Don’t believe Michael Showalter when he tells you that he’s much less funny than his comic ensemble, The Baxter, a smart romantic comedy in which he not only stars, but also lends his considerable writing and directing talents. His inspired turn as Elliott, a chronically lovelorn ‘Baxter’—the guy perpetually dumped at the altar—is an impeccable paean to comic timing, mannered goofiness and everything lovably square about the nice guy as reluctant romantic. It’s showmanship, all right, and Showalter, the veteran of MTV’s The State and the co-creator of the 2001’s smart genre tickler Wet Hot American Summer, stopped in Chicago recently for a chat about his triple-threat turn on a decidedly little film with big laughs.

Lee Shoquist, ReelMovieCritic: This idea is really ingenious—to focus on this character who always loses in love.

MS: I wanted to write a romantic comedy—it’s a genre that I’m not afraid to say I love when it’s done well. I didn’t want to do another that was indistinguishable from all the rest. And from watching movies, I came across this character of this guy who seemed to keep popping up in romantic comedies in various guises, whether he’s Bill Pullman in Sleepless in Seattle or Ben Stiller in Reality Bites, or John Cryer in Pretty in Pink. There’s this guy who is a good guy, a nice guy—but he just doesn’t get the girl. As a movie buff I thought it was an interesting jumping off point for an entire film. So in writing, I tried to imagine that there were two movies happening. One between Bradley and Caroline—the sort of big budget Hollywood movie—and then there’s Elliot’s movie.

LS: You have a terrific comic ensemble here with Justin Theroux, Elizabeth Banks and, why am I surprised about this—Michelle Williams, who is very good here, and even sings! Was making the film as much fun as it actually looks?

MS: Yes, it was very fun! This is a great cast, and they’re starting to become really well known actors, so I just luckily knew them being in New York for a while, and we’re all just starting to work more consistently now! Justin and Elizabeth are both very comedic and very funny. Michelle Williams I saw in The Station Agent and then saw her on the street in New York City, recognized her and thought that she’d be perfect for this part! So she was the one actor in this movie that I had to really go out of my way to convince to be in it. She was actually reluctant about it at first because she didn’t quite recognize the genre—the light, romantic comedy genre. She’s totally amazing in the movie.

LS: The timing feels spontaneous, almost like improvisation.

MS: It was all scripted. We shot the movie in twenty days, low budget, no margin for error and no film to waste, so we really couldn’t afford to have people goofing around. I never did more than three takes during any one shot, and pretty much needed people to say the lines as they were written. If it was ‘okay,’ that was okay with me, and then we moved on, which is why it’s so important to get a great cast, because you don’t have a lot of time to screw around.

LS: Since you wrote and directed, you obviously had a lot on your mind while shooting. There must have been days as an actor when you felt like, ‘I just don’t feel funny today.’

MS: All the time! I just kind of held my breath the whole way through. I didn’t have the experience as a director, nor had I ever taken on a role that big, so I just barreled through the whole thing and then came up for air when it was over. I didn’t have time to be overly concerned with whether or not I was doing a good job. But I certainly had people around to whom I could say, ‘Is that funny? Am I doing okay?’

I think I’m okay at acting, but I’m not great. I think that I’m much happier editing this movie watching Justin Theroux, Paul Rudd and Peter Dinklage. I think I’d like to do smaller roles, and let guys who spend their whole life acting do that. But I may change my mind! Creatively, I’m more interested in the writing and the directing—that’s the bigger challenge. I read a quote that was very appropriate—in the entertainment industry, ‘if you have a fallback plan, you will fall back on it. If you don’t, you won’t.’

LS: The film is very lean and streamlined, and for its genre it moves nicely.

MS: A lot of the way the story was told happened in the editing. I had an amazing editor named Sarah Flack, who did Lost in Translation and The Limey, two great movies from an editing standpoint. Working with her was one of the best experiences on this whole project. And the whole way in which the movie was told in flashback was not the original intention, but it definitely became clear that it was one of the ways to make the movie less straightforward and gave it life, somehow, to tell in flashback.

LS: Very funny character names by the way—Cecil Mills, Benson Hedges…

MS: Yes! Obviously Benson and Hedges is meant to be funny. Ed’s wife is named Stella, which is the name of a TV show that I do right now on Comedy Central. And then Cecil Mills is kind of like Cecil B. DeMille, and then Wendell Wims is sort of like Wim Wenders backwards! And ‘Baxter’ is Jack Lemmon’s last name in The Apartment. But none of that was intentional, actually, except for Stella! I’m very literal, so even Caroline, who is a swan, her last name is Swan. And then the brother-in-law, whose name you only see in the credits, is Louis Lewis!

LS: The tone of the film is very sweet and innocent, and this material could have gone gross-out, like most contemporary comedies. It’s fresh and not cynical.

MS: Yes. I actually very much wrote this in response to the gross-out comedy trend, even though I have participated in that for anyone who knows my work! As I get older, I really miss these old-fashioned comedies, and I tried to write something that had no gross-out humor, and that the laughter was just simple and sweet. Something that my parents could watch, but that still has an edge and sensibility to it that was consistent with some of the projects that I’ve worked on in the past. There is that one kind of moment where Bradley is talking about the cold night with Caroline, and that’s why we’re PG-13—that one line. I wanted to just get laughs in a different way. For my next film, that will be something that I will try to do. It appeals to me personally—a cleaner type of movie.

LS: You like playing with genres, don’t you?

MS: Yes, I love it. I was a semiotics major in college, which is the language of signs and symbols. I love the way a movie tells you what to think. And genre is all about these sort of signs and symbols throughout the movie that tell you what to think. In any genre, starting with the western, the black hat tells you he’s the villain. And I love the little conventions that are the tent posts of any genre that tell you what to think. In the buddy movies, there’s always the angry, Black police chief. Things like that I get such a kick out of!

LS: Were you thinking of Woody Allen at all when you wrote this? It feels like a distinctly New York story.

MS: Oh, yeah! What I like about Woody Allen and my larger ambition is these chapters of a world. The Woody Allen reality is something that I love—his New York, which really isn’t real, but it feels so real and it’s so exciting. I have a vivid imagination and I like existing in my fantasy life.

LS: The Baxter also says that being a nice guy can still get you in first place.

MS: Nice guys finish first, for once. The movie used to end with a quote: ‘Everybody is wrong for somebody, but everybody is right for somebody else.’ You’ve just got to hang in there, and if you’re a romantic like me, there’s always hope!

LS: So what’s next?

MS: I’m writing another movie set in Brooklyn, and this one is about a guy with back pain. And I feel there’s a huge audience for this movie—thirty million Americans suffer from back pain! It’s called the Back Story, which is coincidental.