What Michael Che and Sam Richardson Learned From Their Worst Jobs

In Reunited, Awards Insider hosts a conversation between two Emmy contenders who have collaborated on a previous project. Today, we speak with The Afterparty star Sam Richardson and Michael Che, cohead writer and star of Saturday Night Live and star and creator of That Damn Michael Che. The pair previously worked together in the writers room of the TV series Detroiters.

when Michael Chee and Sam Richardson sign onto Zoom for our Reunited chat, the jokes start right away. Che is calling in from New York, where he just completed a photo shoot in Times Square. “It’s the capital of America. It’s why so many countries hate us,” hey quips.

“Yeah, they envy our lights,” replies Richardson, who is in Los Angeles.

“They envy our giant Forever 21 signs,” says Che.

“That’s right. They too wish they could have Bubba Gumps,” says Richardson.

This easy report will continue for the rest of the conversation. Che and Richardson have known each other for years, but first worked together in the writers room on Detroiters, a 2017 Comedy Central series in which Richardson also starred opposite Tim Robinson.

They arrived in Hollywood on different paths. Che began as a stand-up who joined Saturday Night Live as a writer in 2013 and as the Weekend Update coanchor in 2014. Richardson honed his skills as an improv and sketch actor at Second City in Detroit and Chicago before appearing on shows like The Office, Arrested Development and Veep† They already reunited once this year, when Richardson appeared on the second season of Che’s HBO Max sketch series, That Damn Michael Che, which premiered on May 26.

Both keep extremely busy. Che, who just completed season 47 of SNL, also released his Netflix stand-up special Michael Che: Shame the Devil in November, and Richardson starred in Apple TV+s The Afterparty an ensemble murder mystery comedy set at a high school reunion. Both as writers and performers, they’re often using their own stories and observations to create comedy, though they say putting themselves out there isn’t as scary as it may look. They chatted with Vanity Fair about their recent work, how the opportunities in comedy have changed and who’s the “funniest man in the world.”

Vanity Fair: What do you remember about the first time you met?

Michael Che: I with you before Detroiters, but I got to know you on Detroiters and I think, to me, those writing rooms—I might have been there for like a week maybe, I wasn’t there for very long—but I remember that being the most fun writers room.

Sam Richardson: We’d met before because I’ve come through to SNL a few times, but when we did the writers room for Detroiters and we were doing it in New York…

Che: In 30 Rock.

Richardson: At 30 Rock. That’s when we really got to hang out and a writers room is always, I might not say always, but it can be good.

Che: Not always.

Richardson: Not always, but if a person’s genuinely funny and you really vibe with them, it’s fun because you just want to hear everything that person has to say, or every take they have on a joke or a bit or what they add to it. Everything you said, I was like, “That’s genius. That’s really funny.”

Che: You would love to be around people whose brain goes in a different way like, “Why didn’t I think of that?” I’m a stand-up, so hanging around writers, sketch writers, and real writers and shit, to me, I’m always learning something from you guys because my brain doesn’t work like that. Simple things that you guys probably take for granted that I’m just like, “Oh, that’s so fucking smart. Why didn’t I think of it?”

How would you both sum up where you were in your careers at that point?

Che: I never know how I’m doing in my career. I usually have to read about it and it’s usually bad. [Laughs.] I think then, I was doing kind of the same thing I’m doing now, was just kind of Update writing on SNL, getting one sketch in a month and doing stand up on the side.

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