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Not a Dry Seat In the House: In Conversation With Filmmaker Dean Dempsey

Dean Dempsey
Photography: Ky Digregorio

Queer comedian Greg Mania talks with his close collaborator about their feature-length film, Deadman's Barstool

I'm sitting in a studio in Chinatown where, just one year ago, I was finishing writing the script for my first feature-length film, Deadman's Barstool, with my co-writer, Dean Dempsey. I approached Dean about writing together a few years ago after seeing his previous film, Candy Apple, and asked him if he wanted to write a TV pilot together. He said yes and hasn't been able to get rid of me ever since.

I was enthralled by his ability to paint a portrait (and I mean that metaphorically, although he is quite the accomplished painter, as well; you can see his work often on display at Georges Berges Gallery in SoHo, Manhattan) of a world so many covet and effortlessly blend his unique sense of humor with a coterie of over-the-top characters, instantly making his film one I think will show up under the "We Also Think You Would Like" suggestions whenever someone buys something of John Waters's.

I sat down with my collaborator and best friend in his Lower East Side apartment to talk about Candy Apple, our current film, and his comprehensive knowledge of Taylor Swift.

Greg Mania: Let's start with an ice-breaker: how are your BMs?

Dean Dempsey: Let's just say they're training for a marathon.

What do you mean?

They're runners!

Cute. So, some stuff is festering for you, for us! Tell me what's going on with your previous feature film, Candy Apple.

It's finally in distribution! It's available on most major streaming platforms like iTunes and Google Play. You can also buy a DVD on Amazon, too.

I heard you had a co-writer for your current film.

Yeah, it was a nightmare.

I'm in the room, I can hear you, you know.

Oh, shit, right, sorry.

What was it like writing with me? It's too late to back out now, by the way.

Oh, fuck. No, it was really great to be able to bounce ideas off of another creative person. It's the advantage of the ping-pong; you throw something out there and the other person is says, "Oh, and then what if this happens?" and it goes back and forth and before you know it, it snowballs into this beautiful, collaborative process. I recommend anybody to find a good creative partner to collaborate with on a project or two.

I agree!

What was it like working with me?

I wanted to challenge myself as a comedy writer, so I initially approached you to write a pilot together after seeing Candy Apple. I thought we would have great chemistry because of our respective senses of humor, and I was right!

And write that pilot we did!

You were adamant about working with non-actors for Candy Apple, but took the opposite approach for our film. What was that like?

With Candy Apple it was a combination of things: I couldn't work with trained actors because the resources weren't really there, but more importantly, it was because the film was so autobiographical. These people, these real people, playing themselves or exaggerated versions of themselves, is what gave Candy Apple its appeal and uniqueness. Having these real-life people in this real-life situations--everything that happened in the film is stuff that really happened--all seems so out-of-this-world because they're out-of-this-world people. I think that's what makes it a special film, and probably something I can't do again.

Deadman's Barstool is more fictionally driven. I feel like at that point I had more of a relationship with emerging actors in New York so working with them became more feasible.

We both took a different direction with a murder-mystery comedy. Well, you took a different direction; I took a new one--this is my first feature-length script! What challenges do you think we faced?

I can't think of anything because I'm so talented so there were no challenges.

(Laughs) I want to talk about inclusivity and representation. Candy Apple included non-able-bodied, queer, trans, and POC individuals and when we wrote Deadman's Barstool, we didn't even write character descriptions for our characters. I think it just makes our characters even stronger.

I think you do have to have the details of someone in mind because otherwise finding a conflict makes it that much more difficult, and casting a nightmare.


I think my goal was to sequester each individual's identity-markers are far away from the impetus of the plot as possible.

Yeah, it's ultimately not about who they fuck or what's between their legs; it's more about, "Can the actor embody that character?" I love the fact that, in our film, we have trans, gay, young, old--all ends of the spectrum--and they're all bad people.

We gave them that common denominator.

Right, I think that's the ultimate balancing factor: everyone is equally as bad. In the same that everyone can be equally good. We really just wrote characters you wish you could hang out with. These are characters that are antithetical to the Hollywood landscape.

You've been told with Candy Apple, and now we've been told with Deadman's Barstool, that we're capturing a world that has died. Why do you think nostalgia is so coveted in the cinematic world?

I think because nostalgia comes with a detachment from the current. And not just as an escape, but a fetishization of oneself as younger person. Of course someone who's sixty or seventy says the '70s or '80s were the better because that's when they were younger. But on the other hand, I think nostalgia has a role to play in cinema because I think we look at, say, having a cigarette in a bar, or getting away with a petty crime, as a form of freedom. Everything has been so fucking policed, suburbanized and sanitized, and you face obstacles every time you want to rebel against the norm. I think what we're mistaking for nostalgia is our longing for freedom.

I don't think we really fit a mold, and not just because of the amalgam of genres. Why do you think we don't fit a mold unrestrained by genre?

I think it's just inherent. I don't think I, or we, rather, really intend to write comedy, you know? It's just our natural response to the world, if you don't laugh you'll cry.

It's like a reflex to me.

Yeah. I can find the lighter side of anything. But who knows? Maybe in the future I'll write a horror film. I just do what I fucking do. I'm not very much process-oriented, I really only think about the end product. I just do what I want to do and tell the story I want to tell. Wouldn't you say the same?

Absolutely. I don't really think about how it's going to be received. I try to trust my instincts.

I think you're really just thinking about what you're going to wear to the premiere.

You got me there. How do you, as a filmmaker, want to see your aesthetic evolve? Do you see a hint of where it's going?

I mean, if you're not evolving, you're dead. I would hate to be told one day, "Wow, you made the same seven films in a row." I hope to always be evolving.

What do you see in store for the future of our film?

Good question! I'd ask the neighborhood psychic but she went out of business. (I wonder if she saw it coming?) Ultimately a small theatrical run would be ideal, and later to become available on Netflix or another major streaming platform.

Well, since this is for a queer publication, I guess we should talk about gay stuff. What do you think of Taylor Swift's recent single?

I don't think I've ever heard a song of hers in my life.

For updates on Deadman's Barstool, follow the film's official Instagram and like it on Facebook.

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