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As ‘The Late Show’ Comes to an End, Stephen Colbert’s Sincerity Will Be Missed Most of All
Daniel Fienb · 2026-05-21 · via The Hollywood Reporter

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In January 2010, Conan O’Brien signed off after a truncated run as host of The Tonight Show.

Thanks to NBC’s embarrassing “Hey, let’s give the 10 p.m. hour to Jay Leno” gambit, Conan had barely seven months in the hosting chair — a blunder so egregious it cast a pall over the entire broadcasting lineup for months, and so completely unforced you can mock it to this day.

O’Brien spent five years as Leno’s designated heir, only to get shuffled to the dustbin in less than the gestation time for a hippopotamus, so if anybody had the right to be angry and if anybody had a wide assortment of targets for that anger, it was him.

Instead, O’Brien thanked NBC, his television home for 22 years, and then offered advice to his young audience. “Please, do not be cynical,” O’Brien said. “I hate cynicism. For the record, it’s my least favorite quality, and it doesn’t lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you’re kind, amazing things will happen.”

It was the sort of carefully deployed sentiment that late night hosts often save for moments of national tragedy and their own departures, but rarely utilize as essential components of their daily vernacular. It’s the sort of job in which it’s far easier to use cynicism or glib sarcasm or overarching irony as tonal scaffolding than sincerity.

Stephen Colbert did overarching irony for nine seasons and 1,447 episodes on Comedy Central’s The Colbert Report, one of the most sophisticated, hilarious and astonishingly protracted practical jokes ever conducted on the small screen — an ironic response to a kind of conservative punditry that barely existed when the show began and was extinct long before it ended. The Colbert Report was never a cynical show, but it was a show that often fueled cynicism in its audience, for what ultimately turned out to be good reason. In retrospect, the series was unbearably prescient, but its host still wrapped the show by slipping out of his well-established character with a star-studded cover of “We’ll Meet Again” and heartfelt send-off.

When The Colbert Report ended and Colbert went off to replace David Letterman as host of The Late Show, the big question that people in my job asked repeatedly — asked Colbert, asked his producers, asked each other — was who Stephen Colbert was without the coating of well-applied irony. There was some fear — reinforced in the rough opening months of The Late Show, when it seemed possible that The Late Show With Stephen Colbert might rival The Tonight Show With Conan O’Brien in terms of unplanned brevity — that the answer might turn out to be “the same as all the other guys in late night.”

With both Colbert and The Late Show heading toward their final show on Thursday, May 21, we’ve had 11-ish years to ponder a different answer.

Colbert rose to fame in the politically tinged world of The Daily Show. (OK, fine. Colbert rose to fame on Strangers With Candy, which is streaming on Paramount+ and remains a masterpiece of the niche-iest sort.)

At no point during his run on The Late Show did Colbert’s political humor feel essential to me. It was just essential to anybody doing his job at the time he was doing it. The Colbert version of The Late Show launched and continued in the middle of both Peak TV overall and Peak Late Night TV, a brief window in which there were the usual suspects — white guys named “James,” as the joke so accurately went — offering broadcast yuks for insomniacs, but also shows fronted by the likes of Samantha Bee, Robin Thede, Amber Ruffin, Desus & Mero. Rest in peace to all their shows, gone long before “the challenging late night environment” claimed the life of The Late Show as well.

Everybody responded to the same Donald Trump blunders and ramped up their ire to address the same encroachment on fundamental rights. But when it comes to those jokes that were required from everybody (even if Jimmy Corden and James Fallon did fewer of them), Colbert’s versions never felt like the best or the worst, and when next Monday rolls around, I won’t be sad at not getting Colbert’s take on whatever happened over the weekend. In contrast, I’m still sad that Bee, Thede and Ruffin don’t have regular weekly platforms.

What set Colbert apart, and allowed his colleagues — including Jimmy Kimmel and Seth Meyers — to do their versions of the same, was that lack of cynicism, that abundance of sincerity. For a man who made his name playing an obviously fictional character who shared that name, Colbert’s ability to deliver an unvarnished and unaffected version of himself has been what I will miss the most. (Except that hopefully and presumably, Colbert will still be around in some capacity.) That was the approach that marked what, for me, were Colbert’s best moments on The Late Show.

After its rough beginning, which included a showrunner change and more, the turning point for the show, at least for me, was the live election episode in November 2016, when Colbert had to process the results in real time. An evening that Colbert and most of his peers expected to conclude in relief and vindication instead ended with Colbert’s own version of Conan’s anti-cynicism address, a plea for unity that…well…hasn’t gone so well. In retrospect, maybe it was a tiny bit mawkish and superficial, but in the moment it was what many of us needed.

That streak of sincerity wasn’t bound by political identity.

Colbert wasn’t even code-switching. In her recent interview with Colbert, THR‘s Lacey Rose broached the possibility that his actual political leanings were probably, in many cases, more conservative than most people might guess. As a wealthy white man raised in the South and devoted to his Catholicism, Colbert demographically could or should have been as right-leaning as his Colbert Report character. As himself, though, Colbert used his sincerity to cover terrain conservatives have tried to claim — and to do it better than any conservative pundit on television, without being conservative.

When Colbert talked about his faith, he did it in a way that never came across as feigned or confrontational. I’m still astonished thinking back on his conversation about comedy and religion with Dua Lipa — an interview that sounds like a punchline, like a thing that logically shouldn’t exist, but turns out to be more theologically candid and rigorous than anything expressed by the more overtly godly men and women of Fox News in that channel’s entire history.

When Toby Keith died, Colbert’s reflection on the loss of his friend was more potent than any other tribute I read or saw to the country music star.

People on the right have made “Jimmy Kimmel Cries About Everything” into an ongoing and inaccurate running joke, but nobody has dared do the same with Colbert. Nobody has ever questioned whether Colbert means what he says about grief or creed or J.R.R. Tolkien.

Though he has had the chance for a one-year sendoff, Colbert still deserved better. He deserved better than — if you believe CBS brass — being a victim of a time period that has ceased to be financially rewarding for the multi-billion-dollar corporations fronting it. He deserved better than — if you don’t believe CBS brass — being a martyr for free speech put out to pasture so that the government wouldn’t interfere with one multi-billion-dollar corporation’s ability to acquire another multi-billion-dollar corporation while our nation’s chief executive cackled on social media.

But that’s cynical, and Conan O’Brien told me not to be cynical, and Stephen Colbert would probably prefer that as well.

So instead, I’ll just unironically look forward to how Stephen Colbert says farewell and what comes next.