David Letterman's 33-year journey from cult hero to late-night institution

By Robert LloydTelevision Critic

May 15, 2015 12 PM PT

Los Angeles Times Television Critic

All things change, and everything ends, and after Wednesday we will no longer be living in a world in which David Letterman is on television five nights a week.

The alarm is about to ring on the clock Letterman set ticking just over a year ago, when, nine days shy of his 67th birthday, with a long preamble about trying to identify an eagle, he announced his retirement from CBS’ “Late Show With David Letterman.”

“You can’t help but think about the passage of time,” he said then. “It happens to all of us; it’s the way of life.”

Full coverage: David Letterman retires

After 33 years, he will go out as the longest-serving host in late-night TV — outdistancing his mentor Johnny Carson by two years — a record that will not be challenged any time soon, if ever. Try to imagine Jimmy Fallon doing “The Tonight Show” at 68, and you will fail. (Jimmy Kimmel I can see hanging on, maybe.)

Although the shadow of his leaving has stretched across the year, over the last few weeks things have become positively valedictory as guests arrive for what most can’t help but mentioning will be their last visit to “Letterman.”

Tears have been demurely shed. In a monthlong receiving line, respect is being paid — by the president and the first lady, by Howard Stern and Bill Clinton, Oprah Winfrey and Julia Roberts, Steve Martin and Martin Short. Some come with songs, some with pictures. Everyone has a story about what Dave has meant to them, to comedy, to the late 20th and early 21st centuries. Tina Fey, in honor of “my last time wearing a fancy dress on a talk show and conforming to gender norms out of respect” for Letterman, gave him the dress off her back.

Paul Shaffer, Letterman’s band-leading sidekick since night one, plays them on and plays them off. (He too is on the way out.) The host more or less accepts these tributes — he lets them proceed, anyway — before falling back to a familiar stance of self-deprecation: “This is like buying produce off a prison truck” is how he described his show to Amy Schumer. (“I don’t know if you excel at metaphors anymore, Dave,” said Schumer.)

Letterman was in his early 30s when he set off along this road, which led from a short-lived daytime show on NBC in 1980, to “Late Night With David Letterman” on the same network in 1982, to his present and soon-to-be former post, taken up in 1993. That he wound up on CBS instead of hosting “The Tonight Show” is the stuff of television legend, a whole book, a TV movie based on the book and jokes made by Letterman at Jay Leno’s expense, every so often, ever since.

And yet in the end — long before the end — it was clear that, however magically glamorous the “Tonight Show” brand, where he landed was the place he belonged. In “Late Night,” he had created something new, rooted in Carson but forged in the more intimate and experimental reaches of deep post-prime-time. Surreal, sardonic, mock formal, markedly goofball, it thrived on contradiction and self-critical self-awareness. He carried that over to “Late Show,” where he made its audience into a community and its crew into characters; it took its cameras out through the doors of the Ed Sullivan Theater and into the streets and small businesses of Midtown Manhattan. (Hello, Hello Deli.)

Its big-kids crazy clubhouse mood was adopted by Conan O’Brien, who replaced Letterman on NBC, and Jimmy Fallon, who replaced O’Brien at “Late Night” and then Leno on “The Tonight Show” — if only by proxy, and after a long delay, Letterman left his mark on the House that Johnny Built and Jay Lived In.

New generations have moved in behind the desks and into the crowd, changing the shape of late-night itself. Irony is losing its allure. (It is used only ironically now.) Fun is just fun. But a certain seriousness — especially given the retirement of Craig Ferguson, whose “Late Late Show” Letterman’s company produced — has gone out of the field.

Letterman himself has meant different things at different times; he has been himself, always, but he has not been static. Some of this has to do with economies of age — you get slower, you get smarter. Time turns tenancy into ownership, makes an institution out of a cult figure. Raised above his guests like the emperor he is — Jerry Seinfeld got him to switch seats on his last visit to see how that felt — Letterman has been unflappable, except when getting flapped might pay a comic dividend. He is funny with the very funny and with the very unfunny.

It’s true that after more than 6,000 nights on the air — processing, as Seinfeld put it on his own last “Letterman” show, “every moron with something to sell” — Letterman can run the show on autopilot, throwing in a “sure” or “fair enough” every so often to push the talk along. He has not always bothered or been able to hide his occasional disengagement. Yet by the same token, with the right person, with something more than something to sell, or something he wanted to go after or prize out, he is the most present, intelligent, interested and interesting of interviewers. He can be a terrier, a shark. “A lot of guests, world leaders in particular,” he told Tony Blair, “are here once and don’t come back.”

A highly private person, he has at times been required to violate his own privacy; a shy guy, he comes alive in a public hour. He’s an upright sort, a moralist even, who has done some bad things. His habit of greeting female guests with remarks about their clothes, hair, legs or smell, with hugs or hand-kissing, make a cool uncle momentarily a creepy one. (It’s the thing that makes him seem most out of time and out of touch.) But then he changes back again.

In 2013, he told Charlie Rose that guilt and a fear of failure were “the two great motivators in my life — and I hate it when people started talking about ‘the two great motivators in my life.’” This year he told Rolling Stone that for 30 or 40 years he was “anxious, and hypochondriacal, and an alcoholic, and many, many other things that made me different from other people.” And yet, his obviously complicated inner life, evident even without details, has made him seem all the more human — and paradoxically the most reliable of hosts.

We trust the man who doubts himself more than the one who pretends that everything is fine.

Letterman has been a late-night talk show host through five presidential administrations and many widths of lapels and fashions in ties. The Berlin Wall came down on his watch; at least a couple of Middle East wars were launched. He has had a heart attack; he has had a child.

He has been through some rough patches — the health, the sex-with-staffers scandal, the plot to kidnap his son — and come out burnished. He says “God bless you” a lot, however he means it. He likes to talk to guests about their children, possibly because it gives him a chance to talk about his son. He worries about the world, one would guess, on his behalf.

Some of us have grown up on him; some have grown gray with him. He leaves a hole shaped like a lifetime.

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