Searching for the punchline in the Trump era
Since the inauguration of our 45th president, a new kind of national ritual has emerged: After waking and removing the dental night guard you’ve come to depend on as a necessary line of defense against anxious sleep, you fumble for your phone. Then, expletive hanging in the air, you scroll through an inconceivable number of news alerts that broke while you were sleeping. Threatened nuclear war with Puerto Rico? Signed an order making it legal to hunt zoo animals? Retweeted George Zimmerman? Some may try to ignore them. Most just catch up and move on, with slightly less spring in their step. But I am among a select group of masochists who are obliged not only to follow this onslaught of news but to make it funny.
I’m in my third presidential term as a writer for Conan, and until recently, there was a humming predictability to our days. A batch of headlines (“premises”) would greet us upon arrival at 9 a.m., and my fellow sketch writers and I would cloister ourselves in our offices, poking at those premises for comedy. Typically, we would send pitches to our head writer or meet in his office by 9:45 a.m., where we would “yes-and” promising ideas, fine-tuning them or contributing additional beats. Meanwhile, our monologue writers would be racing to send in their first pass — as many as 70 jokes. After things get weeded out by rehearsal, between mono jokes and sketch, a typical show might end up with around a dozen potential brushes with that day’s news.
Conan is, by its own design, not an especially political show, but there are always certain “big” news stories that can’t be ignored, like a government shutdown or — please, oh please — another Anthony Weiner sex scandal. There are other stories that we simply won’t touch and, depending on their level of magnitude, can even serve to wipe out our desire to present any comedy that night. After the terrorist attack in Paris in 2015, Conan scrapped his whole monologue to speak directly to the audience. Then, on slow news days, you just hope and pray something stupid happened in Florida. (It did.)
The news was once a semireliable friend to a late-night writing staff, often there for you in a pinch, if occasionally flaky. Then, a philandering real-estate and mail-order-steak magnate was sworn in as president of the United States, and suddenly the news was a new kind of friend. The kind who emails you, then texts you immediately to see if you got its email.
Now, after seven months of trying to have fun with headlines that arrive with such frequency they often insert themselves between the delivery of a setup and punchline, or render both obsolete, I feel naïve for ever thinking Trump was a completely useful tool for comedy writers, someone whose buffoonery did all the heavy lifting for us. Remember when he assured the American people that his penis was a very satisfying size right in the middle of a Republican primary debate? I miss that guy — the one who had no shot at the White House.
Spend any time on Twitter and you’ll see even the best comedians abandon their usually meticulously crafted jokes to simply retweet the president, appended with an enraged “FUUUUUUUUCK YOU.” Every permutation of a Trump riff — on his hand size, skin tone, infantilism, relationship with women — has circled the world three or four times.
Of course, some shows have steered into the skid with great results (The Late Show With Stephen Colbert and Saturday Night Live being the obvious examples). Other hosts have continued to offer up entertainment inside a protective, relatively news-free bubble. (I don’t see James Corden doing a freestyle rap battle with Reince Priebus, although, having said that, I am going to set up a Google alert because that is something I refuse to miss.) On Conan, our directive has always been to mine the absurdity from the world, but when the world itself has become absurd, the effect can often be anything but energizing. Lately, our writers’ room has come to serve a new function, as a kind of refuge where, before ever pitching an idea, we first unburden ourselves of that day’s political anxiety. I never thought I’d find myself screaming “Emoluments!” during a pitch meeting, but here I am.
When we finally get to trying to zero in on the most important story to spin, it’s clear that we’re all gamely fighting fatigue. “Is there anything to Andy Richter recusing himself from the show?” (Turns out, there wasn’t.) “Can we offer this show as a sanctuary city for Melania Trump?” (Vetoed.) “What about a product called Are You F’n Kidding Me? which is an extra set of hands you can bury your face in after seeing that day’s news, to keep your own hands free for other activities?” (Too trenchant!)
“Trenchant” has become an emergency brake, a response to ideas that are a little too close to our unfiltered feelings. When a sketch idea sounds like it might elicit a kind of self-satisfied “bravo” (our millennial audiences are so fond of shouting “Bravo!”), it is met by a murmured chorus of “trenchant” from the room. A couple months into the Trump presidency, on a rare slow news day, I pitched a recurring segment where Conan “checks in on” America out of concern for its welfare. Then we’d cut to another part of our studio, where someone in an “America” costume is sitting in a bathtub, holding a toaster. Needless to say, the only way a sketch about our country attempting suicide could exist beyond the writers’ room would be if I used it as an example of what not to do on a comedy show.
In order to preserve what remains of our humor, some staff have found coping mechanisms. One monologue writer told me he avoided using the words “president” and “Trump” together in his jokes for the first couple weeks of the presidency, then gradually began employing just one or the other, as it relates to presidential or personal actions. “The president threatened Nordstrom on Twitter” or “Trump is afraid of stairs.” We’ve also gotten a lot of mileage, and a lot of therapy, out of jokes describing the various things Steve Bannon smells like: old doughnuts, microwaved shellfish, etc. And one writer, striking directly at the heart of our malaise, pitched an idea where Conan, completely fatigued by the assault of breaking news, could periodically take a knee and tag other celebrities to deliver Trump jokes on his behalf.
But the only way to achieve true escape velocity is to find a distraction that makes us so giddy that the world, with all its depressing premises, melts away. A few months ago, I emailed out an idea about a toilet-activated burrito-delivery system from Del Taco that became more intuitive as you used it, eventually allowing the user to achieve an infinite loop of delivery, consumption, and — well, you know. Another writer seized upon the idea, calling this perfect state “Delfinity.” From there it quickly spiraled out, and we turned it into the most ambitious, resource-draining toilet joke we’ve ever done. That same day, Trump accidentally shared an important piece of classified intelligence with Putin’s top diplomats. Like Delfinity, this shit never ends.