The most challenging films about the stand-up world, including Chicago-based filmmaker Ned Crowley’s Middle Man, dwell, sometimes unbearably, in despair. The viciousness of the comedy format is easily accessible, as most contemporary stand-up is fueled by aggression. Even the parlance is violent: to perform well is to “kill,” to fail is to “bomb.”

    Over coffee at Atomix Cafe, Crowley and I discussed the pitfalls of a life in comedy, making a labor of love on a shoestring budget, and how his long-standing friendship with O’Heir inspired his directorial debut. 

    When I started writing this, it was a project for all of my actor friends at the time, and Jim [O’Heir] was definitely the guy. And then it went into mothballs for a while; I didn’t really think about doing it myself. Then about a year and a half ago, we pulled it out, and I was like, ‘You know what, now might be a good time. I’ll take time off of work, and let’s go do it, because I’m tired of trying to get other people to do it.’ And I thought maybe we could figure out a way to make something that looked like we spent a ton of money without having to spend a ton of money. So, we decided it would have to be pretty dialogue-heavy, because we didn’t have a lot of money to do an action picture. 

Middle Man begins with a quote attributed to the silent-film actor and comedian Fatty Arbuckle: “No price is too high to pay for a good laugh.” Arbuckle was accused and ultimately acquitted of the rape and manslaughter of Virginia Rappe, who died in his hotel room under mysterious circumstances. Was Arbuckle’s story the basis of this film?

    I’m Catholic, so I always think there’s a subtext to everything in life. That’s what I like about so many of the Coen brothers’ films, like A Serious Man; I loved how it had an ambiguous ending. So with Middle Man, I wanted other people to be able bring their own ideas to the story. It could be about choices, it could be about good and evil. It is whatever you bring to it. 

    I think anything that you really get lost in thinking you want over what is important corrupts, and can corrupt you. And I’m in a position where I can sit back and pontificate about it, but a lot of people don ‘t have the same opportunities, so they chase what they want, and I get that. But I’ve said this to Jim—Jim is the same guy he is today as he was 30 years ago. We all knew Jim was going to be famous, but the question was, ‘What will Jim become when he does become famous?’ And we’ve had other friends who’ve done it, who’ve gone off and become famous, or become incredibly wealthy, and it is interesting to see what happens to those people. But Jim’s an example of someone who didn’t change. When I  sit down for a poker game with Jim and my other friends, I think, ‘He’s no different than the rest of us’ [chuckles]. You gotta keep your friends, because they keep you grounded.