In case anyone had been able to forget for even a single blissful second, it’s almost been exactly one year since Donald Trump became our president. Since then, he’s tried and failed to enact a travel ban; tried and failed to keep transgender people out of the military; picked fights with Kim Jong Un, the Bushes, and sports; pardoned an openly racist sheriff; defended white supremacists; invented a word; and played a shitload of golf.
Yeah, it’s been a nightmare, one that took on a new shape on November 8, 2016, a day that Esquire felt the need to revisit in a new, extremely thorough oral history. For the piece, the writers spoke with politicians, pundits, entertainers, organizers, and even the heaving blob that houses Steve Bannon, resulting in a piece that examines the expectations and sense of surprise that afflicted both sides of the divide.
As the election unfolded, comedian Neal Brennan was with Dave Chappelle preparing for the latter’s hosting gig on Saturday Night Live. Brennan recalls sitting with the writers as the election results poured in, and the feeling of despair that accompanied the idea of having to cull comedy from what was clearly a despairing moment in American culture.
“Slowly but surely it dawns on us,” he says. “And I had said things like, ‘You know, I’ve heard that technically Republicans can never win another presidential election.’ I’m just saying dumb shit, all things I’d read on Politico or fuckin’ The Atlantic or whatever. And then slowly but surely it happens. It’s like we ... it … fucking Hillary lost.”
Brennan went on to write the episode’s standout sketch, which found a bunch of white people reacting to the results with surprise as Chappelle and Chris Rock laughed knowingly in the background. “It was based on the experience of being in [Colin] Jost’s office and me saying incredibly stupid shit as reality crumbled.”
Chappelle clearly had an influence on the sketch, too, if for no other reason than that he was the only one at 30 Rock who seemed to realize Trump would win. “Chappelle was like, ‘Dude, I feel like Trump’s gonna win,’” Brennan says. “I was like, ‘Dude, I’ll bet you a hundred thousand dollars he won’t win.’ He did not take the bet, thankfully.”
Chappelle ended up addressing the election during his monologue, saying that he was going to give Trump a chance. Surprise, he ended up regretting that.
You can read the whole illuminating piece over at Esquire.