Equipped, Part I: Comedy writer-producer Dan O'Shannon
January 5, 2022
Welcome to "Equipped," a biweekly interview series picking the brains of your favorite showrunners, show creators, EPs, and all-around legends. What makes a successful writer tick? How do they handle bad news? How have others changed their lives and how do they pay it forward? If you want to learn from the best, you’ve come to the right place.
Read on below for a glorious dive into the mind of:
Years in the Writers Guild of America, West: 30+
Show highlights: Cheers, Frasier, Jericho, Better Off Ted, Modern Family, B Positive
We’ll start easy. Do you have any favorite writing utensils?
When I started it was pencil, paper, and typewriters. But now it’s a laptop. No favorite thing, though.
You’re procrastinating on YouTube. What are you watching?
Is there a fictional character you identify with?
I’ve always related to any character that felt misunderstood. I liked Pinocchio, but didn't understand why he worked so hard to be a real boy. I mean, he had it made. Couldn't get hurt, no feelings, no aging. I'd be curious to know if you can think of any characters I remind you of.
Oh, easy; a mix of Will and Sean from Good Will Hunting. Oh! And Jim from The Office. You’ve got strong Jim vibes. Prankster with a heart of gold.
What can’t you live without? (Creatively or just as a human.)
Walking. I find that it’s too easy to sacrifice your brain to writing. You spend years living in worlds that don’t exist, interacting with people who were never born. Then one day you look out the window and you think, “There’s a whole world out there, and I haven’t been in it.” So I walk a lot. And I feel the weather. And I feel the ground and my own weight. And the temperature, and the wind — all of it. I try to be more active in a world that I’d ignored for three decades.
Welp, if that’s the only piece of this interview I post, it’ll be worth it.
Do you have a favorite writing location?
I like coffee shops or busy places. If I’m near a college, I’ll go and sit in whatever area people are working in. It’s kind of comforting to know I’m surrounded by people who also have papers due.
I love homework. I think that’s one of the reasons we get drawn into writing. What are your thoughts on outlining?
Absolutely necessary. Even if you veer from it, at least you have something to veer from.
In the last few years, I’ve started breaking my scripts in Final Draft in the script document. So my descriptions of scenes are written in action lines and then when I think of samples of dialogue, I write them in dialogue lines. That becomes a document that becomes my outline, and then I just keep fleshing out that document and it becomes a script. That switch changed my life.
What are you reading and watching right now?
Squid Game, I just finished that. And the Marvel movies. I watch all the Marvel movies because I love how interconnected they are. And I love that they will put something out there and you won’t know what it means until two movies later. I’m in awe of how they do it. I don’t know if I have the knack to do it. It’s an undeveloped muscle for me.
I’m not sure about that. I’ve been rewatching Frasier, and you’ve got the "Sliding Frasiers" episode in season eight, and Bebe’s long con reveal with Dr. Phil in season 10. A great sitcom like Frasier, Cheers, Modern Family, or any of the others you’ve worked on — they have this classic set-up/payoff that really parallels the kind of narrative you say you appreciate about Marvel. I think a good mystery or twist and a good joke are the same. You’re planting the seeds for a reveal later.
Yeah! And you’re trying to do it invisibly. That’s such a great point. Do you remember the hospital episodes with Niles in season 10?
We were working on that first episode where Niles has a toothache and the dentist tells him, "There’s nothing wrong with your tooth." So the doctor says it’s either a sinus infection, or it could be his heart. But the chances of that are one in a zillion. And then, all of these one-in-a-zillion coincidences start to happen to him and he gets more and more convinced something’s wrong with his heart. So I was getting ready for work and I was thinking about the story and I was just so frustrated because you just know it’s gonna be him getting all worked up and then it’ll be nothing. And then I thought, “Unless it’s something.” And I remember walking to my car, and I stopped and I thought, “What if he does have something wrong with his heart?” And then it’s this punch to the gut. And it means that everything was an omen. It goes back and changes the whole story.
That reveal, it’s the best, I think, for a writer. So yeah, you’ve got that Marvel magic in you, you’re just applying it to comedy.
What got you hooked on writing?
From a very young age, I wanted to write things that were funny. But it’s not like I was good at it. It wasn’t like, “Oh this is good, I want to keep doing this.” A lot of the stuff I wrote was really bad, but I kept aiming to do something that looked like a professional did it.
I think I got hooked around the time I started doing stand-up. I was learning how to make a group of people who didn’t know me laugh out loud. That’s also when I started to veer from “I want to make people laugh” to “I want to make them laugh and cry. I want to make them laugh and feel suspense. I want them to laugh and feel triumph.” And you start mixing all these other things in.
Do you have any advice for up-and-coming writers?
One thing I often find myself teaching young writers is that if they’re stuck on a joke, and they can’t think of a good punchline, they can change the set-up. Every piece of the script is in play until it’s done. Take something from five pages ago and put it into your scene. Scavenge your scenes for parts you can use.
What’s something you know now that you wish you knew when you were joining your first room?
I really had to sink or swim. There are so many things you can do to sabotage yourself in that room. I made all the mistakes people make: I fought for things — which you don’t do if you’re a staff writer. You know, things were getting cut that I was sure were absolutely necessary. And over time you learn, of course, those things weren’t necessary.
I think there were times early on when I was trying to be funnier than I was in the room to prove myself. I got funnier in the room as I got older, but I remember an older writer on my first job taking me out into the hallway and saying, “In your career, you’re gonna find in every writers room there’s kind of a room clown. Someone that makes everyone laugh. …You’re not that guy.” I was super embarrassed. It was horrible, but helpful. Now, half the time I am the room clown, but I wasn’t then, at the age of 23.
So you got into writers rooms at a really young age.
Yeah, I’ve been incredibly lucky.
I’ve heard you talk about luck a bit before. You’ve said a writer’s career is made up of four things: luck, ambition, talent, and politics. I feel like when we try to ignore the element of luck that comes into play, it can be really disorientating, because you think you have more control than you do. You can’t control luck.
Right. You have to let go of luck.
Be prepared, but let go.
Exactly. And giving luck its due doesn’t mean you’re not talented either; it doesn’t mean you didn’t do the work, and it doesn’t mean you don’t have a way with people. All of those things can be true. But they can also be true of someone who just doesn’t have the luck.
If you don’t acknowledge luck, then you either fall into the habit of blaming others or yourself when things don’t go right. And sometimes it’s not that simple. It’s a lot of hubris to assume there’s no luck, and that you have that much control, or that everyone else is the devil because you didn’t make it.
What’s your go-to to-do if you get bad news?
Oh, self-pity is my go-to.
What’s your way out of it?
Trying to keep things in perspective. It’s also a function of being older. You go through it so many times, you learn you’re gonna be okay.
Is there a person or experience that’s been pivotal in your journey from when you were an amateur to becoming a professional writer? Or is it that guy who told you you’re not the clown in the room?
It actually was him! He was the one who got me my first job. And there were people along the way who moved me up a notch, who taught me or said the right thing and zhhmmm! I now had this skill, or they’d help me see things I didn’t see before. I have a bunch of those. But early on, my very, very first person that helped me out when I came to Hollywood was a comedienne named Karen Haber. We got to be friends, and she introduced me to an actual real, live TV writer whose name was Marc Sotkin. And through her, he told me how you write a spec script. I’d never even heard the term before. He was nice enough to read my first spec script and give me notes. I rewrote it. I wrote another one. And he showed somebody who gave me my very first job. So those two human beings were the ones I ran into at exactly the right time in my life, and they gave me the exact right pieces of information to move me up to the first notch of writing. And then from there other people just kept moving me up notches, it feels like.
Is there a writer you’ve never met, but who you admire?
I was lucky enough to work with people who really influenced me. When I got to Cheers, I was working with a room full of people who had written for The Mary Tyler Moore Show and M*A*S*H and all these other shows. And then I was in their ranks. I couldn’t believe it. I’ve also gotten to meet a lot of heroes of mine, like Carl Reiner and Mel Brooks.
But if I could, I would go back and meet the people who were writing the old radio comedies. The Jack Benny show. Robert Benchley, James Thurber, Fred Allen.
What are your thoughts on how content has changed over the years?
I was writing at a time when Cheers was a big show. And if you look at it now, it’s a bit tricky. The lead character was an unapologetic womanizer and all of his buddies celebrated him for it. As an adult now, I can’t write that. It wouldn’t feel right to me. It wouldn’t feel ethical to write that kind of character and make him a hero now.
Young writers today may look back and have a problem with what I was writing and they ask me if I regret it, and I tell them that is where we were. I don’t say that to excuse the past, but rather to acknowledge it, so we can learn from it.
I tell them, “Learn from these things; take what you can and use it to create your content. And years from now, after you’ve won your awards and had a terrific career, there’s going to be a group of people that come to you and say, “We can’t watch your stuff.” And you’ll ask, “Why?” And they’ll say, “Because there’s that scene that happens at a barbecue.” Or, “There’s that scene where someone’s eating a chicken leg, and we don’t do that now. We don’t kill living animals for food.” And you’ll be in a position to say exactly what I’m saying: that is who we were then.
Instead of trying to erase the past, we can use these things in the past as benchmarks to measure how far we’ve come. Because everything we ever write and put out is a report that we’re sending to the future saying “this is who we were.” And those people in the future will have to make the same choices you are about looking at the past. Can we take these lessons and make something better? I hope that’s the choice they make.
I love that breakdown of the past and present. It turns our engagement with complicated or problematic material from reactive to active.
I know you're teaching classes now and mentoring writers, too. What does paying it forward look like to you?
For many years, the system was rigged in my favor in a way I did not understand, or appreciate, or care to look at, perhaps. Whenever I was passed over for a job or I was fired, I had the luxury of assuming it was because I sucked, and never had to wonder if it was because of my color or my gender. And now I understand that by not ever wondering that, I was the beneficiary of a rigged system.
I can’t go back and change that, but what I can do is take the information I acquired over 35 years, and I can now teach to diverse classes and to people who have very different experiences than myself, and pass down what I’ve learned and perhaps they can take that and combine it with who they are and their experiences and create something richer and something that’s more evolved than what I was able to do.
I love talking to you, Dan. This is a master class on philosophy via screenwriting. Thank you so much!
Written by: Liz ThompsonLiz Thompson is a screenwriter and freelance development consultant. She has one show currently in development, is featured on The BitchList 2020, and won the 2019 Tracking Board Launch Pad Julian Silver mentorship. In between outlining and pitching she runs The Writer’s ARC group on Facebook, and can be found on Twitter at @howtoliz.