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With David Letterman's announcement that he plans to step down in about a year, Globe television writer Andrew Ryan picks ten of his favourite Letterman moments. From Bill Murray to Crispin Glover to Oprah Winfrey to Lindsay Lohan, Letterman's almost never at a disadvantage ...

February 1, 1982: Bill Murray

Dave kicks off Late Night with David Letterman
Who was this sassy young man with the bowl haircut and gap between his teeth? The very first episode of Dave’s NBC late-night show was an odd collection of cringeworthy network hype (Dave’s entrance was accompanied by “the Peacock Girls,” a troupe of female dancers) and irreverent weirdness. First guest Bill Murray wore a cardigan and threw false accusations at the rookie host in a prearranged comedy sketch. Murray also expressed a newfound love of aerobics and knocked out a shambling version of the Olivia Newton-John hit Physical. Suddenly viewers had reason to stay up after midnight. 

July 28, 1987: Crispin Glover

Dave nearly gets kicked in the head by Crispin Glover
In one of the few shocking moments on Late Night, the quirky actor Crispin Glover showed up to promote his film River’s Edge. Wearing a wig and platform shoes, Glover rambled off-topic during the interview and behaved belligerently towards Letterman, going so far as to challenge him to an arm-wrestling contest. At meltdown point, Glover declared, “I’m strong, I can kick,” and executed an impromptu karate kick that very nearly landed on Dave’s head. Dave pulled the plug by walking off stage and telling the audience, “I’m going to check on the Top 10,” as the network cut to a commercial. Glover later apologized for his bad behaviour and was allowed to sit down with Dave on three more occasions. 

September 17, 2001: Dave’s first post-9/11 show

Dave’s first new episode following the horrific 9/11 terrorist attack was powerful, moving television. In his patently patient, folksy manner, Letterman eased the viewing audience back to some sort of normalcy in a long opening segment, in which he supplied a succinct précis of the attack on the Twin Towers. In his words: “We’re told that they were zealots fueled by religious fervor…and if you live to be a thousand years old, will that make any sense to you?” Dave helped America heal. 

October 30, 2002: Dave fetes the late Warren Zevon

At Dave’s behest, the entire episode of Late Show was devoted to frequent guest and close friend Warren Zevon, already stricken with mesothelioma at that point. A shaky Zevon came out and revealed his terminal diagnosis in a moving interview with Letterman, who gently asked the questions that needed to be asked. Zevon performed on the show and presented Letterman with the guitar he always played on the show. Zevon also gave Dave the sage life-maxim: “Enjoy every sandwich.” Eleven months later, he was dead. 

January 31, 2005: Dave eulogizes the late Johnny Carson

The passing of the man who invented the late-night talk format obviously rattled Dave: Carson had been his talk-show mentor and Letterman had been groomed to take over The Tonight Show before Jay Leno swooped in and took the job. Dave delivered a fittingly respectful tribute to the man who launched his career, and acknowledged Carson’s place in TV history. “At the end of the day, that’s who you wanted to be there,” he said of Carson. Which is not unlike the way many viewers felt about Letterman. 

December 1, 2005: Dave kisses and makes up with Oprah

After years of making fun of Oprah Winfrey, and countless rumours that Oprah didn’t like him one bit, Dave arranged for a TV rapprochement under the banner title “The Super Bowl of Love.” The culmination was Oprah’s appearance on The Late Show to put an end to a feud that never really was. On his best behaviour, Dave said Oprah was “the most beloved woman in America – despite the fact she gave us Dr. Phil.”

October 1, 2009: The confession

Dave admits to having affairs with female staffers
You could hear a pin drop in the Ed Sullivan Theatre as a contrite Letterman made the stunning admission that he had participated in multiple affairs with women working on his show. Dave’s mea culpa came with a long, and actually pretty funny, story about an extortion plot by a man threatening to reveal his affairs to the public. Shrewdly, Dave beat him to the punch. 

April 10, 2013: Dave makes Lindsay Lohan cry

Lindsay Lohan fulfilled her contractual obligations by showing up on The Late Show to plug her role in Scary Movie 5, but she probably regretted it. Letterman admitted that he had probably gone overboard in skewering the troubled actress in his nightly monologue, then he went all the way off-script (“We didn’t discuss this in the pre-interview,” mewled Lohan) by asking the troubled star about her addictions and personal problems. When Dave told her, “We never thought we’d see you again honestly, because of the jokes and stuff, and yet you have enough spine, enough sense of yourself, enough poise to come out and talk to me,” tears of gratitude welled up in Lohan’s eyes. Viewers, too, most likely. 

Sept. 28, 2007:Dave ridicules Paris Hilton

In the wake of her sex tape and short jail stint, heiress and reality star Paris Hilton foolishly thought she was booked on The Late Show to talk about her new fragrance line. Dave set the tone by asking, “How did you find your time in jail?” And then stayed on the subject by asking Hilton about prison food and whether she lost weight while behind bars. After a few minutes, Hilton declared, “I’m not answering any more questions about it. I’m here for my clothing line, my movie and my perfume.” Cheeky Dave countered with, “How did you like jail?” To which Hilton replied frostily, “Not so much.”

April 12, 1995: Dave gets flashed by Drew Barrymore

What do you get a late-night talk host about to turn 50? In a famous Late Show appearance, actress Drew Barrymore climbed atop the host’s desk to perform an impromptu dance and briefly bare her breasts (with her back to the camera). Dave didn’t seem to mind one bit and remembered the moment fondly years later in an interview: “It was lovely,” he said. “And it’s still something I think about and tell my friends.”

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