Ben Stiller: The Darkest Funnyman in Hollywood - Rolling Stone
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Ben Stiller: The Darkest Funnyman in Hollywood

For over two decades, comedy hero Ben Stiller has been behind the biggest, smartest laughs in Hollywood. So why doesn’t he think he’s funny?

Below is an excerpt of an article that originally appeared in RS 1101 from April 1, 2010. This issue and the rest of the Rolling Stone archives are available via Rolling Stone Plus, Rolling Stone’s premium subscription plan. If you are already a subscriber, you can click here to see the full story. Not a member? Click here to learn more about Rolling Stone Plus.

It is nearly impossible to have a discussion about the past 20 years of comedy filmmaking without mentioning Ben Stiller. As far back as his first shorts parodying Tom Cruise and LL Cool J and his influential sketch series, The Ben Stiller Show, he built a reputation for spotting comedy talent early, and worked with everyone from Judd Apatow to David Cross, Andy Dick, Janeane Garofalo, Jack Black and Owen Wilson. His directorial debut, Reality Bites, captured the zeitgeist of the slacker alt-rock generation at its peak. In 2004 alone, he starred in six comedies. Over the course of his career, he has laid claim to some of the most oft-referenced comedy scenes of his era, from the hair gel in There’s Something About Mary to the Blue Steel of Zoolander, while crossing the funnyman chasm to also become a bona fide lead in everything from romances to dramas to family movies.

Born into a showbiz family (his parents are the comedy team of Anne Meara and Jerry Stiller), he appears to have one of the most charmed lives in entertainment — until you meet him. In person, there’s nothing very funny about Stiller. Wandering through the Man Ray exhibit at the International Center of Photography in Manhattan, he is slumped in a black overcoat, his hair unkempt and a wiry gray goatee spotting his face. There’s a dark weight that seems to burden him, whether due to a hectic schedule or the curse of thinking too much. He describes himself as “socially uncomfortable” by nature, and friends say that they find him quiet and guarded when out of his comfort zone on set. “L.A. is depressing,” he says matter-of-factly as he orders a Caesar salad at the museum cafe. “I was in Century City at night once, and it was such a ghost town, it made me want to slit my wrists.”

It’s almost as though Stiller, 44, is still in character for his latest movie, Greenberg, a Noah Baumbach-directed character study of a neurotic, unemployed 40-year-old still harboring the pipe dream that he can re-form his indie-rock band and win back his high school sweetheart. A romantic comedy so black that it’s a drama, Greenberg is perhaps the first film since Stiller played a junkie TV writer in 1998’s Permanent Midnight where he succeeds in making the audience forget that he is actually Ben Stiller. Those who have worked with him describe him as a driven perfectionist. But as he sits down at the cafe, he explains that, thanks in part to his family (wife and occasional co-star Christine Taylor and their children, Ella, seven, and Quinlin, four), he’s turned a corner and is learning to slow down and let go.

Do you see “Greenberg” as a bookend to “Reality Bites,” where 15 years later it’s not so cool to still be a slacker, and no one gets your cultural references anymore?

People have said that. I never thought that when we were doing it, except maybe in the party scene at the end. Instead of using extras, Noah had the girls who were in the movie invite their friends. We were totally intimidated by these kids who were supercool and superhip. I was not like that at 20. So it was three days where Noah and I, in between shots, would say to each other, “This is like the movie right now. We’re Greenberg.”

In what way?

I wasn’t so confident. I didn’t have my shit together. There’s an air about them that is like, “Wow, they really seem to fucking own the place.” And I guess they do, because they’re young and have it all ahead of them. So it was like, “How does my own experience of being older and my own regrets about things that haven’t come together in my life the way I wanted them to inform that point of view of Greenberg?”

So what kind of regrets do you have?

There are movies that I was supposed to direct that didn’t happen that I still think about all the time. “If I’d done that movie, what direction would my career have gone in?” I don’t blame myself, though maybe I could go back and look at the ways I sabotaged it at the time. And I’ve been in relationships where I’ve screwed things up, where somebody was too there for me — too available — and it scared me.

And you took them for granted?

Yeah, and I made mistakes in the relationship that ended it. With that movie I didn’t direct, it came at a time when I was in a relationship that I’d self-sabotaged and was trying to get back into. At that moment, I was more focused on the relationship than doing the movie. So maybe I didn’t fight as hard as I should have.

You often say you don’t think you’re funny in person. But do you think you’re funny onscreen?

Oh! Good question. Occasionally. I really don’t make a practice of watching stuff that I’ve done, because it’s just too strange and narcissistic, and it doesn’t feel right. But when you’re working on something that you’re in and you’re directing it, you obviously have to watch yourself a lot. So I’ll see things, and more often than not I’m disappointed.

What about after the process?

Every once in a while you’ll be flipping through the channels, and you’ll see something, and if it’s more than five years old, then it becomes sort of an oddity where you go, “Wow, that actually happened? What were we thinking back then?”

You’re often hiding under a wig or mustache or sunglasses in your comedies. Even in “If Lucy Fell,” you’re basically the only actor in a crazy wig.

Yes. I remember I was going through a breakup, and I wanted to just fill time as much as possible. So they asked, “Oh, do you want to get dreadlocks?” And I thought, “That will take up eight hours of my life.” So that was the motivation.

What do you think the difference is between parody and satire?

Parody, for me, is a reductive term, and it can be simplistic. Satire is commenting in some way, and parody is just making fun of things. On The Ben Stiller Show we did a lot of parodies. Something like Tropic Thunder is a bit more satirical. You do parody more when you’re starting out, because you’re influenced by the things you’re attracted to and want to learn more about. But then hopefully you develop past that.

Judging by the parodies from “The Ben Stiller Show,” you were attracted to heroic characters like Bono, Tom Cruise and Bruce Springsteen.

Yes, yes. I love those guys.

Growing up, did you want to be more of an action hero than a comedian?

If anything, I wanted to be like an Al Pacino/Robert De Niro guy, because I loved those movies growing up. But that just wasn’t in the cards. Then when I was 19, I started watching SCTV. That really affected me, and so did watching Albert Brooks movies. So I started exploring that, and it was very derivative for a long time, which is part of the process of figuring out what your voice is.

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