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Letterman, Seriously: Dave’s 10 Most Profound Moments

Sex scandals, heart attacks, 9/11 — when Letterman dropped the funny business and things got real

Most people watch late-night talk shows to forget about their problems for a while. But during David Letterman’s reign, the real world occasionally imposed itself on his show in unpredictable ways. Usually, the results made for hilarious comedy — other times, however, it might prompt Dave to become enraged, philosophical, mournful or even profound. Below are 10 of the most memorable moments when the Late Show got compellingly real.

Dave Letterman

Letterman Responds to Bristol Palin Joke (June 10, 2009)

Irreverent and silly Dave may be, but his brand of humor has never been particularly vicious or hurtful. Still, the host angered people when he made a joke about the Palins' trip to New York in the summer of 2009, commenting that, "One awkward moment for Sarah Palin at the Yankee game: During the seventh inning, her daughter was knocked up by Alex Rodriguez." The politician shot back, accusing him of promoting child rape. (It was Palin's 14-year-old daughter Willow who was at the game — not 18-year-old Bristol, who had given birth in December 2008.) Dave responded to the controversy, acknowledging the joke was in poor taste but clarifying that he would never make light of having sex with an underage girl. "Look at my record, it has never happened," he said angrily. "I don't think it's funny, I would never think it's funny." Letterman invited the former Alaska governor to be on the show, but she never took him up on the offer.

David Letterman

Letterman’s ‘Hurricane Sandy’ Show (October 29, 2012)

As Hurricane Sandy was preparing to make landfall, the Late Show faced an unusual dilemma: The crew was at the Ed Sullivan Theater, but it wasn’t safe to have audience members. So how do they put on a show? The delightful answer was: Like it’s one big game of dress-up. With no crowd, Letterman, Paul Shaffer and his staff went about throwing together something very silly and barebones, bringing on true-trouper guest Denzel Washington to chat for a bit. When jokes bombed, the silence in the studio was a brilliant ironic counterpoint, and the whole enterprise a nice visual illustration of Dave’s self-deprecating wit. “I’m so sad that 500 people couldn’t be here to enjoy this,” he sarcastically lamented to Paul at one point. The whole thing felt like a brilliant meta-comedy throwback to his Late Night years.

David Letterman

Letterman Goes Off on John McCain (September 24, 2008)

Not someone who tends toward political comedy (he's a registered independent), Dave took the gloves off when Republican presidential hopeful John McCain bailed on the Late Show at the last minute, citing the need to return to Washington to focus on the mushrooming financial crisis. But when Letterman discovered that the candidate was instead prepping for an interview with CBS Evening News, the host ripped into him. "He doesn't seem to be racing to the airport," Letterman noted wryly, watching the live feed of McCain getting prepped to talk to anchor Katie Couric. What followed was a nicely surly smack-down: "This is not the way a tested hero behaves," Letterman said of McCain. "Somebody's putting something in his Metamucil."

David Letterman



Letterman Has Fun With Conan/Jay Situation

You may remember back in 1993 that, when NBC gave Jay Leno The Tonight Show, it sent Dave to CBS to be his direct competitor. But the network walked into a similar nightmare in 2009 when it installed Conan O’Brien as host of The Tonight Show; fearing they'd lose the popular Leno to a rival, they created The Jay Leno Show at 10pm and generated considerable tension between the two hosts. Safe in his CBS perch, Letterman had a ball over the melee, trashing his former bosses and laying into Jay “Big Jaw” Leno in delicious monologues over several days. But some of his meanest barbs were hurled at the little-seen and culturally irrelevant Last Call With Carson Daly, which airs after Late Night. "Having a show at 1:30 is almost exactly like not having a show," Letterman said with wicked snideness.

David Letterman



Letterman Gets Married (March 23, 2009)

Dave's never getting hitched again: That was the impression shared by most Letterman observers. After all, he'd been married once in his twenties, and he and his longtime girlfriend Regina Lasko seemed content not tying the knot. But on March 19, 2009 — after 23 years as a couple (and a five-year-old son, Harry) — the two married at a Montana courthouse. A few days later, Dave announced the news on the Late Show, looking pretty pleased but also a little terrified. Letterman told the audience, "People say, 'Geez, Dave, you were together so long — does it feel any different?'" Dave then paused, dramatically, for comedic effect. "And I say, 'Yeah.'" Long pause. "It does."

David Letterman



Warren Zevon’s Final Appearance on Letterman (October 30, 2002)

Enjoy every sandwich. In the summer of 2002, singer-songwriter (and frequent Letterman guest) Warren Zevon was diagnosed with lung cancer. Right before Halloween, Dave devoted an entire show to Zevon, doing a brief interview with the man and then having him play three songs that demonstrated his range: the prickly sentimentality of "Mutineer," the orchestral snarl of "Genius" and the oddball storytelling of "Roland the Headless Thompson Gunner." Zevon would be dead in less than a year, but his acerbic humanity remains: both in his music and in the temperament of a friend like the host, who clearly saw in the musician a kindred spirit. (Near the end of Late Show's run, singer-songwriters Amanda Shires and Jason Isbell feted Dave with their rootsy cover of "Mutineer," which clearly touched the host.)

David Letterman



Michael Richards Apologizes (November 20, 2006)

We've become accustomed to cringe comedy, but Emmy-winning Seinfeld star Michael Richards plunged into ugliness during a failed stand-up appearance in November 2006, which devolved into him hurling racial epithets at audience members. Days later, Jerry Seinfeld appeared on the Late Show, bringing on his longtime friend to apologize via satellite. It was a PR disaster: The inarticulate, flustered Richards rambled, acting not that much different than his daffy Kramer character, which prompted awkward giggles from the crowd. (Among the segment’s many low points is Seinfeld meekly chiding the audience for laughing.) Richards' career never really recovered, and both Letterman and his guest seemed relieved once the disgraced star's spot was over.

David Letterman



Letterman Admits to Sex Scandal (October 1, 2009)

Sometimes when Letterman has to speak candidly to his audience, he finds just the right balance between seriousness and humor. But in 2009 when he discussed with the world a blackmail plot involving secret sexual relationships he'd had with female staff members, he initially stumbled with the tone. "I have a story to tell," he said from his desk. "Would you like to hear a story?" The audience cheered, figuring they were going to be treated to an amusing tale. Only slowly did it become apparent that the details of Dave's story weren't funny: a package of incriminating material, a demand for $2 million, a threat to expose all of Letterman's past sins. As the crowd's laughter grew increasingly more awkward, the host finally admitted his infidelity. The whole incident shown light on the private life of a man who prefers keeping all of that out of sight. "I think [CBS] would have had good reason to fire me," Letterman told the New York Times last week about his sex scandal. "But at the time, I was largely ignorant as to what, really, I had done."

David Letterman

Letterman Returns From Heart Surgery (February 21, 2000)

Dave had long feared that the heart problems that plagued his father — he died of a heart attack at 57 — would claim him as well. At 52, Letterman faced that terror head-on when he went in for quintuple-bypass surgery, which meant taking a break from the Late Show for more than a month. When he returned for his first night back, he made plenty of jokes about his situation, but it was also evident how much the experience had affected him. With typical Letterman-esque flourish, he cheekily brought out the medical team that operated on him, but his usual bite melted away when he told his studio audience, “It was five weeks ago today that these men and women saved my life.” Hearing himself say those words, Dave got teary-eyed, a rare, touching sign of the smart aleck’s charming vulnerability.

David Letterman

Letterman’s First Show After 9/11 (September 17, 2001)

Before the terrorist attacks on Washington and New York on September 11, 2001, we didn’t think of Letterman as any sort of national spokesman. (He’s too irreverent, too self-effacing, to take such a role seriously.) That changed six days after 9/11 when Dave returned to his show, still clearly stricken by what had happened. (“I remember not wanting to go back, not feeling ready to go back, but knowing we had to go back,” Letterman said in 2012.) That first show remains one of his finest hours, precisely because he’s struggling to find words for a tragedy that none of us could quite fathom at that moment. And yet, his extemporaneous comments captured the national mood in all its grief and bruised resolve.

Visibly trying to maintain his composure, Dave talks about dead firemen and policemen, the madness of religious zealotry, and the struggle to be courageous in the face of uncertain times. And then, he tells a beautiful story about Choteau, Montana — the same small town where he and his wife Regina would get married eight years later — that was going through a crippling economic downturn but still raised money for New York. “If that doesn’t tell you everything you need to know about the spirit of the United States, then I can’t help you, I’m sorry,” Dave said. The night transcended great television. For a guy who tends to diminish his own achievements, Letterman delivered a broadcast the country needed.