M: The Secret Life of Ben Stiller

A comedy star tries to live up to his own great expectations.

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Dunhill's wool-cashmere coat and Prada's wool pants.

Photo By Matthias Vriens-McGrath

Appeared In
Special Issue
Menswear issue M Fall 2013

From seventh grade onward, Stiller attended the Calhoun School, not far from his apartment. He was in a band called Capital Punishment in his highschool years. Teenage summers he spent on Nantucket, where he worked at The Sunken Ship General Store. His acting career got off to an inauspicious start when he appeared in an episode of the soap opera Guiding Light. His character was supposed to play chess, but Stiller himself had no idea how to move the pieces, so he froze. Later, he took a stand-up comedy class at the Improv. “It was so hard, and I was so bad at it,” he said.

At 21, having dropped out of UCLA, Stiller landed a part in the 1986 Broadway revival of John Guare’s The House of Blue Leaves, a play in which his mother had had a role during its 1971 off-Broadway run. Between performances, he cowrote and codirected a comedy short, The Hustler of Money, a parody of Martin Scorsese’s 1986 pool-hall drama, The Color of Money. It starred his House of Blue Leaves cast mate John Mahoney doing Paul Newman and Stiller channeling Tom Cruise. His mom played a lusty barmaid.

The Hustler of Money was funny and polished, and Stiller showed it to Steven Spielberg not long after reporting to the set of Empire of the Sun. He had two lines in the 1987 film, which starred John Malkovich and a young Christian Bale. Spielberg had asked Stiller to meet with him after having seen him in the Guare play. “He said, ‘Yeah, so we’re casting prisoners of war,’ ” Stiller recalled. “I was in his office out here. It was like I was on LSD. Figurative LSD. I was tripping out. And I got a call: ‘You’re in the movie.’ He said, ‘Can you lose a little weight? Because these are prisoners of war.’ So I lost twenty-seven pounds. I showed up, and he said, ‘What happened? Are you OK?’ And I said, ‘You told me to lose weight! You’re Steven Spielberg!’ He’s a very generous guy, in terms of the information he’ll give filmmakers. I had made my takeoff on The Color of Money, and he watched it, and we had great conversations.”

Saturday Night Live producer Lorne Michaels aired The Hustler of Money during a 1987 episode. But Stiller’s desire to make himself into a director presented an obstacle for him in 1989, when he joined Saturday Night Live as a featured performer. He hoped to follow in the footsteps of Brooks, who had made six shorts for Saturday Night Live’s first season, but Michaels had other ideas. So Stiller quit. With Judd Apatow he created The Ben Stiller Show, an SCTV-inspired sketch series that ran on MTV before its one-season incarnation on Fox. It won a 1993 Emmy for writing.

He plowed forward as an actor (Flirting With Disaster) and director (Reality Bites)—and then everything changed with There’s Something About Mary, an over-stuffed Farrelly brothers farce that held a fun-house mirror up to the Clinton years and grossed more than $300 million, reminding the film industry that R-rated comedies could do giant business. This was terrific news for Stiller as a movie star and future rich person, but not such a hot development for the shadow man who hoped to be an Ashby-like auteur.

The industry was happy—giddy, even—to plaster his face on movie posters. He went five years between directing jobs, from the dark, underrated The Cable Guy, in 1996, to the poorly reviewed but eventually comedy-geek-approved Zoolander. Since his breakthrough as a box-office actor, Stiller has been the face (or voice) of three separate franchises that have grossed more than a billion apiece: Night at the Museum, Meet the Parents, and Madagascar.

Seven years passed between the releases of Zoolander and the next movie he directed, Tropic Thunder, an action comedy that grossed more than $188 million worldwide on a budget of $92 million, according to Box Office Mojo. During the years he wasn’t directing, he pushed, without success, to adapt the Budd Schulberg novel What Makes Sammy Run and the George Saunders short story “CivilWarLand in Bad Decline.” Now comes The Secret Life of Walter Mitty. With its reported budget of $90 million and the same high-pressure release date that previously saw such debuts as Avatar and the Lord of the Rings, it had better be a hit, or Stiller could wind up in director jail.


The movies that sell the most tickets, whether focused on flying superheroes or dueling wizards, almost always have an element of fantasy. Realism is nice, but it rarely grosses more than $100 million (just ask Baumbach or Alexander Payne). Despite this, Stiller smartly realized that a little of Mitty’s vivid daydreaming goes a long way. With the film’s screenwriter, Steven Conrad, he cut entire set pieces of his hero’s fantasy life before the start of shooting.

“Around draft ten, we could feel like you have to be careful with the daydreams,” Conrad said in a phone interview, “because if you’re into the story, the daydreams can be frustrating. They can take you out of the story.”

Kristen Wiig, who costars in the movie and hopes to direct one day, was impressed with how Stiller ran the shoots in New York and Iceland. “It’s such a huge task to be in a movie and also direct it, and he did it effortlessly,” she said. “That was a helpful thing for me to watch. He’s organized.”

After the wrap, Stiller’s first cut clocked in at two hoursandfortyminutes.“Ifeltliketherewasnoway,” he said. “But it started to come down in increments.” He was ruthless in the editing room, according to Conrad. “He cuts the movie like a director, rather than as an actor,” the screenwriter said. Although Conrad receives credit for the script, he said, “It was every bit a collaboration. We must have done a hundred drafts between us. He’s relentless.” They got acquainted while working on a script called The Parking Ticket. When Fox said yes to The Secret Life of Walter Mitty, they gave it their full attention.

Conrad followed Stiller to Atlanta, where he was filming The Watch, and that’s where shit got real. “We were getting near to having to submit something to the studio,” Conrad recalled, “and he said, ‘No new scenes. Let’s fix what we have.’ ” But with Stiller back on the set, an idea for a new scene popped into Conrad’s brain: In the finished movie, it is the one in which Mitty daydreams that the woman he loves, played by Wiig, is serenading him with David Bowie’s “Space Oddity.” This vision is different from the ones before it, because it kicks Mitty into action. “I remember thinking, I’m going to find out a lot about this guy tonight,” Conrad said, “because he said, ‘No new stuff,’ but I think this is good, and I’m going to find out whether he’s up for it and all the trouble it creates.” Stiller read the scene when he got back. He did not pull a power move, but told the screenwriter, “Man, let’s do it.” “I knew that night he was the kind of filmmaker who doesn’t quit,” Conrad said.

An unexpected cut, for Stiller, came during a scene late in the movie when Mitty gives an emotional speech. “It was a whole scene of him talking about his dad and how he felt responsible—almost his outpouring,” Stiller said. “I watched the movie the first time, and I was like, ‘This is way too much.’ ” He eventually reduced the film to a lean one hour, forty-three minutes.

David Fincher’s The Curious Case of Benjamin Button, which, like The Secret Life of Walter Mitty, has fantastic elements and is based on a wisp of a short story, is two hours, forty-six. Stiller seems more willing to cut his darlings, but he would not be drawn into saying a word against Fincher when I mentioned that The Curious Case of Benjamin Button is too long.

Stiller’s movie, however, includes a scene that skewers its predecessor: When Mitty imagines the lifelong love he might have with Wiig’s character, he envisions himself as a Benjamin Button-like “old-man baby” nestled to her bosom. The daydream does not accurately reflect The Curious Case of Benjamin Button, Mitty explains, when he haltingly tells her about it, because he hasn’t actually seen it. This might be the movie’s funniest and most absurd scene, the one most in keeping with the stuff that fueled The Ben Stiller Show. It is also the scene that most divided the preview audience members who filled out comment cards.

“This is a movie that’s going to go out on a lot of screens, and it has a budget that’s not small, and you have a responsibility to that, which you can’t ignore, or else they won’t let you make it,” Stiller said. “But what I’ve found is that the favorite scene is almost always the most hated scene.” The film’s Benjamin Button sequence, he added, is “a perfect example of that kind of thing. That’s what the movie is, and I’m excited to have a scene that will polarize audiences.” If things break right for him, if moviegoers begin to think of him as a big-time director, it’s the kind of thing that might go down as an example of the Stiller touch.


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