David Letterman on retirement: It's time, but he's torn

NEW YORK -- You don't think of David Letterman as a stop-and-smell-the-flowers type, but here he is, at a major turning point yet savoring his chocolate milkshake.

Perched on a stool in a fast-food restaurant beside the Ed Sullivan Theater, where he has hosted "Late Show" for two decades but will do so only a bit longer, Dave unwinds from that day's taping while, more than once, he comments on his shake's deliciousness.

He also thinks today's show was excellent, a surprising appraisal from this famously self-critical star. Cher did a surprise walk-on. Martin Short brought down the house with his musical eulogy to Dave. Norah Jones sang "Don't Know Why," and everyone got misty.

"I wish tonight's show had been the last show," Letterman said. "Tonight should have been the last show. I don't know what we're gonna do for the next two weeks."

It isn't hard to detect, or understand, the simmering ambivalence in Dave's decision to take his leave after 33 years in late night and 22 years hosting CBS' "Late Show," on May 20.

But by now he's done it all. Letterman has carved a place in cultural history with his pioneering brand of postmodern silliness that collared "Late Night" fans on his arrival in 1982 and subsequently was absorbed into the Age of Irony he played a major role in charting. This legacy-in-the-making was long ago coined "Lettermanesque." But don't talk legacy with Dave. He swiftly raises his deflector shield.

"The real credit goes to the writers," he insists. "It was their show that I was doing, especially early on. And then I got to a point I knew how to do what they were wanting me to do.

"We had guys who had worked at the Harvard Lampoon!" he said, flashing a grin. "I attended university in Muncie, Indiana."

Now he's nearing the end of a record-breaking, surely never-to-be-matched run that exceeds even Johnny Carson's 30 years on "The Tonight Show."

"God, it's been 6,000 shows!" he said. "I used to have these conversations with (wife) Regina: 'How much longer can I do this? How much longer do I WANT to do this?'

"But it was so much fun tonight, just really fun," he said again. "I'm really, really torn. I know why I shouldn't be doing it anymore, but these last few months have been soooo easy."

No wonder. As the days count down, love for Dave is escalating. "With a simple retirement announcement, every day I'm Salesman of the Month."

Letterman's life was anything but easy in October 2009, when an extortion plot compelled him to acknowledge on the air he had been sexually involved with women on his staff. He weathered that storm, largely thanks to a candid and contrite accounting to his viewers.

"It was the worst time of my life. I remember just thinking, 'Oh my God, I've ruined my family,' and that became the only concern. And then: Oh, yeah, you could get fired!"

But on Dave's crisis meter, the scandal far exceeded his emergency quintuple bypass operation in January 2000.

"The heart surgery was fun! People would come and see me and bring me things. And the doctors were wonderful. Those people -- I mean, who does a job that well?"

Another miracle of medical science: An antidepressant he's been taking in recent years.

"It saved my life. I used to wonder how other people weren't always screaming and punching the Sheetrock. And then I started this, and I felt like, 'Ahhh, I see!' And now I don't punch Sheetrock and scream as much."

But nothing, no drug or elixir, can turn back the years.

"There's no cure to being 68," he sighs. So May 20 is closing night.

And then?

"I don't know what's gonna happen," he said, beyond more family time with Regina and their 11-year-old son, Harry. "I hope it will all be good. It's my responsibility to make it good. It's not like heart surgery: 'Could I get a little more morphine?"'

It's not as if he's glum. More like meditative: Where did all the years go?

Meanwhile, he's enjoying his shake and pleased with this day's work.

"If you see how wound up I am," he said, "it's because of the show tonight: Cher, Marty Short, Norah Jones! If the last show goes like that, I'll be like THIS. I hope the last show goes well, because that's what I will take with me. It will reflect nicely on the body of work."

And if it doesn't go so well? He grins: "I'm gonna be miserable for a long time."

EDITOR'S NOTE -- Frazier Moore is a national television columnist for The Associated Press. He can be reached at fmoore(at)ap.org and at http://www.twitter.com/tvfrazier. Past stories are available at http://bigstory.ap.org/content/frazier-moore

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