Demetri Martin on Making a Dramedy and Learning to Not Be a Jerk When Collaborating

As a stand-up, Demetri Martin isn’t usually thought of as an emotional truth-teller. Best known for his short-lived Comedy Central show, Important Things (2009–10), in which the comic would both complicate and simplify subjects like “ability� and “power� through clever wordplay, sketches, and line drawings, Martin’s humor usually relies on intellect and a detachment from the personal. Yet in Dean, pulling triple duty as the screenwriter, director, and star (quadruple duty, if you include the heavy use of his illustrations throughout), Martin drops his aloof stand-up persona for a funny and sweetly sad story about life after loss. The film, which premiered April 16 at the Tribeca Film Festival, fits into the same universe of stand-up-created dramedies like Louie, Master of None, and One Mississippi. Vulture spoke to Martin about his transition to filmmaker and how creating Important Things taught him to be a more empathetic boss and collaborator. 

There seems to be a lot of dramedies with stand-up comedians these days. Louis C.K., Aziz Ansari, Tig Notaro, and now you. Why do you think that is?
I can spitball a theory here, but knowing everyone, maybe part of it is that in today’s comedy world — men and women — guys like Louis, are willing to get up on stage and really bleed in front of the audience, right?

Right.
Audiences really respond to it. There’s so much content, and people are so savvy, maybe they’re hungry for something more sincere. It’s almost as if the audience is saying, “I’m going to give you my attention for this amount of time, and I’m going to need you to give a part of yourself in exchange, and if you do, I’ll come back.�

I’m not snarky. I can’t pull it off that well. I’m always a little bit more earnest, which you can get in trouble for — you can be cheesy, a dork. But it’s still a risk I feel comfortable taking.

It’s surprising for you to make a dramedy, however, considering your stand-up is much more aloof, more cerebral. Like with Louis C.K., there’s a history of him doing really personal material with his stand-up, but that’s not necessarily true with you.
You’re absolutely right. I’ve had conversations about this with my wife and friends who are comics over the last couple of years. In 2002, I wrote my first one-man show, and I went to the Edinburgh Fringe Festival. I went again in 2004, ’05 and ’06. And I also went to the Melbourne Festival in Australia, doing one-man shows that were narrative, personal, talked about failed relationships. It was totally different than what people in the States saw with my stand-up. And I had success, I won a prize and everything, but when I was done doing the shows, people would be like, “Hey, you could tour that around the States — do a little theater tour.� And I was like, “I’m sick of my story and I’m sick of myself.�

I admire the people who can do it. However, jokes are like a parachute for me, where I can share my ideas with an audience: Do we agree that these ideas are jokes? Are they funny? Rather than I like this girl, and I farted. So now, aesthetically, I’m edging my way there, but in the foreseeable future I can’t see myself getting there, like a guy like Louis. But film was a very exciting opportunity to try that in a different way. That’s really a lot of what drew me to it.

Would you say that Louis influenced you, or is it more based on your experiences with doing one-man shows?
This is probably more based on my experience with one-man shows, but also watching Woody Allen and how he developed his voice in films. I saw his films as a kid, but I never knew he was a stand-up until a friend gave me a cassette when I was 25. Then I got Without Feathers and Side Effects, his short-fiction collections, and it was really interesting to hear the jokes nested in those stories. Then you watch his early movies that are kind of like collections of jokes. Then you get to Crimes and Misdemeanors and it’s like, “Wow, these are like philosophical essays.�

Say what you will about Woody Allen — I know a lot of people have problems with his personal life — but if you’re trying to learn how to tell certain kinds of stories, he’s a hell of an example of someone who has tried different things and really evolved. It gives a stand-up like me some kind of hope or some kind of license, like, Hey, you can try stuff like that. It’s not going to be easy, but someone has done it really well. Good luck!

Stand-up is a solo endeavor; do you like collaborating, or do you prefer being by yourself?
Oh, I love collaborating. Being by yourself has certain luxuries for sure, because you can change directions so quickly, and in a live situation I can bail on a joke, I can do crowd work, I can protect myself. Also, I’m not letting anybody else down. Everybody is going to be okay if I have a shitty show. As soon as you get collaborators, the downside is you don’t want to let people down. I want them to be happy with me, I want them to be proud of the work they did with me, and I want them to feel validated that creatively their talents are being used. 

What did you learn from Important Things With Demetri Martin?
I almost have like PTSD from that show, but I’m glad I did it, for sure. I tried so hard to put as much as I could on the screen for the 20 minutes that I had every episode, but probably the best thing I learned about that is you have to pay attention to the work experience for everyone. I was respectful and grateful to have everyone there, but it still felt like the end of the world in a way: I got to get this to work. There were times when I basically drove myself over a cliff, and I took everyone with me. Not in terms of, “It has to be perfect!� but, “Can we please take another take?� No one is going to say no, but if you pay attention, and look at their body language, they’re saying, “Hey, you know, I’m tired,� or, “I have a wife and I would like to get out of here early. I think you have what you need.� And it hindsight, that’s my real takeaway.

Did you realize as you were shooting the show, Oh, wait, maybe I’m being a bit of a jerk in this moment?
No, I didn’t realize. I felt like I was trying to survive. Like, What’s going to happen? The show’s not going to work; we’re not going to get it. In my defense, we didn’t have a ton of money or time. It wasn’t like I was being indulgent. It was all fear. I might also be misrepresenting myself. This is mostly first season. Second season wasn’t as bad and a lot of people did work on the show again. So it wasn’t like a lot of people walked away, “Ugh, never doing that again.� I might have been the one who realized that wasn’t sustainable.

When you were doing the movie this time around you were more conscious of that?
I was. It was still hard for things that were not in my control. What was in my control, and I didn’t realize, was that if you write a lot of locations you’re going to have company moves during your shoot day. And you have the same amount of time whether you shoot in one room one day or three locations around town. You have to add driving time, park the trucks, load the cameras. So now I know. I can think like a producer. That’s why so many indies are four people in a farmhouse.

Do you think you have another movie in you for the future?
Yes. I wrote two scripts before this one actually, but they’re more like concept-y comedies, and I realized quickly that as a first-time filmmaker I’m not going to get the money to make these. And, even if I did, I don’t know if I can pull it off. This was like a half-written script, but I went back to it because my wife said, “You should try to do that one, because you’ve experienced some of that stuff. And you can do that one and it takes place in the real world: No magic, no other planet.� So now the question to myself is do I try to go for the big concept-y thing or do I try to do a bigger one of these? Because I did like the way this one played, and it’s not like there were any robots or any kind of weird devices. It’s just people trying to be okay.

This interview was edited and condensed.