Illustration by Katie Jeanette Wittenberg.

It’s 9:15 p.m. on a Sunday, and I’m in a sparsely populated bar on iO Theater’s second level. At a high-top table by the window I study a lengthy list of questions I prepared for Damon Royster, comedy writer, performer, and teacher. I love comedy. I want to get it right.

I took Royster’s Level A (out of a possible E) improv class at Second City. Watching him conduct the class was itself a crash course in comedy: Everything about him, from the things he said to the body language he used, was funny. It was the first time I’d seen a comedian up close, the first time I could see the gap between your average funny person and a person for whom comedy is livelihood.

He’s got convictions. In class, and during the interview, he was unafraid to criticize shows and fellow performers. All practitioners have field-specific preferences, but Royster seemed especially willing to share his. To me that meant an opportunity to ask the questions I’ve always wanted to ask practicing comedians.

Royster performs all over the Chicago North Side. He can be seen playing with the iO Harold Team Comet, his indie team Regular Girl, The Bar at CIC Theater, and the LGBT improv team Baby Wine at the Annoyance. He was a recipient of the 2017 Bob Curry Fellowship at The Second City. He also teaches beginner improv and writing at The Second City, as well as improv at the iO Theater. Writing credits include: “Love, Factually,” a Christmas parody at the Kennedy Center in Washington, D.C.

Do you do comedy full-time?

No. It’s getting close. I have a part-time legal assistant job at a law firm. It’s about 30 hours a week. It’s not super fun. But, I had a corporate job last year, from which I was fired … unfairly. I like this job better. I like being in an office where someone can just yell out Fuck! real loud. Because it’s not corporate, we can all speak more freely, instead of the fake chipperness at a corporate job. It’s harder to be real in a corporate environment. Also, at that corporate job, I didn’t tell them I did comedy. I worked there for three years, and they slowly figured it out. I was so quiet that people just started asking, “So what do you do?” Sometimes I’d take off for an audition or something and I’d have to tell them. They were just floored.

Is the structure of your life representative of other performers and teachers at Second City?

Yeah, we pretty much all have a day gig. The dream is this, to have a part-time job, and then do comedy at night, because a full-time job plus comedy will kill you. I don’t know how I survived 2017. Did not sleep much, but I did a lot. Most, if not all of us, have jobs, but it’s a lot of baristas, nannies, bartenders, waiters.

At what point can people start paying their bills purely with comedy?

Sadly, I don’t think they can in Chicago.

Not even the Mainstage people?

With that, the pay you get is good, but it’s not forever. You’ve gotta remember that those performers are always being evaluated to see if they’re needed for the next Mainstage show. So there’s always the feeling that it’s a temporary thing, not something you can rely on. There’s a lot of turnover. Each show is only a year-long commitment, and then they start writing the next one. But the Mainstage is the paying gig, so once you get that you can start auditioning for commercials and setting up meetings in L.A. and New York for when you move.

What’s your ideal next step? Saturday Night Live?

I would love to write for “SNL.” I definitely don’t want to be in the cast. I’m a very controlling person. My first few improv classes I was very much controlling the scenes, trying to take them in the direction I thought they should go. In writing you just naturally do that. I’m learning to collaborate more and say “yes” to other people which was not easy for me. I’m learning to let go of control a little bit.

Are you more critical than your peers?

Yes. Easily. I don’t think I’m the most, but I’m definitely one of the most critical. It’s kind of pompous of me, admittedly. But one reason I wanted to get into teaching is that I was tired of seeing people get up onstage, in improv especially, just throwing spaghetti against the wall, hoping it made art. I think that by putting myself in a classroom setting, and giving guidance, even the tiniest bit might help turn the tide. Especially with choices I used to think were right but I now know aren’t.

What separates a good choice from a bad choice?

There’s the basic stuff like not saying no — not denying your partner. I just gave notes on this. The scene was very weird, two people were talking in the shower in a gym, then two more people came in and said, “It’s time for our two o’clock meeting in the shower!” and the other two said, “We don’t do that here, you’re in the wrong place.” That completely shut down the scene. The audience got so quiet. They didn’t know what to believe. It’s all made-up, so when you deny anybody, it makes the audience question what you’re doing. So obviously don’t deny stuff. Also, if you choose to do a more grounded, realistic scene, you’re never gonna hear an audience member say, “Man, I wish they were pirates,” or, “I wish they had been in space.” To that point, if you play a pirate, or a spaceman, no one’s ever gonna say, “Man, do you remember that complicated plot they had? I remember every detail!” They’re gonna remember how you played your pirate, what the relationship was. Or a single funny thing. They remember that more than crazy, extraneous details in the scene.

Has your taste changed over the years?

No. That’s a cool thing I learned from a writing teacher here named Michael McCarthy. He’s written for “Sesame Street,” “SNL,” “Mike and Molly.” He used to tell his students, “You just have to wait for your talent to catch up with your taste.” Because your taste is always right. The stuff you like is always the correct thing that you like, but you need to wait a minute for your abilities to get up to the high standards you set for yourself. That’s a hard thing to say to a class, because it sounds like you’re saying, “You’re not talented.” I would never say that to a Level A class, but I think about it when I see people who are frustrated. You just need to wait for your abilities to get to where your head’s at.

Do you get impatient thinking about career objectives?

I do. I do a lot. Especially recently, I’m seeing a lot of people garner success. There’s one guy I did two sketch shows with at Second City, and he’s now written for “Big Mouth,” “American Vandal,” and he recently got hired as a correspondent for “The Daily Show.” His name is Jaboukie Young-White. He’s great, but he’s also 23, and I’m like, “Oh no, I’m 30, what am I doing?” So that can be frustrating. I wish him luck, because he’s very talented. He deserves everything he has. I try to remind myself of the rule of keeping your eyes on your own paper. Remembering that other people’s success is not my failure. That’s something I have to remind myself at least once a year — well, once a month.

Do you feel pressure to make your comedy political?

No. A lot people, especially a lot of young people, think they need to infuse their comedy with their stance on the world. That’s not my feeling.

Do you think you’re in the minority, having that opinion?

I think I am. Especially the times we’re in now — in the Bush era, I probably would want to do more political comedy. That was poking fun at something that was still trying to be serious. Everything we’re in right now is a total joke. In a recent “SNL,” the cold open was Kanye West in the White House with Donald Trump. But that’s what actually happened. In the Bush era, that would be a fun joke, like, “Oh, what rapper would show up in President Bush’s office? Let’s watch!” I think for this moment in time now, I don’t feel the need to go political. As for social commentary, I’m a gay man, and I do talk a lot in my writing about that, and about how the world feels about the gay community.

What about political correctness? Do you think excessive focus on political correctness blunts comedy?

I think it does a little bit. I do think we are a little too careful with each other. I do miss that era where … there was a “Chappelle Show” sketch where there’s a white family with the n-word last name, and he just did it, but it’s weird because that stuff leads to Trump voters feeling like they can say whatever they want, which leads to Charlottesville. It’s hard. I don’t like how careful we are, but I do think because we weren’t careful in the mid-2000s, people think they can say whatever they want now. Political correctness limits what people who aren’t a part of that particular group can talk about, so I think the solution is to hire more diverse voices. I would be more comfortable if there were more black writers writing about black stuff, or more gay/queer people writing about queer stuff. That’s what we need to help fix it. I love Matt Parker and Trey Stone, but they’re still two white men, tackling all these issues. I think it’s still two of them, plus Bill Hader sometimes. It’s about bringing in the right writers.

In Chicago, do you feel that comedy is a haven for diversity?

No, it’s weird thing I’ve been dealing with. There is a growing pocket of POCs, and they are very vocal about getting their voices heard onstage. I am still performing with majority white people. Sometimes I feel — do you know the term “Uncle Tom?” Sometimes I wonder if I’m seen that way. I know I’m not that, but I worry other people will see me that way. I grew up in an area that was predominantly white, in the Chicago suburbs, and I genuinely find what might be considered “white humor” funny. “Mystery Science Theater 3000,” not a lot of black guys watch that show. Black nerds, yes. It’s fun for me, because I can go back and forth. I love “The Boondocks,” which was a very black show, and I get that humor, but I can also understand “Friends” and “Seinfeld” being funny as well. For me it’s fun, I get to laugh at everything. Sometimes I think POCs feel like they have to like only one type of thing, to make sure their point is heard. I would love if everyone would just come together a little bit more. In the end, funny is funny. I think I can be funny to a variety of people, and I don’t really do — especially in my improv — anything specific to my race or my orientation. I try to do something human. Whenever I perform, I try to make sure I’m doing something that’s relatable to everyone.