It feels like a bit from one of his shows, but I am going to say it anyway—David Letterman is going for unironic sincerity, and that’s how bad things are over in America. Throughout the 80s and the 90s, Letterman’s late night TV missives were the clay with which the edifice of American irony was built. It isn’t a stretch to say the great curmudgeonly comedies like Seinfeld and Frasier, such an essential part of 90s American pop culture, stood on Letterman’s shoulders in their initial days.

As Emily Nussbaum wrote in 2015, around the time Letterman was ready to call it quits, “Now that Letterman’s a flinty codger, an establishment figure, it’s become difficult to recall just how revolutionary his style of meta-comedy once felt. But back when I was sixteen, trapped in the snoozy early eighties and desperate for something rude and wild, Letterman seemed like an anarchist. […] All of us imprinted like ducklings on his persona, the nice guy with the mean streak, making the world safe for smart comedy.”

The establishment-flinty-codger paradigm Nussbaum was talking about in 2015 has now reached maturity. Letterman’s Netflix show My Next Guest Needs No Introduction, which released a batch of new episodes last week, is an exercise in shaving the last remnants of mean streak stubble off its illustrious host. Letterman’s gosh-dang Midwestern niceness and his impressively cultivated cotton candy beard accentuate the effect—the retired hitman of American pop culture is now living out his pastoral years, looking and sounding like a genteel lumberjack. And so we have grandpa Letterman cleaning a pigpen owned by Robert Downey Jr, bonding with his cows, feeding his ridiculously cute alpacas and so on.

Apart from Downey Jr, there have been three other new episodes released so far—with Kim Kardashian West, Lizzo and Dave Chappelle. And apart from the Chappelle episode (to which we shall come presently), the other three proceed along expected lines. Avuncular mannerisms in place, Letterman probes Downey Jr about sharing marijuana with his filmmaker father as a teenager. With syrupy politeness he nudges Kim Kardashian into reminiscing about the big bad OJ Simpson trial one more time. He’s even more guarded around Lizzo, who to her credit chuckles through what was surely the most vanilla 40-odd minutes of television she’s ever been a part of.

None of this is particularly ambitious or pioneering, which is exactly how Letterman intends to play it. This is a strategically crafted show with fairly modest goals, and it achieves most of them with clinical precision. At no point does Letterman even mildly push his guests—these are people he clearly likes, and he’s anxious about stepping on any toes. I suppose if I had been interviewing different people every night for 30-plus years, I’d also be picky when it came to choosing six of them every year (and an inveterate schmoozer once I did so). This is why there’s a general this-is-our-day-off vibe to My Next Guest, something it shares with Jerry Seinfeld’s Comedians in Cars Getting Coffee, a similar retirement vehicle also bankrolled by Netflix (Seinfeld and Letterman interviewed each other in a bonus segment for My Next Guest’s first season).

The façade cracks briefly with Dave Chappelle, who Letterman is visibly enamored with (even by his latter-day gushy grandpa standards). It’s not difficult to see why—Chappelle is and always has been difficult to place in small, comfortable boxes. As an artist, Chappelle has leant heavily on his ability to push a joke or a narrative until it enters truly uncomfortable territory, moments where over half of your audience is sweating. This is, of course, anathema to Letterman and his modus operandi with My Next Guest. For example, Chappelle points out that while slavery was never legal in his home town of Golden Springs, Ohio, neither was suffrage for black people, for the longest time. “Slavery wasn’t legal but neither was freedom,” Chappelle pointed out in a moment that Letterman was visibly uncomfortable with. It’s a classic Chappelle moment, too, assured in its incendiary potential. You know, the way Letterman used to be in the 1980s.

On more than one occasion, Letterman channels some of the self-critical juice that became his hallmark. He scolds himself for being not informed enough, or not as smart as his guests. As the comedy writer Nell Scovell wrote last year in Vanity Fair, “[…] copping to one’s failings after getting caught is kind of Dave’s signature move”. Scovell worked on Letterman’s show as a staff writer in the summer of 1990 before quitting what she later described as an almost entirely male-only writers’ room, a “hostile, sexually charged atmosphere” (On October 1, 2009, Letterman had famously confessed to sleeping with women who worked for him—on-air, no less). The Vanity Fair article described how Letterman apologised to Scovell and the other women he had wronged during his heyday. Sincerity is certainly the order of the day when apologising, it has to be said.

But among the many lessons the Trump era has taught America, I am sure there is room for this one—namely, that sincerity will only take you so far. The late David Foster Wallace (himself one of the biggest beneficiaries of Letterman’s brand of irony-infused humour) once wrote a short story in the voice of an actress who feared an upcoming interview with Letterman. In one of the story’s many hilarious moments, the actress’s husband and a friend are arguing about the relative merits of various late-night shows—see how Letterman’s complicated relationship with ‘sincerity’ and meta-comedy is alluded to.

“”Carson would play along with you,” my husband said. “Carson’s still ‘sincere.’”

“Sincerity is out,” Dick said. “The joke is now on people who’re sincere.”

“Or who are sincere-seeming, who think they’re sincere.””

As Letterman’s (and to a lesser degree, Wallace’s) career shows us, a culture that depends too heavily on irony risks being caught in an endless mirror trick of performing sincerity. The late anthropologist David Graeber called American liberal centrism “a pure set of performative symbols” and in the Double Down News (DDN) video where he explains this, the voice-over is accompanied by visuals like Obama’s dance with Ellen, his ‘mic drop’ moment at his White House Press Corps farewell dinner and so on.

The real challenge before the likes of Letterman, therefore, is to transcend the symbolism and back up the sincerity with actions that accelerate the pace of change. And while Letterman may yet do something of the sort, odds are it won’t be on the sets of My Next Guest.