MM: There are a lot of great cameos from these smaller comedians like H. Jon Benjamin and Kate Berlant in Dean. Do you want talk about casting your fellow contemporaries in the comedy world?
DM: I got great advice from Alexander Payne before I started shooting. I know him a little bit. We’re both Greek. There are like 10 people of Greek descent in Hollywood, basically, and he’s one of them, so I’ve got to know him. He said to me, “I spend a lot of time on casting.It’s just so important. Because of that, I’ve had really good experiences with my actors. But I put a lot of time up front to make sure I get people I want to work with.” So while I didn’t have the kind of time a guy like that does, I tried my hardest to get as much time as I could on the front end of the project for casting. What I was looking for with everyone was vulnerability and sincerity—just a little bit of tenderness. It might sound cheesy, but it’s a personal story. It’s fiction, but I’ve lost people in my life. I just knew that I was looking for people who could trust me and be a little more vulnerable, so that we would not end up with a movie that was too snarky or ironically detached, especially when dealing with grief and loss.
MM: Were you worried about that potential, since there are a lot of comedians involved? Snark could very easily manifest itself if you weren’t careful about it.
DM: Early on when I was getting into casting, there are a lot of people whom I find funny and a lot of things I find funny that are not the same tone that I was going for. I was thinking, “Geez, I hope I can find people that are up for this,” because I guess I’m getting a little older too. It does feel like it’s hard sometimes to find that kind of sincerity when you’re making a comedy. In some ways it’s old-fashioned. The genres seem to drift apart from each other often, it feels like. Comedies: It’s an all-out comedy. Drama: People with great bone structure whispering really serious things. Somewhere in between there is still room for movies that are both. When I think about Mike Nichols, James L. Brooks, Hal Ashby and Alexander Payne—these are storytellers I love. In my favorites of their work, they straddle that line. I’m drawn to that type of material because it feels like the laughs are earned. There’s an emotional weight to them that’s very satisfying.
MM: With all of the various mediums that you navigate, what is it about feature films and the 90-minute storytelling medium that draws you to it? What possibilities exist in film that aren’t possible through your other interests?
DM: I was drawn to film first as a fan, from childhood. The magic of movies is a very real thing. It’s really powerful. I got into showbiz to do stand-up specifically. I didn’t have aspirations of doing anything else. Suddenly I find myself 20 years into stand-up. Along the way, other ideas have percolated out of my notebook that don’t fit my stand-up act. So I started to daydream about getting to make movies someday. One thing I liked about trying to make a movie was the intimacy you can achieve. You have different tools at your disposal. Stand-up, of course can be very intimate, but it does feel presentational. You can do characters; you can out act scenes; you have tons of freedom in stand-up, but at the same time, you are constrained to yourself in real time on the stage. With film there are so many other things you can bring into it to tell your story and move people, hopefully.
MM: What’s next for you?
DM: I’m touring. I’m going to shoot another stand-up special for Netflix in December. So I have some time. I’ll do around 40 shows around the country. I’m working on my next feature script. A couple months ago I figured out the story, and I’m trying to get the script together. I sold a pitch to FX for a single-camera series, so I have to hand in that script in the next couple weeks. I have a book of drawings coming out in the fall. I have drawings that weren’t in my first book of drawings that are in the movie. So I thought, “Hey, I can release another book here.” I’m busy, which I’m happy about, but it’s tricky. MM
Dean opens in theaters on June 2, 2017, courtesy of CBS Films. All images courtesy of CBS Films.