angeles. That’s where he met Merrill Markoe, a brilliant writer, and a group of comics that included Leno, Elayne Boosler and Robin Williams. As a stand-up, Letterman had good nights, he had bad nights. But early on, his peers recognized his calling.
Tom Dreesen, the veteran comic, remembers going with Letterman for his first appearance on “The Tonight Show” in 1978.
“When I saw him walk through that curtain into that television studio, I went, ‘Oh my God, he’s home,’ ” he says.
Much has been written about how “Late Night With David Letterman,” which ran on NBC from 1982 to 1993, revolutionized comedy. There were the characters like Chris Elliott, who played “The Guy Under the Seats” or “Marlon Brando” with obnoxious, nasty glee. There was Letterman’s slate of quirky guests, curmudgeonly George Miller or Gonzo master Hunter S. Thompson. There were also the many bits – Viewer Mail, Stupid Pet Tricks, the Top Ten List — developed under Markoe, who began the show as head writer.
But what set Letterman apart, as much as his material, was his persona. He was a fidgety, self-deprecating figure, either so pleased or so disturbed when a joke failed that he would remind viewers of the biggest bombs by calling them back throughout the show.
“If we were analysts, we could analyze him, he wouldn’t even have to lie down on the couch,” says Paul Shaffer, Letterman’s longtime music director and sidekick. “And he loved having a show like that. And he liked real conversation, even between me and him. He never wanted to plan what we were going to say and it made for a real ‘what you see is what you get’ kind of experience.”
He could be a complicated boss, always unsatisfied with himself and sparing with his compliments. Do you like me? Barbara Gaines, the former receptionist who rose to executive producer, asked him in an insecure moment.
“‘You’ve been here, I’ve promoted you, don’t look for approval,'” she remembers him saying. “‘You’ve seen I haven’t fired you. You’re in. Don’t be a ninny.'”
“Sometimes, when he was really effusive about something you’d offered, he’d go, ‘You’re just nuts,'” says Steve O’Donnell, who was one of the key writers on “Late Night” for almost a decade. “And you’d think it was the best, greatest compliment in the world.”
But Letterman was hardest on himself.
“He would think, I can’t do that, I can’t do that,” says O’Donnell. “But I think he also had an idea he wasn’t going to be a zany, clownish comic. He wasn’t going to put on funny hats. It wasn’t because he thought he wasn’t as good as those broadcasters who went before, but in a way he’s so discriminating and so skeptical about things that it extended to his own abilities as well.”
Eventually, Letterman would define himself as a performer, but on his own terms. There were bits clearly borrowed from Steve Allen, the former “Tonight Show” host and one of his heroes. But there would be nothing approximating Johnny Carson’s Carnac the Magnificent on his program. Instead, Letterman would crack jokes while working the drive-through window at a McDonald’s or haul a crew to a Sears in Hicksville, New York, to confront a viewer, Colleen Boyle, who had criticized him in a Viewer Mail segment for wearing sneakers.
Writer Jim Downey, who left Letterman to return to “Saturday Night Live” in the early ’80s, remembers watching as Letterman grew more comfortable.
“It was like someone who was afraid to ask a girl to dance and suddenly came back and it was like watching ‘Footloose.'”
The past is something Letterman views differently than others. He is not above a nostalgic anecdote, but he doesn’t get dewy-eyed when talking about himself.
Gaines remembers urging her boss to include a clip of his 9/11 monologue in various highlight reels. He wouldn’t. In fact, Letterman won’t even watch old clips. When the John F. Kennedy Center for the Performing Arts asked for help putting together video highlights for the Twain ceremony, he and Mary Barclay, his longtime assistant, sat at a monitor. “Could you turn down the sound?” he asked first. When she pressed play, she looked over and he had his hand over his eyes.
Letterman also doesn’t miss how he behaved in those days. He wishes he had been properly medicated earlier. His wall-punching tantrums were regular, ugly and “triggered over nothing.” Around 2003, he began taking an antidepressant.
“And so now I feel like probably most people feel,” he says.
Since leaving late night, he’s avoided his old playing field. He doesn’t watch. He hasn’t visited as a guest. (The exception being “Jimmy Kimmel Live,” which he did most recently this month.) Which is not to say he’s a shut-in. Letterman has just signed a deal to develop a six-episode Netflix show. He’s gone on Howard Stern, Norm Macdonald’s video podcast, showed up at former “Late Show” writer Steve Young’s class at NYU, and even popped into Indianapolis to speak at the dedication of a statue for retired Colts quarterback Peyton Manning. There was also his appearance on “Them Yo People,” a program that airs in St. Louis at midnight on Sundays.
This summer, Letterman was taking in the Bommarito 500 car race when “Mister Gary,” a former hotel manager who wears a red crown and waves a golden scepter, approached him for an interview.
At one point, Letterman began talking about Long’s doughnuts, an Indianapolis favorite, and how let down he had been when he stopped by the shop before the Indy 500.
“I was so disappointed because they said on their website they would be open,” he said, pausing dramatically. “Gary, they were not open.”
“What do we do about that?”
“Well,” Letterman said, “I have a call in to the governor.”
He left at the right time, though sometimes he wonders if he overstayed his welcome.
Which is when Letterman brings up his biggest regret. It wasn’t losing “The Tonight Show” to Leno in 1992. It wasn’t the embarrassing affair with a staffer he revealed on the show in 2009 after a former CBS news producer threatened to blackmail him. It’s something that has nothing — or everything — to do with TV. He wishes Harry had a sibling. (Letterman says he is too old to adopt a child.)
For years, he fought with his girlfriend, Regina Lasko, 56, about starting a family. She even dumped him at one point. His resistance, he admits, was that he felt he couldn’t do the show and be a father.
Then, in 2003, they had Harry, named after Letterman’s father.
“And then the minute the kid is born I realize: Holy s—, I have made an enormous mistake and tried to defend it for 15 years now,” he says. “I was wrong. I could not have been more wrong.”
Letterman and Lasko, who were married in 2009, spend summers in Montana, where there’s good fishing and enough space to teach the kid how to drive a stick. During the school year, they’re in New York for Harry. As the years pass, Letterman remains grateful that he’s been around to watch his boy growing up.
Letterman likes to tell Harry stories, even if they don’t always wrap up in a bow.
Take a recent Saturday morning when he and Harry went to see “Battle of the Sexes,” the dramatized account of the Bobby Riggs and Billie Jean King celebrity tennis match.
“It’s a very good movie, but what hadn’t occurred to me is that it’s a lesbian love story,” Letterman says. “So you see a lot of good-looking girls in their underpants making out.”
He stares straight ahead. “We’re both eating our popcorn. ‘Uh huh. I see. OK.’ Then it would go away and we could breathe again.”
He thinks back 60 years to a fishing trip he took with his own father. Somewhere along the way, they stopped to use a bathroom. Young Dave spotted a prophylactic machine on the wall.
“And I came out and said, ‘Jeez, there’s a machine in there. It’s not candy. It’s not cigarettes.’ And my dad said, ‘Ah, one day you and I are going to have that talk.’ And we never did.”
This brings a big cackle and he relates to his own son.
“I always think of that and I pester Harry. ‘Have we had the talk? We should. Especially now. Let’s have the talk.'”
His voice trails off and he laughs again. David Letterman knows there’s still time.
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