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An angry crowd, vanished guests and ‘horrible things’: Stephen Colbert tries again after memorably rocky 2016 election special

An angry crowd, vanished guests and ‘horrible things’: Stephen Colbert tries again after memorably rocky 2016 election special
Entertainment
In Stephen Colbert’s quarter-century on television, this might be the ballsiest choice he has ever made. He’s revisiting one of the bigger fiascos of his career by going live on Showtime (and Crave here in Canada) on U.S. election night on Tuesday.

Maybe it’s because there’ll be no live audience, due to COVID-19 ; maybe it’s because, no matter how badly his 2016 special, “Live Election Night: Who’s Going to Clean Up This Mess?” went, he remembers that night as the night his fortunes turned a corner and began to soar again.

His nightly CBS “Late Show” had a famously wobbly start, launching in 2015 with lots of dry chats with respectable people — the guests from just a couple of weeks in its first fall included Justice Stephen Breyer, Jonathan Franzen, an archbishop, Ben Bernanke, and other names synonymous with “hmm, what’s on Jimmy Kimmel?” Ratings reflected this — through 2016 Jimmy Fallon’s “Tonight Show” was clubbing the “Late Show,” sometimes outdoing Colbert and Kimmel combined.

But I have my methods, and the special’s slow descent into political horror was so memorable I’ve tracked it down. I had to; things fell apart in a manner that was sometimes heartbreaking but mostly funny (to me) in an entirely unintended way.

It began with a cartoon relating the rise of Trump’s campaign, spurred by long-ago paternal indifference and Obama’s jibes at his expense at a White House Correspondents Dinner. Animated Donald fumes, rants, snorts crushed orange Tic-Tacs and vows revenge, and then we cut to the cheering and chanting live studio audience, getting us ready for a final dunk on this thin-skinned, graceless creep. Then, well, you remember how the night went.

Clinton was, I doubt I have to remind anyone, the clear favourite going into balloting. As Colbert himself would later explain, in the weeks before the election, his team prepared material for three different versions of the show, for three scenarios: a clear Clinton win, a close fight that seemed to be going her way, and a night where Trump seemed to be leading but it was still unsure. As for material for an emerging Trump victory, Colbert likened such a show to a public execution and decided that no comedy was possible : “My execs and my writers were like, ‘You don’t want to write something for that?’ and I’m like, ‘No! There is nothing you can write … There will be no laughter!’” Somewhere, a monkey’s paw twitched.

Though Colbert would later say the audience wasn’t in the mood, at the beginning there was indeed laughter; the monologue scored and there was gratuitous nudity from a formidably fit male model bearing news on an index card over his groin. “I love women,” Colbert said, prompted by not much, and the mood was buoyant. Then the surest buzzkill of all showed up: journalists. Audience cellphones had been locked away, so they only got an update when someone on stage provided it — and when political analysts Mark Halperin and John Heilemann announced that Trump was leading Florida and was now the favourite, they couldn’t have deflated things more quickly with a stiletto.

A taped fake commercial starring Nick Offerman got an undeservedly tepid response, and an interview with Laura Benanti as Melania Trump got less than that. Touted guests — Katy Perry, Patton Oswalt, Larry Wilmore — did not appear at all. Jeff Goldblum and others dropped by; this could have functioned to elevate the mood, but what we got instead were comments like:

Halperin: “Outside of the Civil War, World War Two, and including 9/11, this may be the most cataclysmic event our country has seen.”

Goldblum: “.”

Comedian Jena Friedman: “I feel as if I’m about to give birth to a baby that’s already dead ... no one’s laughing … Get your abortions now.”

Radio host Charlamagne tha God, contemplating Clinton’s slender prospects, declared “women have done more amazing things,” somehow a more naked act of lady-pandering than the actual naked guy a half-hour before.

It didn’t work. When Colbert announced that Trump had won Florida, moans and angry shouts were audible; after Goldblum tried to lead the audience in meditation, Colbert engaged them directly, asking “How’s everyone?” and getting scattered cries of anguish in response. Pop singer Elle King performed a professional, only slightly downbeat version of “America’s Sweetheart” with a look on her face suggesting she’d rather be reporting for jury duty.

The host managed to pivot back to comedy at the end, segueing from his sincere reaction (an imperfect metaphor about drinking poison) to prepared, winning material about what unites the country: “Americans believe that low gas light on your dashboard is not a warning but a challenge.” A roused, shell-shocked bunch of tourists and New Yorkers went out into a changed world.

It had to have been Colbert’s most draining, difficult night on TV. From a comedy point of view, half of it was a trainwreck. And yet it was an utterly compelling trainwreck — funnier, in its dark way, than what he was often doing at CBS.

However painful election night was, it gave the “Late Show with Stephen Colbert” a clear path and a viable new identity as the TV HQ of the anti-Trump resistance: joke after joke after joke about The Donald. (Elizabeth Warren has appeared nine times.) It was a while in the making, Johnson suggests; the program might have still trailed badly in the ratings in summer 2016, but the “Late Show” ship was being righted, adding showrunner Chris Licht and funny-ing things up generally.

Colbert has become the late-night ratings champ even as the program’s politics surely must alienate half the country. The loyalty of all those viewers now lets him indulge that serious side — he interviewed former UN ambassador and Trump critic Susan Rice for 16 minutes in August, an eternity in TV terms.

Oppositional politics seems to work great in U.S. television — Fox and MSNBC ratings surge and recede, in turn, based on which gets to rail against the occupant of the Oval Office. So the Colbert renaissance might be difficult to sustain in a Joe Biden presidency. “Colbert loves Biden,” Johnson says, adding that Licht might literally .

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Still, these are champagne problems. Given the ratings drubbing Colbert was getting, it’s conceivable that were it not for Trump’s victory, he’d be out of a job by now — worth remembering for those of us mortified by a bad shift at work.

Incredibly, even nonsensically, the misbegotten Showtime special actually got nominated for three Emmy awards — testament to how ready show business was to honour anything sufficiently anti-Trump. One night of cringe paid off, in the end — maybe someday he’ll let people see the evidence.

Postscript: the good luck did not extend beyond the night’s host. Mark Halperin, once a familiar face on MSNBC, was #MeToo’d, and now appears on something called Newsmax. Elle King’s second album produced no hits. The animated opener got spun off, yielding a series, “Our Cartoon President,” that through three seasons doesn’t seem to get praised, promoted, criticized or even observed; no one you have ever met remembers seeing an episode. Charlamagne tha God continues untouched, however.

“Stephen Colbert’s Election Night 2020: Democracy’s Last Stand: Building Back America Great Again Better 2020” airs Tuesday, Nov. 3 at 11 p.m. on the Crave channel and streaming live on the Crave app.
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