Sunday Sitdown with Willie Geist - Michael Che

Episode Date: November 14, 2021

Born and raised in New York City’s Lower East Side, Michael Che grew up with early jobs selling t-shirts and working open mic nights. After being spotted by Colin Jost at a stand-up show in 2013, Che landed a gig writing for Saturday Night Live where he would become the show’s first black head writer and first black anchor of “Weekend Update.” In this week’s Sunday Sitdown, Willie Geist gets together with Che to talk about his rise in comedy and his new Netflix stand-up special, Michael Che: Shame the Devil.  Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey guys, Willie Geist here with another episode of the Sunday Sit Down podcast. My thanks as always for clicking and listening along. Very excited to bring you my conversation today with one of the stars of Saturday Night Live, Mr. Michael Che. Not only does he host Weekend Update with his buddy Colin Jost, has done that since 2014. He also is the co-head writer of SNL, one of the most prestigious positions in all of comedy. We talk about his long journey to the... lofty heights, and it began on the lower east side of Manhattan. We got together in a little bar down there a couple blocks away from where he grew up in a public housing. Youngest of seven children

raised by his single mother, amazing story about how he got where he is. Wasn't really into comedy, was a funny guy, but was more into design and drawing, went to LaGuardia High School for Performing Arts, the famous school. And then after high school made money selling t-shirts that he had designed and produced. There's a great story in here about how Tommy Hilfiger loved his shirt so much. He tried to hire him, but Michael Chee says he just kind of ghosted him after one day on the job and walked away. And you'll hear his rise through stand-up comedy to being spotted by Colin Jost and getting that coveted ticket to Saturday Night Live. There's so much in his story. He's got a new stand-up special out on Netflix, about to come out. It's called Michael Chee, Shame the Devil. I think you'll

enjoy just spending some time. If you don't know his backstory, there's so much in there. And obviously, it's just fun. He's a funny dude. He's a comedian. So please sit back, relax, and enjoy on the Sunday Sit Down podcast now, my conversation with Michael Che. Michael, good to see, man. Good to see you, Willie. Thank you for doing this. Thank you for letting me. So I want to talk about your special, which is great. I told I just finished watching it. I can't believe you watched it. That makes me happy. Of course I did. Good. I get a kick out of people watching anything I'm dealing. Is that exciting to you to know that this thing's about to be out in the world?

Is it nerve-wracking to you? What's the feeling? It's a little nerve-wracking because, as you know, this is not the best time for stand-up comedy. But it is kind of exciting and fun to see how, like I don't watch it. So I don't know sometimes what's in it. You know, like I got to remember it when someone tells you. Yeah. But it is kind of exciting, I guess.

So how do you get ready for that? You say in the special, it's been five years since I did one of these. I've been thinking a lot. I've had a lot on my mind. A lot obviously has happened in the world and the country since then. Yeah. So how do you get that down to 58 minutes or whatever it ends up in? You know, it's, it becomes like a, you know, it's kind of like a typewriter.

It just like kind of fills up and you got to like slam it back the other way. So it's like, it's just like an ever flowing, you know, material or act in your head. And some stuff kind of gets outdated and you don't do anymore. But I think at this point, There's a lot of stuff that I was like, okay, well, this is on time, and this will be fun to tape. You're so effortless in your delivery that it almost looks like you're making it up as you go, which is a tribute to you. It just looks like, you're like, I'm just out here talking.

I'm sitting on a stool. I got my buddy and my Jordan's on. Yeah, yeah, yeah. But that takes, I have to imagine, a lot of thought and a lot of practice to get to the point where you're that comfortable with the set. Well, I don't really write jokes out. And I don't really listen to myself recording it. So I kind of am coming up with it as it is coming out. Really?

Yeah. Even for a Netflix stand-up special, you're just flowing? Yeah, that's just kind of the process. Like, I know the joke, but more so I know why I think it's funny. And once I know why it's funny, then I can tell it any way I want. You know, it doesn't have to be the same every time. So it kind of gives you a little bit more freedom and a little bit more exploration, if that makes sense.

Yeah. So did you try, do you do the clubs and everything? Let me test this out, see how it hits. I did, I was doing clubs. I did Carolines and the seller, a bunch of just to stay sharp, you know, just to kind of hear it and get in a rhythm of it constantly. And, yeah, started kind of coming together. And I wanted to tape it before SNL because, as you know, SNL eats up a lot of the year. Yeah. And you're not allowed to kind of get in that rhythm. them again. So I wanted definitely to tape it before we started. So I taped it in September and I was ready to be out. It's so, I didn't know that, that you kind of, you know the joke, but you craft

it as you go. So what's the feeling there's a cool shot of you at the top of it backstage before the entrance. And I always love those shots, whether it's a band or somebody going out to do some huge thing, but you're going out there alone. What are you thinking in the wings? Are you nervous about or you're like, all right, I'm ready for this? I'm listening to the crowd just to kind of hear what the energy is like to know what to expect. And then I'm also just kind of going through order of what I want to do, what I want to try, what did I do last, you know, all that kind of stuff. It's like a million things going on.

And then also you're trying to like just get a little bit centered and feel comfortable so that you can go out there and just go. How do you get there though? There's nowhere to go. When you're a stand-up comedian by yourself, there's like if it's not going well, you can't kick it to Jost or you're not a sketch. Yeah. Well, to me, I think that's, it's scarier to do sketch for that reason.

Because when I'm doing, if you're doing a sketch or if you're, if you're locked in something scripted, if it's going bad, you know how much more time you have in that sketch to do this bad thing, you know? So you're locked in with stand-up. If it goes bad, I could just do something else immediately. You know what I mean? I could cut it off immediately. If the sketch is going bad, I can't just start a new sketch.

You know, so it's a little bit more freedom in stand-up. You were funny talking about the movement of last summer, two summers ago, what was happening after the murder of George Floyd in the streets. And you paid the comparison to Selma, when you said you didn't want to go out because of this pandemic. What if the people during Selma said, you know, it's flu season. So what commentary did you want to make about what's happened in this country in the last year and a half? I think the most important thing is the validation of feelings.

You know, I think a lot of times we try to come up with answers for struggles, but I think what's more important sometimes is to just let people who look like you or who are going through what you're going through to know that their feelings are valid and we all understand it and we're all kind of going through it in the same way. And I think comedy can do that in a lot of ways because I can tell you my frustrations and you can watch and say, I was thinking that, but I wasn't going to say it, but I definitely kind of on point. So I think that's what I try to offer. Do you find it difficult ever to make comedy out of something that's so painful for so many people? No.

I don't. I mean, it's difficult for them to get the joke, but I've always thinking it's funny. That's probably the biggest hurdle. It's how do I make it funny? How do I make you enjoy it the way I enjoy it? It's the trick. But I'm always kind of laugh. I just process everything that way.

You know, like I just kind of always been the person that process things through humor. You know, and sometimes it's tricky because people think if you find something funny, you don't really respect it or you don't think it's important. You're making fun. Like, you get in trouble for making fun of something. Right.

But for me, it's how I, process the worst things in my life is through making fun of it and laughing and then dealing with it, you know? I think, you think of like Bob Hope going to, going to war, telling jokes to soldiers, you know, going traveling and, you know, doing comedy for troops. And that was very serious. They're facing some real stuff, but also they need levity. They need to be able to feel good too. And they need, you know, someone to be there and, you know, and make them laugh. So I think that's what I like about comedy,

and that's why I wanted to do it as a career. Do you feel like not just you, but any comedian right now, there's almost a responsibility to address all the things that are in front of us as a country? No. No.

No, I think it's not a responsibility. It's, if that's what you find funny, then it's your responsibility to do what you find funny. But whatever you find fun, There's room for all of it. You know, there's not one kind of medicine. There's not one pill. There's a lot of different things that people may need and people may be looking for.

Some people don't want to hear anything political at a comedy show. And that's fine. They can hear something absurd. They can hear something mundane. There's a lot of different ways to do it. So I don't think there's ever responsibility, ever one responsibility for a comedian, other than to share what they find from it. I asked that question.

It was top of mind because I was listening. earlier today to a podcast with Seinfeld, and he was saying made your exact point. Really? Is that your thing? Yeah, you should do it. If it's not your thing, you don't have to do it. Find the little thing in the front door that's funny. Some people have whole specials just about their wife or just about their husband or just

about their kids or just about their family or just about politics or just about social issues or just about, you know, being a woman, being a man, being black, whatever it is, I think if there's an audience, forward, just do it. If you truly find it funny, somebody's going to relate to it. Yeah. You also talk about mental health. Yeah. In relationship to race in this country and how we haven't had enough focus on that. How do you, when you lay out that hour, how do you think about these things that, okay, this is something that's been on my mind and it's going to make it into the last cut of this? It's interesting because comedy is a lot like, you know, being intimate

in that you have to pace everything. You know what I mean? You have to kind of, I'm going to start here. I'm like, you know, and then end up here. So it's a lot of that and building a set of,

you don't start with the heaviest thing first. You kind of want to flirt a little bit and get to know each other. And then, you know, maybe, I don't know what time the show comes on. It's a morning show. Oh, okay, yeah. You know what I'm saying?

You flirt a little bit. as all. So I knew that we'd have to work our way up to that for the audience to kind of not bristle at the mere mention of it. Is that something that had been on your mind though when you were... Of course. I think it's something that's been on everybody's mind,

especially now. I mean, we've been locked in the house for months at a time. Some people are full year even, you know, the country seems to be as divisive as ever. There's so much media and so much, so much of staring at a screen.

And I think people are starting to kind of be ready to have a conversation of how to take better care of ourselves mentally, just like we do physically. I think something you said struck me as true because I'm a little bit older than you, but not much about anxiety and depression and even about autism, which is things we didn't know how to identify when we were kids. And you made it funny,

but there was so much truth in it of, At least we're talking about it now. Yeah. I mean, I'm never trying to be right in a comedy special. I'm just trying to be funny. But also, there is some truth. And when you're just being honest, there is some kind of, you know, actually, it's funny. You mentioned that because X, Y, Z, you know, you might look more into it after you've laughed at it, you know.

There's a bit. I'm not going to give away your act because people have to go watch it. It's also in the morning time. You probably can't. I'm just going to say, the Sesame Street. We'll just leave it right there. We would just leave it right there. Shout out to Sesame Street.

I hope they have a good sense of humor there. Too late now. There's things about to go out in the world. They might not invite you back to Sesame Street, but you've already been, so you're good. I was raised on Sesame Street, you know, and everything I said came from the heart. So we're on the Lower East side right now. You grew up in several different places around here. Yeah, well, this is my city.

This is your city. So I'm interested in how this stand-up comedian came to be. Do you remember the first time somebody laughed at something you said or you realized, oh, maybe this is my thing in life. Maybe I'm funny. Oh, my. Or you got a crowd going or your buddies thought you were funny. I was always like kind of not class clown, but I was always like a smart kid.

You know, I had a real smart mouth and I was always challenging, you know, like that kind of thing. I was very contrarian or whatever. It was stupid. I was arrogant. But I remember one time in high school, Jerry Seinfeld came. Funny you mentioned him. Jerry Seinfeld came to visit the school. I went to LaGuardia High School and he came to visit.

This was right after Seinfeld was over with and people hadn't seen Seinfeld. And it was like excited. This was the biggest show and it ended at the height. And he was probably the biggest comedian in the world at them. Sure. And we were hanging out in the cafeteria, me and my friends. And another friend came home and he goes, Jerry Seinfeld's on his third floor. And one of my buddies was like, so?

Che's funny as in him. I'm not. But it made me feel like I was for like two seconds. I was like, oh, they think I'm funny. That was the first time I ever thought people looked at me as funny. Interesting. Yeah. So you were the youngest of seven.

This was not a thing that was happening inside your house, your mom. I'm like very young compared to my other siblings. Right. So, you know, it was a lot of being quiet. if I wanted to hang around my brother and says I had to be quiet a lot. So I really couldn't be that funny. I was always, I always had a smart mouth, but they were like, look, if we're going to bring you, you have shut up. You know what I mean?

That kind of thing. So with my friends, I could be, you know, insane. But, you know, in the house, I kind of had to always be quiet and be seen and not hurt. So did you feel like you were observing a lot and just taking life in? I think that's where that comes from. I think you just kind of always watch. And everything seems insane when you're the only kid in the house. Right.

So, you know, you're trying to make sense of what already makes sense to them with your own, just with your eyes and just without asking too many questions and being annoying. Right. So I think that's how you become a little observant and you know what's funny. So you said you were the youngest of seven, but I think your next sibling was seven years older. Eight years older. So there's a big spread there. So what do you remember about this childhood around here? What was it like with you and your mom?

A lot of fireworks. Literally a lot of fireworks. I mean, New York City was always kind of, it was always mixy, especially Lower East Side because it's almost like ghetto Olympics because there's poor people from all over the world right here. You know, there's poor black, poor Chinese, poor Hispanic, poor white, poor everybody. So it's like this kind of hodgepodge of poverty. Now it's a lot nicer, but when I was a kid, I remember being very dangerous.

You kind of had to know where you were going and a little segregated in its own way because there's so much happening in your part of the town that you don't really need to venture out. Like I really didn't learn the city until I got to high school and had to, you know, literally be amongst kids of all types of cold for sound

I had to be around a bunch of kids who were like from the Upper West Side from Queens from Harlem from Brooklyn you know it's a then you start to kind of understand you know how big the city is but when I was a kid you kind of only stay in your little bubble and that's really all you know right

you've talked about your family struggling too what was that like how bad was the poverty at times Well, you don't know it until you start talking as an adult to other people who weren't poor and they don't relate to anything you're saying. You know what I mean? But as a kid, you don't really know because everything becomes relative. When you're poor, if there's somebody poorer than you, that's the poor family.

You got, you know what there's, it just becomes relative to what's around. Right. So we were poor, but we wasn't poor for the situation. They were families that were more poor that we thought of as poor. You know, like my whole family is from the Smith Projects. And in the middle of that project, housing project, there's a shelter. We thought they was poor. We had no idea that we was a paycheck away from being in that shelter easily, you know?

So that's kind of the relation of growing up that way. You don't really think of it as that until you're around money. And then you say, oh, wait a minute. That's everybody didn't have these problems. Yeah. And I mean, to get up to LaGuardia, which for people who don't know the city, you're down here on the lower east side. LaGuardia is around Lincoln Center, getting near the upper west side, totally different part of the city. Totally different.

And, you know, you talk about like an all-star game. That's a lot of all-star kids from all around the city. What was your- But as you say that, too, right behind my high school was a housing project. Exactly. Right there. So across the street from Juilliard in the metropolitan. Paulson, you know, literally, literally right across the street is a housing project. So that's New York, though.

You never, right there is an extreme difference, extreme, you know, tucks and tails over here. And, you know, a project next to it. Yeah. So what was your ticket up to LaGuardia? Because they don't just let everybody in. They don't open the door. It was a lot easier when I got there. Everybody says that.

Yeah, no, it really was because now they kind of. they kind of put a priority on grades to get into the school. And I would not have gotten in if it was according to this standard. But when I was there, it was kind of just more based on if you had talent, they'd let you in. And I did fine art. I knew how to draw a little bit. And I learned fine art there. But I became an art major.

And I got in and it was really cool. It kind of changed my life in a lot of ways. but that's not where you ended up. So I'm curious, where's the leap from fine art? You're making t-shirts. You're selling them on the street. You get your folding table out on the corner. How do you know this?

I read a little about you. Yeah, yeah. So you're out selling t-shirts and all that stuff that you drew. That's true. Where does stand-up comedy come in? I think if I had to, I don't really know. Like, I always wanted to do comedy. And I think art is all transferable, you know?

Like, you know, like the way if you play guitar, you could learn how to play piano too, or you could. I think art is transferable. You kind of need to have a brain to want to create, right? And I feel like art was my first language, but comedy was the one I was most fluent. So I would approach it in the same way. And you just wanted to try a new medium. I got bored with painting. I felt like I didn't know how to express myself properly.

And comedy was like immediately. I understood that language way quicker. And I just stayed there. I never needed the pain again after that. Is the story true? Maybe it's urban legend at this point, that you were so good that Spike Lee and Tommy Hilfiger's son saw your stuff, Tommy Hilfiger invites you in, takes you around the office,

offers you a job, and he said no thanks. It's pretty true. Really? Well, it's not that I said no thanks. I just stiffed him. He paid me in cash the first day. And then I just stopped going because I got, I was intimidated. I was like a little, I feel so bad.

I talked to him recently, too, about it on the phone. And we was laughing about it because I don't think he even realized how intimidated I was. Intimidated by what? The culture there, the people there. By the opportunity. Yeah. You know, like you get, sometimes you get an opportunity and you don't feel like you deserve it. And you get scared.

Like, what if I don't do it well, you know? Like, what if it's not that good, like I was thinking it wasn't? What if it's not that good and it let down and disappointed? If I leave, I could always just say, oh, I would have been great and never had to put that to the test. Right. So a lot of times people don't try just because they're intimidated about failing. So they'd rather be able to say it would have been great, you know, but something else happened. But here's what's interesting to me about that is.

So you're intimidated by that. You're worried about failing so you don't do it. And yet you go stand on the stage alone in front of people who may laugh at you if you're lucky or they might boo you off the stage and heckle you and it could go terribly. Yeah. So we're doing something else. That's worse than booing. They're not even listening. They're just looking at their phone and having conversations.

Right. I've been in that situation. You get that too? Oh, my God. Yeah. I run the gamut. So when did you know you had a skill for stand-up and this could become a career for you? I didn't know I had the skill, but I knew I could do it for a living when I did it and it was bad and I didn't care.

Like it was okay. When the worst case scenario happens and you're fine with it, then you can do it. Because then it's like, well, what do I have to be afraid of this? This is the worst case? You know, I'm not a brain surgeon. I'm not, you know what I mean? I'm not on a scaffold or whatever. Like, it's nothing dangerous about it other than people don't like it.

Right. It's a little different now, but then it was a lot safer. How is it? What do you mean? How is it different now? You get in trouble. You could get in a lot of trouble. You can get in a lot of trouble.

It's become important. But I blame comedians for that. What do you mean? By setting new rules? This might be a big swing, but I think at some point, we were always just funny. and then people started telling us we were brilliant and important and we started to believe it and now we kind of have to live up to that standard

of being smart and important as opposed to just being funny and I think that that's what's getting us in trouble a lot of times we're pretending to be something we're not. Stepping into areas that maybe shouldn't be stepped into by certain comedians? I think we're, I think we're missing the plot. We're losing the plot.

We're there to be funny. We're there to have fun and get people's mind off of serious things or at least not be afraid of it. And I think sometimes we think it means something else because a lot of intellectuals gave us compliments. Yeah. I know exactly what you mean and we don't have to mention names. Sometimes I watch a stand of a special

and you almost don't laugh the whole time. People applaud. I say, yes, I agree with that. you're saying. A lot of right answers. It doesn't feel like comedy, right? No, it's not silly. It's like, yeah, I was raised on Bugs Bunny.

And I've been watching like Looney Tunes. It's like, okay, now we're going to talk about the Korean War. Like, good Lord. Easy bugs. But, yeah, so I think sometimes we forget that we're here to have a good time. And then the audience forgets it too. So I try to not take myself too seriously. Hey guys, thanks for listening to the Sunday Sit Down podcast.

Stick around to hear more from Michael Chee right after the break. Welcome back to the Sunday Sit Down podcast, now more of my conversation with Michael Che. So at some point along the way, Lauren Michaels and SNL gives you a phone call. Says come in for a little trial. Colin Jose. Was he the first phone call? Colin Jose was, I seen him in person. I was doing a set at Hannibal Burris's show in Brooklyn.

and Colin was there. And he was like, hey, man, you ever want to write sketches? And I was like, I don't, the same thing, because I was literally, I blew him off. And the same thing, and the time it was like, I don't know how to write sketches. I'm not going to audition or whatever and send a packet. And then they don't like it. And now I got to go through life knowing that I suck. You know what I mean?

So I just, like, kind of blew him off. And he kept messaging me like, hey, come in. We're doing this. they was doing this thing where they were allowing you to come in for two weeks and write as a guest writer. So I just did it. I didn't know

it was like kind of no pressure. It was just like a fun opportunity. I could say I did it. If they wanted me to get coffee, I'd get coffee. I didn't even know what the job really entailed. But I ended up getting a sketch on and they let me finish the season and I've been there ever since.

Do you remember that first sketch? Yes, I do. And it would not be on the air now. Got it. It definitely wouldn't work now. Got it, got it. But it was funny. It was funny at the time.

And so then they say, that went well. Those two weeks are good. Do you want to come on full time? And at that point were you all in? I was all in. Yeah. I was all in, man. It was exciting.

It was like one of the, it was a dream job that I did not know I could possibly do, you know? It was interesting. You have a version of the story I've heard from like eight different people. who get jobs at S&L and don't know they have the job. Yes. Seth Myers tells the story. Yes. He goes, I guess I work here now?

No one has said that to me. I had no idea. They came in. They told me to come back. That's all they said. It was like, what would you like to come back for the season? I was like, yeah, sure. And me and Seth are talking after a table, and I had got another sketch in.

So now I'm like, I'm like, I could die now. You know what I mean? And I'm talking to Seth, who's head writer at the time. And he's watching, I think, like, a Steelers game or something. something on Pirates game. And he goes, you know you work here now, right? And I was like, what? He's like, you work here, like, full time. Like, this is your office. Like, you're here. I was like, no, nobody told me. I had no clue. And he's like, yeah, nobody tells anybody anything. Why is that? I've heard that story from so many people. I think it's like, I don't know.

I think everybody's kind of just doing their job that they forget. Like, there's no real orientation. There's no, like, kind of greeter or anything. You kind of just get in where you fit in and once it works we'll figure out how to get it on television and that's kind of the extent of the show like there's still places that I don't understand or know about the show and I'm head writer the head writer yeah I've been there almost 10 years but there's still stuff I don't know there's departments I don't even know I got to like ask because no one tells you everything you just got to figure it out you got to kind of figure it out you know it's it's weird so you're writing sketches you're getting them on and then they go hey you want to do weekend update what did you

when they said that. No. Again, it's one thing that I learned, I think the most from Lorne is to not sell yourself short in what you can do. You just show up and try it,

you know, because there's a lot of things that I got opportunities to do and I fought the whole way that I shouldn't be doing it. And sometimes I was right, but I'm glad I did it every time they advised me to.

If that makes sense. Yeah. Because now I know I can do it. It just might not be great, but I know I can do it. And I'm not afraid to just do it even if it sucks. Well, and you and Colin are both doing this for the first time, really, in that format. Yeah. Well, Colin was kind of already doing it for like, I think, five or six episodes. Right.

And now he's the longest running anchor ever. I know. I know. Weird. But you guys were feeling your way for a while there. Two guys who hadn't been on the air before. Now they throw you out in this iconic segment of weekend update. What did those early days feel like?

Hell, man, it was horrible. Really? Well, it was just, it was, it's always, I always call it like the step, I have like a stepdad theory that when you're, when you're replacing someone that America loves, like Seth or, you know, Tina and Amy or Jimmy or Norm, whoever it is, when you're taking over that role, they're always like, where's the other guy? We like the other guy. Right. We love the other guy. you're not the other guy. And I felt like for the first year or two,

me and Colin were trying to do what Seth did. We had Seth's writers. We had his kind of format. We was trying to do things he would do because it worked. It worked so well. And it took a long time before we realized, well, we just have to be ourselves and make people love us for us,

not as Seth's replacements. And once we figured that out, then it got a lot easier. once we learn how to write for ourselves, once we learned how to get the writers to write with us and for us and our voices, then it really started clicking. But, I mean, I imagine the writers had it just as hard. I mean, you got to write jokes for Seth and then me.

Like, it's two completely different voices, you know? So that was like the hurdle, the biggest hurdle to get over. Colin has talked about just reading about himself in those early years. Really getting inside his head. He's a glutton for punishment. It really is. Did you have any of that? I always love bad things. Like that's me.

To me it's funny. Some of people hate it. But it was more, I was in my head because I knew what I wanted it to be and it wasn't that. Yeah. So criticism, like, I didn't really care about that because I knew it was bad. It's like, I didn't need you to tell me that I know it's bad. So I don't need to read about it. You know what I mean?

even if you think it's good, I know it's bad. Right. So I knew when it got good, when people started to tell me that it was bad before. Right. You know what I'm saying? They were comfortable to say that. When your friends are comfortable and say, you know, that was rough. The first year, I was like, yeah, now you tell me, you give me all that support

when you thought I needed it. But I hate when people tell me something's good and I know it's not good. Yeah. So it took a while before we kind of learned what we wanted to do with the segment. And now, and then it started to be a strong point of the show. which was like a huge accomplishment. Like from where we started, it felt really, really good. And that's mourn, that's the writers,

that's, you know, everybody kind of sticking with it and giving us that opportunity. You guys achieved something really difficult, which is to create chemistry in that format where it's just one guy at one time, then the other guy at one time. But you have the chemistry part of it is the swapped of the joke,

but also just like the shake of the head you'll give after one, like you shouldn't have that. That was the trickiest part. That was the trickiest part. was learning how to do chemistry in a single. Yeah. And I remember we would try to write things early on for each other where we would, where we would be on camera at the same time. And one would be like, stop writing chemistry.

The chemistry has to be natural. And I never understood what he meant by that until we figured it out. And I realized, oh, I have to address what he says and acknowledge what he says so that they know that we were in the same room. Because we could have shot that from two different parts of the studio. If you're watching it on television, you never see us together. Right. So we had to kind of find little moments to poke fun at each other. And then I think we ended up doing it right.

It's also a way for you guys, not just in the swaps, but to insulate each other. So like the joke the other night where Collins, the squirrels holding a woman's hand, he said, it's like Che always says. Yes. Just put that on you, right? Right, right. And then cut to you and you can shake your head. And I knew nothing about it. Oh, really?

Yeah, I didn't know anything about it. Sometimes it's like change it, tweak it out of air or tweak it. that dress and look where that come from but that one I think I think he said that dress but I didn't know he was going to say that so it was like interesting.

When you write the jokes for each other, everyone just loves that stuff. Is that something that was happening behind the scenes and you said let's put this on the air? Sort of it was Colin's idea because a lot of times we would get we would have jokes that we thought were hilarious

and the audience would be like no you know like all these are hard. So one year like one Christmas we tried to do this segment. It's like, let's do for Christmas. We'll tell, like,

a joke that got cut that we really liked. And we did it, and it would be a joke that already was, like, horrendous when we tried it. We tell it with that setup, and it destroyed.

Because people were like, oh, this is a bad joke. Right. It's okay that it's bad. Right. So then I think Colin came up with the idea. It's like,

all right, how about if we write jokes for each other? And I was like, Colin, suicide mission, where you cannot, you're out of your mind and you think, okay, so I'm thinking he's setting me up. I'm like, all right, whatever. I'm going as hard as possible.

I'm with the writers and we're like, it's got to be hard, it's got to be hard. And they're like, hey man, we know what he's going to say. You might not have to go this hard, go this far. And I was like, no, this is a trick. And I went way harder than he did. And then now we have to do it. Like, people get upset when we don't do it. So it's like, it was a lot of fun.

Collins idea though. You can see when he starts to read the setup and he just starts shaking his head because he knows he's a dead man. He's a glutton for punishment. I keep telling you, man. He reads reviews and he wants to do he's, I don't know what's his problem.

What does it mean? So they name you co-head writer. Yeah. For people out there who don't know the show that, what does that mean in terms of responsibility? It wasn't mean to be the head writer at SNL. I don't know. I still don't know. I still don't know. figured it out. Like it's, you're in a lot of the meetings. You're kind of making sure that

cast and writers are covered and the host is happy. And it also is important for the top of the show, which has kind of been the important part of the show, the cold open, the monologue, and the first sketch out of monologue. This kind of determines whether the show is going to be good or not. So that those meetings and those discussions, you know, becomes a lot of your, your week a lot of times or, you know, a certain time. Like if Dave is hosting the show, Rock is hosting the show, I'm kind of there a lot to make sure that things are running smoothly with them for them. And you're under the bleachers a lot, you know, with lawn watching the sketches and figuring out

how to fix it and what we need to make the show, the nuts and both boring part of the show is kind of now you're, you're weak. So I'm not as good at it as, you know, the other headwriters is Dresden and Kent and Joss, but I do what I can. I've been on the hook for a couple things that turned out okay, but for the most part, they're really doing most of the heavy-lived. So you get a little, you dabble a little bit? Yeah, I'm not as good. Like, I've never been good at like smart stuff. Oh, you know what I mean? Like, it's like, to me, that's like eight student stuff. They know how to do that. I'm like, I can help, but I'm not a great head writer.

I think some people who work with you might disagree with that. On camera, but not if they're being honest. That's Colin privately, see what he says. Yeah. You've also talked a lot in last couple of years about the diversity of the cast and the points of view that come out of that show, changing over the last several years. Totally. Focus on that.

Does it feel like that change is underway at SNL? I think it always changes when new cast come in, you know, especially younger cast comes in because, you know, they start to bring to the show what they wanted to see, you know. And I think that that's how the show's able to last this long because it stays fresh with people that are excited to do it and excited to kind of, you know, be the history that they've already seen. You know what I mean? So it's, I think it's helped a lot. Like when I got there, I was the only black writer. And that's changed drastically, you know. I think Keenan and Jay were the only black cast.

At one point, I think we had six black cast, or five or six or whatever, unless he was there. So, you know, I think they're not just, you know, black. It's a lot of different voices on the show. And it changes the way you write because when the show looks all, all the same color and all the same culture, you start laughing at all the same things and then it becomes redundant. Right. So there will be black sketches that black people might laugh at that the writing staff and

the cast might be like, I don't get it. But with more black people in the room or with more gay people in the room, with more gay people in the room, more, you know, whatever culture in the room, it's like, oh, no, I know what this is. It gives the audience, it gives us a better reflection of what our audience is. Right. And so we could kind of gauge better as to what should be on the show or what could work on the show. I think the best are one of the best examples of that is Black Jeopardy, which is so, so brilliant.

But it requires a point of view. Yeah, I actually wrote that with a, it was Brian Tucker's idea, who's a white guy, but he's, I don't know. I don't know. There's something going on over there, man. He's white, but he writes a lot of black stuff. I don't know how he knows what he know. But, no, he's a white guy. And he's a really, really great writer. And, you know, we would write stuff together.

And Black Jeopardy, he came to me with that. I was like, absolutely, let's do it. So me, him and Keenan kind of just started pitching down on it. And we really wanted to show how people are more similar to him. Yes. Than different, you know, because everybody connects to it. Everybody likes it. So people get it.

And it's one of the sketches I think that he should be very proud of. I know you've got to run. You got a busy and long night ahead of you. So what does this week look like? It's Tuesday right now. I guarantee you work harder than I do. Well, I'm not going to be at 30 Rock till what time are you leave tonight? Probably like, probably like.

We're going to cross paths, put it that way. Yeah, yeah, for sure. I'll be coming in early. You'll be leaving. That's possible. I'll see in the elevator bank. That's possible, yeah. It's funny to see, like, yeah, yeah, that's funny.

It's weird. Isn't that a weird building where all these people are there? People don't even understand how weird it is. It's very strange. It's like you guys are in the elevator, the Today Show and Jimmy and Seth. Yeah. Used to be like Dr. Oz. Yeah.

Sometimes I'm working out, I'll just see Joy Reed. I'm like, what are you doing here? Oh, that's right. We work in the same building. Right, right. So what is Tuesday night like for you? As you start the week, you got a new host, a new, it's a totally new show. Whatever you did last week, it's a clean slate now.

It's the closest thing to be an athlete somebody this out of shape could ever talk about because it's like you said, the show is kind of over with. You could have a great show, you could have a bad show, but once it's over, it's a new week. You know, it doesn't matter. We have to kind of, it's not, we're not piggybacking off of, you know, the last show's success or anything like that. So it's just fresh new ideas. It kind of keeps you sharp because no matter what, you still have to come up with something new. and people are expecting it. It's exciting.

And tonight you're pitching ideas, meeting the host, do all those things. I don't like meeting the host. Oh, really? No. Why? Well, because then, like. You don't like meeting the host? No, no, I don't like famous people.

I don't like, you know, whatever. I mean, it's pleasantly surprised every time, but I don't like meeting the house. I kind of. But don't you have to as the co-head writer. Yeah, that's why his job sucks. No, no. No, yeah, we do. We talk to the host and we kind of get a gauge on what they want to do

and how to make them feel like, you know, their ideas are being heard and trying to make it work or whatever. Because, like I said, nothing works better than when you believe in what you're doing. So they're excited about an idea. They're going to perform it well, and then we end up all looking good. Won't use any names again, but many of your friends have told me, there's nothing worse than a host who comes in with a lot of ideas. You want some ideas.

This is why I don't like me, not a lot of ideas. One or two ideas is great, but when you start to have a lot of ideas, but you got to think to SNL is like, it's like a celebrity's wedding. You know what I mean? Sometimes you're like facilitating this is all the things they've wanted to do and wanted to see and they're excited about it. And it's a big moment. Like this is a very important week for them.

So, you know, we try to be respectful and considerate of that. And if you've got some ideas, we'll try to, you know, help you see them through. Well, a lot of times, it's glaring that you're not a professional comedian, you know. That's also the case sometimes. And you can't just tell somebody, hey, this ain't funny, rich guy. I'm curious, how do you let a huge star down? They come in really excited. They pitch this idea, and you guys are all looking at each other, like, ooh boy.

Oh, I immediately take a phone call. I got to go. Yeah. Coming, you know, like one of them things. Leave it to Colin. A lot, you know what it is? The table read makes everybody, it kind of, it's when it's when it starts. Yeah.

So Wednesday table read, I don't care who you are, nine times out of 10, you're not going to want to do the thing that got no laughs. Right. So when no one's laughing, then they're like, all right, you tell us what I should be doing. You tell me what I should be doing and I'll do it, you know. So everybody just wants to be funny. At the end of the day, when you come on that show, you just want it to work. And you realize how scary it is and how, how, how. fast it goes and then you start to trust us a little bit more as

the week goes on. So, you know. Let them have it until Wednesday and it goes away. Well, Wednesday, when they hear it, they're like, oh boy. But sometimes, I mean, sometimes people come in and they're amazing immediately and you're like, you could easily

I mean, Justin Timberler could easily be a sketch comedian if he wasn't also one of the greatest singers of all time. You know what I mean? like he could have easily done this. A lot of you see like, you look at Donald Glover. I mean, he bounces back and forth from comedy to music and he could easily be anything

you want it. So it's kind of cool when you see somebody that's really good. You got Taylor Swift in this weekend. Any big plans for her beyond the music? Do we think we'll see her somewhere else? No. Yeah, I don't know. I don't know.

We'll see what she wants to do. Sometimes they can't do stuff. Sometimes they can only show up on Saturday. So you never really know how available they even are to do something. But we'll try. Well, we'll look forward to it. Congratulations on the Netflix special, man. Did I answer the question as good?

You did, every one of them. I can keep you here all day, but you got to go do your job, man. Thank you so much, Willie. So good to see you, Michael. This was fun. Stick around for more of my conversation with Michael Che, right after a quick break. Welcome back. Now the rest of my conversation with Michael Che, as we head for a quick walk around the block on the lower east side of Manhattan. Michael, does this neighborhood look and feel the way at all it did when you were growing up?

It really, like, it's so crazy looking at the walls. It's like, like, that graffiti's probably been up there for 40 years. You know what I mean? Like, it's weird. This, Chinatown specifically always kind of feels the same. I could always kind of feel like China. Do you allow yourselves the moment ever of, I grew up here, it's where I came from, and now I'm going to drive up to Midtown, get in an elevator and go be the head writer and one of the biggest stars on Saturday Night Live?

It doesn't make sense. It's honestly, like, that ball could have bounced any other way. You know, but it's lucky, I guess. It's dumb luck. You're too humble. You're too humble. really is though it's dumb luck man you know like i always said like if i had a good if i had a decent job i would have never even tried comedy even if i hated the job only because i would have been

afraid to jeopardize something that i don't even really want you know what i mean right so i wasn't working at all and i was able to try comedy and then i got good at it but you know that was like a luxury to be able to take that change. And you were willing to stay with it, even though it maybe wasn't paying the bills at the beginning, because you enjoyed it. Yeah, I mean, it seemed like, uh, seemed like fun. But no, really, you know, like, it's, I think, I think, like, a lot of times you, you don't want to jeopardize something like that, you know.

Maybe you don't like it. Some people won't try just because they don't want to lose what they already have. Right. I got lucky. I was in a position where I could afford to try something, which is not something everybody has, you know? Yeah. My big thanks again to Michael Che for a great conversation.

Be sure to check out Michael Chey, Shame the Devil. The new stand-up special on Netflix begins streaming on November 16th. My thanks to all of you, as always, for listening. If you want to hear more of our conversations with my guests every week, be sure to click subscribe. follow so you never miss an episode. And don't forget to tune in to Sunday today every weekend on NBC. I'm Willie Geist. We'll see you right back here next week on the Sunday Sit Down podcast.