'Late Shift' Author Bill Carter Pens David Letterman Tribute: Laughs, Legacy and Leno

Courtesy of Photofest
Letterman in 1982, launching 'Late Night With David Letterman' on NBC.

Writing for THR, the former New York Times writer and author of 'The Late Shift' assesses the complications — and legacy — of the brilliant, gap-toothed comic, who is signing off from 'Late Show' on May 20.

This story first appeared in the May 22 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

If you were to synthesize all that has happened in recent years in the late-night arena into one epic inside-TV version of Game of Thrones — in this case, Game of Desk Chairs — the central figure, the comic hero, would be a man whose reign has stretched over three decades, two networks and countless moments of original, memorable comedy as well as personal, unusually intimate on-air revelations.

David Letterman, who will end his 33-year run May 20, has been a compelling, complex presence in American culture since two familiar Jimmys were in braces and another was in the White House. "Letterman is, by any standard, a landmark performer," says Howard Stringer, the executive who brought the comic to CBS in 1993 and put him up in a landmark building on Broadway.

In the fashion of landmarks, something truly groundbreaking took place when Letterman got his hands on the traditional talk-show format in 1982. He spun it on its head, removed the sheen of showbiz slickness Johnny Carson had perfected and in its place inserted irony, parody and a touch of anarchy. Interviews could be fractious (Cher called him an asshole); comedy could be based in "found humor" (Dave going through strangers' vacation pictures at a Fotomat); visuals could be deliberately unhinged (the famed Monkey-Cam).

"With Johnny, you watched because you were being allowed into the sophisticated world of show business, which was polished, elegant and cool," says Rob Burnett, Letterman's longtime producer. "With Dave, it was a brilliantly funny clubhouse."

Letterman did not deserve all the credit. "Merrill Markoe, Steve O'Donnell and some others had a big hand in it," says Burnett, referencing the two original head writers — and, in the case of Markoe, Letterman's decadelong life partner. But Letterman's sensibility was the dominant force. He pushed writers and producers for new ideas, often to the point of exhaustion and exasperation. Markoe described to me how she would present idea after idea that Dave rejected and then would live in fear of his failing with the one bit he had agreed to try — only to see him slay audiences night after night.

Drew Barrymore after flashing Letterman — it was Dave's birthday — during an infamous 1995 taping of CBS' Late Show.

I have seen thousands of David Letterman shows, beginning with his awkward weeks as host of a morning program on NBC. That summer, 1980, a friend was confined to a hospital bed and miserable. I recommended she tune in to this odd new host at 10 a.m. She was instantly enthralled — and feeling better. A year later, when Dave was between NBC shows, I saw him doing stand-up at The Comedy Store in L.A. He electrified the crowd.

I interviewed Letterman for the first time when I was reporting my book The Late Shift in 1993. He was then, and has remained, the most reliably great interview subject I can remember. I met him in his office at the Ed Sullivan Theater. We were scheduled to chat for an hour; we went for five. He held nothing back, offering opinions on comedy, on NBC and CBS, on his rival Jay Leno, on himself. Dave spoke about Jay with great respect for his stand-up talent, but he didn't see Jay as a "friend," as was generally assumed at the time. Jay was too wrapped up in his career, and Letterman never accepted him at face value: Jay always seemed to be running some scheme, as Letterman saw it.

By then, I had heard from his staff about his bouts of insecurity bordering on self-loathing, the episodes of tearing up his office after disappointing performances. The self-flagellation seemed incomprehensible given his talent, but the inability to achieve satisfaction was as much a part of Letterman's makeup as his quicksilver wit. I sent him and Jay copies of The Late Shift just prior to release. Jay made a gracious and funny phone call after reading the book. I never knew if Dave read it (probably not), but he sent a lovely note wishing me good luck with it.

The uncompromising approach often did damage — mainly to himself. Dave mocked NBC executives and once kicked two of them out of a show anniversary party, a decision that came back to haunt him in negotiations for The Tonight Show. He initially feuded with his CBS boss, Leslie Moonves, often dwelling on how the executive once questioned Letterman: "Do you have a problem with me?" Moonves took pains to repair the relationship and later gained Letterman's trust. But to the end, Dave did his own thing. He resisted Moonves' request to take part in the May 4 primetime retrospective special. CBS did one anyway — the news division produced it.

For some, Dave dwelled too long on the might-have-been, never fully getting over not being allowed to succeed his idol, Carson. He told the same joke every spring: Passover is a Jewish feast — but also what happened to him at NBC.

Carson, Letterman's idol, made an appearance on Late Night With David Letterman in 1985.

In the aftermath of his only major performance outside of his show, hosting the 1995 Oscars, Dave lashed himself mercilessly for what he saw as bombing. The reviews indeed had been bad (though the ratings were excellent), mainly because Letterman had been Letterman, not doing a show that sucked up to Hollywood.

That irascibility, the high expectations, left many guests quivering before they went on the show. The counter was that if Dave told a guest he enjoyed their film/show/album, they knew it was not another meaningless compliment from a host who "liked" everything.

Letterman abhorred phoniness. Veterans of his shows come up with the same word to describe what made him stand out: authenticity. That word covered his extraordinary directness when speaking on air about everything from the horrors of the 9/11 attacks to speeding tickets, the woman who stalked him for years, his heart bypass surgery, his joy at having a son late in life — even the sex scandal he owned up to on air, rather than give in to blackmail.

The on-air Letterman had "friendships" with other celebrities; he rarely saw them anywhere else. When Billy Crystal appeared for the last time, during a farewell parade of "friends of the show," he sang a funny, touching song about Dave. But he hit a telling note when he said, "You're my best friend on television." On television.

I saw Dave in later years mainly at group events like NBC's farewell party for Tom Brokaw. He was always receptive and amiable, if not exactly friendly. I never heard him offer a single complaint about any story I wrote, though of course he hated the red wig that got stuck on John Michael Higgins' head in the HBO version of my book. I disavow responsibility for that (though I think Higgins' performance far surpassed the wig in terms of accuracy).

The bulk of Dave's life was defined by a daily routine of scripted laughs and formalized conversations. That is about to change. Associates wonder what it will mean for someone who, at numerous points in his life, conceded he was happy only during the one hour a day when he was taping his show. The birth of son Harry, now 11, clearly added much joy and seemed to mellow Letterman in ways that surprised people.

Colbert, future host of Late Show, during an appearance in April 2014.

Moonves has given him an office inside Black Rock, CBS' New York headquarters, but it is hard to picture Letterman hanging around a towering office building with nothing specific to do. "I hope he finds another outlet," says Burnett. "I believe he still has things to say."

Carson, of course, never really performed again. Leno keeps popping up here and there: on CNBC, online, on James Corden's first episode of The Late Late Show on CBS.

What's left for Letterman is the legacy. That amounts to influence over an army of comic progeny. His wry, ironic sensibility — and delivery — has been the inspiration for countless comedians, movies and even commercials.

The most literal legacy is a late-night franchise. Before Letterman signed on, no late-night show anywhere but NBC had established a foothold strong enough to continue through successive hosts. CBS will have Late Show With Stephen Colbert in the fall — would that be the case if anyone but Letterman had secured that beachhead?

Howard Stringer doesn't think so. He started the succession drama in 1991 when he quietly pursued Leno. Leno famously conquered Letterman in the ratings for most of their mutual run — but he had the Tonight franchise behind him. Could he have done the same at CBS? "I don't think we would have succeeded with Jay at 11:30," says Stringer. "You needed someone of Letterman's individual brilliance."

Bill Carter has covered television for more than 40 years, including from 1989 to 2014 for The New York Times.