Stephen Kessler took an unusual path to underground success as a director. He started directing commercials in 1989, landing high-profile ad campaigns for Snapple and Saturn and the "Got Milk" ads. In 1991, he garnered an Academy Award nomination for his short film, Birch Street Gym. He took his first shot at big-budget Hollywood filmmaking with Vegas Vacation in 1997. That’s where he got his first taste of directing legends like My Dinner with Andre’s Wallace Shawn and comic innovator Sid Ceasar, infamous characters like Siegfried and Roy, and glitzy showbiz kings like Wayne Newton.

The experience came in handy directing his latest film, The Independent (see FinemanFilms.com), a mockumentary that follows the life of fictional b-movie director Morty Fineman. Kessler directed a mixed bag of talent, from the actors at the core of the film—Jerry Stiller as Fineman and Janeane Garofalo, Anne Meara, Jonathan Katz—to fellow directors Roger Corman, Ron Howard, and Peter Bogdanovich to b-movie queens like Julie Strain. Gadfly caught up with Kessler by phone while he was hunting for videos at his local mega-chain store.

Gadfly: How did you go about directing the mix of different actors in Vegas Vacation and The Independent? I know you had to direct Wallace Shawn, Siegfried and Roy, and Wayne Newton.

Kessler: Siegfried in particular did a lot of confidence-building. And it was funny because when the film came out, I guess I hadn’t seen the guy in about a year, and he said to me, "You know, I really want to thank you, because we’re up on the stage and I was very nervous, and you said to me, ‘Just be Siegfried.’" And I said, "Well, you’re welcome, Siegfried."

And even people like Julie Strain... I mean, Julie is someone who really has a great amount of natural ability, and there isn’t much I have to do but tell her, you know, just pull it back, I just want it to be a bit more natural, just be yourself a little more. You know, the stuff she does in the opening scene of The Independent is pretty much all improvised (all her improvising). And it’s great. So whenever people come in front the camera, whether they’re really accomplished actors or they’ve never acted before, you just kind of try to see what their comfort level is and just start making adjustments from there.

So there’s no difference necessarily between directing Wallace Shawn and Wayne Newton?

No. As a matter of fact, [in Vegas Vacation] Wayne Newton had a really great understanding of what I wanted him to do, without my having to say a word. Certainly he’s not playing Wayne Newton but he’s playing a… I mean, he’s actually doing a really good characterization of who people think Wayne Newton is. That’s what makes him so funny.

Wallace Shawn actually said, "I want to see the script before I decide to do it." He read the script, he loved the jokes, the jokes he had to do. And actually we did really try to give him some great jokes. Like, I remember this one joke where Chevy [Chase] has like five dollars left and he says, "What can I do with five dollars?" And Wallace Shawn’s line was, "I don’t know, buy a bullet and rent a gun?" But he also, he had a lot of ideas about… He’s one who was always, "Is it funny if I do it this way? Should I do it this way?" But he was great, Wallace Shawn, you know.

So did the Vegas Vacation folks approach you or did you vie for the spot to direct the film?

Hey, could you hold on for just a second? [To video clerk] Could you tell me if you have a film here called Crimes and Misdemeanors? M-I-S-D… DVD or video… [Back to interview] See here’s the thing, you know, a movie like Crimes and Misdemeanors, brilliant film. You can’t even get it at Blockbuster. And then look how many copies there are of Keanu Reeves’ Hardball. I’m looking at like twenty right now, on one table. [Back to clerk] It’s checked out? That’s DVD rental over there? Gotta get a back-up movie. Okay I’m ready to talk again.

So we were on, how did you come to direct Vegas Vacation?

Well, I had tried—after I did Birch Street Gym, I had tried to do this script I had written, which was kind of a very sincere dramatic comedy. And I thought it was going to be very easy, but it was actually almost impossible. And after a while, I hadn’t been working, and my agent and some friends of mine said, "You should just take some studio job." And so I looked at what was around and Vegas Vacation was something that was happening, and I liked the idea of satirizing Las Vegas as becoming this family destination. And that was the start of it, you know? I had to go through a lot of interviews with Jerry Weintraub, who was the producer. And basically just go through a whole song and dance.

Did the work with the advertising campaigns help you land the job?

Yeah. Yeah they did. I mean, because, it helps if people know you’re working, and, you know, other people believe in you enough to give you money.

I got to see a preview [of The Independent] here in Boston with Jerry Stiller, Anne Meara, Janeane Garofalo, and Jonathan Katz…

Yeah. One of the really amazing things is how devoted these guys are to this movie. Which, you know, basically they made no money on.

You had met some of them at commercial auditions? Janeane Garofalo said that you met when she had auditioned for a "Lunchables" commercial.

Right. For some Oscar Meyer product. I had been looking for like young stand-ups who just hadn’t been in a hundred commercials. You know, and Janeane came in and she was just blindingly funny, and of course not what Oscar Meyer was looking for.

Were all of the parts tightly scripted?

It really was tightly scripted, although some of the funniest lines in the movie were improvised. Some of the stuff Bob Odenkirk said as Death were his improvs, which were great. Brian Possain: "I’ve seen all of your movies. I’ve seen all of Scorsese’s, too, but they’re not half as easy to masturbate to." Brian improvised that line. It was great. Janeane improvised some great stuff. I try to stick to the script somewhat but kind of let people move out from there, and a lot of times you just get really great stuff.

How loving are these parodies of these different films?

I think it’s kind of more for the people that watch them to judge. I really like the films. I try to be really faithful to not only the physical look of the film but the spirit of the film, the casting of the film. You know, we used real motorcycle gang people in the motorcycle gang film. The Eco Angels is actually based on a film called The Mini-Skirt Mob. That kind of thing. So there are films like that. And then there are films like Whale of a Cop. Whale of a Cop was based on a story a friend of mine who was a Hollywood writer told me. And some are just stupid stuff we made up like Brothers Divided.

Are you a big b-movie fan?

You know, oddly enough, I am not a huge b-movie fan. But, you know, I like them. I always find them funny. I always find—the Something Weird video has trailer compilations. Those are always hysterical to watch.

You’re not one of those guys who has a den full of Roger Corman film posters?

No. Even when I was a little kid the movies I liked weren’t Star Wars, they were like Woody Allen. People on a bench talking to each other was the kind of stuff I always liked.

You once said that you just enjoy making funny movies, not necessarily movies where people are getting blown up or that are really violent or heavy. How do you intend to stick to that?

Even though there’s violence in The Independent, the violence is there to kind of make a point. I try to juxtapose senseless movie violence with the reality of how dull it is when one person shoots another person. That’s why when Larry Hankin’s character gets killed in The Independent, I tried to film it in as uninteresting a way as possible. Movie violence, you know, I mean, it’s a fine form of entertainment, but I don’t really feel like I have to entertain people that way or that I want to. So I try to do something that entertains people in a different way.

You don’t feel that there’ll be any pressure to make the kind of films you don’t want to make as time goes on?

No. Nobody’s asking me to do those kinds of movies. No pressure at all. The only pressure I have is to do stupid comedies. That’s kind of the biggest pressure, and I just deal with it on a case by case basis. To me, I have to see something there. Something worthwhile.