Ben Stiller on Hollywood’s Long Journey With ‘The Secret Life of Walter Mitty’

Cover Story: Ben Stiller is one of Hollywood's most bankable comic actors, but 'Walter Mitty' could give him the cachet he craves as a serious director if audiences embrace his movie

The Secret Life of Walter Mitty

At a recent Q&A to promote “The Secret Life of Walter Mitty,” Ben Stiller was asked by the moderator, his pal Jay Roach, if the latest movie that he directed and stars in is autobiographical. “Are you Mitty — is this wish fulfillment for you?” Roach prodded Stiller about the movie’s tale of a middle-aged dreamer who embarks on a life-changing, globe-trotting adventure that finds him skateboarding down a highway in Iceland and swimming with a shark in the frigid waters of the North Atlantic.

It’s a question that Stiller gets often. “Yeah, of course,” Stiller told Roach, who directed the “Meet the Parents” films. “I think that’s what made it relatable.”

It’s not that Stiller, who’s also a producer on the picture, necessarily identifies with the character, but he understands the draw. Mitty wants to be “a better version of himself,” Stiller said later. “A different version of himself.”

At 47, Stiller is searching for his own Holy Grail: to be taken more seriously as a director. He envisions a future in which he acts less and directs more. “I love acting, but what I love is the freedom you have as a director to tell all different kinds of stories,” Stiller says, “where as an actor, to a certain extent you’re just limited to who you are and what you get cast in. The process is less vulnerable when you’re directing, because you’re supposedly in control.”

It’s a job description that fits well with Stiller’s controlling nature. He has a reputation as a detailed perfectionist behind the camera. Many who’ve worked with him say he can be onerous and intimidating. Certainly, he can be exacting. “What Ben needs is time to think and make choices,” says John Goldwyn, who produced “Mitty” along with his father, Samuel Goldwyn Jr. “When he doesn’t have that, he gets frustrated, whether it’s casting, locations or the color of a wall in a scene. He would want four different versions of the wall. It never got nasty, but it did get uncomfortable.” Despite that, Goldwyn says he’d work with Stiller again “in a second.”

Stiller the actor vs. Stiller the director have long been two very different, and sometimes conflicting, versions of the same artist. The movies in which he’s starred have grossed $2.6 billion at the domestic box office, thanks in large part to mainstream family comedy franchises — 2000’s “Meet the Parents,” 2005’s “Madagascar” and 2006’s “Night at the Museum.” Combined, they have so far spawned seven sequels.

But as a director, Stiller is drawn to material that’s more subversive. Even his most audience-friendly film, 2008’s “Tropic Thunder,” a satire that took in $188 million globally, came from an old sketch idea about actors who are so serious about their craft that they made a war movie and returned home with pseudo post-traumatic stress syndrome. Two other instances of Stiller’s dark humor as a director — 1996’s “The Cable Guy,” starring Jim Carrey, and 2001’s “Zoolander” — were box office disappointments, though “Zoolander” subsequently found a cult following on DVD and cable.

“The Secret Life of Walter Mitty” — the fifth movie Stiller has helmed, and the first in five years — might just be the vehicle that finally enables him to achieve the kind of status as a filmmaker he enjoys as one of Hollywood’s biggest comedy stars. But it’s also a big gamble. The $90 million special-effects-laden dramedy is a marketing challenge that has made executives at 20th Century Fox jittery.

During the course of production, the studio kept grilling Stiller about the tone of the material. The story “didn’t have a traditional structure in terms of what people might expect from this kind of movie,” Stiller admits. “There’s no real big third act.”

The film reveals an untapped vulnerability in Stiller both as director and actor. “I think his performance in ‘Mitty’ is extraordinary: sometimes funny and sometimes dramatic,” Roach explains. Now it’s just a question of whether audiences will agree.

As for being a tough sell, “Mitty” is no “Night at the Museum”: It’s not a broad comedy. And despite its adult themes, it’s not a straight drama. There’s no telling exactly who the target audience is, or how many will turn out over the holidays to make the movie the hit the studio and Stiller need it to be. As the picture’s helmer and star, he will be blamed if it doesn’t work. On the other hand, if it resonates with moviegoers, it would raise his stock as a director.

When the film’s first teaser debuted this fall, it struck a kind of wry chord more reminiscent of a Wes Anderson film, not the kind of mass that packs families into multiplexes. “The earlier trailer was trying to make it clear that this is not ‘Zoolander,’ ” says Jim Gianopulos, chief executive of Fox Filmed Entertainment. “It’s not your typical over-the-top comedy. It’s a comedy with a brain.” Production president Emma Watts also believes the film will connect with audiences. “What Ben has done is create something that’s an ode to the working man,” she says, adding, “People always knew it was going to be a challenge. The tough part of it was to find a contemporary angle that would resonate.”

The original, produced 67 years ago by Sam Goldwyn Sr. and starring Danny Kaye, was a musical comedy about a daydreaming book editor — a throwback to simpler times. It was a big box office hit. The source material was a sparse James Thurber short story that appeared in the New Yorker in 1939.

In Stiller’s reinvention, written by screenwriter Steve Conrad, Mitty is a photo editor at an ailing Life magazine. He’s too bashful to talk to his office crush, played by Kristen Wiig, who is dramatically more subdued than the raucous lead she played in “Bridesmaids.” “I love all the comedic roles, especially the broader stuff at ‘SNL,’ ” Wiig says. “But to be able to play a normal person was great.”

When a photo negative for the Life cover shot by a famous photographer, played by Sean Penn, goes missing, Mitty sets out on a global quest to find the photojournalist and tap into the adventurous person he’s always meant to be. As courageous as Mitty’s stunts are onscreen, Stiller’s most impressive feat was landing his friend Penn in that small but pivotal role.

“Ben had been stalking me on projects for some time,” Penn jokes. “The intensity level rose with ‘Mitty,’ and I was advised by security experts that the compromise tactic of de-escalation would be compliance. And given that Ben, apart from the stalking bit, is a sensational person and so committed to the work he does, I relented.”

Penn also cracks about his character and screentime with Stiller: “I’ve been told it’s an upbeat role for me,” Penn says. “It’s not true. It’s just the audience observing me in a scene with an actor I like. I don’t like the others.”

It’s no secret that the “Walter Mitty” remake, lodged in development purgatory for two decades, is one of Hollywood’s most tortured projects. Samuel Goldwyn Jr. began working on a redo of his father’s film in 1994, with Jim Carrey in the title role. Goldwyn set the project up at New Line, where Carrey had made “Dumb and Dumber” and “The Mask,” and the studio bought the rights in 1995 with the understanding that the Samuel Goldwyn Co. would be involved in all creative decisions.

The next decade and a half saw a revolving door of talent on the project, from directors Ron Howard to Steven Spielberg, and countless screenwriters and stars including Owen Wilson, Mike Myers and Sacha Baron Cohen. The Goldwyns filed a lawsuit against New Line for trying to transfer the rights to another studio. In 2002, New Line was forced to revert the fi lm rights back to Goldwyn Jr., who took the property to Paramount, where his son John was president.

In 2007, John Goldwyn, who had transitioned into a producing deal that he still has at Par, set up “Mitty” at Fox after his home studio put the project (on which it had once been so high) into turnaround.

“You have to fall in love with some element of a film to keep going with it, and I was always enchanted by the character,” says Sam Goldwyn, who concedes he was “running up a fortune in writing costs” as the producers kept commissioning new scripts.

Stiller read the current screenplay by Conrad in 2011 and was immediately taken by the tone. He returned a draft with his detailed notes about how to sharpen Mitty’s journey. “Ben had such a global grasp of the movie at that point,” John Goldwyn says. “He was already buying into the vision. I told my father when I finished the meeting that I thought Ben wanted to direct, too.” Fox’s then-co-chairman, Tom Rothman, who had worked with Stiller on the “Night at the Museum” movies, didn’t believe he could both star in and direct such a demanding film.

To convince the studio he was up to the job (which had been offered to Gore Verbinski before he opted to make “The Lone Ranger”), Stiller produced a five-minute short reel he presented as his vision for the film.

“He really was one step ahead of the game with the quality of his thinking,” John Goldwyn says. “He had shots of Greenland and Iceland, which were designed to portray what (the film) would be like for the audience.”

Ben Stiller grew up in a family of comedians (his parents are the comedy duo Jerry Stiller and Anne Meara), but he never wanted to be funny. “Ben has been in show business all his life with his dad and mom,” says Sam Goldwyn Jr. “He was born in the trunk.”

Stiller says that as a kid, he made action and kung-fu movies on his Super 8 camera. “I was like, ‘I’m not going to do what my parents do. I’m going to find my own way.’ That was my version of rebellion. I didn’t go and do drugs. I said, ‘I’m going to do drama instead of comedy.’ ”

That proved easier said than done. Stiller kept auditioning for serious parts in big films, but never quite landed them. His first big break was on Broadway in “The House of Blue Leaves,” a wild, black comedy, although he needed some help landing a meeting with the casting director. “I couldn’t get in on the audition,” Stiller says. “My mother, who had been in the original production of the play in 1970, called up the playwright (John Guare) and said, ‘Hey, would you audition Ben,’ which is the worst way to ever go into an audition: They are doing a favor for your mother. I was desperate enough to get the part that I was like, ‘OK, just do it. I appreciate it, mom.’ ”

The gig paid off. Stiller got noticed by Spielberg, who came to see the play, and cast him in a bit part in 1987’s “Empire of the Sun.” “To me, that experience of just being on his set for 10 weeks in Spain and watching him work was amazing,” says Stiller, who has been studying every director he’s ever worked with since.

Stiller eventually returned to comedy, directing the short 1987 film “The Hustler of Money,” in which he parodied Tom Cruise in “The Color of Money.” That led to the 1992 Emmy-winning “Ben Stiller Show” on Fox and the 1994 Gen X comedy “Reality Bites,” his feature film-directing debut starring Winona Ryder. He wanted to carve out a career in which he both acted and directed, but his trajectory changed when the Farrelly brothers cast him in 1998’s “There’s Something About Mary,” a surprise hit that grossed $370 million globally and catapulted Stiller to stardom. It created a template for the actor as a hapless underdog who finds himself in humiliating situations — and earns the empathy of audiences.

“That was the first movie I was in that actually did well at the box office,” Stiller says. “Up to that point, I was really happy, because I was working as a director and as an actor, and going back and forth. ‘There’s Something About Mary’ came out, and it opened other doors that created a lot more opportunities as an actor.”

In “Walter Mitty,” Stiller’s reluctant hero keeps obsessive records about all the film negatives stored in the Life magazine archives. As a director, Stiller is just as fanatical. He has a reputation for drilling his crew for the tiniest details. “Like other stars with that level of perfectionism, it’s rigorous and it is sometimes hard,” says Shawn Levy, who directed the “Night at the Museum” films and has spent the past few years working with Stiller on drafts of the third movie in the franchise, scheduled for release Dec. 25, 2014.

“Anyone who is looking to just do a gig doesn’t sign up for a Ben Stiller movie,” Levy adds. “You sign up with Ben if you’re down for a kind of hard-working, fully committed experience.”

Stiller concedes his reputation for being demanding is deserved, but maintains that he’s mellowed a bit over the years. “I think what’s great is when you’re making a movie with a bunch of people who have the same commitment,” he says.

A rigorous rewriter, Stiller will chew on the finest points in a script until he gets them right. For example, on “Mitty,” he wanted to make sure that the extras playing Afghani war soldiers opposite Penn’s photographer looked like they were actually from Afghanistan. “He knows what he wants, and he works extremely hard,” says Justin Theroux, who spent eight years co-writing the script on “Tropic Thunder” with him. After clocking long days of constructing scenes on that film, Theroux would sometimes receive a phone call at dinner from Stiller with more notes. “It was like getting a PhD in writing,” Theroux says. “There would be times we’d push to the end of the scene, and I thought we’d mined everything we could. And lo and behold, on the 20th draft, the pearl would pop open.”

Stiller and John Goldwyn go back to when Goldwyn greenlit “Zoolander” at Paramount. The original movie grossed only $45 million domestically and earned mixed reviews before achieving its cult classic status. Stiller was inspired to create the voice of the male model character, based on a skit he did at the VH1 Fashion Awards.“I was kind of doing a bad Marilyn Monroe impression,” Stiller says. And the puckered-lips? “Whenever I would fix my hair in the mirror, my wife would say, ‘Why are you doing this look?’ ” And then (I realized) that mirror look could be Derek’s look.”

When the film went overbudget, Stiller had to chip in $2 million out of his own pocket to cover costs. And the studio released the picture just two weeks after Sept. 11, 2001, leaving audiences squirming at the film’s male-model assassination subplot. He’s now working on a “Zoolander” sequel at Paramount, after spending the past several years on a draft of the script. He’d like writing partner Theroux to direct the film.

“It has such a following of the people who love it, I would want to make sure the sequel could deliver in the way that it needed to,” Stiller says. “That’s hard. I feel good about the script we have — I just want to really make sure it felt right.” When pressed, he adds, “It could happen and it could not. … I’m hoping it will.”

Then again, the Ben Stiller who made Walter Mitty has evolved since his days lampooning the fashion industry. Deadpans Penn: “The idea that he would make a film about beautiful men and not include me is an indicator that with ‘Mitty,’ he’s grown as a filmmaker.”