Dave Chappelle hosted SNL in 2016 following the election of Donald Trump. Now, four years later, he's poised to host again after yet another contentious presidential election that seems to be in Joe Biden's hands.

Whenever discussions arise about the greatest comedian to ever grace the stage, Dave Chappelle always ranks near the very top of every respectable list. His resume includes a plethora of highly acclaimed stand-up specials (with some of his more recent ones earning him Grammy and Emmy awards), numerous film credits, and, of course, his iconic sketch show, Chappelle's Show. Unlike any other comedian of his generation — with the exception of Chris Rock — Chappelle seamlessly weaves social commentary around race and politics, without compromising the integrity of the comedic art form or losing his soul. So when the stars aligned for Dave Chappelle to host Saturday Night Live On November 12, 2016, just days after Donald J. Trump defeated Hillary Clinton in the 2016 presidential election, plenty of people — shellshocked by the election results — tuned in to watch one of comedy's greats offer provocative takes on the political climate.

Accompanied by A Tribe Called Quest as the musical guest — the iconic group would release their politically charged final albumWe Got It From Here….Thank You For You Service just a few days later —  Dave Chappelle wasted no time addressing the zeitgeist of the moment. 

He began his opening monologue by saying:

“You know, I didn’t know that Donald Trump was going to win the election. I did suspect it. It seemed like Hillary was doing well in the polls and yet — I know the whites. You guys aren’t as full of surprises as you used to be. I don’t even know what she’s doing in the news. The whites were furious. I’ve never seen anything like it. I haven’t seen whites this mad since the O.J. [Simpson] verdict. White people screaming on both sides, 'Aahhh!'"

Continuing to connect the dots with Trump’s meteoric rise as the face of the latest iteration of white, racist political leadership, and the social unrest that was spilling over across the nation, Chappelle argued, "I don’t even think it’s the most important thing we’re dealing with. Don’t forget... all the things that are going on. Shootings. What you think about that? All these shootings in the last year. The worst mass shootings in the history of the United States. Pulse Nightclub, which they said ISIS did, and it turned out that wasn’t exactly what happened."

He also took a jab at Trump's unapologetic misogyny and how, despite his flaws, he still won the election. He said:

"Donald Trump, he did it. He’s our president. I feel bad saying it. I’m staying at the Trump Hotel right now. I don’t know if he’s going to make a good president, but he makes a swell hotel suite, I'mma tell you that. Housekeeping comes in in the morning, cleans my room. And I just, 'Hey, good morning, housekeeping.' Grab a big handful of pussy, and say, 'You know, the boss said it was OK.'"

Surprisingly, after critiquing the moral failings of Trump, the political process, and the lack of racial justice for Black and Brown people in America, Chappelle concluded his monologue by extending an olive branch to Trump.

"I’m wishing Donald Trump luck. And I’m going to give him a chance, and we, the historically disenfranchised, demand that he give us one too. Thank you very much," he said.

Chapelle’s quasi, soft-embrace of Trump garnered him much criticism. Eventually, Chappelle would attempt to set the record by offering an apology, saying, during a benefit set in 2017, "I fucked up. I'm sorry." After witnessing the devastation that came as a result of Trump’s inept leadership, it’s fair to say that Chappelle is fully aware now — more than ever — that Trump never deserved a chance.

Of all of the performances on SNL that night, there was one sketch in particular that encapsulated the tenor of the moment — "Election Night." The skit revolved around an election night watch party where Beck Bennett, Aidy Bryant, Vanessa Bayer, and Cecily Strong portray a group of naive white progressives who grow more and more surprised as Hillary Clinton's expected win became Trump's. The power of white supremacy that aided Trump's win came as no surprise to the two Black men in the room — Chappelle and special guest Chris Rock.

Seeing Chappelle sigh at his white friends prematurely calling Florida for Clinton and making a toast to Latino voters was a hilariously subtle jab at the willful ignorance of real-life white liberal voters. When the friends hear that Florida has gone to Trump, Chappelle mockingly tells them, "I guess the Latinos didn't hear about your toast."

Rock also joined in the much-needed mocking. When the friends wondered why Clinton wasn't doing the same numbers as Obama, Rock gave the perfect response: "I mean, maybe because you're replacing a charismatic 40-year-old Black guy with a 70-year-old white woman. That's like the Knicks replacing Patrick Ewing with Neil Patrick Harris." 

But the best moment comes right at the end when Bennett declares that Trump's election is "the most shameful thing America has ever done." In response, Chappelle and Rock trade a bemused look to each other before breaking out into laughter — the pair ridiculing the naivete of whitness masquerading as woke.

Four years later, Chappelle is back in the saddle hostingSNL the Saturday after another polarizing, contentious presidential election. He'll be far from Yellow Springs, Ohio, where he hosted a number of socially distanced comedy shows, as well as delivered his powerful and raw8:46 special, where he spoke out against the death of George Floyd earlier this year. Instead, he'll be at 30 Rockefeller Plaza, where the country will be awaiting what he has to say. With all signs pointing to Trump being a one-term president, he won't have to ask an inept businessman turned inept president for a chance again. This time, he can offer salutations and congratulations to Joe Biden and Kamala Harris, and crack jokes about the anxiety of this year's election while knowing that the nation will be in better hands than they were before. After the no laughing matter of 8:46, it seems like we'll finally be able to share some laughter with Chappelle come Saturday.

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