6 Things Learned From David Letterman's 'Rolling Stone' Cover Story

He's not that involved with preparations for his final show, and he'd like to do a version of 'Comedians in Cars Getting Coffee' involving stars on horses.
Evan Agostini/Invision/AP
David Letterman

Outgoing Late Show host David Letterman conducted another of the handful of exit interviews the press shy CBS star has been doing lately. In this one, which serves as the basis of Rolling Stone's cover story, Letterman and his staff reveal how involved he is with his final show (not very) and how he told them he was leaving. He also talks about life after the Late Show, what he thinks of his late-night competition and his regrets.

Read on for more revelations from Letterman's Rolling Stone cover story.

He's not that involved in preparations for his final show.

Letterman is "dreading" his final Late Show, he tells Rolling Stone in its cover story on the CBS host. "As Regis [Philbin] used to say, 'I don't like going down memory lane' — and I'm afraid that's what this is all about. After we get through with it, then I'll sit back and see what we've done. But for now, I just want it to be over with." He's steering clear of plans for his final episode, in keeping with the somewhat standoffish approach he's taken to the daily production of his show in recent years: He talks to producers, makes phone calls and reviews monologue jokes but he rarely goes to meetings and doesn't rehearse.

"I tell the producers, 'I'm not a producer, you're the producers. You come get me when the show is ready, and it will either go smoothly or it won't,' " he says, pausing before adding, "Which is maybe an indicator that you shouldn't be hosting your 11:30 comedy show much longer."

As for the final show next Wednesday, preparations have been underway for months, Rolling Stone reports, but not with the host, who previously told the New York Times he knows what he'll do but doesn't know what will happen during the rest of the show. He tells Rolling Stone he hopes he doesn't cry, saying if he does, "then something is going terribly wrong."

Executive producer Barbara Gaines, who is working on the final show, offers a bit more insight into what's planned. She's putting together a greatest-hits collection of clips, possibly including the Taco Bell drive-thru segment and "Dave and Steve's Gay Vacation." And, Letterman's producers have invited Jay Leno to be a guest, they tell Rolling Stone, but he hasn't accepted.

"It'd be great to just let them chew on whatever they have to chew on," the CEO of Letterman's production company Worldwide Pants, Rob Burnett, says. "To see Dave turn to Jay and say, 'What's your beef?' "

His family, Jay Leno and Pharrell Williams all played a role in his retirement announcement.

Rolling Stone also goes inside Letterman's announcement last year that he would leave the Late Show in 2015. He used a story about his son and trying to find out the type of bird they spotted over the weekend as an explanation for why he thought it was time to hang it up. But he tells Rolling Stone that was just a convenient anecdote. He and his wife had been talking about retirement for at least a year and half.

"I just thought, 'I don't want this to be mawkish, I don't want it to be maudlin. Let me see if I can't just put it all off on the kid,' " he tells Rolling Stone about how he announced his departure.

Behind the scenes, Paul Shaffer was the first Late Show staffer he told, breaking the news to his longtime bandleader while the two of them were waiting to go on stage. A few days later, Letterman called his staff into his dressing room.

"I wanted to make it as casual and organic as possible," Letterman says. "I felt self-conscious about it. I didn't enjoy it."

He had the radio on in the background, playing Pharrell Williams' "Happy."

"Here he is going, 'This 30-year career, we're finally bringing it to a close . . . ,'" head writer Matt Roberts recalls. "And all I can hear is 'Clap along, if you feel. . . .' "

Still, when he signed his last contract extension, for a year, he was afraid he wouldn't last that long.

"The next day, I woke up in a bloody panic," he says. " 'Holy crap! What if I can't do this for another year?' " Although he'd been talking with his wife about stepping down, Letterman says Leno leaving the The Tonight Show helped him make his decision.

"[Leno leaving] caught me off guard. I thought Jay would have that job as long as he wanted. His ratings were strong; he showed no sign of slowing down. I know he loved it. I know it must have been hard for him," Letterman says, recalling that he called Leno after his NBC rival announced he was leaving. "I was sort of touched by it," Letterman says. "I said, 'Jay, are you actually retiring?' And he said yeah, you know, so and so. And I said, 'Well, I hope this is good for you, and I'm sorry you're leaving.' He was very nice and earnest about it."

He has nice things to say about Jimmy Kimmel and Jimmy Fallon's late night show, but he thinks reality will set in when he sees Stephen Colbert take over.

Letterman calls Kimmel "friendly" and "very sweet" and says Fallon's show is "bright and colorful" and "a commercial for itself." As for Colbert, whom Letterman has previously said he wasn't involved in picking as his successor, the veteran late-night host said the reality of his retirement will probably set in when Colbert's show starts in September.

"I think in the fall, when Stephen's show starts up, that's when my stomach will kind of go, 'Oh, shit. I'm not really on vacation, am I?' "

He wants to do Comedians on Horses Getting Coffee

So, what's next for Letterman? He says he's still interested in doing a talk show, just not a daily one.

"Here's how I would put it: I would like to do this show maybe three days a week, two weeks out of the month," he says, laughing, "Do they have shows like that?" In fact, what he'd really like to do is a more rustic version of Jerry Seinfeld's Comedians in Cars Getting Coffee, perhaps set in Montana, where he has a house and spends a significant amount of time. "Comedians on Horses Getting Coffee," Rolling Stone dubs it.

When he saw Seinfeld's show he was annoyed that his fellow comedian had come up with that show first.

"I thought, 'Well, that's the perfect idea, goddamnit,'" Letterman recalls, adding of his horseback version, "I thought that would be so much better than riding around in a car, because then you see what the guy is made of." Evidently Seinfeld wasn't blown away by the idea when Letterman pitched it to him, but Tom Brokaw thinks it's a winner. "I'd like to see Louis C.K. on a horse, for example," Brokaw tells Rolling Stone.

He wonders if anyone listens to podcasts, and when told they're popular, he says, "Well, OK. That would be good."

He's also likely to continue the lecture series he founded at Ball State, where he interviews people like Oprah Winfrey and Rachel Maddow.

"Those are fun," Letterman says. "That would be an easy place to start. And maybe that's all there will ever be."

He's "a pretty active rancher"

Letterman doesn't just vacation in Montana, he's really gotten involved in the lifestyle. "David's a pretty active rancher," Brokaw says. Animal expert and friend Jack Hanna adds: "This is not boutique stuff ... in the last four or five years, Dave has become one of the greatest conservationists I've ever met. His land, his grasses, his water, how he plants his fields — he knows everything. It's absolutely amazing. He studies like you wouldn't believe."

With the help of his ranch manager, Andrew Bardwell, he's started raising a bison herd of more than a hundred animals that he sends to market.

His 2009 sex scandal was "easily the lowest point in my life."

Letterman still seems to cringe when he recalls his admission on the air that he had sex with multiple female staffers.

"It was easily the lowest point in my life," he says. "I don't know how else to describe it. I felt like I'd dug a bottomless pit, and I was falling into it."

While, as he's said before, he was convinced he'd get fired, he reveals he was more worried that his wife would leave him.

"The biggest panic was on a Friday night, when we heard Regina was on her way to file for divorce," he says. "It turned out not to be true. But that just turned me inside out. The only thing that's important to me, I just ruined. I remember when they first handed me my son, thinking, 'Oh, look — something perfect.' And now I've jeopardized him as a part of my life and me as a part of his life."

His son, who was five at the time, doesn't know about it, but Letterman acknowledges he'll have to talk about it with him one day.

He has a few regrets.

Letterman is reluctant to reflect on his legacy, but he does share a few regrets with Rolling Stone, wishing he'd done a better job on a more consistent basis and not have been distracted by "the wrong things." But he also regrets that he didn't make more out of his production company, Worldwide Pants, so "it could have an afterlife, whereby some of these people who've worked so hard all these years could continue to be employed."

And he would like to have had more children, at least a second one, preferably a girl.