Writing Jokes with Ilana Gordon (Second City, iO Chicago)

It’s more important to fart out a terrible first draft than it is to sit on a good idea forever.

[@IlanaAbby on Twitter]
‘ We’re not adults, we’re just old babies.’

When did you realize you wanted to be a comedian?

Growing up, I did a lot of musical theater, which I was fundamentally not good at. But I took this one acting class where we would do these improv exercises that I really enjoyed and felt really comfortable doing, so I thought there might be money in that. I was wrong.

What did your parents do for a living when you were a kid?

My dad was a computer programmer for an insurance company and my mom’s career evolved as I got older. She’s a cellist, so she did a lot of performance stuff when I was young, then she became a music teacher and now she’s a school psychologist.

What kinds of tools did you pick up studying screenwriting as an undergrad?

I came into college very green, so learning things like formatting and narrative structure were huge for me. But I think the biggest tool I picked up in college was discipline. I love to procrastinate and I’m also a huge perfectionist, so my first inclination is to put off writing something until I can write it perfectly. School taught me that it’s more important to fart out a terrible first draft than it is to sit on a good idea forever.

What do you enjoy most about humorous fiction?

The great thing about writing for the Internet is that now some of these platforms have such big audiences that you know people are going to see your work. And that’s a nice perk — especially when you’re used to working in live comedy.

In terms of the work itself, I love the challenge of taking something in the news and figuring out my take on it. Plus, I love how short the pieces are. I feel I do my best work between 350 and 472 words. Anything over 473 and it’s all garbage.

How did you first get involved with iO Chicago?

I spent my last semester in college studying comedy at The Second City and I fell in love with Chicago. I ended up staying after my program ended and taking classes at iO. I got placed on a team in 2011 and I started coaching teams two years later.

Sweet! Which teams have you coached?

I’ve coached four Harold teams at iO (Attica, JTD, Blood! and Cecilia). It’s one of my favorite things I get to do.

A harmless game of telephone goes terribly awry.

How does sketch-writing compare with writing for your own stand-up?

I like sketch writing because for a long time, I was scared to write or say the things I actually felt or believed. And with sketch, you can kind of filter your thoughts and ideas through the eyes of your characters, which makes it feel safer.

With stand up, everything I say has to be rooted in something I actually feel or believe, otherwise I feel weird talking about it. So in some ways, I’m finding writing for stand up easier, because it’s just me talking about the things that make me laugh.

Why do you think comedy works well in Chicago? Especially improv?

I think Chicago gives comics a lot of freedom to fail — there’s not a huge industry presence here, so people are able to focus more on doing the work and taking cool risks than on building their personal brands. Also, there’s an incredible sense of community here that I haven’t seen anywhere else.

Why do you think comedians become comedians?

Because the world doesn’t need any more happy, well-adjusted dental hygienists.

What makes a joke funny?

A smart, fast set-up and a punchline that takes you by surprise. Also, ham-fisted references to Arby’s (this portion of my thoughts brought to you by Arby’s).


Ilana’s work has appeared on Mashable, The Huffington Post, Reductress and The Second City Network. She coachs and performs improv at iO Chicago and does standup around the city.


For more on humor, follow @jokewriting on Twitter.

Interview by Zuri Irvin (@withzuri)