By Jeff Jensen
Updated May 21, 2015 at 05:04 PM EDT
Credit: John Paul Filo/CBS

David Letterman retired from television Wednesday night, a historic passing that takes from us one of the medium’s greatest broadcasters and biggest icons. Naturally, Letterman being Letterman, the self-aware imp tried very hard to take a pin to a moment inflated with so much hot air. His last act as a snarky, unsentimental saboteur of TV tropes: Subverting himself.

He opened his 6028th and final hour with a gag that had four living presidents quoting Gerald Ford’s famous line about Vietnam: “Our long national nightmare is over.” It culminated with President Obama making deadpan clear that said nightmare was the three decade reign of late night’s most unlikely commander-in-chief.

10 stars performed the night’s Top Ten list (“Things I’ve Always Wanted to Say to David Letterman,” starring Bill Murray, Chris Rock, Tina Fey, Peyton Manning, and more), and Foo Fighters performed a closing musical number (“Everlong,” a song that gave Letterman inspiration during his heart problems in 2000). But otherwise, Letterman eschewed celebrity guests and recollections of infamous encounters with famous people. Instead, he filled much of the time with clips that focused on his interactions with everyday people—including a package devoted to all of his insanely talented kid guests and a mid-’90s Dave-in-the-field bit in which he frustrated and harassed customers passing through a Taco Bell drive-thru. He also showed a surprising number of excerpts from his first, short-lived daytime talker, The David Letterman Show. (For many, the finale might have been their first exposure to this obscure Letterman ur-text.)

The entire show seemed rigged to minimize the potential for self-aggrandizement and mawkishness—even as it fed the just-folks image Letterman prefers for himself—and to shape how we will remember him: He was, from beginning to end, a late night talk show host, nothing more, nothing less. And it meant everything to him be just that and only that. At least, until now. His closing remarks—a series of sincere thank you’s to his partner, musical director Paul Schaeffer, his staff, his family, and CBS bigwigs—were delivered without a catch in the throat or a discernible tear in the eye. Letterman’s last stand was a controlled burn, and it’s possible it needed to be for its host to get through it without falling apart.

Yet for all of the finale’s reserve and modesty (and, sure, whiff of false modesty), I wouldn’t call it anti-climactic. It appreciated that Letterman tried to ring out with something that resembled a typical show, at least in structure. His bid to manage the tone and tenor of his exit was a powerfully poignant, sincere act into itself. During the protracted ovation at the start of the show, Letterman repeatedly asked his audience to stop it already. When they wouldn’t, he squirmed. “Please be seated,” he said. “I don’t know what to do.”

That was the first moment in which I found myself getting emotional, for him and for myself. David Letterman—an innovator who became an institution; a cultural touchstone for at least one generation, maybe two—is gone. We may never see the likes of him again. But I hope we do.

It’s fitting that David Letterman leaves us the same week Mad Men signed off. His arc mirrors that of Don Draper—an outsider turned insider; a cracked genius with an ironic persona, brilliant shtick and angry ambition; a man whose greatest growth was found in humanizing the character he had created as a vehicle for success.

Letterman made his name as a fringe hour Alfred E. Newman, a cartoonish wise-ass whose satirical target was TV itself. He began his showbiz career as comedy writer, performer, and actor. (A fave FUN FACT! about Dave: He tested for the lead in Airplane!)

But Letterman believed that television, not movies, was his milieu, and that the talk show format was his proper stage. He found his identity and voice by working within and against the conventions of a genre, and he did so with the help of comedian and writer Merrill Markoe, who produced The David Letterman Show (1980) and served as head writer on Late Night With David Letterman during its first six years.

The gimmicks that expressed his sensibility were viscerally absurd, knowingly contrived, and often just plain weird. Stupid pet tricks and stupid human tricks, viewer mail and Top Ten lists, the Monkey Cam and the Alka-Seltzer and Velcro suits, throwaway gags like throwing pencils through the windowless lattice behind his desk and triggering a shattering-glass sound effect. Late Night with David Letterman, which ran from 1982 to 1993, created a marvelous meta-verse that that turned NBC into a mirror maze funhouse, populated by a mix of fictional characters and real players, from bumbling, cackling Larry “Bud” Melman (actor Calvert DeForest) to Chris Elliot’s The Guy Under The Seats to stagehand Biff Henderson to Tom Brokaw to Al Roker. One of my favorite early Letterman gags involved putting a camera on a track mounted on the ceiling and sending it over the heads of his audience, out of his studio, and into the halls of 30 Rockefeller Center—each day venturing deeper into that monolith. This was ’80s Letterman in a nutshell: a roller coaster ride of pranky, winky mirth that overshot the masses, aiming for TV-savvy freaks and geeks who required next-level surprises and subversions of the medium to be entertained by it.

He was the tortured genius type, by all accounts. He was certainly as awkward as one, nerd-endearing and nerd-alienating. Yet he owned that discomfort and wore it comfortably, with equal amount of self-deprecation and self-confidence. The funniest moments of a monologue were often the joke-fails—sometimes it seemed like Letterman told bad jokes on purpose just to score the sure laugh of mocking himself—or simply standing on his stage mark and playing with his ti,e or sucking his teeth, or making silly faces, all while watching himself on the monitor, alternately totally pleased with himself or totally aghast. Letterman was shocked—shocked!—that anyone would let someone like him on TV.

He could be smug. He could be mean. “Acerbic” is a word many critics used to describe him in the early days. Even with late-stage Letterman, you often couldn’t tell how he really felt about his guests or even his audience—and you weren’t sure if could believe him when he told them. Cher famously called him an “asshole.” She wasn’t wrong.

But Letterman, a developing master broadcaster who began his career as an Indiana weatherman, was always careful to round out the prickishness with humility, cultivating an everyman air that at least felt sincere. He made his mom one of his stable of recurring players—phoning her at random, sending her to the Olympics—and he gained much by letting her mother him on national television.

And Letterman was capable of feeling bad about being an “asshole.” One Letterman moment that frames my complex feelings about him was the time he sent Larry “Bud” Melman on a road trip to Tierra del Fuego, the southern tip of South America. Larry was becoming increasingly miserable during the trek, and Letterman, determined to milk as much comedy out of the adventure and his suffering as possible, kept denying his pleas to come home—until a teary meltdown in Guatemala finally broke Letterman. I’m sure Letterman felt horrible. I’m also sure he knew it was great television.

During the run of the NBC show, Letterman led, joined, and ran parallel to a number of fringe cultural movements that connected with coming-of-age Gen Xers and college kids on the make for cultural rebellion. Ultimately, it precipitated the pop culture we have today. Letterman’s subversions of form were no different from, say, Alan Moore’s superhero comics in the ’80s, or grunge rock in the ’90s. His idiosyncratic and ironic persona were deeply meaningful to his audience; he was an authentic original in a bland, plastic decade. Letterman’s influence can be felt not only in the stand-ups and talk show hosts that followed him, but in SportsCenter anchors, podcasters, and, by his own admission, our current president. Letterman infected everyone who loved him with his sense of humor. His legacy extends beyond the screen. It lives in us.

At the same time, Letterman also embodied the limits—and even the lie—of the mainstream pop artist playing the part of punk insurrectionist. During the NBC days, Letterman often ribbed the network and its owner, General Electric. It was punchy but empty irreverence. I’m sure he pissed off the suits—and according to legend, it might have cost him when he made a play to replace Johnny Carson as the host of The Tonight Show. At the same time, I’m sure those same suits saw value in his impudence. It made him cool, and cool is always good for business. You know how the machine overlords in The Matrix allowed occasional, short-term patterns of internal rebellion to flourish for the sake of maintaining the status quo in the long run? That’s how I imagine NBC’s relationship to the rogue element that was making lots and lots of money for the company in the wee, cheap, largely unwatched hours of the morning.

Moreover, Letterman couldn’t ever give himself over completely to the anarchist joker that his fanboys like to make him out to be. He loved the provocative likes of Andy Kaufman, Howard Stern and graphic novel memoirist Harvey Pekar—but he tolerated provocation only to a point. Pekar—whose unlikely and memorably belligerent appearances nurtured the Late Night’s outsider-friendly, anything-might-happen rep—finally wore out his welcome on Letterman’s NBC show in 1988, when Pekar told him he was “full of shit” and called him a “shill” for G.E. (Letterman would later express regret for losing his patience with Pekar.) For years, the signature Letterman moment – outside the Cher/”asshole” business – was the time an incoherent Crispin Glover seemed to terrify Letterman with an impromptu, out-of-control karate kick that came close to nailing Letterman in the head. Letterman left the set, and Glover was asked to leave

Letterman may have stood for irreverence, but he also insisted in decorum. He recognized the value of outré antics, yet he often appeared (or pretended to be) exasperated or even scandalized by the most extreme examples of them. It was a paradox that I could never fully reconcile.

Letterman is often described as the “anti-host”—a walking, talking send-up of a late night talk show host—but it doesn’t ring true for a simple reason: For all his tomfoolery, Letterman loved the conventions more than he did subverting them. Nothing proves that more than his hope—and perhaps expectation—to inherit The Tonight Show, late night’s brass ring. I consider myself a Letterman fan, but I was conflicted about the idea of him giving up the franchise he built for the franchise that inspired him. I remember wanting him to get the gig, perhaps more for my sake than his, but also in some arrogant belief that it was for the greater good of pop culture: His election to 11:30 and his inauguration as late night prez would have represented the affirmation and validation of my taste in comedy, my pop culture sensibility… which, obviously, was the correct taste and the correct sensibility. Certainly superior to whatever Jay Leno represented.

At the same time, I worried that Letterman would lose something in the translation to an earlier hour, that he would trade away some of his edge to gain—or rather, retain—the larger, broader audience that watched The Tonight Show. NBC chose Jay over Dave, and CBS gave a jilted Letterman a platform and perch to prove his doubters wrong in the form of the Late Show with David Letterman, which premiered on August 30, 1993.

Letterman was an instant hit for The Tiffany Network, at least compared to what had been in that timeslot before him. Which was… what? Nothing? No one remembers, and it doesn’t matter. Letterman on CBS was a bit more formal, and he had to change the names of his signature gags—NBC owned the legal trademarks—but he made the transition without much compromise or heat-loss. Of course, CBS didn’t buy him to be anything less than what he was. They wanted a brand, not a revolution.

The early years of Late Show were Letterman in full: the legendary, sexy sassing with Madonna, going door to door in suburbia with fellow geek chic pioneers Roger Ebert and Gene Siskel. The only people who could have been even a little bit disappointed with Late Show were those who hoped that Letterman would dare to try something bold and new, that he would attempt to deconstruct and then reconstruct the 11:30 hour—just as he had made something novel and relevant from the hour after it. You wonder what would have happened if he had tried. Could Letterman have made something that was more popular than Leno’s version of The Tonight Show, which more often than not beat the Late Show in the ratings? We’ll never know. Letterman chose not to reinvent the wheel. He chose to become an institution.

Not that Letterman never changed again, or never changed for the better. In 2000, Letterman transformed into what has been, for me, his most compelling incarnation. After undergoing a quadruple bypass for a heart condition that could have killed him, Letterman returned to air after two months away more humble, vulnerable, and winning. “These are the people who saved my life!” he declared while introducing the medical team that performed the surgery.

The reborn Dave engaged us with his heart as much as his headiness, no more so than on his first post-9/11 show, in which he tried to help us through our shock, confusion and grief by unabashedly modeling it with a moving monologue that searched for meaning in the madness. Fatherhood humanized him further. So did a confession to workplace affairs that left him vulnerable to blackmail and humiliated his family and his associates. (Let’s not confuse “legendary entertainer” with “sainthood.” He is anti-hero, not hero. Again, see: “Asshole,” Cher.)

For the most part, all of this, the good and the bad, worked to enhance Letterman, not diminish him. The detached ironist had given way to a guy who genuinely gave a shit. You saw it in the way he challenged periodic guest Bill O’Reilly, in the beard he grew in solidarity for the striking Writers Guild Of America, in his dismay over Indiana’s “Religious Freedom Act.” It’s been said that Letterman has lost relevancy to a new generation of talk show hosts that speak the social media language of today’s hyper-mediated young people. But I’d like to see Letterman acolytes Fallon or Kimmel try to speak with any kind of authority about the social issues of the day in the way that Letterman has or can. Hipster irony and irreverence can be easily replaced. Authentic, hard-won humanity can’t.

Letterman leaves a legacy that deserves to be called “untouchable.” But I hope to heck someone tries. Because what late night needs is not more Letterman clones, but more innovators like the one Letterman used to be in his earliest days—and deeper, wiser, more culturally engaged voices like the one Letterman has now. It would be nice to see someone who dares to blow up the talk show conventions Letterman didn’t dare destroy (the desk, the suit, the sidekick bandleader) but retains the others that he (thankfully) preserved and got better at over time—like, say, a good conversation between a curious, intelligent host and an interesting, intelligence guest.

Stephen Colbert will replace Letterman. He’s another white guy in a suit, and we do need less of this, too. (Good on Chris Rock for calling that out in the finale—and good on Letterman for basically agreeing with it.) Still, in Colbert I trust. He’s hungry, he’s naturally funny, he has the weapons that today’s viral-minded, variety show talk show emcee needs to compete. (Put another way: He sings!) He’s a comedian who, like early Letterman, made his name by being an innovative ironist who subverted television conventions (in his case, those of cable news, and Fox News in particular), and who, like late Letterman, clearly cares about the world outside his show. The challenge he faces is connecting with us as himself, stripped of his faux-O’Reilly “Stephen Colbert” character. I think the genre will benefit from that effort.

In this way, the narrative of re-humanization represented by Letterman continues. May Colbert honor the house that Dave built—and may he have the ingenuity and guts to blow it up as needed to improve upon it.

Late Show With David Letterman

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