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How Liberal Late-Night Talk Shows Became a Comedy Sinkhole

‘Every single person in late night knows it’s a dumb factory of lazy ideas,’ one fed-up writer tells me. ‘I will never be happy with anything I make.’

In 2005, I attended the taping of what turned out to be a landmark episode of The Daily Show. The front half was the usual skewering of that day’s news, nothing too memorable — but the guest was the infamous Christopher Hitchens, a prickly proponent of the Iraq War, something the audience and host Jon Stewart regarded as a colossal mistake. While the two men on stage began their conversation with the obligatory chumminess of the late-night TV interview, it was bound to become a fierce debate on Iraq, and that’s exactly what happened: For around 20 minutes, Stewart challenged Hitchens’ excuses for a disastrous invasion, and Hitchens punched back, impressively enough that he could at one point observe the crowd had gone quiet.

It was an electrifying encounter — one of the early examples of the breathless “so-and-so DESTROYS political opponent” fare that has choked the internet in years since. When Hitchens left, Stewart more or less apologized for the intensity of their debate, joking that the production team would have a great time trying to edit it down into a coherent segment. In truth, it wasn’t that common for him to go on the offensive, and anyone in that room intuitively understood why: It may have been cathartic, and even enlightening, but it wasn’t very funny.

Talented as Stewart was (or is) at sneaking punchlines into a thorny discussion of geopolitics, those moments found him resisting a deep well of gravity created by bloody, corrupt and spiraling American empire. When you slice right into that issue, it will never be a laughing matter. The brutal reality of lives destroyed and a region in chaos cannot be domesticated for your living room.

Understandably burnt out and ready to pass the torch, Stewart left The Daily Show in 2015 and has largely kept to himself in the Trump era. This makes the demarcation between the remarkable run of The Daily Show and The Colbert Report during the Bush and Obama presidencies and the current ecosystem of late-night talk shows especially crisp. In fact, Stewart’s career tells the story of what I regard as the three phases of political consciousness within the format. He took the reins of the show in 1999, right as the comedy hacks finally ran out of bad Monica Lewinsky jokes. From there, he (and soon Stephen Colbert) walked the tightrope of cogent, biting political satire, incidentally gifting mainstream network shows with freedom to ignore or address Washington at will.

Then Colbert transitioned to that platform (theoretically leaving his political commentary behind), Stewart bounced, Trump took power in a shock election, and we entered a third act for TV writers expected to cull humor from the state of government and its leaders. Remember, the late-night model wasn’t really built for this: Johnny Carson, presumably liberal, explicitly avoided such topics and guests of that orbit; David Letterman wrapped his opinions in a hundred layers of irony; Jay Leno remained safely noncommittal and recently complained that today’s hosts are one-sided, begging for a return to every centrist’s favorite value: “civility.” But while it’s easy as ever to hit Leno as the epitome of uncool and brush off his asinine prescription (rudeness is hardly a hindrance to good comedy), the diagnosis from which he proceeds is inescapably true:

These shows are fucking unwatchable.

‘Everyone Is on Autopilot’

You could fairly accuse me of hating late-night talk shows long before they transformed into entertainment for Resistance Boomers who think that calling Trump “the Cheeto-in-Chief” is devastatingly clever. For me, they are a frustrating waste of awesome talent. It’s painful to watch someone like Colbert, who makes me double up in laughter with his performance in the oddball ’90s sitcom Strangers With Candy, go through the paces of yet another weeknight monologue on the president’s bald hypocrisies. Then there are the people behind the scenes, toiling at bits they know are jarringly uncomical, with no way of challenging the hierarchy that demands them.

One such writer, a man with an impressive résumé, reached out to me as I started this piece. He works at one of the major network late-night shows, and he’s despondent. (For obvious reasons, I won’t reveal his identity or other specifics on his employer.)

“I have been venting about this very shit to [a friend] for about five months now,” he writes to me in a Twitter DM. “To me, this is all because of two big things, one being that the late night writers’ rooms are all extremely homogeneous groups of cynical, miserable white comedy dudes who figure out the ‘formula’ for the show early on and then never really work harder than they need to. Which makes sense, because the other big thing is that the people who make the actual decisions on these shows are all older, white dudes who are out of touch (but don’t think they are) and are never thinking in terms of comedy or upending power or doing anything interesting with the format, they just maintain the status quo and follow a formula of ‘thing we’ve done + a celebrity = hit.’”

No doubt this was the same dynamic that gave us the first wave of late-night political hackery, when Bill Clinton’s rampant horniness and abuse of office turned into a parade of repetitive innuendo and cruel jokes at Monica Lewinsky’s expense (for which Letterman, at least, has voiced some regret). This time around, the stagnation makes for a punishingly superficial critique of Trump’s tenure and the man himself.

It’s only natural that these Trump “takedowns” would lack the substance of, say, the Stewart-Hitchens confrontation. With rare exceptions, Kimmel, Corden, Colbert, Conan, Fallon and Meyers aren’t trying to push us anywhere uncomfortable; they’re who you watch to unwind at bedtime. This means papering over much of the true horror of being alive in this country right now — migrant family separation, emboldened Nazis, environmental and kleptocratic plunder — to feast on low-hanging fruit.

“Monologue-wise, there’s just a bunch of shortcuts-to-jokes that every writer knows to hit for Trump stories now,” the exasperated TV writer tells me. “Talk about Trump loving fast food, reference a photo where he looks awful, call him orange, mention the Stormy Daniels thing (always in some not-so-thinly-veiled anti-sex-work way), say he tweets a lot, use one of his catchphrases like ‘Fake News,’ etc. Everyone’s on autopilot.”

He adds, “Trying to push any new idea, even if it’s low-risk, is a series of hurdles that almost always ends in different producers saying they ‘don’t see it,’ or shutting it down because they don’t get a reference that the entire rest of the world would get, or bristling at the idea of even mentioning race/gender/sex in any creative way that isn’t already some catchphrase on a department store T-shirt.”

In his writers’ room, he says, they don’t even have the freedom to pursue different, “evergreen” subjects, because “the Trump stuff got more engagement and sort of legitimized them as a ‘show with a point of view,’ which is nonsense. It’s really just trying to chase John Oliver.” But if they wanted to follow the model of HBO’s Last Week Tonight With John Oliver, arguably the best comedy/news hybrid of the moment, they’d have to renovate their show from top to bottom. Besides, the success of Last Week Tonight has less to do with its roasting of Trump than a willingness to wander into the weeds on arcane or poorly understood stories to make sense of America’s fundamental brokenness. You get real information there.

The TV writer explains that this isn’t something most late-night talk shows are equipped to offer, at least not anymore, so long as they cling to an outmoded approach: “At this point it feels like the only reason they acknowledge Trump is because he is the news, and ignoring him would be noticeable,” he says — though that also means we’ve had our fill of him already. Who in the goddamn hell is hungry for extra Trump analysis? “I’ve honestly never understood the notion of commenting on the news in late night anyway,” he adds, “but I think it’s just a relic of a time when you might legitimately be learning about things for the first time at 11 p.m. But now, with Twitter and a million different outlets for news, late-night monologues are [hacky] by 11 a.m.”

‘They’re Not Trying to Beat the Internet — Just Your Boring Coworkers’

Whereas the Lewinsky gags, abhorrent and vapid as they were, may have felt fresh to people who didn’t have the chance to make those jokes online, no lighthearted potshot at Trump taken by a late-night host will compare to the scabrously funny, unbroadcastable shit people tweet about the president 24/7. As the writer puts it, in terms of the race to land a solid blow: “They’re not trying to beat the internet, they’re still just trying to beat your boring office coworkers.”

These shows are, however, nominally online, and equally banal in that medium. These social accounts are defended with zeal by the shows’ loyalists — people with avatars of bald eagles in pink pussy hats and tenuous web literacy. When I quote-tweeted a particular groaner posted by the staff at The Late Show With Stephen Colbert, wondering if they couldn’t do better, these folks came out of the woodwork to call me a snowflake, a Trump supporter and an unfunny nobody. Some just showed up to reply with their own incoherent Trump “jokes,” and one woman, having assumed my avatar of Ben Affleck smoking was a photo of me, said to “keep puffing on the cigarette.” Lung cancer: a fine punishment for disrespecting her favorite TV show.

What motivates these weirdos? Why do they care what I think? And how did they even stumble across that tweet? It’s telling, of course, that their political identity comprises bromides and parody songs from a barely-left-of-center media machine. I can only conclude that they are the last true believers in this mealy dreck that late night is pumping out. They’re nourished and sustained by the consoling lie that Trump is an aberration of the system, not an avatar of its very nature; that everything will go back to “normal” one day, provided we keep ridiculing his hideous combover and fake tan. They are the dim bulbs who adopted Robert Mueller as a daddy figure and still defend grope-y Democrats like Al Franken and Joe Biden.

And they definitely think they’re the good guys.

‘Their Version of Liberal Just Means Not Being White Trash’

Another man in the industry (he describes himself as a “mid-level TV writer,” though not of the late-night sphere) tells me via Twitter DM that the skin-deep stabs at Trump aren’t intended to be apolitical — rather, they’re coded as courageous. “They think [joking about] ‘covfefe’ is brave,” he argues. “These are people whose version of ‘liberal’ just means not being white trash. And not calling their coworkers gay slurs.” Of course, that doesn’t stand in the way of their homophobic gloss on the Trump-Putin relationship.

This derangement presumably stems from a refusal to face the America that propelled Trump to the White House. For all they hate him, they yearn, as he does, for a “lost” country that younger generations view with skepticism. “No one wants to confront the fact that they grew up in a time that was pretty sexist and racist because then they’d have to stop being nostalgic for everything,” this writer says. “See: Aaron Sorkin.” As such, the anti-Trump Boomers — faithfully catered to by the older, more powerful figures in TV while, allegedly, the newcomers there are told to shut up and use the tired playbook, because that’s what “works” — settle into a smug superiority that lets them vent their classist contempt. That’s true of some of the hosts and writing staffs, too. “Bill Maher isn’t actually liberal, he just hates people from Alabama,” the second writer says. When I reframe that idea as “‘I shop at Whole Foods, so I’m not a reactionary,’” he replies, “[This is] the politics of 75 percent of Hollywood writers.” And so that’s the ideology served.

‘They’re Literally Upholding the Status Quo in Every Way’

The first late-night TV writer gives me the impression we probably aren’t going to break out of this bind anytime soon. The system is complacent in its abject shittiness. “I think the worst part is that every single person in late night knows it’s a dumb factory of lazy ideas,” he says. “[The host] makes fun of it, the head writers make fun of it, the staff writers watch the tapings and just lament it all. But the alternative is taking a risk, and network TV just isn’t about that. Safety is the key.” He tells me that he plans to leave the job soon. “[N]o amount of money can validate how consistently miserable it makes me feel to waste so much time, knowing I will never be happy with anything I make,” he says.

Still more dispiriting than that, he says, is his fellow creatives’ hostility to the aspirants capable of changing things for the better. He mentions his anger at writers mocking people who used the Writers Guild of America–associated hashtag #WGAStaffingBoost to seek work, “making fun of [the tweets] and reading them out loud. A bunch of privileged, white, staffed WGA writers, cackling at unemployed writers who are just trying to break into the industry but don’t have connections.” He laments this “bunch of cynical jerks who live by the law that vulnerability is embarrassing and worth looking down upon, and that they’ve gotten to where they are by just being better. No perspective to even realize how many times the [tweets] they chose to make fun of were … people saying they focus on diverse voices.”

It seems that for every youthful, fun, excitingly nonwhite talk show like Desus & Mero, there are a dozen depressingly bland legacy series whose doors are firmly closed to innovation, lacking both the means and will to do anything with Trump besides “tick off the ‘we-mentioned-him-and-said-he’s-bad’ box and move on,” as the late-night writer describes it. And so that becomes the weak standard of defiance.

Which is to say, the awful talk shows are complicit in this barbaric regime by diminishing any rebuke of it to the scope of a half-assed Alec Baldwin impression. In truth, it would be better if they didn’t mention Trump at all; that would possibly sting his ego. Alas, the not-long-for-late-night writer says, they will continue hitting him with an inflatable hammer, because a genuine crisis isn’t enough to disrupt business as usual, and these places are “full of people who think they’re doing so much better than everyone else, with no perspective to see they’re literally upholding the status quo in every way.”

Personally, I can’t find anything funny in that.