Ben Stiller’s good sense of direction

The year is 2024. You are Ben Stiller. You have a film out in January. Another in March. One more in April. Then in June. Again in July. And, for good measure, one in December. That’s six films in twelve months; all comedies. Among them, Dodgeball, Meet the Fockers, Along Came Polly and Starsky & Hutch. Together, they make over $1 billion. It’s a multiplex monopoly! A box office bonanza! Next year, you’ll star in the first Madagascar film. The year after that, the first Night at the Museum movie. And so on, and so on.

The year 2004, then, was Stiller’s Super Bowl: his highest-flying, fastest-living moment. And yet, in March of that year, at the storybook Chateau Marmont on L.A.’s Sunset Boulevard, he still found time to give a charming, effusive exclusive to The Observer Magazine. It’s a fascinating, insightful interview – made even more so with two decades of hindsight. Why? Because, rather than puffing up his half-dozen new movies to The Observer, a “laid-back and low-key” Stiller spends much of the meet-up discussing small screen matters.

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“I watched a lot of TV,” says a 38-year-old Stiller in The Observer piece of twenty years ago (which also sees him cite The Partridge Family as his favourite childhood show, and reveal a lapsed crush on The Bionic Woman). “Too much TV, probably. You know, it’s like a drug.” In our new age of bingeing, there’s a whiff of intoxicating prescience to his throwaway words. But that’s Stiller: ever-switched-on, ever-tuned in, a man abreast of the times. It also may be why, 20 years later (when, once again, he has a new film to promote) we’re still mostly talking television. This time, the subject is the fluorescently perplexing psycho-thriller Severance, which returns to Apple TV+ for its second season in January, and which Stiller directs. He’s even back at the Chateau Marmont.

“You know, I saw my first topless woman at the Chateau,” laughs Stiller today (now 59; equally laid-back and low-key). “Really! It was by the pool, and I was probably only about eight years old. I was there with my folks, and this famous American television star, Tony Randall – a very funny man – just pointed her out to me. It’s a ridiculous place, in terms of the crowd that comes in and out, but so many formative moments of my life happened there.”

The legendary hotel exists behind something of a looking glass, at once unmistakable and unbreachable to all but the most capital of A-listers. But that’s why Stiller’s parents held a much-coveted key. Jerry and Anne – better known as Stiller and Meara – were a comedy duo who stood atop American show business for decades. The family, however, lived together in New York, where Stiller’s childhood home was captured on countless rolls of Super 8 film by his father. Stiller was gifted his own camera, a Fujica, when he turned 10, and he’s currently sifting through reel upon reel of old footage for a documentary he is making about his parents. “I’m living in those movies,” says Stiller, “and it’s amazing. They seem to get more and more valuable as I get older, like a window onto the past. They really are something else.”

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Amongst the videos can be found Stiller’s first films as a director – ambitious, choppily edited efforts created with his friends. Together, the teens would return from cinema trips and attempt to recreate blockbusting special effects of the time. Jaws in a bathtub, say. “Or making people disappear. Or even stop-motion animation” says Stiller. “Living where we did, it was a bit rough-and-tumble, and I’d get mugged once in a while. So lots of the movies would also be about kids going out for revenge, beating other kids up.”

When Stiller first saw The Fabelmans, Steven Spielberg’s recent semi-autobiographical drama, it unlocked a long-dormant childhood memory. “I told this to Steven,” he smiles, “that I loved the sound in the movie of the editing process – those little editing machines they had to cut the film. I remember them so well. But I was a less-accomplished Steven Spielberg! I wouldn’t even finish my movies all of the time. But I did make a lot of them...”

“So many formative moments of my life happened here...”

While acting on Broadway (Stiller’s debut came in a 1986 production of The House of Blue Leaves), he even corralled his castmates into filming a short spoof of The Color of Money. Stiller, not for the last time, took on the task of impersonating Tom Cruise. “It was post-college, and I was just trying to figure out what to do,” he says of dreaming up such sketches. “And I wanted to get on Saturday Night Live.”

He did. But, preferring to pre-record skits over performing them live, Stiller’s SNL tenure lasted under a month (during which he imitated Bruce Springsteen and, once again, Tom Cruise). In Los Angeles, however, MTV was crackling into life and, in 1990, The Ben Stiller Show arrived. It lasted just two seasons, but subsequently won an Emmy for writing and became another of Stiller’s formative moments. “Although I wasn’t quite ready for the prime time back then,” he laughs. “We were kind of figuring it out as we went along. But I was really into the directing back then, and MTV were willing to take chances on people for low budgets.”

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A group of film producers, including Danny DeVito, saw The Ben Stiller Show and decided that they, too, were willing to take a chance on the fledgling director. This led to Stiller’s feature directorial debut, Reality Bites, in 1994. With a soundtrack featuring Lenny Kravitz, New Order and Squeeze, the film is a haystack of excellently deployed needle drops, including ‘My Sharona’ by The Knack (which Stiller successfully snatched away from Pulp Fiction). “I also remember wanting ‘All I Want Is You’ by U2,” he adds, “which we were only lucky enough to get because Winona [Ryder, the film’s star] knew Bono. She just called Bono up and we got it.

“But [music] is so powerful when it’s done right by directors like Tarantino or David O. Russell. There are some incredible montages and sequences set to songs.” 1978 war drama Coming Home, Stiller says, uses ‘Sympathy for the Devil’ by The Rolling Stones to excellent effect – so much so that he broke out the track for Tropic Thunder, his fourth film as director (after Reality Bites, The Cable Guy and Zoolander). Recently rediscovered on streaming, Tropic Thunder has developed something of a contentious reputation today, one it only flirted with upon release in 2008. It features a pre-Marvel Robert Downey Jr. lampooning method actors by wearing blackface, a move Stiller admits was always “incredibly dicey”. Yet, incredibly, Downey Jr. received an Oscar nomination for his performance.

“And comedy has always been overlooked in the awards world,” says Stiller. “But I always stand by that movie because, to me, the intention is so clear: it’s to make fun of actors. And we do need to be able to push boundaries and take chances. Otherwise, when people say ‘no’ too much, when the studios and people making those decisions keep saying ‘no’, the people who are trying to make things, after a while, don’t have the will anymore. They stop trying. That’s why it’s up to creative people to keep trying.”

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Tom Cruise, Stiller says, is an example of an actor who “gets it”. Cruise, too, pops up in Tropic Thunder as a loathsome, large-handed caricature of a Hollywood mega-mogul. But he first worked with Stiller in 2002, during a now internet-famous skit for the MTV Movie Awards in which Stiller plays Cruise’s Mission: Impossible stunt double. “He was willing to go there with that,” nods Stiller. “I think most serious actors have a sense of humour about themselves, and Tom’s always had that – while being able to maintain his brand. He’s been very smart about it.”

When Tropic Thunder landed on streaming, Stiller requested that the director’s cut version be shown. “Because it’s so much better! There are things you might tighten up in the moment but, sometimes, when we did test screenings back in the day, I feel like I let myself get influenced too much by wanting to get a good score because of pressure from the studios. The great thing about streaming is that there’s an opportunity now for stuff to live on, stuff that would otherwise just sit on the DVD shelf.”

Streaming is also home to Stiller’s latest acting gig, a sugarplum-sweet festive comedy on Hulu called Nutcrackers – his first lead role in over seven years. The film sees Stiller’s workaholic Mike whisked away to a farm in rural Ohio to care for his four unruly nephews, his sister and her husband recently killed in a car accident. It’s a gentle callback to the wound-too-tight types that characterised Stiller’s earlier work. There’s a little of his hen-pecked Meet the Parents protagonist, Greg Focker, in there. There’s a hint of Stiller’s bereaved Chas Tenenbaum from Wes Anderson’s seminal The Royal Tenenbaums. There’s even something about There’s Something About Mary’s dorky-but-determined Ted Stroehmann in the mix. But painted with more pathos.

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Because this is new Stiller. Still-here Stiller. Today’s Stiller is a vintage; a man matured. He’s the Chateau’s best bottle, a well-rounded, well-grounded performer who has knocked the brasher, bluer corners off his comedy. These days, he’s flecked with grey instead, slightly unwound – slower, but sharper. The last 20 years have put a new lens on his life, and left it happily focused. The break from lead roles (his last, in 2017’s Brad’s Status, saw him directed by The White Lotus’ Mike White), has helped.

“There was this moment, after Zoolander 2,” says Stiller of his underperforming 2016 sequel, “where nobody really liked it, and it wasn’t a great time for me. Stuff in my life wasn’t great, but that was more on me than anything else. But it became my outlook. So I was trying to figure out what to do. There was this moment where, I think, if that movie had done well, they might have said: ‘Let’s do [Zoolander] 3. But nothing was coming in. It really wasn’t.

So Stiller stopped. He pressed pause, and asked himself: What should I do next? What do I want to do? What actually makes me happy? “And I had this realisation,” he says, “that I didn’t want to direct and act at the same time – for a while.” He slipped more completely behind the camera, beginning work on crime drama Escape at Dannemora (which also recently arrived on Netflix). Based on a real-life prison break, the show was eulogised upon release, with Stiller’s direction even scooping him a Directors Guild of America Award. “I have no idea why I won!” he laughs. “I was incredibly gratified, it was such a great feeling. But every time you go out there, you try to do your best. In any creative process, there is this ‘thing ’ of, like, is this going to be good or not? But the thing is, you can’t control it. You just have to jump in and go for it. So, for me, making that was incredibly fun and I didn’t feel any pressure or anything, I just felt the enjoyment of being able to work on that scale, on that story. And every day of it was really just a fun process.”

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Stiller has found a new home in the television industry, but is quick to add that the big screen will always be his first love. “I always loved movies,” he says, “although I was talking to my daughter last night, and she said that some friend of hers can’t watch movies anymore – because they’re ‘too long’. So it really has all changed, you know? Social media has really affected attention spans. The long form on television is interesting, though. I look at them as if they’re little movies, you know?”

Which brings us neatly to the carpet-tiled world of Severance. Stiller directs and produces the Apple TV+ hit, which follows a team of office workers who have surgically split their brains between their work and personal lives. It’s mind-bending stuff, trippy enough to trip you up if you don’t pay attention to every unexpected twist and highly stylised turn. Covid postponed the first season’s filming several years ago. Last summer’s SAG-AFTRA strike disrupted production on season two. But the team has overcome difficult second album syndrome – they’ve sidestepped the sophomore slump – and they’re back to see in 2025.

“It’s mostly about trying to keep the DNA of the show,” says Stiller of Severance’s return, “and that’s something that I think gets affected, in a way, when people watch the show. You’re trying to stick with what people feel they’re connecting with. And, while we’re not adjusting it based off people’s tweets or anything like that, it is amazing to have that engagement with the fans, and to hear people pick up on different things. Some people connect to the production design, some people to the humour, some people to the mystery of what’s going on. But, for me, it’s just about figuring out how to expand, not staying in one place with the show and expanding our horizons – leaning into the things that only this premise can do.”

“We definitely need to bring back comedy...”

The second season opens with the ‘ping!’ of Adam Scott’s hassled protagonist emerging from a lift, before he frantically takes off along the bright white, Kubrick-coded halls of the show’s setting, Lumon Industries. It’s an arresting sequence, one that grabs you by your Lumon lanyard and doesn’t let go. “We wanted to do something really special to kick off the season,” Stiller says of the opening. “To ratchet it up. That’s the fun thing about getting to work on a second season – everybody’s got a rhythm going with each other, and you can figure out what to do to push the boundaries.”

This meant reaching into the toybox, and pulling out the ‘bolt arm’, a “computerised motion control arm” that Stiller first saw used in the 2020 remake of The Invisible Man. They made a previs of the Severance sequence, he explains, then broke it up into over a dozen pieces that they’d seamlessly reconnect in post. It’s technical talk, but there’s a certain vim and vitality to Stiller when discussing direction that keeps you engaged. Perhaps it’s the performer in him, but his every note and explanation whips along like tightly written dialogue. ‘Director’ is a character Stiller inhabits with ease; his speeches of re-shoots and storyboards like soliloquies. Listen closely, and you can almost hear that Spielbergian film cutter clicking away behind his eyes. “Well I’m much more comfortable as a director,” he says of this professional happy place. “I don’t consider myself a showrunner-type of person. I feel that I can best express myself by directing.”

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Stiller has several options for his next directorial project. There’s the documentary about his parents, for one. A film about the first American to win the Tour de France, for another. Perhaps even an adaptation of podcast Bag Man, which detailed the audacious cover-up of Vice President Spiro Agnew taking payoffs while in the White House, for a third. “That one I thought was very topical,” says Stiller, “and probably will remain topical for a while.”

But there’s also more acting to come. Stiller recently bristled up some attention with a (sadly fake) horseshoe moustache in New York while filming legacy sequel Happy Gilmore 2. He’ll star as literary titan Norman Mailer in true crime story Belly of the Beast alongside Colin Farrell’s real-life, long-time convict. And he’s also producing The Dink, a sports comedy about competitive pickleball in which he plays a small role – alongside Andy Roddick and John McEnroe. “That one’s really fun,” he says, “like a comedy from back in the 2000s. A flat-out comedy. And I just feel as though, lately – and maybe this is since doing Nutcrackers – that for all the tension and strife in the world, for all the divisiveness, that something in me is just enjoying jumping in and doing comedy. Because it seems like now is a time that people can appreciate it. We definitely need to bring it back in the movies.”

There’s another sports comedy that could deliver just that. Since 2013, Hollywood has been awash with whispers of a certain Stiller sequel, a follow-up to one of those half-dozen 2004 releases, and one of the several films in which he has starred with Christine Taylor, his wife of 24 years.

But does he know anything about Dodgeball 2? “Not on my end,” says Stiller. “I think they might be trying to make it, but I’m waiting for the day that Rawson Thurber, the writ- er-director of Dodgeball, calls up and says: Hey,I have an idea and I want to do it. I would love to work with Vince [Vaughn] again, I think he’s a genius – and one of the funniest people ever. But I feel like that was Rawson’s baby. And not every movie has to have a sequel. But if Rawson felt that he had an idea and wanted to do it, then I would jump in.”

For now, however, Stiller is happy where he is. He’s happy to be directing, producing, and pushing his limits as a filmmaker – on screens small and big. When he was making The Secret Life of Walter Mitty, his fifth film as director, he felt the first flicker of this total immersion; his creative sweet spot. “I remember,” he says, “when I was making that movie, I was really in it. Every piece of music that I listened to, everything that I watched or thought about was about it. And that’s the great thing about being in process with something, I think, when you’re making something, is that you’re kind of attuned, and you’re just trying to put all of that energy into the project that you’re making. That’s the joy, I think, of being creative. It’s really a gift, that you can spend your time doing that.”

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It’s a healthy, high-yielding outlook, one that surely comes with age. It also calls to mind something a younger Stiller said in that decades-old interview for The Observer Magazine. “People have told me that I tend to be a little bit obsessive,” he’d admitted. “But I’m trying not to be that any more. I’m a recovering obsessive.” If today’s Stiller is anything to go by, then consider him recovered. He may be eager, over-enthusiastic at times – perhaps even emotional when describing his passion projects. But not obsessive.

The year, then, is 2024. You are Ben Stiller. You’ve got a bittersweet, snow-dusted comedy currently streaming. In January, the second season of your acclaimed television show will be unveiled to its adoring international fanbase. Soon after, you will start piecing together the story of your parents’ lives. Work is steady, but more rewarding than ever. And, after decades of challenging norms and taking risks, you’ve learnt to trust your sense of direction.

Thanks to...

Lighting Tech: Ram Gibson

Photography Assistant: Trevor Smith

Grooming: Natalia Bruschi

Tailor: David Viato

Style Assistant: Bin Nguyen

Production: Freya Anderson

Location: Chateau Marmont, LA

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This feature was taken from our Winter 2024 issue. Read more about it here...

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