Why Michael Che Thinks His Big Break Is Still to Come

Prior to starting as a writer at “Saturday Night Live” in 2013, Michael Che had never written a sketch before. Now, eight years later, Che is one of four head writers at the venerable program, co-anchor of the show’s Weekend Update segment, and creator, writer, and star of his own show, HBO Max’s “That Damn Michael Che.” Here, Che explains the challenge of pivoting from standup to sketch writing and why he believes his big break is still to come.

How does writing for “SNL” differ from writing for “That Damn Michael Che”?
At “SNL” your writing starts and ends in the duration of a sketch. This show, you’re able to stretch out over 20 minutes a sketch where the punchline is further down or or there are running tags that run throughout the show that make it feel more cohesive. Every sketch doesn’t need to be six minutes long. You can write a little bit freer as opposed to on “SNL,” where you have to write a tight five minute sketch and once it’s over it’s over.

How did being in your own sketches as yourself inform your performance?
That was mostly an HBO Max demand. I really didn’t want to be in the show that much. I don’t like acting that much. They wanted me to be in it more. I accommodated and I’m glad I did. I always write a little bit where anybody else can do this so might as well let somebody else do it. They felt like if they were paying me, I should be in it–and I don’t know that they’re wrong.

What has “That Damn Michael Che” added to your writing and acting skills?
It’s less spooky: Acting, I'm always way too far in my head. “Does that suck?” People are like, “It’s fine man, relax.” It makes it a little more natural. Just like anything you do more, it feels more natural. 

You’re an artist, and you also worked for Tommy Hilfiger. What made you pivot to comedy?
Everything I did felt so unnatural. I never felt good at anything deep down. When I started doing standup, I just wanted to try it but I didn’t know what else to try. I just wanted to try everything I’ve always wanted to try and standup was always something in the back of my head, like, That would be so fun to do what Chris Rock was doing. I tried it and as soon as I tried it I was terrible at it. But I loved it more than anything else, so I stuck with it and kept doing it every single day. 

Every comic bombs, but is there a story that sticks out for you as being the worst bomb?
The first time I really, really bombed was at this club in Newark. I remember I had never really bombed before and I told my friend whose show it was. We were at an open mic somewhere in the city and I had only really done open mics and bar shows and he said, “I have this show in Newark if you want to get on.” I was telling him I never really bombed. It makes me cringe how arrogant I must've sounded to him—his name is Richie Redding, by the way, a really great comic from Philadelphia. I probably sounded like such an ass. Oh my god, I bombed. I couldn’t even get out “Hello.” They booed immediately. As soon as they saw me onstage it was like, Nope, you’re not ready. It was soul-crushing being up there. It was one of those railroad style clubs where the only way out was to walk through all the people who just booed you. There was a lady standing on her chair booing me, that’s how bad it was. I remember leaving the club because I was mortified and just started laughing hysterically. I snapped. I called my best friend and told him what happened and that’s when I realized if the worst-case scenario is bombing, there’s nothing to be afraid of. It taught me that no matter who you are and who you think you are, it can happen and you have to be prepared and you have to be professional and you can’t go in thinking you’re going to do well because of who you are. It was a good lesson. But also I’m not a brain surgeon, I'm not a fireman. If I don’t do my job correctly, they just boo me. No one dies, it's not that serious. That frees you up to take chances and take risks. What’s the worst that could happen, they don’t like it? 

What other advice would you give your younger self?
To get onstage as much as possible, which is something I was doing. The more comfortable you are onstage, writing comes second. Learn how to be a performer. Learn how to hold an audience’s attention. The jokes will come. Being comfortable onstage, at least for me, allowed me the freedom to try to take different kinds of risks.

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How did you land your first agent?
I got lucky. I didn’t know anything about agents or what the benefits of having one even were. I remember my agent, who’s still my agent to this day, Mackenzie [Roussos], came to my show and after the show she was like we want to sign you. I had this bar show in Brooklyn at a bar that doesn’t exist anymore and I remember that there’d be agents there all the time and you could always spot them. They’d be like cops, they're the only guys in this dive bar in Brooklyn at 10 o’clock at night dressed like they had insurance. Everyone else was wearing the same clothes all week. I remember they were just standing in the back of the show, and I’d be working out jokes and terrible premises and Mackenzie was like, “Great, I love your stuff. I want you to come be a part of our team.” I kept her ever since, she’s one of my best friends. 

It was very serendipitous. It’s high stress when you know there’s a difference between being fearless and not being smart enough to know you should be afraid. That, for me, is where I didn’t care because I didn’t know what it was. I didn’t know the benefits of having an agent. I didn’t care that there were people at the show who wanted to work with me. I was like, Cool, I’ll give it a shot. If it were now I could see how it would be more stressful.

What’s the wildest thing you ever did to get a gig?
I never cared about that stuff! I was never trying to make it. I was so obsessed with just doing standup comedy that I didn’t care about anything like that. I didn’t care about being famous or even making money, I would do it for free, I would pay to do it, I would do it for beer. Not just me. I think there’s a class of comics that came up that way, where making it was such a pipe dream. I just liked doing it and getting 10 minutes and hanging out after the show with all my friends laughing at that performer high. 

How do you think your writing has progressed over time?
It’s hard for me because I’m too close to it but I hope it’s gotten more thoughtful. When you’re doing standup by yourself, there’s a lot of things that push a joke over the top as a performer that you don’t really know about. You’re not really even conscious of what the audience is truly laughing at. It gets you into these lazy habits of saying things that make people laugh. But when you’re writing sketches and when you’re writing for other people, you’re trying to create a world, every voice matters and counts and sets something else up. So you take yourself out of the equation and it makes you a little more well rounded. You start to think, This is what I would say. But what would she say? And what would the people looking say? And what would be happening during that time? I think it helps you paint more of a world than just one person’s perspective. 

How did you get your first big break? 
I don’t think it’s come yet. I think it’s just been a lot of small breaks and consistent breaks that put me where I am. I don’t know that I had a big break. Obviously, “Saturday Night Live” is an awesome platform but I wasn’t good at it for many years so I wouldn’t say that was a big break. It was the biggest opportunity I ever got. I think the consistency of the show and developing on the show helped me be a better performer, [but was] not necessarily a big break. It helps you to know that if someone keeps putting you on TV, you feel like you belong there. And when you feel like you belong there, you grow up very quickly and you have a responsibility and you sink or swim. It taught me how to be a professional.

How did you first get your SAG-AFTRA card?
Maybe I was doing a VH1 talking head show, “Best Week Ever.” I think that was my first regular gig that got me my union card, which was before “Saturday Night Live.” I think “SNL” was my first writers guild. That was my first writing job ever. I had never written a sketch before “SNL.” 

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What was your first day at “SNL” like?
Have you ever seen “Trading Places”? It felt like when they were trying to tell Eddie Murphy this was his job and this is his house. At some point, it’s a practical joke and someone is going to end up taking it away from you. If you really give it to me, I’ll take it. It's that kind of a feeling of I know I don’t belong and at any point I’m going to be found out but might as well have fun while we’re here. It turned out it wasn’t a trick but it was so bizarre and so outside what I thought. I did standup. That, to me, was the best thing. That’s all I came for. Getting to do anything else and getting those kinds of opportunities, it’s all been icing.

What performance should every actor see and why?
As a standup, it’s going to be biased, but Richard Pryor live, I think, is the greatest display of comedy ever shown or captured. I watch it every so often just to beat myself up as to what I’m not as a performer. It’s the best comedian that’s ever lived doing his best work. And I think anybody that wants to do comedy should watch how he’s able to tell a story with his entire body, and effortlessly. And he’s following Patti LaBelle. I don’t know if you’ve ever seen Patti LaBelle perform before but she’s an absolute killer of a performer. He’s going on after that with jokes and I just think that’s the most spectacular thing I’ve ever seen.