Revisiting Stephen Colbert’s Live 2016 Election Night Special, an Artifact of Bygone Shock (Column)

Caroline Framke
·6 min read
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Four years ago, Stephen Colbert stood onstage, looked out at his hopeful audience and told them that they didn’t know yet who had won the 2016 presidential election. “But for the life of me,” he continued, “I cannot understand how Trump’s candidacy even got this far.”

Cut to: Jeff Goldblum, standing to the side with a pensive look on his infamously elastic face. “Well, I’ll tell you, Stephen,” he said, before launching into a monologue about the GOP and chaos theory that ended in a “Jurassic Park” line (you probably know the one). By the time a shellshocked Colbert and Goldblum talked later on in the show, Trump had won Florida and was well on his way to becoming President of the United States. Colbert’s earlier setup, it turned out, wasn’t for a joke at all: he didn’t understand how Trump’s candidacy had gotten that far, and really didn’t understand how he had just won.

On Nov. 8, 2016, the “Late Show” host’s live special unfolded on Showtime over one increasingly bewildered hour from 11 p.m. to midnight — a crucial moment in time hanging on the precipice between the moment Hillary Clinton still had a shot at the presidency and the moment it became clear that she had lost it. What began as a madcap political circus show with Colbert playing ringleader quickly devolved into a stunned reckoning as Colbert, his guests and his audience processed Trump’s probable win in real time. In the words of Variety’s Brian Steinberg in his report on the ill-fated event, it was “the late-night equivalent of a wake.” So when Colbert announced that he would be doing another live election-night special this year, he might as well have announced that he would be doing a televised séance to summon the ghosts of missteps past.

Looking back at the 2016 version now is difficult on several visceral levels, the most basic of which is that it’s almost impossible to view in its entirety. Unless you taped it the night of, it’s not available anywhere. The segments that do still live on the internet in some way, however, are perversely fascinating. No one in the Ed Sullivan Theater — not Colbert, not his producers, not the liberal, overwhelmingly white in-studio audience — expected Clinton to lose, let alone Donald Trump to win. Their instinctive attempts to grapple with that failure highlight so much of what went wrong before the election, and so much of what would happen next.

The first minutes of “Democracy’s Series Finale” (a supposedly tongue-in-cheek title that was never really that funny) are dedicated to a wacky cartoon of Trump fuming through Barack Obama’s 2011 roast of him at the White House Correspondents Dinner all the way to his own presidential campaign. Afterwards, Colbert delivers a jaunty opening monologue that acknowledges the possibility of a Trump victory (“it’s too close to call and too terrifying to contemplate”), but still with enough levity that a punchline like “you don’t have to cheer my name, America doesn’t have dictators — yet” manages to get laughs absent any dread. He pulls up an interactive electoral map and says that states Trump wins will flash bright orange (like his hair, get it?). A nude model traipses onstage with a precarious sign hanging just above his penis, ostensibly to help announce the results but moreso to underline that this special, unlike Colbert’s “Late Show,” was airing on a network that would allow it.

At this point, Colbert and company are rattled by the electoral college contest skewing closer than they expected, but are still hoping for the best. But by the time “The Circus” hosts and pundits John Heilemann and Mark Halperin join Colbert for double old fashioneds, the writing’s on the wall. Trump wins Florida mid-interview, inspiring a small ripple of horrified gasps, and the best Colbert can muster is, “does the election have a safe word?” Eventually, he concedes, “I can’t put a happy face on that — and that’s my job.”

From there on out, Colbert’s job became about mitigating expectations and finding an even vaguely optimistic way forward for the audience and himself both. Sketches like one with Laura Benanti playing Melania Trump — a role she’s played on and off “The Late Show” for years now — fell flat and were swiftly abandoned. Guest interviews like that with Goldblum turned into de facto therapy sessions. And when Colbert finally had to sign off, he noticeably shifted his rhetoric from that of a comedian to more of a preacher delivering a sermon with some occasional jokes, because “you can’t laugh and be afraid at the same time — the Devil cannot stand mockery.”

Watching the special now, it’s impossible not to notice details that either foreshadow future talking points or would never unfold the same now. On the former count, Heilemann’s immediate inclination to compare Trump’s supporters to Bernie Sanders’ on account of “populist rage” remains a knee-jerk pundit response today despite the enormous gulf of beliefs between them. And as for things that look a bit different today, well, look no further than Halperin, who was fired off “The Circus” in 2017 when several women came forward with allegations of sexual harassment during the height of the #MeToo reckoning. The world changed, whether or not they liked or were ready for it.

In that respect, it’s downright jarring now to watch Colbert’s melancholic, impassioned sign-off in which he waxes poetic about the days in which “we” didn’t have to pay as close attention to politics. “Politics was something we used to think about every four years, maybe every two, if you had no life,” Colbert mused to his now silent audience, a half-drunk glass of bourbon sweating on his desk. For now, he continues, “You can take off your ‘I Voted’ stickers and get back to your life.”

It’s understandable that in that uniquely public moment, Colbert could improvise nothing but bone-deep exhaustion. (His only joke that still holds true today is that the election’s constant chaos has made us all “feel the way Rudy Giuliani looks.”) But as the subsequent four years would prove beyond a shadow of a doubt, the sentiment that people should feel free to disengage was only true for a vanishingly small, privileged echelon of people. The domino effect of Trump’s election would go on to have horrific for repercussions for most anyone not rich, white, or both. This year alone, as his administration continues to diminish the devastating effects of the coronavirus pandemic, hundreds of thousands are dead. And now, with another crucial election looming just over the horizon, the idea that this could be“Democracy’s Series Finale” is very, horrifyingly tangible. Making a joke out of that possibility, no matter how tempting, was never a useful way forward. Four years and countless tectonic shifts in just about all walks of life later, it may be just as instructive to see how Colbert deals with this election no matter who wins it.

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