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In some parallel universe, Ben Stiller is having a career like that of Hal Ashby or Albert Brooks, directors he greatly admires. “When I think about the movies I’ve directed—that, to me, is where I have the most personal investment,” he said. “Directing has been what I enjoy the most.” In this world, however, Stiller is a bankable star who has helped various movie studios bring in a few billion by playing put-upon schlumps in big comedies.


This story first appeared in the October 1, 2013 issue of WWD. Subscribe Today.

We all imagine lives different from the ones we have ended up with—lives more dazzling or eventful, or maybe just easier and happier. What if we did something about it? That’s the subject of the fifth movie directed by Stiller, The Secret Life of Walter Mitty, which shares something of the premise (guy who has intense daydreams) but not much else with the compact 1939 James Thurber short story of the same title.

It is also far removed from the 1947 musical adaptation that starred Danny Kaye. Stiller’s Mitty is a dutiful son who, like George Bailey in Frank Capra’s It’s a Wonderful Life, has shelved his desire to see the world in order to concentrate on taking care of things at home—in his case, a widowed mother and kooky sister. As the head of the photo library at Life magazine, revived in all its analog glory for the film, Mitty is tantalizingly close to adventures he has not experienced firsthand, until one day—well, I won’t ruin it.

Stiller and I met in a wide-open section of the Catch restaurant of the Hotel Casa del Mar, in Santa Monica. He had some trouble getting through a late lunch (tuna crudo, fried artichokes) because of all the people who kept stopping by the table. The first person to say hello was baseball announcer Joe Buck. Then came the tourists—more than a dozen in all. They approached on gentle cat feet, only to whip out inevitable iPhones and request photos. Roughly half were from Asia or France, a testament to the reach of the comedies Stiller has starred in. They were exceedingly polite, even as their requests grew more and more exacting.

The American visitors, on the other hand, were almost backslappingly familiar. This was not, after all, some billboard god they were encountering, like Brad Pitt or George Clooney—this was Ben Stiller. They had seen his body and ego take a beating in comedy after comedy, and they felt like they knew him.

The attention seemed to embarrass him. He apologized to me more than once, as if his celebrity were a condition he should be able to control. The waiter asked him if he should shoo people away from the table.

“If they can get deflected before they come by?” Stiller said. “But once it’s happening, it’s too late.”

After a premiere at the New York Film Festival in October, Fox will release The Secret Life of Walter Mitty on Christmas Day, when studios tend to roll out blockbusters with decent Oscar chances. It has a shot at doing huge business, too, partly because its theme of the road not taken is, to use a Hollywood term, so relatable.


“That’s the thing,” said Stiller, who seemed to be suffering a case of prepartum jitters. “When I’m in the process, that’s when I’m the happiest, because everything is possible. But then you have to put it out into the world. Of course you want everybody to love it, but everybody’s never going to love it. So then it becomes: What do you have to do to get it out into the world? And then there’s the acceptance or nonacceptance of it. I do think that’s the biggest challenge, for sure.”


One of Stiller’s favorite movies is Sullivan’s Travels, the 1941 Preston Sturges comedy that examines the value of comedy itself. It tells the story of film director John L. Sullivan, who abandons his life as a Hollywood hack (his oeuvre includes Hey, Hey in the Hayloft and Ants in Your Plants of 1939) and hits the road, guised as a tramp, to gather the material he needs to make a movie out of a social-realist novel titled O Brother, Where Art Thou?

In the universe of Sullivan’s Travels, conveniently for Sturges, there are two types of films: fluffy comedies and heavy dramas; the movie provides no room for something that’s a little of both, like, say, Sullivan’s Travels itself. Now, some twenty years into his stop-start career as a movie director, Stiller seems to have hit upon the elusive middle way. The Secret Life of Walter Mitty, which I saw at a press screening, has meaning and heart to go with the laughs. It’s a big-canvas picture, a real movie-movie, and it speaks in the language of classic Hollywood, with its echoes of It’s a Wonderful Life and Victor Fleming’s The Wizard of Oz. (Early in the movie, an office bully calls the stiff-bodied Mitty “Tinman,” although he seems to lack courage more than heart.)

“It feels very much like Ben, even though it’s a different aspect of Ben,” said the filmmaker Noah Baumbach, who directed Stiller in Greenberg (2010). “In a way, it feels like the kind of movie the studios used to make a lot more of, and we wish they would continue to.”

The last two movies Stiller directed, Tropic Thunder (2008) and Zoolander (2001), were satires more interested in tearing down established institutions (big-budget Hollywood in Tropic Thunder, the preening fashion industry in Zoolander) than in building up a fictional world in which audiences could lose themselves. His new movie risks more than his earlier work as a director. It takes Stiller further than ever from his spiritual home base—the piercingly satirical television series SCTV, which he has loved since he was a kid.


Stiller, 47, lives with his wife, actor Christine Taylor (Arrested Development, Zoolander), and their two children in Chappaqua, New York (home of Bill and Hillary Clinton). The family left Los Angeles three years ago. “I wanted to move back east while my kids were still young enough to give ’em a shot at seeing how they felt about it,” Stiller said. “We moved in the middle of the winter, and they had four or five snow days. They were like, ‘What is this? You never go to school here?’” His kids now experience some of what he went through as a child of working parents who were often on the road.

Stiller grew up on Manhattan’s Upper West Side, where he now keeps an apartment, as the son of comedian actors Jerry Stiller and Anne Meara. Bickering and affectionate, they were beloved on the New York comedy scene as the Stiller and Meara comedy duo. Throughout the sixties, they appeared on The Ed Sullivan Show, despite the host’s habit of introducing “Stiller and Meara” as “Stiller and Mara.” “That’s just how he pronounced it,” Stiller said. “He was Ed Sullivan.”

As a kid, Ben shared a bunk bed with his sister, Amy, now a comedian and actor. He started making movie shorts at an early age, using a Fuji Super 8 camera his father had given him to shoot scenes with his friends in Riverside Park. “I started when I was 10, 11 years old,” he said. “I was actually looking at some of them with my kids the other day. They’re pretty crude, and they’re all the same story: a kid getting mugged, and a friend coming up and then beating up the mugger. Revenge stories.”

He got to know the nightclubs and comedy rooms of New York and Los Angeles. “My parents were at the Improv in L.A.,” he recalled, “and there I was, with my mom, and it was really crowded, and I heard this voice behind me, going, ‘Stay close to your mother—you’ll be safe!’ I turned around, and it was Robin Williams. It was right at the height of Mork & Mindy.”

He saw a lot of Rodney Dangerfield. “He was good friends with my folks,” Stiller said. “He would come over. I went to his club, actually. I met John Belushi at Dangerfield’s. I was maybe 10 or 11. He was sitting at the bar, and I walked in with my parents. I’ll remember this forever. He was sitting at the bar, and he said, ‘Hey, how you doing?’ I said, ‘I’m OK.’ He said, ‘You sure you’re OK?’ And that was it.”


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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