On the face of it, David Letterman and Stephen Colbert don’t seem to have that much in common. Perpetually cranky and never much of a people person, Letterman grew up in the Midwest with dreams of getting into broadcasting or comedy, maybe as a standup. A vocal Catholic with an ebullient personality, Colbert was raised in the South, thinking that perhaps he’d become a dramatic actor until he realized that getting laughs was more fun. Letterman has made his name being his lovably ornery self. Colbert has made his playing a fake person who’s the opposite of him: a raging right-wing blowhard.
And yet, the announcement today that Colbert will be replacing Letterman on CBS’s Late Show wasn’t just unsurprising — it felt right. Their journeys to late-night might be different, but in the ways that matter — their sensibilities, their daring — they share a kinship.
It’s easy to overlook now because Letterman has long become an institution, that reliable presence on CBS who genially mocks the lameness of his own monologues. But his genius, starting with NBC’s Late Night With David Letterman, was in the margins; his program looked like a talk show, albeit in a public-access cable kind of way, but rarely felt like one. It wasn’t just the Stupid Pet Tricks and the presence of Larry “Bud” Melman so much as Letterman’s notion that the hallowed institution of late-night TV shows could be reinvented with a combination of aw-shucks modesty and satiric wit. Tucked safely away at 12:30am where he presumably couldn’t do any harm, Letterman reveled in the possibility of “what about this?” — whether it was having Chris Elliott eat dog food or bringing on Andy Kaufman for whatever new surrealist idea that had popped into his head. But the coup de grâce was always Letterman’s nonchalance to the anarchy he concocted. “You’re not supposed to be impressed,” he told Playboy in 1984. “If you happened to see me perform and I happened to make you laugh, great. That’s all I’m in it for.”
That same mixture of folksy charm, irreverence and irony has powered The Colbert Report since its inception in 2005. Developing a show based around Colbert’s popular red-state correspondent from The Daily Show With Jon Stewart seemed smart — and incredibly risky. There was no guarantee it would work. Reviewing The Colbert Report a little more than a month after its premiere, The New Yorker‘s Nancy Franklin wrote, “For all the delightful wordplay and nonsense, Colbert comes across pretty stiffly much of the time, because he remains in character during the whole show. There’s not a lot of breathing room, or room for any real seriousness, as there is on Stewart’s show.”
Colbert soon found himself, however, letting the persona be a launching pad rather than a destination. Segments like “Better Know a District,” where the clueless character would interview eerily peppy members of the House of Representative, recalled Letterman at his peak, when he would interact with the public by, say, driving to random McDonald’s drive-throughs and harassing the employees.
But where Letterman’s sharp bits could sometimes flirt with meanness — hey, they’re just regular people trying to do their job, Dave — Colbert’s satirical interviews had no such sour aftertaste. Whether it was the politicians of “Better Know a District” or the actors, celebrities and authors wanting to sell something, they had willfully signed up for the bizarre grilling that “Colbert” gave them. What soon became fascinating on The Colbert Report was observing how certain guests would respond to the character. A decorated actor like Ben Kingsley could seem absolutely intimidated by Colbert’s irreverence and blatant phoniness, while James Franco rose to the occasion, connecting with Colbert on their shared interest in how performance is a form of lying. Where Late Show served as a gleeful middle finger to corporations—particularly Letterman’s GE bosses—and a certain kind of outdated talk-show chumminess, The Colbert Report made late-night feel like a carefully manicured variety show, upending the format as stealthily (and with as much relish) as Letterman had a generation ago.
But what also bonds the two men is the deep sincerity beneath the smirk. Some of Letterman’s all-time greatest shows came in moments of personal or public turmoil. The program he did shortly after 9/11 was incredibly raw, the ironic funny man so eloquently articulating the pain, anger and sorrow that Americans (and especially New Yorkers) were experiencing after the attacks. (“We’re told they were zealots fueled by religious fervor,” Letterman said, trying to contain his emotions. “Religious fervor. And if you live to be a thousand years old, will that make any sense to you? Will that make any goddamn sense?”) But he could be just as riveting when bringing out the doctors who conducted his 2000 emergency quintuple bypass surgery. (“These are the people who saved my life,” he told us, fighting back tears.)
Colbert has been no less bighearted. His on-air tribute to his mother, who died last year, was poignant, remembering the woman who raised nine children after Colbert’s father and two brothers died in a plane crash in 1974. But the sentiment comes through in other ways, noticeably on the recurring segment “The Word,” in which Colbert thunderously trumpets a current right-wing talking point and, with a nimble verbal sleight of hand, contorts it until it become ludicrous, exposing the lie in GOP thinking and sneakily articulating a deeply humanist message. If that point wasn’t clear, he made it manifest when he testified in 2010 before the House Judiciary Committee’s Subcommittee on Immigration, Citizenship, Refugees, Border Security, and International Law. Speaking up for the rights of immigrant farm workers, he broke character for a moment, saying “I like talking about people who don’t have any power” and then paraphrasing from the Book of Matthew: “Whatsoever you do for the least of my brothers, you do unto me.” We watch these men not just because they’re funny, but because there’s a sense of substance underneath — a common decency that elevates the joyous shenanigans to something resembling grace.
Colbert has already made it clear that his Late Show won’t feature the satirical Colbert character, which has caused some fans of The Colbert Report to be concerned that we’re losing a beloved friend. But that doesn’t seem entirely out of keeping with those who, 21 years ago, worried that Letterman would somehow lose his edge transitioning from 12:30 to 11:30. That turned out pretty well, and so might this, especially since Colbert’s brilliance extends far beyond his character. “I really respect people who can walk out onstage alone and with no other tool but their own minds and can make you laugh and maybe even think a little,” Letterman told Playboy 30 years ago. He could very well have been describing the man who will soon try to fill his sizable shoes.