EO

How old were you when you got hired at Saturday Night Live?

CY

I was 23 years old. [Laughs.] Wait, is that true? I think so.

EO

That’s so crazy. I didn't realize that you were that young.

CY

I know. Me too.

EO

These next three years, 27 through 30, are insane.

CY

Everybody’s been saying that to me recently.

EO

Because it’s a thing. I just got through it. [Laughs.] You should write a book or something.

CY

What was that like?

EO

I feel like a different person from that time. My life just happened quickly. It goes all back to 25, I got into graduate school and that was a succession of events. But my priorities are different—socially, energetically, et cetera. I’ve done this several times before in my life where I’ll completely strip everything away and then I’ll rebuild. Being 27, specifically—that period of time is when you become really focused. Certain friends of mine are in that time where they’re dating and have decided, “This is my forever person,” or they’re making insanely big decisions and committing to jobs. You submit to yourself, essentially.

It’s an exciting time. You also make your best work because you’re not thinking. I recently interviewed this painter in her 40s now, and she was saying, “30 to 36 was the roughest time for me, because I felt lost.” And I’ve been thinking about this now, and thinking about my 20s. They were a really intuitive time for me. I was thinking on some level, but I didn’t really think about the consequences. You weirdly have vision, but you don’t think about context. Even if you are thinking about context. [Laughs.] You’re rawdogging reality. I just turned 30 and things don't feel as intuitive now in the way they once did.

CY

Interesting. I wonder if there’s also a function of having seen more horror and felt more, and that makes things less accessible. There’s some Steve Martin quote about that, that’s along the lines of, as you get older, fewer and fewer topics become available to you because you've just experienced too much pain. [Laughs.] It’s so easy to joke about stuff when you’re young.

EO

I’d first like to start off by asking, what do people not know about you that you even want people to know? Do you ever think about the politics of being known?

CY

I don’t really want people to know things about me. That is my general mode. [Laughs.] I don’t know why—I’m generally a very open person, I think.

EO

When does your story start? Where does your story start?

CY

I’m from Toronto. Born and raised. Always wanted to write, to be a writer. Started reading and writing pretty young. Never really could do anything else but that.

EO

What kind of writing did you want to do?

CY

I think for a long time I wanted to be a journalist. A serious news journalist. And in high school, I was very much on that track and was like, “That’s what I want to do. I’m going to be a writer, I’m going to be a famous journalist.”

EO

But did you know that you were going to be famous?

CY

No, I didn’t think I was going to be famous. [Laughs.]

EO

Right. Okay, keep going. [Laughs.]

CY

You cannot be having reactions like that. [Laughs.] But then I basically became addicted to watching SNL. And I was totally obsessed with Steven Wright. Do you know who that is?

EO

No. Who is that?

CY

He’s a famous one-liner comic. My dad told me about him. And I looked him up on YouTube. From there, I became engrossed with contemporary comedy, with the comics performing at UCB in New York. I would never make plans on Saturday nights. I just loved watching SNL live too much. I submitted to the fandom. I would watch it on Tumblr with other sad teenagers. [Laughs.]

EO

So you were on Tumblr too?

CY

Of course. Were you?

EO

Yeah.

CY

What kind of realms? Probably cooler than what I was looking at.

EO

Shut up! The thing is, sure I seem cool, but I’m actually not. I live in my brain, I’m just a nerd basking in grasping my own fantasies. I do care about structure and systems and histories. But Tumblr was crazy. My life is still the sum of Tumblr’s parts then. I wasn’t big on Tumblr. I was just lurking. I was there and I could see what was happening and I was absorbing everything I could. I went through so many different iterations of it also, because I was on from such a young age, from 2008 through college. I still have mine. I occasionally will go on and will see stuff that people are posting because it’s where I grew to become interested in fashion and literature. Tumblr was really not essential, but instrumental. Tumblr was really instrumental for feeding my love of literature, and it really cemented my cultural references for everything from the niche to the masses. Because I had always been really literary and I was more academic and rigorous because of the schools that I went to. But Tumblr was like, “Oh no, this is a feeling,” or all the quotes and the images that were swimming around. And that really changed my relationship to art, image, and words. I try to bring it up, and I’ll shorthand reference it for people, but people who weren’t there to experience that machinery don’t understand how serious it was.

CY

You literally had to be there. It’s impossible to recreate. The speed at which I was consuming words, images, and texts, if you will, was just totally nauseating. It’s crazy to imagine now. [Laughs.]

EO

Also, you didn’t know who was famous. You weren’t aware of people’s followings, though you knew who had influence. That wasn’t why people were curating and mainstaging this content, which is such a different apparatus now. So how did it affect you? You were on Tumblr, you weren’t going out on Saturday nights. What was the vibe?

CY

It’s interesting, I look back now and I think, “How did I move to New York?” The path to getting to my life now feels so unlikely. But I think at the time it all felt extremely accessible.

EO

What felt accessible? Or are we all just productively delusional? [Laughs.]

CY

I was like, “Okay, so I’m going to be a stand-up comic. I’m going to work in comedy and I’m going to be a TV writer, and great.” I think that I just followed so many people on Twitter who had this kind of life that was a fantasy of sorts to me. And at the time, I thought, “Cool, I’ll just do what they did.” Looking back, I’m like, “Hello? Why did you think that?” [Laughs.]

EO

But how did you know what to do? What’s the real story and how did you time your move to the US? Why didn’t you just immediately go to college here?

CY

It was extremely expensive, and seemed impractical to me. And I also lived in Toronto, which I felt was a big city. I was like, “Why don’t I go downtown and go to school? And I know people do stand-up downtown, maybe I’ll just do that.” So that’s what I did. I remember there was this girl in the year above me who went to NYU for undergrad, for film or something. And I remember thinking, she has my dream life, which basically I’ll never have. [Laughs.] Then I did undergrad, and I would say that my vibe in undergrad was that I would sometimes go to school but that I was mainly living downtown working as a stand-up. I was barely a student. I was really like, I’m an adult.

EO

I know. I’m fully aware of the plight and inner workings of that thinking. [Laughs.]

CY

Where did you go to school?

EO

I went to The New School for college. And then Columbia University for graduate school. When I was in high school in Los Angeles, I took this Writing Workshop my junior year, and I realized I had the dream of being a writer. [Laughs.] I was like whoa, I know how to do this, tell stories and understand the tools of structure and the whole gamut. I can tell stories that aren’t mine but I understand the severity and rigor and intensity of them. With my own move to New York at that time in my life, I also know what it’s like to be that young person who says, “I’m in a city and it’s so different.” Though there’s a difference between people who go to school in cities versus those who go to campus schools, maturity-wise.

CY

It’s interesting because it’s different, right, but it’s also a total delusion. [Laughs.]

EO

100%.

CY

It’s a lot like, “Sweetie…” [Laughs.] You’re not a working person, you’re basically a child who is not being supervised living in a/the big city. But I love that feeling of “I can go fucking anywhere, right now.” [Laughs.]

EO

So you’re in school and doing comedy downtown. What was the scene like? Had you already been thinking about the structure of comedy and writing in that way, and were you reading any specific kinds of books?

CY

There was one big sketch group that had a lot of funding that I did not get into in a pretty devastating way. When I first approached them, I thought, “Great, I’ll just go there, I’ll get in, I’ll probably be the head writer maybe two weeks in,” whatever. Went there, met them, didn’t get in—probably by a long shot—wasn’t even in the conversation, not in the mix.

So then instead, I joined this dinky one. You know when you join a wayward college group and randomly one person there is 45 years old, but a student, and then it’s like, six gay people. And you’re all living in fear. This one old man who’s technically a student, so he’s in the group, but he’s being scary, basically. [Laughs.] Is this an archetype or just my experience? [Laughs.]

EO

I was going to make a Julia Louis-Dreyfus joke, but then you ran with the man story thing...[Laughs.]

CY

Anyways, I joined this group, right, and it was so disorganized, had no funding. I remember one time we performed in a bar that had a theater area, but it had rained the day before, so it was totally flooded. Instead of performing in the theater part, we stood in the middle of a busy bar with no microphone. Basically, we were just talking to each other. Nobody could hear us. It was that kind of situation. And then at the same time I was doing a lot of open mics.

EO

How did you seek those out?

CY

Definitely online. It was probably through Tumblr. . .I don’t know how it works now because I’ve been out of the game for a bit, but normally there’s some kind of master document online of every day of the week, and it lists what bars and who runs the shows—the open mic comedy community is a robust, organized community. [Laughs.] I’d show up to these bars. The legal drinking age in Toronto is 19. I was 18 for a lot of it, so I would just not order a drink and wait for my turn to tell my jokes, well into the night. And there just weren’t that many people like me doing stand-up, so I was booked a lot, pretty quickly. I was performing most nights of the week. It all happened pretty fast. The comedy scene there is a pretty small community, it was easy to get to know everyone. I don't know if I was good immediately, but I was confident immediately.

EO

Why do you think that was?

CY

I don’t know. Just total delusion.

EO

What were you studying in school? And what was happening in that life? Because there are two lives that were happening at the same time, no?

CY

I changed my major a million times, but at the end of college, I cobbled together enough for two minors and a major. I ended up being a women and gender studies, of course, and media studies minor and majored in English. I kept taking classes that I was bad at, dropping them. The only thing I was good at was women and gender studies. [Laughs.] I wasn’t that focused in school. Then I ended up doing Second City, and was on this weekly sketch comedy show in Toronto—it was the premier sketch comedy show that was on every week. I was young, and very much played the role of “woke police” in it. But by the end of college, I was like, “I’m sick of stand-up. This is crap. [Laughs.] What am I doing? Comedy sucks.” At the time, it became this totally irresponsible, reductive, simplistic form of art and communication. I was so angry with it. And I decided, I’m going to be a real serious writer. And I need to write on a meaningful TV show.

So I basically Googled “Top MFA programs.” I didn’t know what an MFA was, had never met anyone who had done one. I had gone through this crazy breakup in my last year of college and was thinking, “I’m sick of this, I need out. I need a different life.” And so I applied to all five that were on a listicle: NYU, USC, UCLA, AFI, and Northwestern.

EO

Specifically for dramatic writing or something else?

CY

I applied for TV and film, and whatever each one required. I got in everywhere. I think I got waitlisted at USC. I can’t remember. And NYU offered me a big sum of money, and I was like, Yes. This is amazing. I called them and asked, “Can I have more money?” And they said yes. So I decided to go, I moved to New York to be a TV writer and write the next Fleabag or whatever. I got here and I immediately thought, “I’m going to quit comedy. Fuck this, fuck Second City.” And I got duped into doing playwriting. I started seeing shows. I had a couple of really good playwriting profs. I was like, “This is amazing. It’s so fun. It’s basically what I’ve been training myself to do.” It’s so similar to comedy. It’s live and it’s ostensibly wanting to be funny and it’s political by nature. So that was really my graduate school experience. That became the plan: to make unproducible plays, not make much money, quit comedy. [Laughs.] And then I basically got the most corporate comedy job in the world.

EO

I’m curious how involved you were in the New York comedy scene? That narrative you’ve given is the professional you, but what’s the social aspect and what was happening that reinforced what you were doing in school?

CY

I had been doing live stand-up shows for, at that point, about four years in Toronto. I also knew some comics here just from when they had visited Toronto, or if I had come to New York during the summer or hopped on two or three shows. Even though I had maintained that mindset of I’m done with comedy basically, so forget my name, I was still doing some shows. I was wanting friends in comedy and I still liked hanging out with comedians, I liked the scene of it. And it was hard, I didn’t know anyone when I moved here. It was nice to have something outside of school.

EO

Was school intense? What was the culture of it?

CY

It was intense. But the culture was pretty nice. Not so competitive or anything, and very nice and very normal. And by that, I mean not so alternative. That surprised me and I didn’t like that so much.

EO

But I think that that depoliticization probably allowed you to hone your craft, because politics weren’t foregrounded as much. There was space to dream.

CY

I would say it was more the repetition of the craft. Truly how much I was writing and working on trying to understand, what makes a story? How does it work? Trying to sit in the passenger seat of so many movies and plays and TV shows that I really liked and trying to understand where they go, exactly.

EO

Yes, how they get there. What were the questions you were asking yourself?

CY

My big question was: “How did anybody turn any of these crazy feelings into something that was legible, something with tension that's suspenseful?” And, “How does anyone turn any of their ideas into a narrative structure?” It was so hard for me to understand and it honestly still is. My biggest challenge in writing and being a writer is the legibility of it. It’s interesting—at my job now, that’s the whole job. [Laughs.] It’s trying to take any idea or any big feeling into the most succinct, funniest, clearest sketch. So much of comedy is just clarity.

EO

What was it like leapfrogging from Toronto? From Toronto to NYU, and then from NYU to SNL. Can you describe what that experience felt like?

CY

Toronto to New York was really a scale difference. In Toronto there were five comics who I thought were so interesting and singular and doing interesting things and making me laugh and structuring comedy in this totally original way. When I moved to New York, I realized, “Okay, there’s 25 people here who are doing that.” The scale is just so much bigger.

EO

Then NYU to SNL. Three letters to three letters. [Laughs.]

CY

So, starting there. I don’t know...I graduated in May 2020. So the last few months of grad school were total fucking hell.

EO

We were in grad school at the same time. Which was mostly that pressurized moment of COVID-19.

CY

Definitely. I had a total mental breakdown writing my thesis, a play. It was the hardest thing I’ve ever done, just finishing this fucking play. Writing is this solitary thing, but you need to not be alone to do it. For some reason it just felt like this total behemoth, and getting to the end of it and how I wanted it to be quality-wise was so tough. And I ended up being really proud of it. But it made starting SNL, which is notoriously the most difficult job in the industry, feel pretty manageable. Not to do an NYU advertisement placement or something. [Laughs.]

EO

How did you get the SNL job?

CY

Basically, I was on a student visa and it was about to finish because I was graduating from school, but the way it works is that you can work for one year on it. So I was like, “All I have to do is just get a job—any job—and then I’ll be able to stay for another year.” I could not get one. I applied to maybe 200. I was just sitting down and applying to jobs every day. But then I went to my friend Max’s birthday party in June. It was a park party and it was the first park outing I went to. And Bowen Yang was there. And think we had hung out maybe one time before that. I think literally one time. He told me that SNL was hiring writers, and I decided to submit a packet. As I said earlier, I was obsessed with SNL, but by this time the dream had been long gone.

And then I DM’d [directly messaged him on Instagram] Bowen about it, and he sent me the guidelines and told me to submit three to five sketches. That’s how you apply. I had not written a sketch in years. But I wrote them in one day, in one sitting. And at that time too, my metabolism for writing was so high. I sent the packet through. I didn’t really think anybody would read it, but I knew there was a chance Bowen might read it. So I told myself, “This just has to be good enough so that if Bowen reads it, I’m not going to be embarrassed.”

EO

Yes, I’m into it. Let’s keep the flame going.

CY

It reminded me that I can write a sketch. I had been writing hundreds and hundreds of pages of total nonsense at school. But I can write a very simple idea in five pages. So, I did that. I sent it to him. This was around August or July, and I had to go back to Toronto because there’s a small window of time with the visa that you need to find a job within. So I went home, had no plan. Was totally depressed. And my friends suggested we take a trip to the middle of the woods in Canada. We were driving on a road called Dump Road, and I had service for the first time in five days. I had all these emails and DMs. There was one from a producer at SNL being like, “Hey, we’ve been trying to contact you.” And the head writer had DM’d me on Twitter, being like, “Is there an email that is better to reach you at? We haven’t heard back. We are doing one more day of interviews tomorrow. Can you Zoom in?” So, I went back to the house I was staying at, packed it up with my friends, and went home to talk on Zoom. It was done, and then I didn’t hear anything for weeks. I’m just depressed again, thinking, “I blew it. My ticket back to New York.” Then online I see that production is starting—from my Tumblr days, I know what day of the week each production thing is happening—so I’m like, “Obviously, I didn’t get it. It’s writing night.”

But I got a call from Lorne Michaels during that first week of production. There’s a show on Saturday. He asks me, “Where are you?” And I was like, “Um, Toronto. Ever heard of it?” Because he was from there. He did not laugh, obviously. [Laughs.] He basically went on to say, “Okay, I’ll see you as soon as possible,” and hung up. And I was like, “What?” I called my manager at the time, who told me to get a flight immediately. [Laughs.] So I flew in the next day, and I started in the middle of the week.

EO

Wow. What were the working conditions like in COVID?

CY

They were crazy. There was obviously no vaccine at the time, so we were getting PCR tested every single day and masking.

EO

You had to physically be there. You couldn’t Zoom it in.

CY

Looking back, I’m like, “Why did we do that?” [Laughs.] We could have died for that. What?

EO

Comedy. [Laughs.] Was the viewership significantly bigger because everyone was home at that time?

CY

I don’t know. Probably. It’s amazing how little I think of that. At work, there’s television monitors everywhere, right, and they feed to the studio so that we can watch rehearsals and blocking. And we do a dress rehearsal for the show, and then the live, on-air show. It’s all obviously on the same monitors. Sometimes when the show is live, I’ll look at the monitors and I’ll have this pain of remembering that people are watching this outside of the studio, and it literally scares the shit out of me. [Laughs.] Because I just don’t think of it that way.

EO

Right. I was recently talking with a friend about how we were professionalized through COVID. I was 25 when I started and I got all these big jobs throughout the pandemic. So I don’t think about the audience because I wasn’t socializing in the same way. You weren’t being social in the same way that you are now; there weren’t parties and dinners to go to. But in a weird way, we got to really focus on the work, and there was nothing that eclipsed that. It was so pure.

CY

Interesting. I never thought of it that way. I think that must be true for me as well. But I always thought of it as a transition from performing live to writing for some unseen audience.

EO

What was your experience working with Lorne like? How involved is he in the process?

CY

He’s very involved. He’s there every day of the show.

EO

How does it feel occupying a public stage in that same way? Do you inherit a community or is it something that you go into blind? What are the mechanics of it?

CY

It was interesting because I started alone and that is not so typical. There’s normally a cohort, and they hire five, six, seven writers at a time. The whole show operates on an excess to pick from, where every week we make way more sketches than we need and we cut them down. Every part of the show works that way.

EO

I was reading about the Beavis and Butt-Head sketch with Heidi Gardner and she was talking about how that was a sketch that they’ve been working on for a long time—five years or so, right?

CY

Yes. And in my time, they tried it at least once.

EO

And it didn’t work?

CY

I don’t know. I don’t know why it got cut before.

EO

So you the writers are proposing these sketches and they get put to the side, and then people are constantly bringing them back? What’s the protocol like for this process?

CY

Yeah. But in my experience, when I get things cut, I usually don’t bring them back. Every time I’ve tried to, it has not been successful. It’s diminishing returns.

EO

What’s your success rate with getting sketches on?

CY

It’s pretty high. I actually recently counted how many sketches that I've got on—I believe it’s in the area of 100 sketches, or a little over 100.

EO

And is that typical? What is the average?

CY

I would say it’s not typical.

EO

Is that structure something you’ve had to learn, and is it a structure that you then create for yourself?

CY

Well, it was an interesting process, because it’s both yes and no. Yes, where I had to figure out how to put my own ideas into a typical SNL sketch of a game show or whatever. But then also no, because I had basically been studying the show for 10 years.

EO

Were you still watching throughout your college years though?

CY

I wasn’t, but when I was watching, I was addicted. Like, watching every sketch more than once—I would play them like songs. They became like my favorite song, my favorite artist. The sketches were on repeat. But more generally, SNL takes up such an interesting space in the culture because it’s so mainstream, so monoculture. But then at the same time, some people will ask me, “What days do you film it?” Or, “Is Bill Hader still on the cast?” I’ll be like, “No.” [Laughs.] “What are you talking about?” It’s totally present, but also not.

EO

Of course. It’s a kind of shorthand, but it exists ambiently. What has it been like working with Bowen Yang? He is masterful, and he really has the Kristen Wiig-ification thing going where you can totally see him crafting these scenes and characters in a masterful way. What you guys have done is crazy with and for each other is crazy. Aside from him being an Asian counterpart and the first Asian to be a cast member. . .

CY

He’s amazing.

EO

And a visionary. It’s not just another body in space, it is like another mind completely.

CY

His mind is so expansive. So it makes my job really, really fun, and basically pretty easy. Obviously it’s hard in volume, but what he can access at any given time is so beyond what a normal person can. He has this encyclopedic nature, but is also so iterative. Saturdays are long days, we’ll get to the studio at noon or 11:00 AM, and we’re working through the night. We’ll run each thing on camera in full dress and are also doing rewrites. So, all day everybody’s working. But there’s long stretches of time, so for a lot of the cast and writers, it’s a lot of chilling, reading books, hanging out, going to get food, watching TV, whatever. But Bowen is in his dressing room studying, paper and pen out, writing out different pieces of dialogue, writing out different lines that each of the characters he’s playing on the show are going to say. That’s how he works. I feel like I worked at SNL to work with him, or it felt like everything was leading up to working with him. I’m just so lucky.

EO

But how does his approach vary from the standard, typical approach, or what you even knew of the show?

CY

I always write from a big idea, and then I try to find how to fit into it or something. He writes from a single sentence he’s heard or just a way someone has a certain kind of posture. It’s always from such a specific idea, and then he expands on it. And so we make a really good team. We can turn anything into a sketch. I think most people will work from a solid joke, a solid idea, or a character that’s in an environment that’s not for them or an idea that’s subverted–a totally structurally sound joke. And for us, it can be that, but it doesn’t need to be that. You know what I mean?

EO

Yes, it’s more like a feeling.

CY

Yeah. We’re both very feelings-based.

EO

When did you feel like you could take more risks with the form? After a point in time, you’re like, “I know I’m successful. I know I can do this or that I can place a sketch.” But when did you shift into a more experimental approach?

CY

In some ways I feel like I started there, and then learned how to do it and then went back, if that makes sense. For instance, I feel like when I first started, I immediately wanted to do different forms and sketches that I didn’t have the skills to do, or know how to do. I tried to write this sketch that was about people’s email signatures. And so the sketch was all emails—an email chain, basically. And it didn’t work because I didn’t know how to produce a sketch like that at the time, or write it to be producible. But then last year, this writer, Jimmy Fowlie, told me this story of him running into somebody that he’d already met and them being like, “Hey, nice to meet you.” And he was like, “Actually, we’ve met.” Then the next time seeing this person, she said, again, “Hey, how are you? Nice to see you.” And he pretended to not know her and was like, “Oh, I’m sorry, have we met?” [Laughs.] He was like, which is always the fear on the other side of that, where you’re asking yourself, “Is this person pretending? What the fuck?”

He came to me with this story, and I knew we had to write a sketch about it. I knew that it needed to take place at least two different times. Because first of all, it is funny to say, “Actually we’ve met”—like, what’s your problem? Why are you being so aggressive? [Laughs.] And then I think it’s literally crazy to be asked, “I’m sorry, have we met?” after the fact. It’s being stubborn in two bad ways, both times. And so this sketch became about this guy who is this stubborn character [Barry the Midwife]. And because time was passing, we made his hair grow longer and shorter based on where he was in time.

EO

Tell me more.

CY

Formally, it’s obviously not a typical SNL sketch. There’s very rarely time jumps in our work. But at the time, I remember Bowen and Jimmy, both being like, “It won’t work. We can’t jump in time." And I was like, “Why not? I know exactly how it’ll look and how it’ll work and how we can do it.” So that question is tough because it’s a bit of both. I always wanted to do something like that sketch, but I needed to know how to do the job first.

EO

Yes. You need to understand the rules so you can do your own thing.

CY

Totally. And at the job specifically, it becomes really fun to take risks in that way. With that Beavis and Butt-Head sketch, the guys who wrote it—Mikey Day and Streeter Seidell—are amazing formalists.

EO

That structure was deeply formal.

CY

If you look at their body of work, it’s clear that they’re amazing genre writers. And obviously they’re funny too. Lorne is a total formalist. The show is all about form, because you have to do so much so quickly.

EO

Speak more on the formalist angle. Where do you live in that?

CY

I’m totally obsessed with that part of the show—which is that you can basically make any structure, do anything on the show. Any existing film or TV structure, you can use for your take. That’s a very exciting thing because we can get the sets for it, looks and sound, we can land the performances. It’s so fun. It’s like being able to do fanfiction on American culture. [Laughs.]

EO

But speak more to the formalist sensibility and inhabiting that culture at SNL. How did you develop your own take on it? Because being a minority, you’re occupying that structure, but the joke still has to land. There are gimmicks that people try to employ around, othering and minorities, but it doesn't mean that it necessarily lands. I was watching the Pride Month sketch with Anya Taylor-Joy and I was like, “This is so stupid.” [Laughs.] The set up and structure of the joke were so perfect you could slot in any subject matter and it would work.

CY

That’s true. It’s almost like a point system though, where if you aren’t using some kind of borrowed form, then the content has to hit on something deep within the psyche. If not, then you’ll need a form to communicate or telegraph something about what we need to understand to get the jokes. An example: I wrote this Black Eyed Peas sketch years ago, that, for whatever reason, I wasn’t confident about how it would look because I had just written it. I’m not very good at writing visually. So sometimes I’ll write scripts for a podcast or something, and I’ll be like, “Well, I don’t know who should stand where and what it should look like.” And with this particular sketch, if you go and watch it, you’ll see what I was saying. I thought, “I think everyone just needs to stand in a line.” [Laughs.] “Let’s not make it complicated. I know the jokes will work. It’s all about the Black Eyed Peas…” What’s not to get.

EO

Like a chorus line. [Laughs.]

CY

Exactly. The sketch is about them spitballing on ideas for song lyrics. They’re like, “What about something that is meaningful to all of us? Okay. Mazel tov.” Whatever. I think that is a pretty good example of that formally being nothing. We would never see a band standing around pitching in the studio, it’s an abstraction and not something that exists. But I knew that everybody would know the lyrics and that the jokes work on total nostalgia, what is buried in the brain, which are Black Eyed Peas lyrics. We’re going to be on our deathbeds reciting those lyrics.

EO

"Shut up." and "My Humps." and "I Gotta Feeling.” and “Boom Boom Pow.”

CY

So it’s a balance. It’s always a balancing act.

EO

I’d like to hear more about your ‘podcast’ writing approach. Because when you’re working on sketches, as the writer, do you have to know where people are standing? Or in making the structure you have to vaguely understand where people are, with sequencing of choreography, for it to make sense?

CY

It’s a mix. Because sometimes, especially with comedy, the shot will matter, and the cut will matter. Where it cuts. Something I’ve learned time and time again from SNL is that comedy is up-close, it’s hard to laugh at something that’s in this wide shot with all the stuff in it. If there’s a joke, you want the camera to be on someone. Comedy is just as much timing and sound as it is space and distance. So, I do have to think about it a lot. And, again, it’s always about what’s funny. It’s also always what’s legible. It needs to be clear. I see so many stand-ups who struggle with clarity. We need to know what you’re talking about. We need to be on the same page for us to laugh. It needs to be understandable. I think that’s a very underrated quality.

EO

Is it something that cemented itself once you got to SNL, in terms of the machine?

CY

I think so. I was very formally strict in graduate school with writing. I wanted to truly understand how to translate the feelings into a legible piece of writing. And then I think at SNL, it was more about asking, how does it have just enough elements, formally and in terms of legibility, to then also go ahead and be totally loose, fun comedy that people can enjoy and not think too much about?

EO

Boom. You don’t want people thinking.

CY

Yes, you don’t want people thinking. You want them to feel as if it’s already happened. [Laughs.]

EO

Do you go back and watch your sketches?

CY

No. Of course not. There’s always something that I wish was different. With basically every single thing I’ve written—there was something that even right before it went on air—I was like, “It should have had this.” And then that’s my memory of it, is the piece that didn’t have that thing that I wanted it to have.

EO

What’s your process of writing and keeping track of ideas, do you just note that difference in a notebook? Or is it something that you do in your notes app on your phone? Where does it happen?

CY

I try to make little notes after every show, just because you always think you’ll remember and you don’t. And a huge part of the show is working with celebrities and they say things that I want to remember them saying and doing and how they’re being.

EO

Working with celebrities, how does that change and inform the work that you do?

CY

It’s been useful in a lot of ways, just because of the show. I’ve been there for four years and everyone comes through the show, basically. It’s been very useful to know how so many different people work, in terms of learning what is required for some people, and what is totally rejected by others.

EO

Hm, is it a climb or is it more of a conversation to get people to do things?

CY

I would say a climb.

EO

You have to prepare like 30 sketches for certain types of people, or it’s like you can get by with five?

CY

It honestly depends. With some people I’ll sit with them and I’ll have 10 ideas and I’ll go through each of them, they’re like, “I don’t know. Yeah, maybe, but I know that person, so I don’t want to make fun of them.” That kind of thing. [Laughs.] And some people are like, “My brain is empty. I am not funny. Help me. Tell me what to do and I’ll do it. And tell me how to say it and I’ll say it like that because I trust you.” It really depends.

EO

What has surprised you about this work? Being the little know-it-all at 18 and now doing this—almost 10 years later—with what you thought you knew then, what’s the most surprising thing about it now?

CY

I’ve definitely been extremely humbled by the work. I’ve been humbled by the volume and by the visibility of it, and by the straight-up quality of it. There’s so many sketches that I didn’t even put a brain cell into, I wrote it because I had to write it because it’s my job and because I had to show up to get my paycheck. That ended up being made. And then there are so many sketches that I poured my heart into and felt so emotionally, deeply connected to, that will literally never be seen or spoken about or remembered. So, that is a very humbling thing, my feeling of what I am writing has no bearing on the outcome of it. It’s very tough, but also a relieving reality to constantly live in.

EO

Why is it relieving?

CY

Because who cares? If it’s good or bad, who cares? If people like it, if they don’t like it, it doesn’t matter so much to me anymore in this job.

EO

You said you were humbled by the volume and visibility. What did you mean by that?

CY

The visibility is humbling because no matter what I think of it or what I do to it, if it’s going on the show, it’s going to be seen by millions of people. There’s something that’s a bit rough about that. We don’t get enough time to make the show. It’s just not enough time. Tuesday to Saturday. It’s not normal.

EO

Yes, that is what makes it work though. It’s its own specific architecture. It requires its own apparatus. There’s this Leonard Bernstein quote where he says, “To achieve great things, two things are needed: A plan and not quite enough time.” [Laughs.] Story of my life.

CY

Exactly.

EO

What does this mean for your practice generally? How has this experience driven how you now relate to the practice of comedy writing?

CY

I think it’s the best thing that could have ever happened to me, having so much structure and such a real deadline and so many resources beyond my wildest dreams. And in some ways I need to get back to what I really enjoy about writing, which is a very slow, meandering, convoluted process that I don’t really have at the show. It’s actually not about process at all there, it’s all about production. And we’re just making things all the time, nonstop.

EO

And how does that feel being an artist? To me it doesn't sound like you’re a writer. It sounds like you’re an artist, because of how you relate to craft, process, and discovery. It’s like you have the tools and the mechanical aspect of being able to produce and be a producer but now it’s time to hone your craft and make that solo magic happen.

CY

In my head, I would like to be more able to—outside of the show—just follow the process more. I have this friend Vincent who is an architect, and he is also into ceramics. He became obsessed with the revolutions of the pottery wheel. He was so obsessed with the revolutions that he wanted to take up another practice that involved revolutions, and so he started DJing. [Laughs.] And I was literally like, “Bro, that’s how I need to be. I want to be following different shapes and how things are moving naturally. I don’t really want an office or a badge to get into a corporate building. I don’t want to be getting Sweet Green for lunch.” I want to see a circle and have that take me to my next play.

EO

Any other thoughts that follow that?

CY

No. [Laughs.]

EO

That was perfect. [Laughs.]

CY

Print it!