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The Evolution of Ben Stiller

His journey from nerdy New York kid to hip Hollywood royality proves there’s something about him

Ben Stiller

Ben Stiller, March 14th, 1997

Paul Drinkwater/NBC/NBCU Photo Bank/Getty

BEN STILLER’S LOS ANGELES apartment is striking for a number of reasons (the penthouse deck with a view of the Wilshire Country Club springs to mind), but what stands out most is why he feels at home there. “What I really like,” says Stiller as he shows you around, “is that it feels like a New York apartment.”

He’s right. Much like Stiller himself, the home seems slightly out of place in the high glare of Hollywood, more subdued, the kind of space as likely to have the curtains drawn as it is to have the sun pouring in.

Stiller points out the hardwood floors, the Twenties-style kitchen, the original moldings. In the large main room of the duplex’s bottom floor, there is a collection of black-and-white photographs, nothing else – like a SoHo gallery space.

As he gives the tour, Stiller is warm; yet, for someone who has made his mark in comedy, he does not strike you as the casual sort. He is unfailingly polite; he is friendly; but there is also a quiet intensity and a nervousness that seeps into the air around him. You like him. You just wouldn’t call him to entertain at a child’s birthday party.

“I’ve never really felt like a funny, funny guy,” says Stiller as we make our way to the deck. “I’ve never really felt like Mr. Life of the Party. People who know me know that I’m not the most gregarious person. I’m trying to open myself up more. I’ve realized in the last few years that my state of mind affects how I live my life.”

Stiller’s mind these days must be in a dizzy state – a career high induced by the sheer goofiness and phenomenal success of There’s Something About Mary. Stiller has always been one of the most versatile talents of his generation: an Emmy-winning writer (for The Ben Stiller Show); a director of major stars in major motion pictures (Winona Ryder in Reality Bites, Jim Carrey in The Cable Guy); and a steadily employed actor drawn to small, intriguing comedies such as Flirting With Disaster, Zero Effect and the controversial Your Friends and Neighbors. But rarely have the heavens been better aligned for a performer than they are now for Stiller. First comes There’s Something About Mary, the summer comedy that won’t quit even deep into the fall and the kind of colossal hit that every star needs. At the same time, Stiller nails a performance as a junkie TV writer in Permanent Midnight that most serious actors wait a lifetime to deliver. After a career spent working diligently, Stiller has finally hit the big time by shooting dope, donning braces and getting his penis caught in his zipper.

But then, the map of Stiller’s world has always been drawn with blurry borders between reality and pop-culture fantasy. As a child, he was taught to swim, in Las Vegas, by the Pips; he watched home movies of Rodney Danger-field holding him when he was an infant; Stiller even had the Swami Satchidanada borrow his skateboard outside the Stillers’ apartment building, on Riverside Drive in New York. When one of the Beatles’ robed gurus of choice borrows your skateboard, it’s tough to talk about a normal childhood with a straight face.

Stiller’s parents, Jerry Stiller and Anne Meara, are a veteran comedy duo and were thirty-two-time guests on The Ed Sullivan Show. (Today, Dad is best known as Frank Costanza on Seinfeld, and Mom from movies like The Daytrippers.) The pair often traveled for work, leaving Ben and his older sister, Amy, alone. Upset that show business had taken their parents out of town, the two would fill the void with show business. Not surprisingly, both are now actors. From the moment Ben began to look at the world around him, he has been building his body of work.

“Ben and Amy did a lot of films together,” says Anne Meara. “They would do show tunes and do our act. We weren’t there a lot, and I think that was painful for them.”

“But we didn’t want to go to L.A.,” says Jerry. “We thought a bigger danger was growing up in a community where the neighbors were all stars and the kids were in competition with their parents’ roles.”

The irony is that while his parents agonized over whether to live in New York or Los Angeles, Stiller was learning to exist in the entertainment industry. Today, at thirty-two, Stiller lives comfortably in all three.

Scene 2 – AS STILLER lounges on his deck in L.A., he tips back in his chair and tries to make some sense of it all. He has spent a great deal of time in therapy – “I haven’t been going for about a year, but I actually really like it,” he says – and his approach to answers often seems rooted in those sessions.

“I’m working on that whole happiness-balance issue in life,” says Stiller. “I think you’re always working on that. I tend to lean more toward the work side of life. It’s important to find happiness outside of your work.”

Yet, if you listen to the people who know him best, you wonder how precarious that balance really is.

His friend (and Permanent Midnight memoirist) Jerry Stahl: “I’ve never seen anybody put in the sheer man-hours Ben does. Being a forty-five-year-old guy with a liver that lives in an adjoining county, I sure as hell can’t keep up. It’s amazing.”

His father: “He works much too hard, for my money. I just wish he would take a rest.”

His friend and frequent collaborator Janeane Garofalo: “He works harder than anyone I know. He never, ever, ever is not working. It’s actually bizarre.”

Not that Stiller seems unhappy. On the contrary, as he sits on his deck, feet propped up, Stiller is content, almost unable to imagine another way of life. It’s as if because film was his source of pleasure as a child, his work and life have morphed into one. Still, it’s difficult to understand what drives him.

“As a kid, I was just fascinated by the mechanics of filmmaking,” says Stiller. “I thought I was going to be a cinematographer for a while. The idea of making movies was so much fun. Then, as I got older, acting and writing and the content became more important.”

The question is rephrased. His fascination with film is a well-known fact, but what drives Stiller personally?

Scene 3 – STILLER’S FIRST films were highly derivative. Based mostly on his favorite television shows and on movies like Airport 1975, they articulated his obsession with popular culture yet displayed little vision of his own. Of course, he was barely a teenager. But still. His seminal work had actually blossomed earlier – when he was able to locate his demons. He found them on Eighty-fourth Street in Manhattan.

Stiller’s apartment was on Riverside Drive; his best friend lived on Central Park West; in between was Brandeis High School. “Those four or five blocks were like a gantlet,” remembers Stiller. “I used to live in fear of those Brandeis kids.”

“One day he was mugged twice, once on the East Side and once on the West Side,” says Jerry Stiller. He laughs. “And once they came back and said, ‘We don’t like this watch.'”

All this helped young Ben evolve a personal style of film. “One guy would get mugged and then we’d run after them through Riverside Park,” recalls Stiller of his earliest works. “They all had names like They Called It Murder or Murder in the Park.”

As Stiller’s adult career blossomed, it followed a similar path – The Ben Stiller Show showcased his ability to ape his favorite movies before homing in on his darker depths. Yet Stiller’s range almost never came to light. Perhaps having missed his dramatic turn in They Called It Murder, the producers of Permanent Midnight first offered Stiller’s role to David Duchovny and (no, this is not a typo) Jon Bon Jovi. Even Stiller had his doubts.

“The biggest challenge was convincing myself that I was allowed to play that part,” Stiller says. “I was fascinated by it. There were a lot of similarities as far as Jerry Stahl as a person – this Jewish comedy writer in L.A.”

Based on Stahl’s autobiography of his descent into the hells of heroin and Hollywood, the film is as relentless as any in recent memory, and Stiller – who barely ate during the course of filming – is riveting.

“Meeting Jerry and talking about this role really changed me as a person,” says Stiller. “The key for me was that he showed me I didn’t have to be a drug addict to understand why addicts take drugs – it’s about not wanting to feel pain. I figured out what I did in my life to keep away that pain.”

And that is?

“I’d rather not talk about that,” answers Stiller. He pauses. “But work is definitely one way.” In the end, what emerges from Stiller’s work in Permanent Midnight is that perceptions of him have been permanently, chemically, altered. “There’s a moment in Permanent Midnight when Ben’s in the front seat of a car, shirtless, sweating, baby next to him, ready to shoot up,” says Stahl. “It took a long time to set that scene up. I got into the back seat and was talking to him, and Ben said, ‘The gaffers are looking at me like I’m a fucking creep. It’s like I’m not even human. I’m like an animal.’ I said, ‘Yeah, that’s exactly what it was like. You got it.'” Stahl pauses. “He became it. He became a thing – the way, in that moment, as a dope fiend, you’re completely isolated, you’re not a part of the human race, you’re a thing. And then he had a moment of presence of mind to realize what he’d become and shook himself up. That is a transcendent moment.”

Scene 4 – STILLER’S FIRST major drug experience was not your standard fare. Unless it’s common for a sixteen-year-old to drop two tabs of acid and, just as the visions are ripping through his brain, phone his parents while they film a guest shot on The Love Boat.

BEN STILLER: I was scared, and I didn’t know who to talk to. I didn’t have that many close friends in high school. Luckily my dad was really open.

JERRY STILLER: We were on the phone for a couple of hours. He was scared that he’d done something terrible. I didn’t know what the hell he was talking about, to be honest with you. He said something about acid, and, to me, acid was marijuana. So he started explaining that this was tough stuff.

BEN: For about six months afterward, I was really freaked out and scared I was going to have a flashback.

JERRY: One night we were driving and he said, “I have to talk to you about this.” To this day, it’s something that really sticks with him.

BEN: I remember sitting in the car. My dad’s a very spiritual guy. For all the personae he has, he’s really not like that. When I was going through that, he was incredible and open and warm and spiritual.

JERRY: I said, first, that I didn’t want him to feel guilty and, second, that Anne and I were working in L.A. and it wasn’t like we were abandoning him. He felt at the time that his parents had disappeared on him. So he did something that kids do when their parents go away. I also had to explain to him that his mind was OK. He was so concerned. [Pauses] It was one of the closest places we’ve ever been together.

BEN: Even though he didn’t really understand, he was able to somehow empathize. I have a strange relationship with my parents. I admire both of them, but it’s not the easiest relationship in the world, and we feel it on both sides. Yet we both have respect for one another. I’ve always wanted just more of a friendship with them. To a certain extent I’ve been able to develop that more with my mother than my father. My father is always going to be looking at me as his son.

Scene 5 – IT’S MIDAFTERNOON in New York, and as we walk toward Stiller’s childhood apartment on the Upper West Side, he suddenly changes his mind, hops in a cab and heads downtown to wander the neighborhood where he now keeps a place of his own.

Immediately it’s clear that being a hometown celebrity is not an anonymous condition. There are the There’s Something About Mary fanatics on Second Avenue, the guy near Third who displays the article he’s reading about Stiller in today’s New York Post, the students on University Place who invite him to pop in to the NYU Jewish center. Stiller even bumps into comedian Gilbert Gottfried and stops to laugh about a plane ride the two once took together. Finally, as we make our way to his block, Stiller signs a few more autographs and looks up to see a college-age kid approaching sheepishly.

“Ben, um, hi,” the kid says.

“Hey,” says Stiller.

The kid fidgets. “I just wanted to say I’m a big fan of your dad’s.”

Stiller is silent for a moment. “Oh,” he finally manages. “Yeah, well, so am I.”

For Stiller, the shadows of the Upper West Side still have a very long reach. Many of Stiller’s childhood memories are fond: skateboarding and playing handball on the street where he lived; trick or treating without ever leaving the building; creating code knocks on the walls to send signals to his sister. But, as in many families, there were issues that would surface. And, as in many New York families, they finally brought those issues out, as adults, in group therapy.

“Our need to get closer as a family overrode any fear,” says Meara of the sessions. “We had a need to clean up stuff. You have to remember, when my kids were six years old, I was emotionally about three. Now that I’m older, I feel like I’m a better parent.”

There were certainly plenty of conflicting pulls on Stiller’s family, starting with the simple fact that the kids were half-Jewish, half-Irish-Catholic.

“The Irish side gets lost,” says Stiller. “It’s just because I look Jewish. But I’m half-Irish, and I feel very in touch with my Irish roots. I’ve gone to Ireland twice, and I love it there. I’m actually closer to that side of my family than my dad’s side. Yet in the media, it’s just the Jewish side. And I have all sorts of feelings about that because, after my bar mitzvah, that was really it for me in terms of being a religious Jew.”

Most of the Stiller family’s issues centered around its primary religion: show business. “Our whole family is so unique,” says Amy Stiller. “There are no twelve-step programs for my and Ben’s situation.” All four Stillers would travel during the summer, when mom and dad took their act on the road. (“Flint, Michigan; Dayton, Ohio,” recalls Ben. “It was fun. I have really fond memories of that.”) But during the rest of the year, one or both of Stiller’s parents were often working out of town.

“My sister and I really bonded when my parents were away,” says Stiller. “Hazel, our housekeeper, would stay with us. I love Hazel, she’s really warmhearted, but we could always figure out how to get away with a lot.”

A few times, when Stiller was thirteen and his sister was seventeen, the pair even went to Studio 54. “She dressed me up in, like, a Fiorucci yellow polka-dot shirt and Mickey Mouse sunglasses and, like, an Army jacket,” says Stiller. “We just hung out together all the time. We acted out movies and things like that.”

Oh, yes, show business again.

It would be unfair to cast the role of the entertainment industry in Stiller’s life in an entirely unflattering light. It was, after all, not only what inflicted pain but also what was there to give comfort. And to this day, though the dynamics might be complicated, the Stiller family is quite close.

“Was my mother guilt-ridden about the way she raised us?” asks Amy Stiller. She laughs. “It’s like, ‘Mom, get over the guilt.’ You know what? My parents are really good people. They love us.”

Says Jerry Stiller: “I think the kids knew that although we were in the business, we were also there for them. Even though they resented moments when we were away and acted out their own anger, they understood that we were, number one, a family.”

As if to prove the distance that the shadows of those early days can travel, Ben Stiller has signed a deal to develop television shows for ABC. One project in the talking stages is a series about what it was like to be a child in New York in the mid-Seventies.

Scene 6 – AS BEN STILLER’S evolution continued, he flirted briefly with college but decided to drop out of UCLA after less than a year. Met with resistance from home, Stiller marched his father to class with him. “He really was right,” says Jerry Stiller. “So I said, ‘OK, but you’re not just going to lay around.’ Sure enough, he got his body in shape, he got rid of his acne, he started studying and auditioning. At that point, I realized this was a rather serious young man.”

A pattern emerged. Namely that the moment that Ben Stiller has felt comfortable in one arena, he has abruptly moved on to another. He landed a role on Broadway, in The House of Blue Leaves, only to follow that up with a short film, The Hustler of Money, which led to a five-year contract, in 1989, with Saturday Night Live. Unhappy that he was not allowed to make the short films he desired, Stiller quit after just five episodes. Word was that Stiller found the atmosphere far too cutthroat.

“That’s kind of out of context,” says Stiller. He pauses. “Especially since I’m hosting on October 24th.” And then he bursts out laughing.

By the time The Ben Stiller Show debuted, in 1992, it seemed that Stiller was absolutely in his element. Featuring inspired collaboration from Garofalo, Bob Odenkirk (of HBO’s Mr. Show With Bob and David) and NewsRadio’s Andy Dick, the show was a pitch-perfect reflection of Stiller’s twisted sensibilities (Eddie Munster replacing Robert De Niro in Cape Fear) and pop-culture vocabulary. Though the show was canceled after thirteen episodes (which tends to happen when you finish 138th in the ratings out of 138 shows), Stiller won his writing Emmy. Naturally, he turned his back on sketch comedy and began his career as a director, with Reality Bites.

“You can’t do everything at the same time,” explains Stiller. “For me, in my head, I’m always a director, and I’m always an actor and always a writer. I feel like I’m seeing what feels right. I just happen to be doing it out in public a little bit. I’m just trying to find my voice.”

Scene 7 – IT’S SATURDAY night, and Jerry Stahl is reading from Permanent Midnight at Book Soup, seemingly the only bookstore in the entire Los Angeles metropolitan area. Stiller has come to offer moral support. The two have known each other for just two years but have already collaborated on a screenplay based on What Makes Sammy Run?, the classic Budd Schulberg novel about society’s simultaneous repulsion and obsession with Hollywood fame. Each considers the other his best friend.

“Ben has an emotional acuity and reads situations like no one I’ve ever seen,” says Stahl. “It’s truly a level of depth that I haven’t encountered very often. The last place you’d look is in a movie star. Go figure.”

It is the type of friendship that Stiller prefers, low-key but with an obvious mutual respect and trust.

“I have a lot of different kinds of friends, but I don’t have a lot of close friends,” says Stiller. “I wish I had more. A lot of my friends don’t hang out together. Whenever I have a birthday party, we get all these people together and it’s a weird hodgepodge. It always makes me really uncomfortable.”

It seems that Stiller gets uncomfortable easily. “I do,” he says. “I do.” When Stiller first arrived in L.A., he spent most of his time at the Improv (where he met Garofalo and many of the artists who repeatedly surface in his work), yet Stiller was never a stand-up comedian and was not likely to be entertaining the troops at the bar.

“Ben does not feel comfortable in groups,” says Garofalo. “For his humor to come out, it has to be basically one-on-one. He’s not loud, and you have to be sitting very close to him to hear it. He doesn’t laugh very often. He laughs occasionally very heartily, and then I consider it a big victory.”

Still, the biggest recent change for Stiller socially is that he has broken up with actress Jeanne Tripplehorn (Basic Instinct, Waterworld) after five and a half years with her.

“I’m alone for the first time in my life, relationshipwise,” says Stiller. “It’s weird. To deal with being alone has always been a challenging thing for me. I’m having trouble even dating. I really do feel that at this time in my life, I want to concentrate on work. But it can also be really empty if you don’t understand how to nurture whatever side of your life isn’t about the work.”

Stiller doesn’t particularly care to discuss the details of the split outside of what is already known: that the pair were engaged but have ended things amicably. They still speak, but, even if they didn’t, both are in the public eye, so there are always reminders.

“It’s impossible to avoid it, so you have to be in a place where you’re OK with whatever comes along,” says Stiller of seeing Tripplehorn in the press or onscreen. “Luckily, now, I feel that way.” He pauses. “I wasn’t always like that.”

Scene 8 – STILLER IS JUST beginning a new thought when he is hit with a dental emergency. A temporary cap on one of his front teeth has come loose, leaving him to clutch at his mouth every time he tries to utter a word that begins with an f. At one point, attempting to explain a connection he felt with Stahl, whose father was at one time the attorney general of Pennsylvania, Stiller says, “His fa … his fa … Everybody knew his dad.” We call a timeout for some quick oral surgery.

Stiller’s car is parked in front of his building, and as we climb in, he gives an embarrassed grimace.

“I just got this car six months ago, but I think I’m going to get rid of it,” he says. “Every article always says, ‘Stiller drives a new black Jaguar.'”

You tell Stiller he shouldn’t worry about what anyone thinks.

“Yeah,” he almost yells. “Right. Exactly.”

Such is Stiller’s relation to his fame. He works tirelessly for it yet seems awkward with its existence. Sensing that There’s Something About Mary could be the enormous hit it has been, Stiller fought for the role even when studio executives were less than enthusiastic.

“The studio didn’t want me at all,” he says. “Even going into the first day of shooting, I thought I might get fired.”

And now that Stiller’s vision has proved prophetic, he seems almost apologetic. You begin to realize just why he has worked doggedly for almost two years to turn What Makes Sammy Run? into a reality.

Stiller has tested the waters of major studio pictures only twice, and the results have been sink and swim. We’ll start with the swim. “Working with the Farrelly brothers was the most stress-free experience I’ve ever had,” says Stiller of the There’s Something About Mary directing team. “They’re fun, open. It’s, ‘We’re going to finish early and then go play golf.’ There was no stressing about what the camera angle was going to be. I really learned from that. It was, ‘Wow, you don’t have to stress out, and you can still have this incredibly funny movie.'”

Then, however, there is Stiller’s other, unhappy dip into the mainstream. The studio imagined The Cable Guy as another Jim Carrey romp to a box-office bonanza. As Stiller envisioned the film, it was a twisted morality tale of what can happen to a generation raised – as he was – on television. The studio, as it turned out, was not pleased with what TV had done to Stiller’s mind.

The Cable Guy really affected me,” says Stiller of the savaging he took when the film failed to live up to box-office expectations. “I felt really connected to the movie, I’m proud of it, and the experience of making it was incredible. But then it came out, and it was not fun. It made me much more aware, for better or for worse, that I have to take responsibility for my own work. I haven’t directed anything again yet because I don’t want to just direct something for hire.”

He continues: “It’s much more important to me now that I relate what I do to my personal life somehow. Not that I want to bore people. I just don’t think I want to be directing big, broad comedies. I’d like to get more into the Albert Brooks, Woody Allen state of mind. It might not reach everybody, but it will be funny.”

Because Stiller cites Brooks continuously as an influence – from Brooks’ early days making short films for Saturday Night Live to his later features like Lost in America – you wonder whether Stiller almost looks down on the mainstream success he’s poised to achieve, whether he would give it all up if he could use Brooks’ career as a blueprint.

“It’s not like I have these people on a pedestal or anything,” says Stiller, a tad defensively.

Of course not, you answer. You’re not trying to imply that Stiller has an Albert Brooks poster up in his home.

Stiller shakes his head slowly. “I do, actually,” he says.
Excuse me?

“I have a Real Life poster,” says Stiller. “I love Real Life. It’s one of my favorite movies of all time.” He laughs and then stares at his lap. “Sorry.”

Scene 9 – AS THE MOVIE OF Stiller’s life unfolds, what is most striking is how little has changed. Today, Stiller is still doing what he’s done forever: hanging out, watching television, making conversation about pop culture, excusing himself for a moment to be a part of pop culture, repeating. Except for hosting duties on Saturday Night Live and cable awards shows, Stiller has rarely indulged in the sketch comedy that first put him on the map. He has precise reasons for walking away, among them close encounters with the objects of his comically merciless parodies.

On one occasion, Stiller came face to face with Tom Cruise – whom Stiller had portrayed a number of times, including in a sketch featuring an aging Cruise trotting out his greatest hits on Broadway – when Tripplehorn co-starred with Cruise in The Firm.

“Someone had told Tom Cruise about it, and he wanted to see it,” says Stiller of the sketches. “We went to his house and he said, ‘Come on, let’s see it.’ I was like, ‘No, I’ll drop off the tape for you. I do not have the balls to sit in the room with you while you watch it.'” Stiller laughs. “He was extremely nice and cool about it, but it’s not something I want to spend my whole life doing – worrying about it.”

And yet, in many ways, these sketches could not be a better introduction to Stiller’s psyche. Funny, twisted, well-written, they are sharp comments on pop culture that can be articulated only by using more pop culture. For MTV’s Video Music Awards, Stiller played Bruce Springsteen going on the show FANatic, MTV’s stalking enabler, in order to meet Puff Daddy. You’d swear Stiller was making fun of Springsteen if it weren’t for the obsessive detail his characterization revealed.

“That’s me,” says Stiller. “I’ll take responsibility for it. I’m the guy who was a huge Bruce Springsteen fan but does the Puffy-fanatic sketch because it’s the only way I know how to express it. That’s one thing I’m sure of: I’m that guy.”

And so it is nice to see Stiller once again comfortable with the work that first showcased his talent.

“I don’t want to disown it,” he says of sketch comedy. “It’s part of who I am. But after my show, I felt I really needed to go off and do something as a filmmaker or an actor. Now I feel like I can do these sketch things again.” He smiles. “Of course, after I do that, I won’t want to keep on doing it.”

Stiller smiles again and glances across the stretch of L.A. laid out before him. It has been, in many ways, a liberating year. He’s had the breakout comedy hit his career always promised, as well as the startling dramatic role that only he could have known he had in him. Next he will direct one of a pair of scripts he has recently co-written. It’s as if the show-business life that Stiller began rehearsing for as a boy has finally revealed its adult shape. He still obsesses over the details. But as its star, director and writer, Stiller has finally gained creative control. Only he can decide when to type The End.

In This Article: Ben Stiller, Coverwall

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