David Letterman Leaves Us, Laughing

9 minute read

Would he leave us laughing or crying?

The David Letterman who crashed late night on NBC in 1982 was hilarious, but not exactly the sentimental type. (A 1986 Viewer Mail segment ended with him being dragged off by the cops for indecency after trying to refute a viewer who said “you don’t have a romantic bone in your body.”) In his later CBS years, he learned to open up—about his heart surgery, 9/11, becoming a father. But there was always that reserve, that distance, that resistance to being self-serious.

So Wednesday night, his last as a TV host after three and a half decades, the man who introduced TV to a new kind of comedy show left us with … a comedy show. Letterman’s last Late Show was nostalgic but not maudlin, gracious but not mournful, valedictory but not a eulogy. Letterman’s last minutes behind the desk were as heavy on the laughs as on the thank-yous, an hour-plus of an entertainer being an entertainer and enjoying it. It was true to Dave, it was fun and it was terrific.

And why not? Letterman was leaving on his own timetable, not being defenestrated by the network. He remade his art and his business. He got to spend more than three decades of his career doing more or less what the hell he wanted on national TV and left widely acknowledged as the best at what he did (whatever his ratings). Sure, goodbye is sad, but then again—as he said in sheepishly acknowledging the effusive, lugubrious praise of the past weeks—”Save a little for my funeral.”

So the night kicked off with typical self-effacement, as well as by-special-celebrity-guests-effacement. After a clip of President Gerald Ford saying (after Nixon’s resignation) “Our long national nightmare is over,” Presidents George H.W. Bush, Bill Clinton, George W. Bush and Barack Obama repeated the line at Letterman.

He took the stage with a brisk monologue including one last joke at the disappointment he could never stop picking at: “It’s beginning to look like I’m not going to get the Tonight Show!” Stephen Hawking, he said, called to say he’d crunched the numbers on Letterman’s more than 6,000 shows and said, “it works out to about eight minutes of laughter.” And the night’s classic-quality Top Ten list (Things I’ve Always Wanted to Say to Dave), delivered by frequent guests, was like a mini-celebrity roast, with Julia Louis-Dreyfus, in the presence of Jerry Seinfeld, saying, “Thanks for letting me take part in another hugely disappointing series finale!”

Trust Letterman to deflate showbiz hyperbole and cheerfully let some of the air out of the own celebratory float we’ve been parading around for him. The bulk of the middle of the show was a look back at his career, but it felt less like an In Memoriam than a highlight reel assembled by a man who was simply damn proud of the work he and his crew had done.

The sweetest of the prepared reels was devoted to a day behind the scenes at Late Show: polishing and pitching jokes, riffing one-liners over White House Correspondents Dinner footage, dealing with the million small details of the daily production. What came across wasn’t grieving but pride in the machine that Worldwide Pants had built over the years, and the comedy force that began with Letterman and Merrill Markoe’s bizarrely brilliant daytime show in 1980 (generously highlighted in the clip reels).

At one point in the backstage film, the camera stopped on Paul Shaffer, with a droll observation about what it’s like to be the boss: “There’s a parade of people coming and they all say the same thing: ‘Dave, I know you hate this.’ And then they go on to do what he hates.”

It was in the last segment, as the episode ran into overtime, that Letterman unleashed his emotion, settling in for one of the “desk talks” that have been the highlights of his second great period at CBS. But characteristically, his sentiment was fond, not wistful.

He remembered touring the Ed Sullivan Theater before moving to CBS: “It was a dump… crawling with rats—big rats.” He thanked CBS President Les Moonves and Biff Henderson, the gang in the control room—”Let’s keep it to three drinks tonight!”—and his writers. He thanked, of course, Paul and the band. And he thanked—with the kind of personal touch he’s been showing in his later days—his son Harry and his wife Regina, while giving a shout-out to Harry’s friend Tommy. (The closing image of the show was a home video of Harry skiing.)

Were his eyes a touch pink? Maybe, but his voice was steady. He seemed to feel good—in the zone—knowing, maybe, that he’d just put on a good hour of TV. His last minutes on the air were like his favorite song, “Everlong,” which the Foo Fighters played over hundreds of stills from Letterman history: emotional but driving, ever letting up, hurtling forward to the end. Until simply, steadily, honestly: “All right, that’s pretty much all I got. The only thing I have left to do, for the last time on a television program: Thank you and good night.”

David Letterman, our host, our comedy uncle, our after-hours pal, delivered the laughs one more time. I would have to supply the tears myself. Sorry, Dave. I know you hate this.

Paul Shaffer

The colorful Canadian bandleader was really two sidekicks in one: an Ed McMahon—Doc Severinsen hybrid with the talent to back up A-list guest musicians and the ability to banter with Dave as an equal. Perhaps more essentially, Shaffer served as the simple syrup to Letterman’s bitters, undercutting the host’s grumpiness with wacky irreverence.

Larry “Bud” Melman (Calvert DeForest)

A celebration of oddness, actor Calvert DeForest was an awkward, unassuming Truman Capote lookalike and soundalike who came off like a stranger trying to befriend you on a bus—the guy you’d prefer to avoid but can’t help liking. As Melman, he was Dave’s clutch hitter, used for everything from serving as New York’s official greeter at the Port Authority to appearing in commercial parodies for Toast on a Stick. Whatever strange errand he ran, his warm humanity was always apparent.

Dave’s Mom

When a man is as uncomfortable in his own skin as Letterman, few things are more squirm-inducingly funny than watching him deal with his mother. Dave’s mom Dorothy Mengering was a frequent guest, baking pies on the show every Thanksgiving and serving as a correspondent for three Olympics. Viewers lapped up her small-town charm, and she explained her appeal like this: “People enjoy seeing a mother and son together.”

Chris Elliott

Late Night writer Chris Elliott was the incarnation of the show’s sense of the absurd. His characters, like the Guy Under the Seats, were often just thin disguises of his own frustrated and bitter showbiz-failure persona, made brilliant by the crumbling of Elliott’s cheery facade.

Rupert from the Hello Deli

Letterman smartly deputized Times Square denizens as co-stars, and Rupert Jee, owner of the Hello Deli, was up for any game or prank, including approaching strangers with a hidden earpiece and repeating whatever Letterman said. His unassuming manner lent great comedic contrast to Dave’s bizarre instructions, leading to such moments as Rupert posing as a newsstand vendor and offering to remove his pants with every purchase.

Richard Simmons

Simmons was the show’s Tasmanian devil, a cheerleading dervish delivered to earth in inappropriate short shorts to make Dave cringe. Dave’s insults and Simmons’ defensive yet loving incredulity gave the pairing an opposites-attract spark.

Mujibar and Sirijul

The Bangladeshi souvenir salesmen became Letterman’s roving correspondents. Stiff yet friendly in ill-fitting suits, they gave halting responses to his queries that helped serve Dave’s deconstruction of the conventional wisdom about what constitutes entertainment.

Tony Randall

One of the Late Show’s most frequent guests, with 70 appearances, Randall would stop by for a chat or surprise the audience by popping off a quick joke from the cheap seats. Randall’s acquiescent warmth created a wonderful, watchable bond with the host.

Alan Kalter (announcer)

A kinetic presence with psychotic tendencies, Late Show announcer Kalter became a powerful character. Kalter’s fictional (we hope) dark side kept a hostage in a metal locker and cursed Dave for ignoring him. As Letterman grew warmer and more personable, Kalter’s character insured that the show’s bitter aspects remained part of the mix.

Harvey Pekar

Letterman and comic-book memoirist Pekar had an uneasy bond. They didn’t seem to like each other much, turning insult-filled interviews into compelling can’t-turn-away TV. Letterman once banned him from the show, but given their chemistry, it’s unsurprising that the ban didn’t last.

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