It gets annoying, doesn’t it? All the experts–and yeah, me too–telling you how to write dialogue? As if it were actually possible that I could teach you how to be funny

Between Columbia College and Chicago Filmmakers I’ve had maybe a thousand students in the last decade. Yet the question remains…can I actually teach you how to write dialogue?

Here in Chicago, Second City has built an empire. I don’t think they would answer this question of teaching comedy writing with any sort of general yes or no. It would be more complex in terms of them providing you with tools to bring out your natural gifts, or in educating you in terms of those who came before you, improvisation exercises, etc. It’s arts and craft, or more specifically, the craft of the art.

One of the exercises I use is to have students transcribe some conversation they heard that week into screenplay dialogue format. Take it from the air, lay it out on the page. When you look it over you see that it doesn’t play out in straight noun-verb, perfect grammatical sentences. Far from it….

It’s the hearing of dialogue that’s the key. You want to write better dialogue? Use your ears. Yeah, it’ll be painful to listen—to really listen—to your fellow man, but it’s the only way to sus out true to life dialogue. What’s so great about true to life? Because something gleaned from a real world source always plays out less artificially, at least it seems to me.

Let’s look at some of these conversations submitted to me by students through the years….I’ll lay them out on the page without consideration for screenplay format:


Setting: A restaurant, table for two, man and a woman eating.

WOMAN: What are you thinking about?

MAN: You, us.

WOMAN: Doing what?

MAN: Oh, we’re happy.

WOMAN: We’re always happy.

MAN: I know.


MAN: How’s your food?

WOMAN: Oh, it’s good.

MAN: Yeah?

WOMAN: Mhmmm.

MAN: I’ll have to order that sometime.

WOMAN: Yeah, you should.

THE TAKEAWAY: Great subtext. Think about how many ways the actors could play this dialogue…. Anywhere from the way it plays out superficially, these being two people, bland but happy enough…all the way to these two utterly hating each other. Lesson? Subtext = say it without saying it.


Setting: A party,  two kids locked in a debate about the 51st State. Saturday around 11 and they are not drunk.

VINCE: I fucking hate Canada.

DANNY: Yeah, it’s like the 51st state.

VINCE: No dumbass, the 51st state is Hawaii.

Danny pauses for a few seconds.

DANNY: Are you sure? What about Puerto Rico?

VINCE: Puerto Rico is not a state.

DANNY: Yeah, I guess. It’s a race like the Jews…they don’t have a country.

VINCE: You’re the one in college, you should know that.

DANNY: You’re right. Hawaii is the 51st state.

**THE TAKEAWAY: Stupid is funny? Columbia needs to up those eligibility requirements?


MAN 1: Yo, listen to this shit, yo. You heard about that shit roofies, right? The date rape drug.

MAN 2: Oh, I didn’t know about that shit.

MAN 1: A’ight…peep this right…this kid, I was chillin’ with him and shit, right…he was telling me—

MAN 2: Wait, roofies are for what?

MAN 1: A date rape drug. Makes you like…pass out, unconscious. Check this right, tell me this shit ain’t ill. Shit just freaked me out. This guy met a girl down the club. She was like, ‘wanna go back to my place?’ He woke up in a bathtub full of ice, gets us…his whole side is stitched up. He freaks out and goes to the hospital and they x-ray him. They stole his kidney!!!”

TAKEAWAY: Sounds like a well-known urban legend the student grabbed off the internet. Listen to the passage though. Speak it out and you’ll hear this pop with a couple choice words, the repetition and tone. It’s got interruption, some black humor…it’s funny, long as it’s not my kidney they removed!


Setting: An elevator. Older Man in a business suit, joined by a middle-aged Woman, waiting for the elevator doors to close.

WOMAN: Hi, Norman.

MAN: Hello, Denise.

The door begin to close. A girl sprints toward the elevator, reaching her hand through to stop them from closing.

WOMAN: We’re not going to play the save-late-people-from-waiting-for-the-elevator game, are we?

Girl enters the elevator, awkwardly squeezing by the Woman.

WOMAN: How’ve you been, Norman?

MAN: Fine. Tired.

WOMAN: I know, me too. I’m so done with this. Honestly, Norman, I can’t even handle the sound of my own voice any more. I hear myself rambling at the podium about the dumbest shit. And I’m thinking: ‘Is this what it’s come to?’

MAN: Mhmmm.

WOMAN: Christ Norman, I feel like a puppet, don’t you? What are we but giant puppets getting paid to spout off the most useless information? Don’t you feel like a puppet, Norman?

MAN: Mhmmm.

WOMAN: Do you ever think about giving it all up? I’m thinking about it. I’m serious about it this time. Do you ever think about it?

MAN: Uhmm….

WOMAN: You should. You really should.

MAN: Ok.

WOMAN: It was good talking to you, I have to get off. I’m late for class again and the TA never unlocks the door.

MAN: What are you teaching?

WOMAN: Children, Family, and the Community

MAN: Ah….

TAKEAWAY: “So good talking to you again!” The gag—which the audience gets— is it’s a monologue punctuated only by his grunts. The confined space helps, his pain in being trapped with this bore of a woman. You see this essential exchange in lots of TV and movies. Laughter in the selfishness of her POV, in his pain at having to deal with her. Pity the kids of that class!

Here’s another extended monologue, masquerading as conversation….


Setting: A construction site. Two guys talking, a piece of blue plastic between them and the listener.

GUY 1: Motherfuckers lie all the time.

GUY 2:  Who?

GUY 1: Babies. You think they don’t know how to talk? If they can make those sounds, you know, baby sounds….it’s ‘cause they know how to talk.  If one day I have a son and I talk to him he’ll have to answer no matter how young he is. If he comes to me with this ‘daddy, mammy’ shit he’ll have it for sure.

GUY 2: Mine too.

GUY 1: Don’t you think?  Babies know how to talk, they just like to fuck with us because they think that because they’re small we won’t do anything about it. Fuck them! If they don’t answer me they’re gonna get it for sure. Another thing is this shit with the moon. It’s all bullshit. What’s that guy’s name…Reagan? All bullshit that guy Reagan told us. The man never went to the moon! Can’t fool me. Uhuh, not me.

TAKEAWAY: Some very disturbed people walking around the Loop! Sure, I can point to this “extended monologue”/rant model and recommend you fill it with your own content or POV. You can clearly see and hear the model but ultimately it’s you alone who have to sit down in front of the typer and execute that sound. Not easy. That’s why it’s called craft and why many say it takes not classes or well meaning advice but years of pounding away at the writing to really make a difference.

I’ll throw some more examples by you next week….

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