In November, Dave Chappelle hosted a highly praised episode of Saturday Night Live, which just so happened to air a few days after Donald Trump was elected president. The dour circumstances would make a difficult task for any host — even for a consummate comedian like Chappelle — but he (unsurprisingly) managed to knock it out of the park with his politically charged monologue and some Chappelle’s Show shenanigans. However, as you might imagine, it didn’t come easy for the SNL team to write a show that week, and Chappelle was seriously concerned that the writers weren’t going to come up with anything substantial by the weekend. “At a certain point [on Election Night], we were all in the writers’ room, and as the night went on, and Trump was picking up these Electoral [College] votes, everyone stopped writing,” Chappelle explained in a rare interview with the New York Times. “And then everyone was just staring at the TV. I saw people tear up sketches they were writing. They’d assumed Hillary was going to win. Now there was essentially no show on Saturday. It was like the wind got knocked out of the writers’ room. I was really worried.”
Chappelle also noted that the best advice he got for his poignant monologue came directly from Louis C.K., less than 24 hours before showtime. “I went to a comedy club Friday night [before the show] and saw him,” he explained. “And Louis told me: ‘Forget the rest of the show. The monologue is all that matters.’ I was stressed out all that day. But right before I went onstage, this calm just washed over me. Everything just felt right.” And the rest, as we know, is history.