Lisa DeMoraes TV badge vertical“Everything he did seemed wrong. He didn’t look right. His manner, his affect, everything seemed wrong because he was so profoundly original.” That’s Conan O’Brien talking about David Letterman, the gap-toothed Indiana weathercaster who went on to become the longest-serving late-night talk show host in TV history, ending his run this week at more than three decades. Letterman’s final announced guest, for tonight’s night’s penultimate broadcast, is Bill Murray, who, not coincidentally also was his very first broadcast TV late night guest, making good on this threat made back on that Late Night unveiling in February of 1982, to “make every second of your life from this moment on a living hell.”

Letterman’s credited with turning late-night TV into a super-smart showcase of stupid, catering to increasingly elusive young viewers, ushering in the era of viral videos, and celebrities willing to play games as the price of hanging with the cool kid. “I couldn’t get a show now,” Letterman said recently of the daypart, going to his famous dark place.

“He was for me and I think for many comics of my generation, an incredible epiphany of how a talk show or entertainment — for god sakes, the man put a camera on a monkey!” Jon Stewart said days ago in his The Daily Show tribute to CBS’ Late Show host.  “It seems so simple now but back then it was mind blowing. I fell in love with the joy they brought. There are so few people who can innovate that format, and then to have that kind of longevity…The list is: Dave”:

“My behavior was aberrant,” Letterman said more simply over the weekend, describing his style, in an interview with fellow Indiana native Jane Pauley for CBS Sunday Morning:

In the long walk-up to Letterman’s final night tomorrow, there’s maybe nobody who hasn’t heard the story of how he broke into TV in Indiana, doing local weather and a late-night show called Freeze-Dried Movies. Pauley said his program was great. Letterman, however, once described it as “like robbing 7-11’s. The money’s good but you know you’re going to get caught,” according to Pauley.

Letterman — who has said he carved out a broadcast career after giving an impromptu two-minute speech about himself in a high school public-speaking class and realizing, “Wow, THAT was easy!” – was a made man after he moved to Los Angeles, knocked around on the game show and comedy club circuit, and got the call to appear on NBC’s Tonight Show Starring Johnny Carson.

“It’s white-hot adrenalin,” Letterman describes his first Tonight Show set. “Then you go and you sit and you talk to Johnny and it’s like you’re sitting on the knee of the Lincoln Memorial and Lincoln is talking to you.”

NBC gave him a daytime talk show. It debuted on June 23, 1980, was cut from 90 minutes to 60 in August, and canceled in October. “I just didn’t see the housewives diggin’ you at 9 AM,” Tom Hanks admitted to Letterman on this past Monday’s show, in re that short-lived daytime program. Letterman, meanwhile, had described that show as “like standing on an overpass looking at a chain-reaction collision. OK! Nine cars, 10 cars – oh, look – it’s 100 cars! It couldn’t have been more poisonous. They had to get away from it.”

Instead of sacking him, NBC gave him a show called Late Night, after Carson’s, that debuted on February 1, 1982 with Bill Murray as his first guest:

There he developed a following with Stupid Pet Tricks, Top 10 Lists, and particularly his take-no-prisoners interview style. All of Hollywood’s “cool kids” wanted to hang out with him, because of/in spite of his cynicism about celebrity. “He was so not about show business, and so outside of show business, and his show felt like a revolution,” Conan explained recently to Charlie Rose:

When Carson retired, NBC gave Tonight to Jay Leno instead of presumed heir Letterman, triggering an inter-network dust-up that HBO would turn into an Emmy-nominated TV movie The Late Shift, based on the best-selling book of the same name, which Letterman called the “the biggest waste of film since my wedding photos,” saying actor John Michael Higgins portrayed him as a “psychotic chimp.”

CBS, a relative non-player in late night, having foisted such product on the American viewing public as a Pat Sajak late-night talk show and Crimetime After Primetime, snagged Dave, who recently noted, any enormous uprooting change in my life has petrified me…really petrified me. But once I have come through the other side the reward has been unimaginable.Sentimentally, he had Murray back as his first guest again; Tom Brokaw also made an appearance, to take back a couple gags he said were the intellectual property of NBC. His first reading at CBS of his Top 10 List was electric, given reports of a battle between the two networks as to whether Dave owned that bit, or NBC. The first show attracted an average of 23 million viewers:

During his early CBS years, Letterman’s antics often made headlines. And you can’t swing a dead cat without hitting someone who wants to remind you about that time, in 1995, when Drew Barrymore flashed her breasts at Letterman to celebrate his birthday/keep all eyes on her.

But, as Jon Stewart noted in his Moment of Zen Letterman send-off last week, it’s not about the Stupid Pet Tricks, or Drew Barrymore’s flashing tits. “At the core of it, David Letterman is an American wit. He has an authentic, witty mind… For everyone in my generation, David Letterman was, and is, the gold standard”:

Frequent guest Julia Roberts, admires another quality about Letterman, recently confiding her reluctance to guest on his show when she was promoting Mystic Pizza, because, she told Dave, “I had seen you absolutely dismember young actresses” of a certain IQ, and assumed she would meet with the same fate.

“I’m not going to dispute this, but what do you suppose was wrong with me?” Letterman said. “Why would I behave that way?”

“I think stupid people annoy you,” she observed, accurately:

Same goes for politicians who stand up Dave. Nobody knows that better than FOS Sen. John McCain, who’d announced his candidacy on the program in ’07, but canceled a scheduled appearance at the last minute, on September 24, 2008, telling Letterman he had to fly back to Washington for an important vote on an economic bailout. Letterman explained the last-minute guest change to his studio audience and Keith Olbermann stepped in. But, mid-taping, Dave learned McCain was down the street, about to tape an interview with CBS’ evening newscaster Katie Couric. John McCain David LettermanLetterman showed his studio audience, and viewers at home that night, the raw feed of McCain having makeup applied to his face as he got ready to chat with Couric, and eviscerated the senator on air. “First of all, the road to the White House runs right through me!” Letterman snarked as viewers watched a makeup artist apply late-minute touch-ups on McCain’s face. Letterman ran the Couric interview taping as it was going out on the in-house feed, while shouting questions at the monitor: “Hey, John, I got a question — You need a ride to the airport?!” Letterman did not let up on McCain for weeks, until the senator finally appeared on the show to eat crow:

But Letterman can also be comforting. He was the first late-night comic to go back on the air after September 11 attacks on the World Trade Towers and the Pentagon, delivering an eight-minute opening monologue that made it okay for TV viewers to laugh again and for all the other late-night hosts to get back to work. “We needed someone,” Jimmy Fallon said, describing the scene in the city back then. “The city was in shock and we were all looking for answers. We all wanted to see what Dave had to say and we looked to him to say something.”

When his frequent guest, friend and sometimes Paul Shaffer fill-in Warren Zevon was diagnosed with terminal lung cancer, Letterman devoted his entire program to Zevon on October 30, 2002, to ask him what he’s learned about life and death. “I may have made a tactical error in not going to a physician for 20 years,” Zevon said, calling Letterman “the best friend my music’s ever had.” Zevon died less than a year later:

More than five years before TV newsmen Brian Williams and George Stephanopoulos exacerbated inadvertent career self-immolation with botched on-air apologies, Letterman delivered a master class on How To Perform TV Mea Culpa  (No. 1: it helps a lot to have a live studio audience) with what remains for many, the most riveting night of late-night in the history of TV.

That night, in early October 2009, Letterman surprised his studio audience when, coming back from commercial break after his opening monologue, he started telling them “a story” about having been the victim of a recent extortion attempt. Dave told his somewhat baffled crowd — after all, they thought they’d come to see a comedy show — that three weeks ago he had received a letter from a man threatening to write a screenplay about “everything terrible thing you’ve ever done in your life.”

“He’s going to take all the terrible stuff he knows about my life…and he’s going to put it into a movie unless I give him some money,” Davie said. His studio audience guffawed.

“I want to reiterate how terrifying this is…I’m motivated by nothing but guilt — I’m a towering mass of Lutheran Midwestern guilt,” Dave continued.

The crowd applauded its approval.

“Now of course we get to what was all the ‘creepy’ stuff,” Dave continued. His audience tittered.

“And the creepy stuff was I have had sex with women who work for me on this show. Now my response to that is: ‘Yes I have’.”

The studio crowd erupted in gales of laughter.

I have had sex with women who work on this show.”

Thunderous applause:

Over the years, Barrymore was not the only guest to turn a Letterman visit into a viral moment for themselves. Dave recently played Tina Fey’s straight man and, in return, got his name printed on her belly, though the more important Twitter handle #LastDressEver emblazoned on her butt, made no mention of Dave. Less than two weeks later, that viral video is closing in on 16 million views:

But Fey already had delivered what remains the best Letterman tribute ever, back in 2012, when he was being feted with a Kennedy Center Honor, broadcast on CBS, in which she named him “professor emeritus at the Here’s Some More Rope Institute”:

Speaking of CBS: in marked contrast to NBC when it was saying so-long to Carson, pushing Letterman out the door, pushing Conan out the door, or pushing Leno out the door – twice – CBS has shown TV viewers how to do this right. Among other things, Letterman got to pick his end date; CBS CEO Leslie Moonves having said he was not going to be the guy who told David Letterman when to bow out. Letterman, in turn, gave Moonves a few minutes’ notice, on April 3, 2014, that he was going to announce it on his show:

Back in 1995, when Letterman, moved to CBS, appeared on the final night of canceled The Jon Stewart Show, a depressed Stewart had asked Letterman, hypothetically, “Let’s say you decided to stop doing your show. I know there’s plenty you would miss. I need to hear what you WOULDN’T miss at all – what you wouldn’t care to ever see again about doing your show, so I have something to think about.”

‘What have you heard about me stopping doing the show,” Letterman joked. Then, he offered, “Sometime what you love the most also provides you with the most pain,” adding, “I’m kinda getting tired of reading about myself.”