Jim O’Heir And Ned Crowley Talk About Their New Film ‘Middle Man,’ And That ‘Walking Dead’ Cliffhanger

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Actor Jim O’Heir is known for playing a lovable oaf, a role he perfected as Jerry Gergich across seven seasons on NBC’s Parks and Recreation, and one he played even more recently as a guest star on Fox’s Brooklyn Nine-Nine. But that doesn’t mean we’ve seen everything O’Heir can do. He breaks with that type in his new film, Middle Man, where he stars as Lenny, a man who wants nothing more than to become a stand-up comic, despite the fact that he’s a terribly unfunny guy. After his mother dies, leaving him nothing but debt and her 1953 Oldsmobile, Lenny decides to follow his dream, and heads out to Vegas to make it big on a stand-up talent competition. On the way, Lenny meets Hitch (Andrew J. West), a hitchhiker (hence the name) who takes his quest for fame in a much different direction.

Currently making the rounds on the festival circuit, Middle Man recently had two screenings in Austin, Texas as part of the Austin Film Festival, and we got the chance to chat with both O’Heir and the movie’s writer/director, Ned Crowley. Together, the two of them discuss their shared history, the sensibility of dark comedy, as well as that notorious season-ending cliffhanger from The Walking Dead.

Where did the story of Middle Man come from originally?

Ned Crowley: We met in ’87 in improv class, and we formed [our own] group, so Jim and I have been friends for 30 years. We had a sketch comedy troupe, and we did shows for about 10 years in Chicago. And then he and my writing partner at the time decided to make a go of it in Hollywood, and I stayed in Chicago, I had a family and I was working in advertising. So, with no one to do stage stuff with anymore, I turned to writing. I wrote a ton of stuff over the years, all of which goes out into Hollywood, land of “soft yeses,” where nothing ever quite gets produced and nothing quite gets picked up. Then, after the Parks thing, Jim was ready to do something, and I was ready to take a little break and try something new, so I took a sabbatical from work and we went out to the desert for four months to create this thing. It’s a long history but that’s how we got here.

Jim O’Heir: My involvement was that Ned has pictures that I don’t want released, and I had no choice. That’s my involvement. He has stuff on me that would make Trump blush. [Laughs.]

Well, if that is the case, seems like it would lend itself to this sense of unease that runs throughout the movie.

O’Heir: So, you’ve seen the film?

I have. You guys have really crafted the dark comedy’s dark comedy.

Crowley: That’s pretty good! One writer said we’d created a new genre of film called the bleak comedy, and I sort of liked that. You know, you call it a comedy, you’ve gotta call it something. But people might look at the poster and go ‘Oh, it’s like a little madcap caper in the desert,’ but it goes pretty dark.

Where did the character of Lenny come from, and how did Jim step into the role?

Crowley: Just from the creative standpoint, I’d written the script about 10 years ago, and stuck it in the drawer. Jim had thought he might even be too old to play the part when we pulled it back out. I originally wrote the script with a lot of different friends in mind, guys from our improv class and things like that. But Jim was always thought of as that character, and this was well before Parks, when he was playing a sweet sad-sack, and I also knew he was a very funny man, so I said why not play him as a sort-of straight man with all this insanity around him.

He gets a lot of laughs in the movie, but he doesn’t have funny lines, you know? So it was trying to counter-cast and trying to write stuff for Jim that I knew he was capable of, but was very different from what he’d been cast in. At the time it was, like, “Here’s a big guy, so, you know, give him a donut and a cop uniform and we’ll put him in this TV show, and that TV show.” And we all knew Jim was gonna become famous at some point, [but] we still like to sit around the table and talk, and Jim can become a very dark, irreverent person, and [we joked that] he was gonna drop us like a rock as soon as he gets any taste of fame at at all. So, it was sort-of like that, too. And I hate the whole “everybody wants their 15 minutes, everybody wants their YouTube show, everybody wants their shot at fame,” I think it’s soul-crushing and destructive, so that became the impetus of this.

O’Heir: It totally did happen, I don’t speak to Ned or any of those people anymore. I’m better than all of them. [Laughs.] No, obviously we’ve all stayed dear friends, and the timing was perfect for me. I did seven years as Jerry Gergich, which was the gift of a lifetime, it was my lottery ticket. I loved every single day of it, and I’d do it again tomorrow if I had the opportunity. But I’m also an actor. I live in L.A., and I’m the funny big guy, like Ned was saying. But what Lenny lets me do is say “There’s more to me than the fat joke.” Are there laughs in this? Absolutely, but it is the melting down of a man. It is one terrible, terrible mistake that changed his life. Literally changed his life. So to get the play that kind of a role, where you get to see a man breaking down was awesome. I give Ned all the credit for my performance, because he kept me in check. He knows me, he knows my bullshit, and he knew I could do other stuff.

Crowley: I wanted to get Jim cast in a different role. It’s interesting that, over the years, the quote-unquote “heavy,” as they used to call it, was played by a comedy actor. Like Jackie Gleason in The Hustler, or Bill Murray in Mad Dog and Glory. I think it’s interesting to cast comedy guys in the villain roles.

So, Jim, when you played this character of Lenny, did you play him as a straight sad-sack, or do you keep the darkness of the character somewhere in the back of your mind?

O’Heir: For me, for Lenny, he really is a sweet guy. I know what you’re saying, but I truly didn’t [think that]. He really is a sweet man, very delusional, had a very odd upbringing, with a mother who would memorize bits from old radio shows and stuff like that. So, I always thought he was the sweetest man, but near the end of the film, he just snaps. As humans, we can only take so much. This is a guy who’s never done a mean or a wrong thing in his life. That’s where I was coming from the whole time, until I couldn’t, and for me, that was the scene where I leave the jail and start walking through the desert. For me, and again, this is in my mind, is “Fuck you, now it’s getting real,” but it was all happy-go-lucky until that moment.

The first time we see Lenny do stand-up, all we hear is the orchestral music playing drowning out his material. Did you film a scene where he just bombs on stage like he does in the film?

Crowley: It was always meant to be dream-like, but I think we wrote a routine for Jim, and we tried to get the most old-school, really bad jokes, and Jim did get up there and do it. But the jokes we found in we found, our art director [Bob Feffer] found this box of old business cards from the ’50s, and on the back of each one was a really bad joke, so we used those.

O’Heir: And they were horrible. Just absolutely horrible.

Crowley: You know, stand-up is funny when you’re there watching it, but when you see a movie about stand-up, the jokes aren’t quite as funny, so I kinda just wanted to avoid all that.

Did you have any trouble when Josh McDermitt, who plays Eugene on The Walking Dead, was on set with people trying to pry some spoilers after their big cliffhanger last season?

Crowley: Josh is a sweet guy, I tell ya. And he did us a real solid, he loved the script and wanted to do it. Those guys make a lot of money at those comic-con things, and filming fell right during one of those, and we couldn’t rearrange our schedule. He’d have done very well, but Josh said he’d rather do our movie. But no, we didn’t have any trouble with that. But, since then, the last six months have been so secretive, he won’t tell us anything.

O’Heir: I was shooting in Atlanta for a couple of weeks, and Josh invited me to a party at one of their houses. And I’m a huge fan, too, I want to find out who gets whacked, like everybody. So, I will tell you this, without giving anything away, there were people at that party that I didn’t think would be at the party. I thought they were dead! I had no idea, it really threw me, but it was really cool to be around them. They’re a very tight cast, and they’re very sweet together.

Crowley: And they’ve been good for us. The Walking Dead fans have been great about retweeting and pushing, and they’ve got an amazing rabid fanbase. I think they’re gonna like seeing Josh in a different role, even though he’s still got f*cked-up hair in our movie.