Charm and Disarm: David Letterman, Late-Night TV’s Midwestern Hero

Comedy Features David Letterman

When you hail from the Midwest, people’s biggest assumption about you—besides the expectation that you’ll say “pop” instead of “soda” and hit all your vowel sounds especially hard—is that you’re “nice.” And that’s one of those stereotypes based in truth; I’m not trying to brag (that’s a cardinal sin where I come from), but we Midwesterners are extremely friendly and kind, for the most part.

But “nice” sometimes gets confused for “passive” or “meek,” and it’s not until you spend some time outside the region that you realize there’s another predominantly Midwestern trait people are less aware of—a certain directness, an aversion to pretense. An allergy to bullshit. This is why celebrities feared David Letterman, and one of many reasons why the Indiana native was able to completely change late-night TV for the better.

From the get-go, Letterman refused to play the Hollywood game. Small-talk and fake smiles to promote movies were never his thing; Cher famously called him an “asshole,” telling him she could always tell when he didn’t like his guests, that “if you don’t like ‘em, you might as well take a picnic lunch.” Letterman barely missed a beat: “I think a lot of people feel that way about me, though.” And he was right—that’s become his persona, the country’s grumpy uncle, subverting the entertainment industry from within. Even in recent years, though he’s softened with age, he still has turned in memorable interviews with entitled celebrities. In 2007, he opened his chat with Paris Hilton with a softball, asking her if she preferred New York or LA before following up with a sucker-punch: “How’d you like being in jail?” When Justin Bieber was on in 2012, he asked the newly 18-year-old Bieber about voting, and after the pop star made an excuse about not being an American citizen, Letterman’s trusty Midwestern bullshit detector went off and he pressed the issue: “Who would you vote for?” Bieber’s silence and sheepish grin said it all.

But there’s a difference between a distaste for phoniness and plain-old maliciousness, and though Letterman would often toe that line, he rarely crossed it. When Lindsay Lohan—the butt of countless late-night jokes, including many on the Late Show—came on in 2013 right before a trip to rehab, Letterman was happy to play the self-deprecating aggressor, reading off some of the one-liners he had made at Lohan’s expense before eventually laughing and saying, “For the love of God, what is wrong with me?” He was still blunt, asking Lohan point-blank “Do you drink too much?” but there’s a certain tenderness to the whole thing, with Letterman—himself a recovering alcoholic, sober for over 30 years—offering up some tough love and advice like “the best way through this, the victory is to succeed and have a wonderful life ahead of you.” He wraps up the interview with candor, saying “We never thought we’d see you again, honestly, because of the jokes, but yet you have enough spine, enough sense of yourself, enough poise to come out here and talk to me honestly.”

Letterman’s always been frank about his own trials and tribulations, and when he was the victim of a blackmail attempt, he dedicated a 10-minute segment to it on his show, where—after deadpanning “I’m just a towering mass of Lutheran Midwestern guilt”—he opened up about the sex scandal his blackmailer had threatened to reveal. It was a victory of sorts, taking away his enemy’s ammunition by setting it off himself, but it was also an unprecedented display of honesty in an industry where scandal so routinely gets swept under the rug.

But that openness and resistance to Hollywood charades (figuratively and literally speaking—you won’t see any viral clips of Dave playing party games with his guests) aren’t the only reasons why we count Letterman as one of the Midwest’s finest TV heroes. He’s never tried to hide where he came from—on the contrary, he flaunts it, the way anyone who grew up enduring harsh winters and hot summers wears it as a badge of honor. He has always been happy to paint himself as an other on his show, an outsider looking in at New York City. Aw, shucks. He’s a sucker for tradition, too, like the rest of us; when he loves something, you know it. I can recite Jay Thomas’ Lone Ranger story line by line, because Letterman insisted he come on the show every Christmas and tell it—the same show where he’d have Darlene Love sing the same song every year. The punchline, “they’ll believe me, citizen,” still cracks him up every time.

The phrase “Midwestern dry wit” gets tossed around a lot, and we don’t have enough space here to talk about how it applies to David Letterman’s irreverent comedy (read our cover story from this week for more on that), but as another Hoosier, Jim Gaffigan, pointed out on the show a few weeks ago, people from the area are all kind of half-nuts. Dave’s always embraced his oddness, made it part of his shtick, and in doing so, he popularized an unabashedly weird comedy. It’s fitting that his final guest is Bill Murray, another unapologetically Midwestern folk hero, a kindred spirit who served as Letterman’s very first guest in 1982, ushering in what would go on to become a TV institution by cracking “I’m just waiting for the other shoe to fall on you, man, and I want to be there when it hits the floor.”

We all like to see ourselves on television—not literally (although, hey, if you’re on TV, that’s great, congrats), but people we can relate to, people who remind us of our goofy relatives or the guy who lives down the street. For anyone who grew up near the Great Lakes, or in what those on either coast sometimes callously refer to as “flyover country,” David Letterman was that guy. When he steps down on Wednesday, it will be the end of something—not just of his show, but of an era when a celebrity could come out from behind the curtain on a late-night show and have no idea what they were walking into. That retires with Letterman…for a few decades at least, until a new late-night spot opens up and we can meet the next self-deprecating weirdo to walk the trail he blazed.

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