Colin Jost Of 'SNL' Knows You're Laughing At His 'Very Punchable Face'

Jul 14, 2020
Originally published on July 14, 2020 4:32 pm

Saturday Night Live's Colin Jost knows there's something about his clean-cut image that rubs some people the wrong way. When he joined SNL as a writer in 2005, he worked off-camera — and didn't have to think about his looks.

"When you're not on camera or on television, you don't really consider what you look like," he says. But all that changed when he began working on-air in 2014 as the co-anchor of the show's "Weekend Update."

"Some people look at me and have sort of a visceral, angry reaction [to me]," he says. "You see it in our audience. When I get hurt or hit on camera — like when [castmate] Cecily [Strong] throws drinks in my face or throws up red wine on me — the audience really loves it."

Jost's new memoir, A Very Punchable Face, describes his experiences growing up in a middle-class household on Staten Island.

"Part of writing this book was being excited to talk about parts of my life and weird episodes in my life that I thought that would be entertaining for people," he says. Or, he adds, for people to "just get another chance to laugh at me."

Jost has been a co-head writer at SNL, following in the footsteps of Tina Fey and Seth Meyers. While he's not ready to leave the show just yet — he does think about it.

"It's a world that I love so much," he says. "You just don't know how often you get to work at a place like that, and the odds are zero other times in my life will I get to work at a place like that. So it's a scary but a necessary decision to face at some point."


Interview Highlights

Penguin Random House

On gravitating toward writing because it was difficult for him to articulate what was in his head

I think the feeling is a lot of ideas and words are jumbled around, and I want to get it all out, and it's like I can't. It's almost like you're trying to funnel a lot of words or ideas, and they're not getting through that hole at the bottom of the funnel. They're backing up, and you're trying to get them through either in an orderly fashion or all at once. But it's not happening. There's almost like a slight delay sometimes when I'm talking because I'm trying to kind of get things together in my head before they come out.

On how he didn't speak until he was 4 years old

I remember a feeling of frustration at that period of my life. It's always hard when you're looking back because what your memories are at that age are also informed by what your parents tell you about that time. I definitely remember having angry outbursts, like physical outbursts, because I felt frustrated that I wasn't communicating with words — that I remember. I remember my speech therapist. I remember meeting with her, and I remember a profound sense of relief that this other gate was open or something ... [being] able to finally talk. It was just a relief, I would say, more than anything.

On his mom working as chief medical officer in New York for more than two decades

She was in the fire department for 40 years. ... She has lung issues from [the Sept. 11 attacks]. Obviously it's scarier in this time we're with COVID and stuff, but she's a healthy person who tries to be conscious of that and make decisions that help her health. ... One of the first things she did [after Sept. 11] was to set up a triage center that was like in an old Duane Reade ... and then set up another center later at Pace University. I think that she was expecting, everyone was expecting, waves of people who were injured, and there was a little bit of an initial wave. But very quickly, people realized that it was not an injury situation, it was how many people had died. And so it became more of a search and a recovery than it was like treating individual injuries. ...

I was very worried about her, and I didn't talk to her for a long time. ... [Growing up] my mom was always on call, like she'd be on call certain days, like all night. So I was used to late at night, my mom coming and waking me up and saying, "Hey, I got to go to work." And I'm like, "Oh, why now?" And she's like, "Well, there's a fire." ... But when someone's just survived something, you want them to be in a safe place and not put themselves in more danger. That was scary for a while.

On having many firefighters in his family

There's very few people in my family, [on] my mom's side, who are not firefighters. My grandfather was a firefighter. My great-grandfather, my uncle is a fire dispatcher. I think I have three cousins who live on our street [on Staten Island] who are firefighters. ...

They loved it as a community, and they also loved it as a steady, city job. They really appreciated that you could earn a living as a firefighter, build a family as a firefighter. And they love the people they worked with. So I just grew up thinking of it as this great community in this great world. When I didn't get jobs as a writer or my brother was struggling to get jobs as a writer, [my mom] would always tell us, "You can take the fire department test. It's coming up!" I think she's still told my brother that about two months ago, even though he's been very gainfully employed for 10 years.

On his SNL 'Weekend Update' co-anchor Michael Che writing jokes for Jost to say about race that sometimes he doesn't see until he says them live on TV

The hard thing is you kind of need an audience to guide you about what's too far. Some of the jokes that we do, I have not seen the joke until air, so I'm pretty much putting my life in Michael Che's hands a lot of times and hoping that he knows what that line is. But it's a very terrifying moment ... when Michael Che makes me read a joke that I have not seen before on live TV, which occasionally happens; I'll hear things backstage in passing like one of the other writers saying, "You can't make him say that!" But I don't know what it was. And I don't think anyone particularly knows what's too far or not too far. People have different opinions about that. I think you really have to trust ultimately that if you're coming at something from a good-hearted place and you're well-meaning and what you're doing, I think you have to go for it and then hope that the people are open-minded.

Sam Briger and Seth Kelley produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the Web.

Copyright 2020 Fresh Air. To see more, visit Fresh Air.

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. My guest Colin Jost has been a head writer at "Saturday Night Live" for six years and has co-anchored Weekend Update with Michael Che since 2014. He co-anchored with Cecily Strong for eight episodes before that. He was hired as a writer for the show in 2005 when he was 22, and the new cast members included Andy Samberg, Bill Hader and Kristen Wiig.

Colin Jost has written a new memoir called "A Very Punchable Face." He says he came up with that title because he's often been told he has a very punchable face. And he's been punched on "SNL" by Lorne Michaels, Leslie Jones, Tiffany Haddish and Cecily Strong.

Colin Jost, welcome back to FRESH AIR. Let's get to your punchable face. So you write, I look like a guy who's always on the verge of asking, do you know who my father is? - even though your father was a public school's teacher on Staten Island, teaching mechanical drawing to high school freshmen. And you write you also look like you're the president of the Young Republicans club even though you're totally a Democrat. And you've been called the whitest of white people (laughter). So what is it - what do you think it is about you or your face that makes people think that you're, you know, so privileged or so, like, white in a tone-deaf kind of whiteness?

COLIN JOST: (Laughter) That's a good description of it. I don't know. The weird thing - the strangest part of it is, like, I didn't - you know, no one knew who I was until I was, like, 30 years old. Like, no one - I wasn't - you know, I was a stand-up, and no one knew who I was until I started doing Weekend Update. So you really don't consider - when you're not on camera or on television, you don't really consider what you look - like, how other people perceive what you look like. So you're just kind of living your life, and you just assume you're, like, just a regular human-looking human, whatever that means. You're kind of like, I don't know. I didn't - wouldn't think anyone had a crazy - like, a whole preconception about me based on seeing me. But, of course, that's what every human has. We all have that for - in different ways, so you have to understand that.

But, yeah, I don't know. I think part of it is I don't really talk a lot about myself. Obviously, part of writing this book was being excited to talk about parts of my life and weird episodes in my life that I thought people would - that would be entertaining for people or would - they would learn something that they didn't realize about me or just - really, just get another chance to laugh at me. But they - you know, I think some people look at me and have sort of a visceral, angry reaction. I don't know, right? And then - or it feels like it would be fun to punch me, right? I don't know - something like that.

GROSS: But why? I don't (laughter) - why would people think that?

JOST: (Laughter) I mean, I don't know. I think part of it's a sense of privilege or a sense of - maybe it's - I don't know if it's entitlement, that people feel like I have a sense of - I don't know. I'm not sure what it is. But people see - clearly see something in my face sometimes, and you see it in our audience. Like, when I get hurt or hit on camera, like when Cecily throws (laughter) drinks in my face or, you know, like, throws up red wine on me, the audience really loves it.

Even when I make jokes about, like, my relationship with my dad being bad on Weekend Update, people (laughter) - that's, like, one of the things people laugh at the most. And I think there's some sense of - it's funny to see bad things happen to me, which is OK. I kind of get it. And I also - it's sort of enjoyable, and a part of it is so - the reaction is so extreme that it's funny.

GROSS: You write that you wanted to write a book all your life because you have difficulty taking what's inside your head and saying it out loud and that it's easier to write because you don't have to be afraid of what you're going to say. Would you describe that feeling that you can't say what's in your head?

JOST: I think the feeling is a lot of ideas and words are jumbled around. And I want to get it all out, and I - and it's like I can't. It's almost like you're trying to funnel a lot of words or ideas, and they're not getting through that hole at the bottom of the funnel, you know? They're, like, backing up. And you're trying to, like, get them through either in an orderly fashion or all at once, but it's not happening. And - you know, so I think that's just - I kind of - there's almost, like, a slight delay sometimes, I feel, when I'm talking because it's - I'm trying to - I don't know - get things together in my head before they come out.

GROSS: So is that a kind of shyness thing, or is that some kind of disorder that you've got - actually gotten a diagnosis for?

JOST: I have no idea on a disorder level. I - you know, I only know as a kid - you know, as I write about, as a kid, it was extreme to the point of not having any words come out for a long time. And so I don't know what - I never got, like, a diagnosis of what it was. I just had speech therapy that helped me, you know, form words or start articulating whatever was inside my head.

GROSS: You didn't speak until you were 4. And you write that you could understand what people were saying, but you couldn't speak. Was it a physical thing? Were you physically unable or just afraid? Do you remember? I mean, do you remember when you were 4 and didn't speak?

JOST: I remember just a feeling of frustration at that period in my life. I mean, I - it's always hard when you're looking back because your - what your memories are at that age are also informed by what your parents tell you about that time, you know? But I remember - I definitely remember having, like, outbursts - you know, angry outbursts, like, physical outbursts, you know, like, because I felt frustrated that I wasn't communicating with words. That I remember.

And I really remember - I remember my speech therapist. I remember meeting with her, and I remember a profound sense of relief that this other gate was opened or something, that it was - that - I remember feeling, like, a sense of being able to breathe or, like, you know, you're able to - I don't know. You're able to finally talk. I don't know. I - it's a - it was a real - it was just a relief, I would say, more than anything.

GROSS: Are you more comfortable speaking on stage or on TV?

JOST: Sometimes. You know, I think the most comfortable I am is if I'm acting if something's filmed. That is a huge feeling of ease for me. I don't know why. I hadn't thought about it till you asked me. But when you're - whenever I'm doing - like, if I - even if it's improvising in a - in the limited things that I've filmed or if I'm - if I've memorized dialogue - either way, on film, for some reason, that is liberating. Like, that's a huge feeling of liberation. And that never - it's stressful leading up to it because you're preparing for what that part is, or you're preparing, you know, for what your part of the scene is. But your - when I'm actually going, that is the most freeing feeling that I have. And I think, you know, yeah, I don't know if it's the filming-of-it part or the - just the release of starting to perform or feeling like there's some distance between what it is, like, that I'm doing someone else's material or - I don't know. But that's the most freeing version of speaking for me.

GROSS: You grew up in Staten Island, went to a Catholic school in Manhattan. And it was a school where you had to apply - 120 spots. And thousands of people would apply. And you managed to get in. You were in debating club in high school. And you qualified for national championships and original oratory declamation, student congress, duo interpretation and oral interpretation of poetry and prose.

And it's just making me think again of what you were saying about getting words out and how it's easier when there is, you know, a performance or a script. And it's just so interesting that you were having trouble with words, and yet you were so good as a debater or making speeches or, you know, interpreting prose and poetry.

JOST: It took a lot of work to get better at it. I mean, even when I started doing it, I wasn't great at it. When - I mean, I wasn't good at it when I started. I was never really great at it. There were - even though I had some success doing it, there were kids that were significantly better at it than I was. But I - you know, it was what I - you know, I worked at it a lot. We, you know, I was basically doing it every single week at a different - traveling to a different school, traveling to a different city for tournaments. And you kind of slowly build over time. I just - again, it was the most fun thing for me to do.

Like, going - and, you know, I had a partner for duo interpretation - Pete DeFalco (ph), who was from Staten Island, too, who was one of my best friends. And we - like, performing together, going and traveling and doing that was, like, the most - it was like a traveling show that you did every week. And it was so fun to, like, be on the road with your friends, get to do that, be away from home, like, have your full freedom and go and do something that was creatively rewarding like that was like - you know, it was like a miracle. It was so fun to do. And, you know, we - I don't know - I think that was a - it made me feel good. It gave me a lot of self-esteem because, again, it was such a struggle early on in my life that I've really liked the challenge of trying to get better at it.

And, you know, you learn - like anything, you learn from - there were other kids who were way more naturally gifted at doing it. And it was - you learn from them. And you - you know, you were inspired by them because you - they were doing things, like, I couldn't do. It was, you know - it was the beginning of kind of learning about how much we learn from our peers.

GROSS: It's interesting because a lot of people think of, like, debating club as being so kind of nerdy. But for you, it's way...

JOST: They're correct.

GROSS: Yeah (laughter). But you were on the road. You were on the road performing. Like, that's pretty cool.

JOST: Yeah, it's very - I mean, it's the absolute nerdiest version of - it was very cool to us. But we were all gigantic nerds. We were...

GROSS: (Laughter).

JOST: Happily. We were...

GROSS: Yeah.

JOST: We were not trying to be other - I mean, we - I was in school where - we all came from schools that had bullies. And we went to a school where there were not really bullies in the same way. I mean, even - every school has bullies. But we didn't have, like, bullies the way we were escaping from our hometowns. So, you know, almost everyone - almost no one at my school lived in Manhattan. Almost everyone lived in one of the outer boroughs or Jersey or Pennsylvania.

And almost everyone had, like, an hour and a half or two-hour commute to school. And part of that was everyone wanted to kind of get out of where they were or find who their people were in the world. And I think that's what our high school was for so many people and also for - speech and debate was kind of a group within that. It was like a group of people who wanted to do that. I mean, it's a profoundly nerdy activity. But among nerds, it's a pretty fun - it's the closest that we're going to get, probably, to sports.

GROSS: So let's take a short break here. And then we'll talk some more. If you're just joining us, my guest is Colin Jost, a head writer on "Saturday Night Live" and co-anchor of "Weekend Update." He has a new memoir called "A Very Punchable Face." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to my interview with Colin Jost. He's written a new memoir called "A Very Punchable Face." He's a head writer on "Saturday Night Live" and co-anchor of "Weekend Update."

So your mother was the chief medical officer for the New York City Fire Department for 20 years?

JOST: She was - I think she was the chief medical officer maybe for 25 years. And she was in the fire department for 40 years.

GROSS: Got it, OK. So while you were at Harvard, 9/11 happened. And your mother was the chief medical officer for New York City at the time. So when she heard about the buildings collapsing, she got in her car and drove right to ground zero and nearly got killed because one of the buildings collapsed while she was very close to it.

And then when she was able to see again after the debris started to clear, she just stayed at ground zero and then went back every day. Your mother sounds amazing and incredibly courageous, too. I'm hoping she doesn't have any, like, medical problems left over from being at ground zero for so long, like so many first responders have.

JOST: She has lung issues, you know, from that. She's - that it's like - you know, obviously, it's slightly scarier in this time where - with COVID and stuff. But she's - you know, she's a healthy person who tries to - you know, she tries to, like, be conscious of that and make decisions that help her health. But she - you know, she'll - she has lingering effects of it, but I think she's grateful that she's still relatively OK.

GROSS: What did she do on 9/11 after she was able to start moving again?

JOST: You know, the first thing she did was to - you know, after a bunch of things, obviously, that I talk about in the book - but she - you know, one of the first things she did was to set up a triage center that was, like, in an old Duane Reade there - not old, but probably somewhat beat-up Duane Reade.

GROSS: For people who don't know, Duane Reade is a - it's a drug store. It's a, like, pharmacy kind of store. There's Duane Reade's all over New York.

JOST: Yeah. But my - yeah, she set up a triage center in a Duane Reade, and then set up another center later at Pace University. And everything was - it was - I think that she was expecting - everyone was expecting, like, waves of people who were injured. And there was a little bit of an initial wave, but very quickly people realized that most of the people had not - it was not an injury situation; it was how many people had died. And so it became more of a search and a recovery than it was, like, treating individual injuries.

GROSS: You must've been so worried about her.

JOST: Yeah (laughter). Yeah, I was very worried about her. I didn't - you know, I didn't talk to her for a long time. I didn't - I mean, I couldn't. And it was - you know, it's - when - I was, on some level, used to - you know, my mom was always on call - like, she'd be on call certain days, like all night. So I was used to, late at night, my mom coming and saying, hey - like, waking me up and saying, hey, I got to go to work. And I'm like, oh, why now? And she's like, well, there's a fire.

And so it's a - you know, I got used to a mom saying, I'm going to go to this fire. But when someone's just survived something, it's also your - you want them to kind of, like, be in a safe place and not put themselves in more danger. And so that was very - that was scary for a while. And she's - you know, she's tough, and she's a sensible person. But yeah, of course, that was very scary.

GROSS: Are there other firefighters in your family?

JOST: There's very few people in my family, on my mom's side, who are not firefighters. My grandfather was a firefighter, my great-grandfather. My uncle's a fire dispatcher. I think I have three cousins who live on our street who are firefighters (laughter), like, on Staten Island street. And, you know, I think it's just been - that's been our - my mom's family has all had that.

And they - you know, they really - they loved it as a community, and they also loved it as a - like, a steady city job. Like, they really appreciated that you could, you know, earn a living as a firefighter, you know, build a family as a firefighter. And they loved the people they worked with. So I just grew up knowing - like, thinking of it as this great community and this great world. And, you know, my mom - even when things - like, when I didn't get jobs as a writer or I didn't - or my brother was struggling to get jobs as a writer, she would always tell us, like, you can take the fire department test; it's coming up, you know? And I think she still told my brother that about two months ago, even though he's been very gainfully employed for 10 years.

She - I think she - part of it, she loves the community of the fire department so much that she's - wants it to continue in some way in our family. And the other part of it is she does feel like there's - I think she really - she values it a lot and hopes that her - you know, would love it to continue in some way in her family, you know?

GROSS: I think we have to take another break here. If you're just joining us, my guest is Colin Jost. He's a head writer on "Saturday Night Live" and co-anchor of Weekend Update. He has a new memoir called "A Very Punchable Face." We'll be right back. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Colin Jost. He joined "Saturday Night Live" as a writer in 2005 when he was 22. He's been a head writer for six years and has co-anchored "Weekend Update" with Michael Che since 2014. He's written a new memoir called "A Very Punchable Face."

Let's talk about "Saturday Night Live." You were 22 when you joined, which seems really young. What was your audition like?

JOST: It was - you know, I applied as a writer. So I sent in - you know, the year before, I had sent in a sketch packet, which is, you know - people apply every year. You kind of do - a sketch packet is basically five or six sketches. They can be - usually people include, like, a commercial parody and something that's topical and maybe something about pop culture in some way, but, really, just five or six sketches that you think are funny that you write out. And you're looking at them, like, you know, in a final draft document or a Microsoft Word document. And you submit, you know - I didn't know at the time. But every summer is when people submit those and when we read all those submissions.

And the first time I submitted was the year before. And I submitted - I, like - I attempted to email it in just in the middle of the winter when no one at "SNL" would ever read it or be hiring. And so I, like, put this whole packet together. And I was like, all right, I got - like, I feel good about it. I'll send it in, and then never heard from anyone. And then in the summer, I realized that that was the window to actually submit and that my previous submission had basically just gone into the trash.

And so I wrote a new packet, which was actually a great process because it made me, you know, come up with a whole different set of sketches that I'm sure were better and stronger than the one I had done the year before. And I submitted that. And then I didn't know what the process would be and then got a call from an associate producer on the show who asked if I - if I could come in to interview with Tina Fey and Andrew Steele, who were the head writers on the show.

GROSS: What was something in the packet of sketches that you sent to "Saturday Night Live" as your audition (ph)?

JOST: (Laughter) You know, a couple of them eventually got on the show. I wrote one - I remember, the most Catholic submission that I had was - it was a commercial parody for a birth control called the rhythm method. And it was just - I remember hearing, like, the rhythm method was you just, you know, you have sex at certain times. And then other times, you don't. And that's a nice - that's a great way of birth control, too, natural way. And it was Amy Poehler explaining the rhythm method and how great it is for birth control. And every room she walked through in her house, there were more and more children...

GROSS: (Laughter).

JOST: ...And more and more - like, she was in the kitchen. And you revealed kids that were, like, in the cabinets and everything.

GROSS: (Laughter).

JOST: Like, she clearly had 35 kids (laughter). And that was one I remember.

GROSS: One of the great cold opens that you co-wrote had Matt Damon as Brett Kavanaugh. This was during the Kavanaugh hearings. And it was right after Christine Blasey Ford had testified about being sexually assaulted by Kavanaugh. And then Kavanaugh came back and gave his side of the story and was, you know, asked about his drinking and everything. And so Matt Damon played Kavanaugh in this sketch. So who thought of Matt Damon to play Brett Kavanaugh? He was so terrific. But I wouldn't have thought of him.

JOST: Me and Kent Sublette, you know, wrote it together. And he was, like, our dream person to do it. But we didn't think he'd do it. Or we didn't think he'd physically be able to because he was - I think he was in LA. Or he was either shooting in LA or he was shooting, like, in Northern California. And so we said to Lindsay Shookus, who runs our talent department and is a producer at our show - we were like, well, do you think Matt Damon would ever do it? And she was like, I'll ask him, you know?

It was kind of in a - none of us really had any hope (laughter) that he would do it. And then she came back. And she was like, he's in. Like, he's going to do it. He's going to fly overnight to New York, land and basically go right into it. And that was - you know, there were - she was like, he'd love to see a script by the time he lands...

(LAUGHTER)

JOST: ...If that's possible, you know? And he flew in and nailed it. And I remember he drank, like, half a beer sort of to get into character, maybe (laughter).

GROSS: You're most famous for "Weekend Update" because that's when you're actually on camera. You write that when you started doing "Weekend Update" with Michael Che that you realized you should each be yourselves as much as possible and not just accept jokes from other writers that seem like they're - yeah, they'll get laughs. But your heart isn't really in the joke. Can you talk a little bit about learning to do things that you really believed in, jokes that you really believed in?

JOST: Yeah. You know, first of all, we have writers for Update who are fantastic joke-writers who I really think are some of the best joke-writers in the world. Like, they're really great. And part of, you know, starting out and learning how to do it was - the way Che put it was, he didn't ever want to tell a joke that someone else could tell as much as possible.

Like, he wanted the jokes to feel like they were purely his or no one else would do it the way he would do it, you know? That's what he said early on. And I remember thinking - I remember that, like, really clicking for me, like, as a concept. And I still struggle with that. Like, I still sometimes fall out of that, you know? And I'm aware of that. I think Che is better at doing that and sticking with that. But I think that's such a great goal.

GROSS: On "Weekend Update," you and Michael Che often make a lot of jokes about race. You're white. He's Black. Have you been thinking, like, if you were doing...

JOST: What?

GROSS: (Laughter) If you were doing the show during the height of the protests against police brutality and systemic racial injustice in policing and in the Justice Department, the George Floyd protests, would you have addressed that head on? As those protests were going on, was part of your mind thinking if - even though "Saturday Night Live" was not doing new shows at that point, was part of your mind thinking, how would I have handled this on "Weekend Update?"

JOST: Yeah, of course. I mean, certainly, Che would've talked about it. And I would've talked about it, too. I don't know how. It's really a - you know, you kind of have to, when you're doing Update, you have to figure out some way. But I don't know. I honestly don't know. I think it would've been really hard. And I don't know. It's a - you know, it felt like a time - it definitely felt like a time to listen and not be the one talking, for me, personally. And, you know, I think - I don't know.

I mean, I think Che would've had a great - would've figured out a great approach to it. But I'm sure even he doesn't know exactly what it was. You know, part of it's being forced in a moment to come up with something that you have to figure out what you - you know, what you're going to say. I don't know. I think it would've been really hard.

GROSS: When you and Michael Che do "Weekend Update" and you make jokes about race, how do you calibrate, like, what's going too far, what's going to be taken in the wrong way and what's going to just read as really funny? And along with that, I'm wondering if any of the jokes that you've told that seemed really funny but didn't land right and were totally misinterpreted pertaining to race?

JOST: With jokes about race, you know, I think we don't - the hard thing is you kind of need an audience to guide you about what's too far. Or - I don't know. But you - some of the jokes that we do, I have not seen the joke until air. So I'm pretty much - I'm putting my life in Michael Che's hands a lot of times and (laughter) hoping that he knows what that line is (laughter). But it's a very scary - it's a very terrifying moment because you also hear - you hear things backstage.

You don't - like, when Michael Che makes me read a joke that I have not seen before on live TV, which occasionally happens, he - I'll hear things backstage in passing, like one of the other writers saying, you can't make him say that (laughter). But I don't know what it was. And I don't think anyone particularly knows what's too far or not too far. I think everyone is - people have different opinions about that. And you - I think you really have to trust, ultimately, that if you're coming at something from a good-hearted place and you're trying to be - you know, that you're - I don't know - you're well-meaning at what you're doing, I think you have to go for it and then hope that people are open-minded.

GROSS: OK. It's time for another break. So let me introduce you here. If you're just joining us, my guest is Colin Jost. And he has a new memoir called "A Very Punchable Face." We'll be right back after a short break. This is FRESH AIR.

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GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Colin Jost. He joined "Saturday Night Live" as a writer in 2005 when he was 22. He's been a head writer for six years and has co-anchored "Weekend Update" with Michael Che since 2014. His new memoir is called "A Very Punchable Face."

You and Michael Che do a bit sometimes where you write jokes for each other. And they're usually jokes that are going to be very uncomfortable for the other person to tell.

JOST: (Laughter) Yeah.

GROSS: What is one of the more uncomfortable ones that Che wrote for you?

JOST: Oh, my God. I mean, seeing what the straight line of the joke is is almost more terrifying because you're imagining where - you're trying to think about, like - (laughter). Like, if the devil wrote a joke...

GROSS: (Laughter).

JOST: ...What kind of joke would he write to get you (laughter)? - because you know - because I know that's what Che's thinking. And, you know - and I remember, maybe last year, one came up about Martin Luther King Day. And I saw that as the through line. And I was like, oh, my God. And that was, you know - you know, it's a very honest moment of television because it's - you see that I'm pretty scared, I think - I think that comes across - and how uncomfortable it is. And I think that's fun for people to watch and even though it's sometimes pretty cringey.

GROSS: We happen to have that Martin Luther King joke standing by. So let's play it. And again...

JOST: Oh, great (laughter).

GROSS: ...This is a joke that Michael Che wrote for Colin Jost. And Colin Jost had to read it cold without ever having seen the joke before.

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JOST: Oh, come on.

(LAUGHTER)

MICHAEL CHE: Oh, no. I think this...

JOST: Just the graphic.

(LAUGHTER)

CHE: No. This will be good.

JOST: Yeah, I'm sure.

(LAUGHTER)

JOST: A substitute teacher in North Carolina has resigned after she reportedly told a class of elementary students that Martin Luther King Jr. killed himself. In her defense, he is the one who decided to keep running his mouth. Why?

(LAUGHTER)

JOST: You're going to get me murdered.

(LAUGHTER)

GROSS: So that was my guest, Colin Jost, on "Weekend Update" reading a joke cold that Michael Che had written for him. What reaction did you get to that? You sounded just so appalled that you had to tell that joke.

JOST: (Laughter) I mean, it's a pretty appalling joke. A lot of friends contacted me after that. And backstage, a lot of - there were a bunch of comedians around. I remember Godfrey (ph) was around, who's a comedian I knew from, like, the Comedy Cellar and stuff. And I remember he was like, oh, my God (laughter). He was like, I can't believe you said that. Like, how could Che do that to you? And yeah, I really - I think - you know, my friends were like, I don't - I can't remember anyone ever doing a Martin Luther King joke on "SNL" before. And they definitely did not expect that joke to come from me. So yeah, I don't know. It was - it's a very unique moment to go through.

GROSS: Yeah, it's always like - in those things, on Weekend Update, where you write jokes for the other person to read, it's really funny because you can tell you both really like each other, but this is your opportunity to really, like, embarrass the other person (laughter) by giving them jokes that they should not tell.

JOST: Well, you know, when you're at a club, like, among comedians, the jokes you love the most are the worst, meaning, like, the - either most offensive or the darkest jokes. And that's what you're always watching - it's, like, why we love watching Dave Attell from the back of the room 'cause we were just, like - we love hearing whatever he's going to say because you know something in there is going to be horrifying (laughter).

And that's the - that's, like, the most fun you have as a comedian because there's this - whatever - like, some weird, dark pleasure about it. So to force another person to tell one of those jokes is just - is very satisfying, I think, because I think anyone can imagine, if they just had to cold-read a joke like that, that's a pretty awful situation to be in. And, again, people like seeing me in pain. So...

GROSS: (Laughter) That's right. That seems to be a theme. You write in your book that you're preparing mentally to leave "Saturday Night Live" in the near future, and you say that's a very scary sentence to write, even though it's intentionally vague. Of course, filling in the blanks in my mind, I figured, like, oh, you didn't sign your contract to renew (laughter). So I don't know where you are with that now...

JOST: You always get - you always go straight to the contract. You just - your...

GROSS: (Laughter).

JOST: That's where your mind always goes, your legal mind.

GROSS: Yes. Yeah. But anyways, I was wondering if, like, this book and the film that you're working with Pete Davidson are - if you saw that as kind of creating the pathway out. You - if you leave, you want to know you have something that you're doing; you don't want to just leave and then go, like, now what?

JOST: Well, of course, yeah. I mean, I - definitely. I want to - there's just a lot of other things I want to do. There's a lot of things I want to do in my life and also things that I want to do creatively in my life. And, you know, I want to start that because I don't want to - because I don't know. I'm just - I'm anxious to get going on that.

But I - you know, of course - I have a real deep fear about ever leaving "SNL" because I - it's a world that I love so much. Like, I've never - you know, you just don't know how often you get to work at a place like that, and the odds are zero other times (laughter) in my life will I get to work at a place like that. So it's a scary but a necessary decision to face at some point.

And even though it's a crazy job and an all-over-the-place job, there is an odd routine to it of knowing what each week could be and just the structure of the schedule. I mean, we're basically on a school schedule, from September to May, at "SNL." And there's a way in which we're still a little bit in an arrested development of being in a world like that of not quite a school world but a - I would say maybe a less mature world. And that's a fun world to be in and a scary world to leave.

GROSS: Well, if and when you do leave "Saturday Night Live," I will miss you very much, but I wish you the best of luck in whatever you decide to do. And I really want to thank you so much for talking with us. It's really been a pleasure.

JOST: That's so nice. Thank you very much. It's a - it is always a pleasure to talk to you, and thank you for taking time to read the book and to talk to me.

GROSS: Colin Jost is a head writer on "Saturday Night Live" and co-anchor of Weekend Update. His new memoir is called "A Very Punchable Face." "SNL" alum Andy Samberg is starring in a new movie called "Palm Springs." Justin Chang will review it after we take a short break. This is FRESH AIR.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.