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I Was Trapped with Stephen Colbert During the Last Election and Watched Comedy Reinvent Itself

True, Colbert's 2016 election special was a harrowing ordeal. But sitting in the studio that night, I came to a revelation.

Stephen Colbert

Stephen Colbert

Scott Kowalchyk/SHOWTIME

Many television hosts struggled through election 2016, but few endured the scale of cringeworthy moments faced by Stephen Colbert. Much has been made about the late night figure’s dreadful Showtime special and the way it flailed about in search of feeble punchlines. Yet even as Colbert stumbled through ill-advised bits and banter while the electoral map bled red, the more apt broadcast was taking place outside the Ed Sullivan Theater.

It was there that the network placed a “Screaming Booth,” where passersby could vent their anxieties in real time. Live-streamed on Facebook, where it played alongside cable news anchors issuing unnerving live commentary as results came in, the “Screaming Booth” feed eventually amounted to two hours and 18 minutes of pure existential terror — the essence of November 8, 2016.

Standing in line that evening outside the Ed Sullivan and waiting to join the studio audience, I eyed that booth with a mixture of annoyance and queasy uncertainty before concluding I had no need for cathartic release. Surely, there was no reason for such abject eruptions of fear and frustration … right? Trump was doomed, of course! The prospects of a presidential campaign rife with misogyny and racism, powered by ineptitude, and pitted against the potential of a shattered glass ceiling somehow taking charge of American society just didn’t add up. Some people lived in a bubble that year; I relaxed into its boundaries, until they burst into a teary mess.

But then again, so did a lot of people. Later that evening, as I sat in the studio and watched Colbert struggle through a hellish evening for any kind of levity, the room became a hermetic embodiment of the emotional whiplash experienced by millions across the country. Colbert’s team had projected the electoral map onto the ceiling of the room, so the cameras could capture it as they swung across the audience, as if were were literally crushed by the impending results.

To his credit, Colbert worked every angle to inject some measure of energy into the room, singing “The Room Where It Happens” from “Hamilton” during a pre-show Q&A with the audience and grasping for every possible means of eliciting laughter from a visibly uneasy crowd. One early line: “America doesn’t have dictators — yet” kind of worked, in a nauseating sort of way, but it was hard to envision how the writers thought it would play when Jeff Goldblum surfaced at the top of the stairs above the stage for a glib “Jurassic Park” reference (“Trump finds a way”). By the time the Florida results came in, however, Colbert’s best means of eliciting cheers from the crowd arrived when he took full advantage of the uncensored cable format. “If Trump wins,” he said, “how about bursting into tears and screaming ‘Fuck’ for 45 minutes?”


Stephen Colbert during the taping of his 2016 Showtime election special.


For all its failings, the “Live Election Night Democracy’s Series Finale: Who’s Going to Clean Up This Shit?” special illustrated the fundamental disconnect between live television and the art of comedy writing steeped in expectations. It was fascinating to watch Colbert fidget in between commercial breaks, tap his toes in a nervous patter as he waited for the camera to go live, and mutter to his producers about the best way to improvise around an abrupt shift to their plans. (He would later admit that he avoided writing jokes before the broadcast about a possible Trump win.) His profound closing monologue, about the poisonous nature of American discourse and prospects of moving ahead in dire times, ranks as one of the greatest moments in improv history. (Even if it was partly scripted, Colbert’s delivery was dictated by the grim atmosphere around him.)

Colbert found his groove by the end of the show in part because he could he could work through the tension that surrounded him at every turn. He could roam the room and scan the crowd, tossing out shreds of reflective ephemera in the hopes that anything might stick. With bandleader John Batiste following Colbert’s cues, the space transformed into a surreal, free-flowing musical thriller, the invention of a new TV genre before our very eyes.

The rest of us were muzzled. Sure, the studio audience could cheer or mutter or groan at the appropriate moments, but the microphones couldn’t capture what it was like to sit in a room where talking was discouraged even at a whisper and cellphones were banned. (We snuck them out at commercial breaks anyway.) At a moment when so many people needed to huddle with the people they cared about and contemplate a jarring new world, there was nothing to do but wait.

Jokes couldn’t save us then. Bone-weary and shellshocked by the time we made it back to Brooklyn, my partner and I turned to nature shows and toyed with our cats. It was a desperate attempt to change the mood, and worked, at least until sleep found a better solution. Humor had no depth that night. It wasn’t funny. But the failure of comedy to wrestle with those circumstance helped clarify its purpose as much as its limitations.

Looking back on the experience four years later, it’s easy to consider the viewer-host dynamic of Colbert’s program as a form of collective trauma. Perhaps, but it was also the moment that sincerity made a comeback. Colbert’s initial plans for the night reportedly included a group of naked men with the words “I’m With Her” spelled out across their rear ends in the event of a Clinton victory. Instead, he delivered a startling edict about how America had “overdosed” on the divisive inclination of political discourse. Sure, he slipped in a trite stab at leaked emails and one prescient line about what it was like to “feel the way Giuliani looks.” However, Colbert’s greatest moments came when he stopped searching for punchlines, and his tone became no more exacting and powerful than CNN commentator Van Jones’ own sobering words across town: “You have people putting children to bed tonight, and they’re afraid of breakfast,” Jones said. “This was a whitelash against a changing country … and that’s the part where the pain comes.”

Colbert stopped short of talking about race. (He let some of his guest comics, including Charlamagne the God, juggle the brunt of that.) A year after “The Late Show With Stephen Colbert” debuted on CBS, he finally, thoroughly, shed the mock anchor figure that put him on the map with “The Daily Show” and charted out a path to become himself. He had to shrug off his confidence and let the fragility take charge. He was all of us.

And fortunately, he wasn’t toast. Colbert remains an entertaining and personable character whose TV persona has calcified over the last four years into a zany, charismatic source of earnest curiosity, a kind of dopier Jack Paar. Meanwhile, though every attempt at satire in the age of a cartoon presidency faces dire consequences when it doesn’t connect, acerbic comedy works wonders when delivered in the appropriate context, as everyone from John Oliver to Sacha Baron Cohen knows well. Democracy dies in darkness; humor doesn’t. The 2016 ride taught us that the best comedians know when it’s time to get serious. I hated the experience of sitting in Colbert’s studio throughout that miserable night, but given all that we went through — the room, the nation, my future wife and me — I wouldn’t trade it for any other.

“Stephen Colbert’s Election Night 2020: Democracy’s Last Stand: Building Back America Great Again Better 2020” airs live on Showtime at 11 p.m. ET.

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