I feel like I’m talking too much. You tell me some stories.”
It’s 10 till seven in a conference room high above West 53rd Street, and David Letterman has just exhausted his capacity for self-reflection. We were scheduled to talk for 45 minutes; we’ve been at it for 44. After nearly 50 years of live broadcasting, he knows instinctively when a segment is about to run long.
Normally, Letterman doesn’t love talking about himself; what he wants to say, he says on his show. But today, he’s sitting for an exit interview of sorts. A few weeks from now, at approximately 5:30 p.m. on Wednesday, May 20th, Letterman will wave good night, the lights at the Ed Sullivan Theater will go dark, and the Late Show With David Letterman will have taped its last episode. There’s a long goodbye scheduled before then, featuring a once-in-a-lifetime lineup of A-list guests — Hanks, Clooney, Seinfeld, Winfrey, Murray, Roberts, at least one Obama — as well as plenteous highlights from his 22 years on CBS. It’s shaping up to be the kind of star-studded send-off television may never see again. And Letterman, of course, is not looking forward to it.
“I’m dreading it,” he says, grimacing. “As Regis 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.”
Today is the first day of April, and Letterman has just finished taping his 5,994th show. He’s changed from his suit into his evening wear: long-sleeved brown Carhartt T-shirt, green canvas pants and beat-up hiking boots that aren’t so much unfashionable as they are unacquainted with the concept of fashion in the first place. His nose is slightly sunburned — a souvenir of his spring-break trips to Wyoming (for skiing) and St. Bart’s (where he keeps a home) — and behind his amber-framed glasses, his 67-year-old eyes look tired. “When Johnny Carson left, I remember asking him why, and he said, ‘I just don’t have the energy,’ ” Letterman recalls. “That rings true to me.”
He’s leaving as the champ, of course: Maybe not Sandy Koufax, quitting after a 27-win season, but at the very least Ted Williams, hitting dingers in four different decades. He changed not just late-night TV but the very nature of comedy itself. Self-awareness, Stupid Pet Tricks, sneakers, irony: He taught multiple generations what it means to be funny. “Everything about his show informed not only our writing but our actual human interactions,” says Tina Fey, a Letterman fan since his short-lived morning show in the summer of 1980, when she was 10. Sixteen Emmys and a few thousand Top Ten lists later, even Jay Leno has acknowledged that Letterman’s the better broadcaster. At this point, it’s Copernican: settled science.
Preparations for his farewell have been underway for months, but for now, Letterman is largely steering clear. “It’s funny,” he says. “In the old days, if there were any kind of special show, I’d want to be right in there. And now I just feel like, ‘Let’s do something polite and happy, and get out of here.’ ”