The Importance of Being David Letterman

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Ken Tucker
·Critic-at-Large, Yahoo Entertainment
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The long goodbye David Letterman has been making from The Late Show concludes Wednesday night. Over the past few weeks, many stars have filed out to express their dismay, respect, and love for the man, who squirms with real squirminess, understanding it would be rude to halt the praise but unable to fully accept it as truth.

That’s partly because Letterman was raised to comport himself with Midwestern humility and reticence, so displays of emotion make him uncomfortable. But it’s also because Letterman is a complicated show-business figure: compelled to seek the spotlight yet never convinced he deserves the attention, ashamed of his ego even as it requires care and feeding from audience and staff. And it is this complexity that helps explain why Letterman is the most important talk show host who’s ever read a joke off a cue-card. He’s the last man in front of the camera who carries the whole history of the genre in his head; he has both honored and messed with the tradition on a nightly basis.

Why and how? It’s worth explaining before Letterman does his disappearing act. 

Letterman was born early enough (1947) to appreciate a folksy radio host like Arthur Godfrey, an early hero, and he thoroughly absorbed the deconstructive self-consciousness that Steve Allen brought to his reign over the nascent Tonight Show from 1954-57. Where Allen once covered himself in tea bags and had himself dunked into a cup of hot water, Letterman would later bedeck himself with Alka Selzer tablets and lower himself into a giant glass of water for some fizzy fun.

To break into show biz, he went the Hollywood comedy-club route during the 1970s, and slid into television, doing game shows (The Gong Show; The $25,000 Pyramid), variety shows (he became buddies with Michael Keaton when the two were part of the ensemble of Mary Tyler Moore’s one-season singing-dancing bomb Mary), and sitcoms (a 1979 Mork and Mindy episode that actually required him to approximate acting). 

All the while, he was plotting his own talk style. He had little use for the naked emotionalism of the other great host of his childhood, Jack Paar (who Tonight-ed with wracked sobs from 1957-62). No, Letterman wanted to be like his fellow Midwestern-born exemplar, Johnny Carson, who had turned The Tonight Show into a well-oiled machine gleamingly efficient at both star-joshing and star-grooming. To do stand-up for King Carson was to be anointed a punch-line prince, and Letterman received the blessing after a sharp set in November 1978. Letterman gave off the right vibes, and ended up guest-hosting for Carson 20 times before NBC said, Hey, let’s give this smart-aleck his own show.

Unfortunately for Letterman, that show was in the morning, a time of day when viewers were unaccustomed to the sort of amiably ramshackle, anything-can-happen program Letterman devised. The David Letterman Show premiered in June 1980 and was canceled in October.

NBC and Carson, a strong ally, kept the comedian on retainer until 1982, when, on Feb. 1, Late Night With David Letterman premiered, slotted after The Tonight Show. This was, in the memories of many, Letterman’s golden era, with characters like faux-naif Larry “Bud” Melman (Calvert DeForest); staple segments such as “Stupid Pet/Human Tricks”; the early, far more absurdist Top 10 lists; and even a vertiginous episode broadcast upside down. Working with a shrewd, cutting writing team that included Merrill Markoe, Gerard Mulligan, Steve O’Donnell, Randy Cohen, and Jim Downey, Letterman was doing the most innovative, ironic comedy on the air. 

Letterman appreciated the nuttiness of Allen as filtered through Carson, but in his soul, he really identified with Carson’s control and, above all else, power, which on its most interesting and least harmful level meant the creation of a mystique of aloofness. Fundamentally insecure, shy, and guilty about his success (all traits of Carson as well), Letterman used his initial NBC late-night success as a way of accumulating a power that would occasionally lead him astray (three words: affairs with staffers) and more often manifested itself as a hearty enjoyment in seeing others squirm.

In 1993, when he lost the job he’d wanted most — succeeding Carson on The Tonight Show — to Jay Leno, it proved to be a blow that strengthened him. In making the move to CBS, Letterman threw off what the literary critic Harold Bloom would call “the anxiety of influence,” and, relieved of the Carson legacy, became his own sort of entertainer.

While much of his fame centered around the notion that he was rough-edged and didn’t put up with any show-biz guff from celebrities (you know the litany: Cher, Madonna, and Joaquin Phoenix, among others), Letterman was ultimately a good Midwestern boy, in thrall to the outreach of broadcast television and a constant, eloquent admirer of people who did their jobs well, whether they were famous (such as his friend Paul Newman) or obscure (the team that performed his quintuple-bypass heart surgery in 2000). It was this dichotomy — the rhino-skinned softie in tortoise-shell glasses and sneakers — that defined Letterman’s initial greatness as a TV personality.

Related: The 2 Times David Letterman Risked Blowing Up His Show

Irony and sarcasm characterized the first phase of Letterman’s career — no host had brandished these two weapons as skillfully: He revolutionized the format by lampooning it until it became something new. But Letterman’s barbed humor was also a defense. At his truest, he was a worrier, a fretful perfectionist. He avoided interviews, parties, even off-camera palaver with celebrities. 

Partly because Leno surged past him in the ratings after Leno’s 1995 “What the hell were you thinking?” Hugh Grant interview, and partly because he’d simply come to feel boxed in, tired of the format for a while, Letterman underwent a creative dry spell of depressive crisis in the late 1990s. “We know the show is tired; it’s the same crap night after night,” Letterman fairly roared one evening in September 1999, sitting at his desk. “But here’s the thing,” he said, turning to the camera with a grin whose twitchiness slid somewhere between arch playfulness and suicidal self-contempt: “We just don’t care.”

At least three events served to burn off that protective layer of cynical irony and compel him to enter the second phase of his career. His heart surgery in 2000; the 9/11 attacks in 2001 (he was the first network host to return to the air after that event, his perfectly measured broadcast an instant classic and a model for all others); and the birth of his son, Harry, in 2003, all brought out a sincerity, a fresh wonder at the world, that has informed his humor ever since. His comedy now breathed fresh oxygen; he seemed more comfortable in his own aging skin.

Letterman is crucial because he’s the bridge between the first generation of great late-night hosts (Allen, Paar, Carson, Dick Cavett) and the generation that followed (Conan O’Brien, Jimmy Kimmel, Jon Stewart, and, I’m hoping and betting, Stephen Colbert). 

He’s the most three-dimensional talk-show host ever — hell, he’s probably the most vividly revealed person who’s ever been on television. The sheer number of hours, combined with a compulsive honesty that trumps reticence, mean that he has exposed more moods and aspects of his personality than any human in front of a TV camera. 

No one other than Letterman has done it with the same combination of furthering historical precedence, extending the lineage, and attempting to unite a mass audience. Jimmy Fallon — who I didn’t include in the list above because he comes out of a different tradition, the SNL one — has spearheaded a successful, fundamental shift: to break the talk-show format into bite-sized bytes to be watched on your laptop, your phone, your watch, or — as soon as Apple gets around to it — on the inside of your closed eyelids. 

As a result, talk shows are no longer about gathering as big an audience as possible. That’s yet another reason, I suspect, Letterman has decided it’s time to let the kids take over the genre. After Wednesday night, Letterman effectively takes the talk show format as we’ve known it since the 1950s with him. 

What Letterman really needs Wednesday is the late Warren Zevon — his musical soulmate, his fellow survivor in fighting demons and raising hell — to sing him off to the tune of “My Ride’s Here.” 

David Letterman’s final Late Show airs Wednesday, May 20 at 11:35 p.m. on CBS.