Che sits down for Boardroom Talks to discuss pranking Colin Jost, confronting Ye, learning the language of a writers’ room, and why a joke still comes down to the joke.
Every week at Saturday Night Live, Michael Che sits in a room and reads sketches aloud to the entire production. Roughly 40 get read, and “about eight or nine” make it to Saturday. If the room doesn’t laugh, the sketch is dead. Most writers would call that a problem. Che calls it the whole point.
“If you could say whatever you want, then it’s not that interesting when you say whatever you want,” Che told Boardroom’s Damien Scott.
He brought that philosophy to the latest episode of Boardroom Talks ahead of his Shot in Minnesota, his first special as director, which landed on Netflix on Oct. 13. And the date wasn’t an accident, at least not on purpose. Nine years ago, Che wrote a $1,000 check on The Tonight Show and told the recipient not to cash it until that very day. He’d forgotten. “That would be an insane plan,” he said. Then he came around. “I love it when a plan works out.”
Che’s own path through the pressure began in a smaller room. When he arrived at SNL, he was “the only Black writer on the show,” and every sketch with a specific perspective had to land with people who didn’t share it. “So I had to learn their language.” He calls the setup a “huge disadvantage,” but says it paid off. “It also makes you stronger.” When he later became the first Black head writer in the show’s history, the milestone barely registered: “It just felt like a promotion at a job that I was working at.”
He’s convinced the walls are what make the work worth watching. Dave Chappelle calls the weight of a live mic “The Gat,” and Che agrees that when comedians can’t say anything they want, “people appreciate it more.” He applies the same logic to the outside world. “Anybody could be brave when everything goes.”
For his own special, he picked his constraints carefully. He shot in Minnesota, in a music venue “not even made for comedy,” packed until it felt “very warm and crowded and feels like a rock show.” He kept the title plain — “I like titles that are sort of just clean and simple” — and he kept the focus where it always is: “It all comes down to the material.”
The pressure peaks live, where he and Colin Jost read jokes the other has never seen from the other. That’s where the roast beef joke came from, a line Che won’t repeat and admits was “a little far.” It’s never left him. “That’ll follow me forever.” He doesn’t seem to mind. “There’s very few times where a large segment of the world feels like they’re in on the same joke.” And the cost? “And if I got to sacrifice Colin’s marriage to do that, then I think it’s…”
“So be it,” Scott said.
“So be it.”
The prank war between the two is “very real,” and one stunt crossed a line. On an April Fools’ show, Che told the audience not to laugh at any of Jost’s jokes. Jost bombed and scribbled on his notepad that it was the worst show ever. “He was shook,” Che says. He understands what he did, because he knows what that stage demands. “You could work all week on that show just to get it right for one moment.” His verdict: “I’m glad I did it, but I wouldn’t do it again.”
Not every high-wire moment has aged well. Che says he can’t sit through the viral clip of him confronting Kanye because “it makes me cringe,” and he still doesn’t know who was recording. “I have no clue.”
By the end, he’d made it through all of Boardroom’s curveballs, including a request to name comedians who make him laugh. “Everybody’s good,” he said, before coming through with Reggie Conquest, Kevin Iso, Marie Foster, and Derek Gaines. Rap was the one topic he conceded. “I’m 43. They don’t make rap for me no more.”
At the end, Scott asked if any of it had been tough. Che, a man who has spent his career thriving under pressure, grinned. “None of these questions was hard, by the way. I had a blast.”
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