Interview: Award-Winning Comedy Writer Kyle Dunnigan of "Inside Amy Schumer"

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Photo Credit - Jenna Szabo (4)

Emmy award–winning comedy writer Kyle Dunnigan is a writer/producer on “Inside Amy Schumer” who’s also written for FOX’s “Cedric the Entertainer Presents,” Comedy Central, MTV, and more. In addition, as an actor and standup comedian, he’s made appearances on “Reno 911!” “Conan,” “Jimmy Kimmel Live!” “Late Night with Seth Myers,” and in 2015’s major motion picture Trainwreck, to name a few. A well-versed member of the sketch writing and comedy scene, Kyle sat down with Writer’s Digest to discuss his writing process, what’s he’s learned from the biz, and his tips for aspiring comedy writers.

  • Do you have a daily writing routine? What does that look like?
    When I’m working on something, I have a weird—well, not really weird [thing I do]: I usually go to Starbucks. I know it’s cliche to go to Starbucks, but it forces me to write. I get there, and there’s no television, it’s not comfortable; the seats there are not comfortable so I just go, well, I guess I’ll start writing. I see it as my office. When I’m really working on finishing something, that’s where I go. When I do write at home, I’m so lounged out­—like flat on my back with like a pillow on my stomach, the laptop on my pillow—[and] there’s a lack of focus there. But, I do love that too; that lounge writing time.
  • What kind of prep time does an hour of stand-up require?
    I do little pieces at a time, although I actually was just thinking of changing that. I really haven’t focused on my stand-up too much at this point; I did when I first started, but [now] I really enjoy writing sketch or story more. It’s something like, when I’m about to go up on stage [to do stand-up], I’m like, oh god,why didn’t I write something? I want to write, I just forget until I’m about to go on stage that I wish I wrote something.
  • What is writing sketches like? Is it a pretty collaborative process?
    [For “Inside Amy Schumer”] you come in with a idea on Monday, and you’ll have like 5 different basic ideas, like, I have an idea about a guy who’s obsessed with, I don’t know, Minecraft, and his girlfriend hates it. Something very big. Then Amy [Schumer] and the head writer will hear all the pitches and say, OK, write up the Minecraft one and the one about the talking hair dryer, or whatever. And then you go home, and you write alone; you write the whole thing yourself. Then they read [it] and give you notes and you do a second pass at it and then, after that, everybody punches everybody’s up. So it becomes very collaborative after the second draft. That’s how they do [at Amy’s show.]
  • Is that true of other shows too?
    It depends on the show. I think every show is different.
  • As far as performance, do you play a role in how a sketch is executed?
    No, not at all. Like for me, I do do some stuff: like I did a sketch with Amy this year, an HSN kind of thing, and I painted my face orange and no one told me to do that. And you can kind of improvise lines. But if I wrote a sketch, I’m not involved in like, directing it or anything.
  • Is there any time a joke works on paper, but falls flat in front of an audience? Or vice versa?
    Oh yeah, it happens more often than not. I just finished shooting a pilot I wrote, and [in it] things would read funny, [but] then it would come out of the actor’s mouth and I’m like, that’s boring. That would happen a few times, where it would read funny and then, that. In making comedy, you really have to be willing to throw out your whole script when you start shooting, and just find things that come out of the actor’s mouths funny, because it just happens. Maybe you can write something really great the first time, but I find I have to do a lot of reworking.
  • Is there a certain sort of “anatomy of a joke” that you’ve found to work?
    I think surprise is important—and that entails avoiding anything that’s hack-y or been done before. It’s just kind of deadly if the audience has heard the same kind of joke before, or done a certain way. Surprise is a big part of it. So much of stand-up [is like that], people don’t want to hear you do your joke again, because the surprise is gone. You can sing a hit song over and over again, and people will be screaming if you don’t sing it, and you can sing it for like 30 years, but your hit joke, [people] hear it more than one time and they’re like, OK, we’re good.There are other elements, but surprise is the big thing in comedy. I mean just like someone tripping; it’s simple, but you didn’t think they were going to trip, and so it’s funny.
  • Where do you get your ideas for your sketches or jokes?
    Most of the time it just sort of hits me. There’s some things I take from real life, but most of the time I just try to drum something up. Which is [usually] drumming up something that happened to me that I kind of forgot about, or that I saw, that sort of didn’t really register [at the time] or I didn’t consciously remember. More so things that happened to me personally rather than like current events or anything.
  • You did some work on Trainwreck. How does the screenwriting process differ from sketch or stand-up?
    I did. I didn’t write write it, but I was around when it was being written and stuff. The way they did it was really great: They’d write it and then rewrite it and then there were table reads in front of a lot of people, so it was this process of constant feedback and taking notes from people, [all] while it was being written and shot. And while it was being shot, there was a lot of improv. It seemed like a good system and I kind of stole from it [method-wise].
  • I see you have a more formal theater training from the University of Connecticut.
    [Laughs.] I was terrible—I don’t know why they accepted me. It was all this Shakespeare, and Russian, and Shakespeare just…doesn’t come out of my mouth right. I did better at my math class [there] than my acting classes.
  • It seems like a lot of comedians or sketch writers generally studied English or something along those lines. Do you feel like your different background informs what you do in any way?
    Yeah…not really. I felt like in high school I got some attention from doing the plays there, so I wanted to continue that in college. But it just wasn’t there for me. I started to feel lost. Then I kind of figured out, I think I’m more of a comedy person, not a serious Shakespeare person. And I started to do stand-up after that.
  • What’s the biggest lesson you’ve learned from the business, as far as writing goes?
    I think, and this is something that took me so long to learn, [because] no one ever told me: You have to know what you’re selling. I’m not saying sell out and do something just to make a lot of money—you can do something that is sort of artsy, but you have to realize, you’re not going to get very rich. You’re not going to get hired for bigger, mainstream jobs. If it happens [that you do something more mainstream because] you’re not that wealthy, you shouldn’t feel shame or bad for what you were selling. These are business places that have to make money, and if you’re not selling a mainstream thing, these people are going to get fired if they give you money to make something that won’t make money. So they can’t give you money. I don’t know, I just never really thought about what I was selling [before], and I’m just starting to. I kept kind of changing and moving around with the wind and people telling me to do this or that, and I was like, OK, I never really thought about what I want to sell or project, what my value is that I have to bring. I kind of wish someone told me that earlier.
  • What do you have coming up next?
    I’m editing this pilot right now. I was given money to make two short sketches, and I ended making that a whole pilot, because I just felt like it. I got in way over my head, had no idea what it would cost, and actually ended up losing money, but I learned a lot, which is cool. So I’m editing that now. It’s for this app called Go90; I’ll own [the pilot] after awhile so I might try to make it into a TV show. But the thing is, it was not a good financial move, I did not think it through: I could have pocketed all this money and [just] done the sketches, but I’m glad I didn’t. If nothing else, I learned how to make a pilot, so.
  • Any tips for aspiring comedy or sketch writers?
    I think it’s to find a way to do it where it’s not a chore. Whatever you do, if you can get it to be a habit, that’s what you need for success. Because cranking it out [regularly] is really important. Find a way to make it like a therapy—therapy to write, therapy to get on stage—otherwise it’s a long road if you don’t [feel that way.] Writing can be annoying! But so can brushing your teeth. But after awhile, [it ’s a habit] and you just brush your teeth; you just do it. Make writing like that. I mean, I don’t brush my teeth, but some people do.
  • For more tips on comedy writing, check out Comedy Writing Secrets 3rd Edition: The Best-Selling Guide to Writing Funny and Getting Paid for It, on sale now at the WD Shop.
  • Baihley Grandison is the assistant editor of Writer's Digest and a freelance writer. Follow her on Twitter @baihleyg, where she mostly tweets about writing (Team Oxford Comma!), food (HUMMUS FOR PRESIDENT, PEOPLE), and Random Conversations With Her Mother.
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