Adventures in Trumplandia: And The President Laughed

John Oliver and his team have subsequently been held responsible for the events that follow, chastised in the more conservative media channels as “instigators,” “disturbers of the peace” who “got what they deserved,” but at the time, it must have simply seemed like a golden opportunity. For comedy. For America. That Oliver et al. could have fully anticipated the chaotic fallout that would accompany their actions that day is highly unlikely.  More-so, it will be argued here that Oliver and the many comics followed his lead were simply doing their jobs, showing up for work where and when there was work to be done.

The documentation of that morning that has been made available to the public opens with the Last Night Tonight’s rented van rolling up and parking as close as was lawfully possible to the White House’s North lawn. Oliver pops out, followed by several cameramen and an intern with more coffee than seemed strictly necessary – but as Oliver may have anticipated, this was only the beginning. ‘Are we rolling?’ Oliver is said to have inquired, and then the cameraman hits record.

OLIVER: Less than an hour ago, and that hour of course being six in the fucking morning, President Trump issued the following tweet. “The so-called late night comics think they’re SO FUNNY (so funny is in caps in case you can’t tell from my accent) but I bet they couldn’t make me laugh if they tried. Not funny! Sad!”

You can see the White House in the shot now as Oliver antically makes his way towards the gate between the lawn and White House itself, coffee cup in hand.

OLIVER: And all right, he’s got a point. Trump has notoriously never laughed once in his life in such a manner that one would deem heartfelt or authentic, not even while firing someone without cause or when those Russian prostitutes urinated on the Obama bed right in front of him – which was hilarious and had everyone else in the room in stitches, even the prostitutes themselves, but Trump just sat there with his hands crossed awkwardly between his legs looking as though he was suffering from a fit of gasbut anyone can change, am I right? Instead of assuming that he’s not laughing because he’s got the sense of humor of a starving polar bear or a grumpy lawn gnome that’s been shat upon by a seagull, what if – and it’s a big what if, America, but what if he’s simply never been told a joke that was funny enough to laugh at?

The camera jiggles slightly as the cameraman pans the lawn, early morning, dew drops on the grass just beginning now to evaporate in what would be another steamy day in the nation’s capital. Oliver looks directly into the camera.

OLIVER: Comics everywhere, let’s raise the ante, shall we? SHALL WE? I’m here just outside the gate facing the North Lawn of the White House, and I hereby issue the following challenge. Gather here with your best joke, and we’ll tweet our way into the White House wherein the first comic to make Trump laugh wins.


OLIVER (turning away from the camera, which is quickly pointed at the ground): Maybe a hat?

Without a reliable source willing to go on the record from inside the White House itself, it’s impossible to say with certainty how Oliver’s subsequent taunting tweets were brought to the attention of the President, or if perhaps Trump acted alone. What can be confirmed is that roughly seventeen minutes past the hour of seven o’clock in the morning, Trump tweeted the following response:

Very boring Owl Face Oliver says I don’t know whats funny. I KNOW WHATS FUNNY.

And then this one, two minutes later:


Oliver, reportedly over the moon with delight at this, tweeted back:

Face To Face, Oh Great One? #MakeAmericaFunnyAgain

Then there was a pause, possibly while Trump ate one of his morning cheeseburgers and received a highly classified update, which in all likelihood he ignored while coming up with his retort, which hit the air at seven forty-nine a.m.:

Make line outside BIG WALL at South Lawn. Will receive first so-called comic at noon. Five minute to each. All invited! #MAGA

Reportedly, Oliver hopped around for at least fifteen minutes after the second tweet crowing, ‘What do I deserve? What do I deserve?!’ There is no collaboration on whether or not he came to a conclusion on this particular point of contention.

By nine o’clock, there were no less than forty-six comedians lined up outside the South Lawn (where had Oliver quickly re-parked his van and set up cameras which were set to stream on Facebook Live.) By ten o’clock, the crowd had swelled to more than one thousand.

At 10:11 a.m., a black SUV rolled around the corner and halted near the numerous parked cars and media vans, which now dotted the outer lawn area. Several helicopters hovered overhead, capturing the spectacle. The window of the SUV slowly rolled down. Several witnesses claim that the occupant of the vehicle was none other than Louis C.K., wearing dark sunglasses, and it is reported that he peered out from this vehicle over the raucous crowd for quite some time. His lips moved, as though repeating a mantra or perhaps the beginnings of a joke or an apology. He looked, as one onlooker put it, sad. Eventually he said something to the driver and the car drove away with the window still rolled down, Louis C.K.’s face made momentarily visible to most in the crowd. Oliver’s cameraman captures the moment just as the SUV takes a right and disappears down the boulevard.

By this time, Trump’s comic challenge tweet had been retweeted more forty million times. A full blown phenomenon was taking place, with no precedent. Somewhat strangely, the hashtag #Princess&Pea took off, trending 700% above norm, despite its reference to a dissimilar fairy tale. Many crude renderings of what artists assumed Trump might look like in the midst of a hearty midday laugh flooded the internet. Some photoshopped actual laughing mouths onto Trump’s head. It was an unsettling morning on social media overall.

The West Coast comics did the math. Already, according the various feeds and tweets and posts, there were more than a thousand people in a line outside the White House. At the allotted five minutes per, and not taking into account transitions between comics and the scheduling delays that seemed inevitable from this particular White House, that was only twelve comics per hour – less than one hundred would be able perform with an eight hour span, making the trip east seem foolhardy at best, unless for some reason the president decided to make a lottery out of it. Even then, arriving so late in the afternoon after the 12 p.m. cutoff seemed unlikely to pay off in the long run. No one wants to be last in line, after all. So, many of the LA comedians opted to stay at home. This time zone dissonance resulting in the west coast comedians’ refusal to risk the long six hour flight from various locations in order to arrive in Washington DC and then stand in a line full of other comics had the unintended effect of wildly unbalancing the West Coast versus East Coast comic rivalry for years to come, and could not have been predicted by anyone, except possibly Jerry Seinfeld.

Seinfeld, on the morning of the “comicalypse,” as it would be come to be described, was filming one of his ubiquitous “Comedians In Cars Getting Coffee” episodes with guest star Bob Einstein, inexplicably appearing in his third episode on said TV show despite not being particular funny or that into fancy cars. There is actual footage (not aired in the TV show itself) of Seinfeld looking at his phone just as the tweet war was heating up, sighing to himself, muttering ‘Well this is gonna be bad,’ and swinging a U-turn in his 1958 Porsche Jagdwagen, with Einstein hanging on for dear life. Einstein can be heard asking, ‘Jerry, where are we going? I thought we were going to get some coffee,’ to which Seinfeld responds, ‘West, Bob, we’re going WEST!’ Although there isn’t a lot further west one can go than Santa Monica, which is nearly they started out in the first place. Seinfeld rescues the episode by walking with Einstein along the beach.

Back on the East Coast, Oliver was gerrymandering the line so that actual comedians would be nearest the front.  ‘Come along Sarah!’ he crowed, pulling Sarah Silverman along by the elbow. ‘We must have you in that room!’  Silverman deflected his enthusiasm. ‘John, you’re first, he’s going to laugh at you and then it’ll all be over before it started.’ But she did not complain further as Oliver installed her in the seventh position from the gate. Oliver waded back out into the crowd in search of Amy Shumer, who was rumored to be trapped behind a team of high school improv comics, while Silverman discussed strategy with Gilbert Gottfried, who has arrived early and had started out in the #2 slot behind Oliver but now had been pushed back to #9. This exchange was captured on tape:

SILVERMAN: I was just thinking about, you know, not what’s funny – we know what’s funny – but what would make him actually laugh, so that he’d admit to it publicly. We can’t prove he laughed, so it has to be a joke that makes him look good –

GOTTFRIED: My game plan is that he’ll just laugh at me.

SILVERMAN: Isn’t that always your game plan, Gilbert?

GOTTFRIED: (unintelligible insult in response while others laugh)

SILVERMAN: No but like one of those wise men jokes where someone has to climb the mountain in search of great wisdom and the punch line is something the wise man says except in this case I’ll just have the wise man be Trump? It has to be a joke at the expense of the climber, right? And the climber is us.

GOTTFRIED: A wise man joke? You’re going in there with a wise man joke?!

SILVERMAN: So what, you’ll just march in and make fun of midgets for five minutes?

At this point, Oliver returns victoriously with Shumer, and subsequent cross talk overwhelms the recording.

According to those in attendance who made it out, there was no consensus as to an approach. Some comedians settled upon their regular methodology, assuming that making changes would cost them in the long run. ‘You know what I mean?’ said Dave Chappelle. ‘I make the motherfucker laugh with a knock knock joke, what’s that say about me?’ Kathy Griffin, overhearing this, crowded in on the conversation, calling out ‘If you’re not going to use the five fingers bit, can I?’  Chappelle did not appear to hear her over the clamor of the other comics in line.

The five fingers joke works as follows:

PERSON ONE: What did the five fingers say to the face?

PERSON TWO (confused): What?

PERSON ONE (slaps person two across face while yelling): SLAP.

It is not clear as to whether Griffin ultimately used the joke.

At one minute prior to noon, a cloud passed over the sun, causing most in line to fall suddenly silent. They waited for the gate to open. At 12:02, it did. Behind it, a convergence of black-suited Secret Service and presidential aides were standing around. In the center of the group, White House chief of staff John F. Kelly stood, holding waivers. He looked decidedly annoyed at the day’s activities as he handed out waivers to the comics in line. ‘You have to sign these,” he said. ‘Then you can go in.’ All but one of the comics signed. (The dissenting comic, Stephen Colbert, pocketed his waiver instead, and read it out loud on his show the next day to record high ratings. It helped, perhaps, that he was the only remaining East Coast host to go to air that night.)

The last of the footage made available by John Oliver’s camera crew shows Oliver, alone, standing on the precipice of the entryway into the White House. He looks over his shoulder and grins, gives a thumbs up. He is then encompassed by a swell of Secret Service agents, two of which appear to put their hands on his shoulder as Oliver disappears from view.

All in all, forty-one comedians passed through the gate before the event concluded at roughly 6 p.m. In addition to Oliver, Silverman, Gottfried, Chappelle, and Griffin, also among the notable lost were Mike Birbiglia, Aziz Ansari, Jim Gaffigan, Chris Rock, Trevor Noah, Jimmy Fallon, and Ali Wong.

Tig Notaro was next in line when the gate finally closed, and would later work it into her next routine.

EXCERPT FROM NOTARO’S COMEDY SPECIAL: I was number forty-two. You know what else was forty-two? Ever read Hitchhiker’s Guide to the Galaxy? Don’t answer that. It’s supposedly the meaning of life. What’s the meaning of life, they ask? Eventually, an answer comes back. Forty-two. Did that used to be funny? Did we think that was funny? I’m just saying, we used to laugh at things. Remember that? Remember when comedians just… you know… made you laugh?

I know. We’re survivors. Laughs don’t come as easy. And now when I hear a shitty joke I have to be like, ‘You know, as a comedian, I don’t think that’s actually very funny.’ You’re out there like, ‘As an paying audience member, I would like to laugh now.’ And I’m like, ‘AT LEAST WE’RE HERE.’ As a survivor. As survivors. Our new collective identity. At least one thing to unify us. We’re still here.

None of the forty-one joke attempts were ever made public, either by the Trump administration or by any of the comedians themselves, who of course were heavily constrained in their capacity to speak out. It is not even clear whether the comics were given an opportunity to tell their jokes once admitted into the White House, although they did seem to be allotted their full five minutes before another was granted entrance. It was only when a member of the news media remarked that while the comedians were certainly going in, they did not seem to be coming out that those still in line began to experience a mounting sense of uneasiness.

For a time, it seemed possible to rationalize what might have happened inside the White House that day. Perhaps the comedians were being held so that they could all gather for a group picture? By the next day, when Fallon did not appear for work at The Tonight Show, it become apparent that things were more serious than had previously been imagined. Protests followed. #FreeTheComedians trended across social platforms. Days turned to weeks. Lawsuits were filed. Trump, after initially shrugging off the accusations of kidnapping and unlawful imprisonment, claimed that the comedians, in signing the waiver, had entered into an unbreakable agreement and had to be held accountable for their actions, or in this case, lack of action. ‘I never laughed once,’ the President claimed on Fox News repeatedly. ‘I never laughed.’

The subsequent TV show Live at Guantanamo Bay, executive produced by President Trump himself, in which the forty-one detained comics compete for food, drink, and the chance to do a routine in front of the rest of prison in exchange for their “early release” (which was never granted) ran for five seasons. The first two were actually pretty funny, if one is being objectively honest about it. Season Two even got an 82% fresh critical rating on Rotten Tomatoes.