Ben Stiller Is Esquire's March Cover Star

In 2001, Ben Stiller unleashed Derek Zoolander, the world's top male model, on the big screen. The movie bombed — initially — but over the years it gained a cult following, even among the fashion world it satirised. Now, 15 years on, Derek is back, but is the world ready?

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No one in fashion is hotter right now than the designer Don Atari. His most recent autumn/winter presentation – which was held in the middle of the night in a former medical-waste facility in Rome last summer — was an exclusive beg-borrow-steal happening in the industry. Lewis Hamilton, Mrs Sting, one of the Jonases, a model called Ana Beatriz Barros and "noted" fashion photographer Nigel Barker were all crammed into the front row. Olivia Munn, the US actress, flew halfway round the world to perch on a steel chemical drum. Old-media editors and new-media upstarts sat elbow to elbow, and all — no exceptions — had to wade through calf-deep toxic sludge to take their places.

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Don Atari's new showcase, which was cheekily and half-ironically entitled Old and Lame, did not disappoint. To specially commissioned music from A$AP Rocky, street-cast models — literally old and lame senior citizens in the main –— were paraded, seemingly befuddled, along a conveyor belt. Terrifying female glamazons called Angels of Death clad in leather and gas masks cracked whips, thrust pitchforks and discharged fire extinguishers. The clothes were audacious, tiptoeing a tightrope of bad taste: one old man was dressed as a boxer in a robe and heavy leather gloves; another wore a visor, body warmer and smoked a fag. Eventually, the moving runway appeared rather realistically to dump them into the jaws of an oversized meat grinder while the celebrities took snaps on phone cameras.

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For the finale, though, Atari did fall back on professional models. And he chose two of the biggest names the fashion world has known. Both have been in exile of sorts and neither had appeared on the catwalk for more than a decade. Epitomising Atari's vision of Old and Lame were Derek Zoolander and Hansel. They arrived on the scene in a pair of coffins.

Yes, Derek and Hansel, the world's least self-aware male models, the protagonists of the adored 2001 comedy Zoolander, are back. Much has happened since we last saw them foiling a plot to kill the Prime Minister of Malaysia. (If you remember, Hansel, played with louche flamboyance by Owen Wilson, engaged in a breakdance battle with an evil DJ, while Ben Stiller's uptight Derek pulled off a signature pose so revolutionary — the long-awaited Magnum — that it defied many of nature's laws.) But the intervening years have not always been kind to the pair. The Derek Zoolander Center for Kids Who Can't Read Good and Wanna Learn to do Other Stuff Good Too collapsed — literally. Hansel's face was horrendously scarred and he disappeared, with a sack over his head like the Elephant Man, and was last seen in India. Derek, for his part, fled the spotlight for a life of seclusion and perhaps, who knows, even reflection in the high mountains.

"It's really hard to satirise the fashion world," says Stiller, who as well as starring in the original movie, co-wrote the script and directed it; he undertakes the same duties on the new film, Zoolander 2. We are in Rome where the fashion show scene is being shot under an elevated bypass in the shabby-chic hipster enclave of San Lorenzo ("Rome's Williamsburg," a local helpfully suggests). Stiller has to be ready to jump both in front of the camera and behind it – this, on occasion, means he will be talking about camera lenses while wearing crotch-tight, gold lamé trousers – and now he's trying to make sure that the Don Atari show is both realistic and completely ridiculous. It's not easy. "It's hard to figure out how to top what's going on in reality," he continues. "Everything is so out of control."

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This is just one of the challenges that Stiller faces with Zoolander 2. Comedy sequels are notoriously difficult to pull off: do you repeat the formula and the jokes, but risk looking a pale imitation? Or strike out into new territory and potentially alienate your core audience? The decade-and-a-half that has elapsed since the original seems only to have intensified the pressure on Stiller to strike the right balance. Meanwhile, the fashion world has changed and the movie industry – attendances and profits down; DVDs and above-the-title stars facing obsolescence – is pretty well unrecognisable. Is there a danger in 2016 that Zoolander 2 could be so last season?

Stiller has a tendency to overthink everything as much as Derek underthinks it and is well aware of the challenge he faces. Zoolander 2 needs to be funny. "Well, hopefully people will laugh," he says. "There's this wonderful thing you get with a comedy. It doesn't matter what you're thinking, what ideas you have about visually what it's going to be, or tonally what it's like. If they are not laughing, I don't care how beautifully designed the shot is. They want to laugh, that's what they care about. If people say, 'I'm going to go see a comedy…' I appreciate that, I do, but it's a high bar."

For a silly film, it's a serious business. And with that Stiller returns to directing duties, making sure an industrial-sized vat of Don Atari stewed prunes is in place so that it can be disgorged over Derek and Hansel at the end of the runway — the ultimate indignity.

Zoolander — the original; the one with the gas-station fight; the one with the walk-off presided over by David Bowie where Hansel removes his underpants without taking off his trousers; the one where Derek is chided by Hansel to "Dere-lick my balls, capitan"; the one where Will Ferrell's deranged Mugatu splutters, "I feel like I'm taking crazy pills!" — was pretty much an unmitigated disaster. You might have liked it, perhaps you have even watched it more times than you can remember, but in film-industry circles, it is a cautionary tale.

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It was released in September 2001, a couple of weeks after the 9/11 attacks on the World Trade Center, at a time when a mass audience wasn't ready to be engaged by a male model's crisis over whether there's more to life than being really, really, ridiculously good-looking. Zoolander failed spectacularly to chime with the national mood in America and some reviewers felt its problems went even deeper. "There have been articles lately asking why the United States is so hated in some parts of the world," wrote film critic Roger Ebert. "As this week's Exhibit A from Hollywood, I offer Zoolander." Malaysia banned the film, after taking affront at the key role assigned to their fictional prime minister, and neighbouring Singapore joined them in protest.

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But Zoolander's troubled existence began long before the movie's release. Derek Zoolander first appeared in a pair of short films for the VH1 Fashion Awards in 1996 and 1997. The character was created by Drake Sather, a Saturday Night Live writer; his name was a nod to Mark Vanderloo and Johnny Zander, two of the most successful models of the time. Stiller recalls, "Derek came out of Drake saying, 'Hey, I want you to be a male model in this little sketch that we're doing.' And I go, 'Well, that's ridiculous.' And he says, 'Yeah, that's why it'll be funny. It's you doing it.'"

It's a few months after our meeting in Rome and we are in the Tribeca district of New York City now, having lunch around the corner from his office, while he finishes off editing the new film. Stiller orders a prawn salad with extra prawns and a Coke Zero. Zoolander in those VH1 skits is already not an ambi-turner — that is, he can't spin left at the end of the runway, only right — and has two signature looks: Ferrari, his "bread and butter"; and Blue Steel, which he saves for catalogue work and shoe campaigns. They are, of course, effectively identical. "It came of looking in the mirror when I was brushing my hair or whatever," says Stiller. "My wife would say, 'Why are you making that face? Why are you doing that?' And it's just that thing you do that you think makes you look good. Which really has no correlation to reality."

New Line Cinema, a division of Time Warner, wanted to make a Zoolander feature film with Stiller, who had recently completed a career-defining turn in There's Something About Mary. Stiller was inspired by Mike Myers' Austin Powers: International Man of Mystery, which New Line had released in 1997 — "he was taking these very broad characters and making movies that were incredibly funny and somehow worked in the long form" — and wanted to write and direct. There was a snag, though: because Derek had first appeared on VH1, the rights to the character belonged to Viacom, which owned the music channel, and its subsidiary Paramount Pictures.

Paramount was never especially enthusiastic about Zoolander, but the interest of a rival was enough to push it through. "I don't think they quite got the tone we were going for," Stiller says. "I don't know if they actually wanted to make it, honestly." The script, which Stiller drafted with Sather and John Hamburg, who co-wrote Meet The Parents (2000), went through multiple versions and a disastrous read-through. Meanwhile, Paramount — seeming to miss the essential joke of the piece — engaged another writer for the project and lined up hunky Brendan Fraser, flying high after George of the Jungle (1997) and The Mummy (1999), to play Derek Zoolander. Nothing came of this, but when Stiller was finally given the go-ahead to shoot, the budget was dramatically reduced; he then overspent by $6m and had to put in around $1m of his own money as a penalty to complete the film. On release, Bret Easton Ellis was paid an out-of-court settlement because the film's plot —solipsistic models who become assassins — bore a similarity to his 1998 novel Glamorama.

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Stiller is phlegmatic about that time, even about having to dig into his own pocket to pay the forfeit for going over budget. "Honestly, I don't think the studio understood the movie enough to say, 'OK, we want to pay the extra money'," he says. "Which is their prerogative, it's not personal, I really don't think it's personal…" He laughs unconvincingly, "Though it did feel like that at the time."

Such details, of course, are largely ancient history, but they came up for Stiller again when he started thinking about Zoolander 2. This first happened in 2005, just as the wounds from the poor reception of the original film were starting to heal and DVD sales finally meant that it had turned a very modest profit. A script was written that took place in Miami, but Stiller couldn't agree with Paramount again on the budget and Will Ferrell, on the back of Anchorman: The Legend of Ron Burgundy (2004), wasn't sure he wanted to appear. A version was hastily drafted without the Mugatu character. "That was considered," says Stiller, "but I always felt that Will and Owen were as much Zoolander as I was."

Another five years passed, the popularity of Zoolander grew. Now Justin Theroux, who appeared briefly in the first film as the DJ Hansel scuffles with, and who co-wrote Tropic Thunder (2008)  with Stiller, came in as the lead writer. Theroux, who cops to actually being genuinely interested in fashion, spent time "boots on the ground" at shows in Paris and industry parties. "I don't think most people saw the first one in the cinema," he says. "They saw it on DVD or cable or satellite, so it became [like] this rare piece of vinyl almost, that people discovered and really enjoyed sort of at home. So, in that way it was an indie that everyone got to discover on their own as opposed to being an opening-weekend smash. And that's part of the reason I think it's such a beloved movie, because everyone has a personal connection to it.

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"But it was weird because the numbers didn't add up to make a second one, even though it was a cult classic," he continues. "With studios, when the accountants recommend making a sequel they often point to the first one and say, 'How much did the first one make?' And it really did die at the box office, the first one."

As time moved on so, in some senses, did the appetites of cinema audiences. Zoolander was unabashedly silly: when Matilda, a journalist writing an article on Derek, played by Stiller's wife Christine Taylor, confesses to suffering from bulimia, he replies, "You can read minds?" In 2011, Adam Sternbergh in The New York Times Magazine called the film: "one of the last all-out, joke-driven comedies released before the rise and stifling reign of the jokeless comedy" – referring explicitly to The Hangover (2009) and Judd Apatow movies such as The 40-Year-Old Virgin (2005), which tend to favour crude visual gags and improvised bro-ishness over conventional jokes. In this climate, Zoolander 2 started to look even more of a risk.

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All the while, Derek and his crew were getting older and, in fashion terms, lamer. "Every time we'd go back into it another five years had gone by or whatever," says Stiller. "So in the first script Derek Junior, his son, was like four years old and now he's 10. Now he's 14! Literally we had to change the story. But eventually we got to a place where all the planets aligned."

So, it's a small miracle that Zoolander 2 exists. But the draining, soul-sapping experience of making the original has never left Stiller, as becomes clear very quickly when you speak to him about the new film. From the outside, it is easy to paint Stiller's career in primary colours: he has been in huge films (Meet the Parents, Night at the Museum and Madagascar, all of which became billion-dollar franchises) and very credible ones (The Royal Tenenbaums (2001), and two Noah Baumbach pictures, Greenberg (2010) and last year's acutely observed While We're Young). No modern comic actor has been successful for as long and in such volume as Stiller. Investing money in him is the Hollywood equivalent of putting your savings into premium bonds: over almost 30 years, his films have averaged $77m at the box office.

But it is the failures — if you can call them that — that rankle Stiller. Especially the ones he himself directed: Zoolander, and the very dark comedy The Cable Guy (1996), which starred Jim Carrey as a deranged TV installer. Carrey at this time was the biggest movie star in the world and received $20m for appearing in the film, the first time that barrier had been broken. The film did in fact turn a profit, but the reception was mixed, and it is this memory that has stuck with Stiller.

"Nobody wants to set themselves up for failure as a film-maker," he says. "You don't want to be: 'I'm going to make this movie that I know isn't going to work! For this studio, to lose them money! To show how different I am!' I don't think even the most anarchic film-maker wants that. You want to go: 'I want to make this movie for the right amount of money, that is different, have it make sense and hopefully not lose money. Maybe make money so I can make the next movie.' That's the economics of the business. You just want the opportunity to make the next one. That's the baseline."

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Stiller continues, The Cable Guy still apparently fresh in his mind: "It didn't do well and lost a bit of money at the time and people got upset. That's what I wish I'd been more aware of back then, but I wouldn't have known that unless I learned from that experience. And also thank Jim Carrey for not caring. For a guy who's at the top of his game, to make that movie at that point, because he was kind of anarchic and said, 'I'm going to do this.' Most movie stars do a certain thing that they do and stay in that lane because they are very smart about knowing how far they can take a chance. And Jim is that smart but also decided that he didn't care."

A large part of Stiller's longevity is down to the fact that he really does care. He is a famously tireless worker who — even when he is only being paid as an actor — involves himself in every aspect of a film's production. Often he will re-write the script, handpick the director and then cajole friends or people whose work he admires (he has a particular weakness for British comedians, especially Ricky Gervais and Steve Coogan), to appear in it with him. His attention to detail isn't always intentionally comical. While making There's Something About Mary, he argued endlessly with the Farrelly brothers, who directed the film, about the scene where he has sperm hanging from his earlobe. Stiller couldn't fathom how he wouldn't have known it was there, and wanted a scene written in earlier where his character was knocked on the head and lost sensitivity in his ear. The Farrellys, on this occasion, ignored him.

In person, Stiller is easy, entertaining and attentive company. He maintains eye contact intently and wouldn't, say, dream of checking his phone while he is in conversation with you. For any human being these days that's notable; for a star of his magnitude, it's definitely commendable.

But it is clear that Stiller is feeling the pressure with Zoolander 2 and he takes his responsibilities to promote it very seriously. On set in Rome, I was surprised to be joined by an exotic cluster of journalists from Germany, Mexico, Brazil and Australia. But overseas markets are of huge importance to films now and Stiller, especially, is an established draw abroad. It's expected that only 10 per cent of the audience for Zoolander 2 will be in America, a statistic unimaginable when the original film was released. Back then, being banned in Malaysia was something of a punchline; this time round, it would be a disaster.

Stiller has taken the publicity for Zoolander 2 very much into own hands. The film was announced in March 2015, when Derek and Hansel strode down the runway at the close of the Valentino show at Paris Fashion Week. At the end of the catwalk, Stiller grabbed the phone belonging to social-media entrepreneur Jérôme Jarre, who has more than 8.5m followers on Vine, and shot Blue Steel direct into the lens. When production began, Stiller used a Zoolander Instagram feed to drip-feed exclusives from the set. These have included a selfie with Justin Bieber, who has a cameo in the film. "In the last year of working on the movie, every time someone wants to take a picture, I'm almost trained now to do the Blue Steel thing," says Stiller. "Even when I think I'm not doing it, they're like, 'Oh, you're doing Blue Steel!' 'No, I'm not.' And I look at the picture and go, 'Oh my God, I am.'"

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For Stiller, who recently turned 50, social media is a skill that he is learning. "I'm in that generation that are kind of aware of it and can play with it a little bit, but it's not naturally my thing," he says. "I'm never going to be that person who feels comfortable Instagramming selfies going to Starbucks or whatever, but for this movie in particular, it felt very organic. Because that's what Derek is about, Derek should be taking selfies of himself and putting them out there."

The alter-ego experience also emboldened Stiller for Esquire's photographs. While Derek favours zebra print, jaunty cravats, matching driving gloves and luggage, Stiller is dressed both times I meet him head-to-toe in black. "There's a certain freedom to go for it and be silly and ridiculous that I don't feel when I do a photo shoot as me," he says. "And I don't think I ever will. But with Derek it's always a pose, it's always with his lips like that. It's much more licence to just do the things you'd probably be embarrassed about, but to go for them even more. And that's what the character is."

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Stiller would mostly prefer that people knew as little as possible about Zoolander 2 before seeing it. He originally hoped to keep it a secret that Benedict Cumberbatch is appearing in the film – he plays a new transgender model called All, who usurps Derek and Hansel – but he eventually decided to put some footage in the trailer, which unwittingly and distractingly led to a campaign from outraged LGBT protesters to boycott the film.

The involvement of Bieber is out now, too, but Stiller is satisfied that at least some of the plot twists will remain a surprise. "Justin's such a polarising figure, so there are people who freak out and say, 'I can't believe Justin Bieber is in the movie!' That makes me happy, and I'm excited for them to see him in the movie in the context he's in the movie. And for the fans of Justin, it's great, they get to see him in the movie and they'll probably have their own reaction when they see the movie."

Cameos have not been hard to fix. With the first Zoolander, though, very few people involved in fashion wanted to be involved. In its opening scenes, there is a council of the leading industry figures who are made to resemble the likes of Karl Lagerfeld and US Vogue editor Anna Wintour, but they were backlit and shown in silhouette. This was, Stiller admits, because he couldn't find anyone who would agree to appear. They feared they were being ridiculed. To get some actual celebrities involved, Stiller went out on the red carpet of other fashion events to solicit soundbites. That was how Paris Hilton, Natalie Portman and, perhaps the next president of the United States, Donald Trump came to appear in Zoolander.

For Zoolander 2, the task was much more straightforward. Most major fashion houses sent samples for Derek and Hansel to wear or made specially commissioned garments: Derek is mostly in Valentino, Saint Laurent by Hedi Slimane and Costume National; Hansel tends to favour Haider Ackermann and Dries Van Noten. Many of the designers turn up in odd roles; Anna Wintour negotiated the Valentino coup and counselled Derek and Hansel pre-show on their runway walks. "It's one of the most beloved movies in the fashion world now. So it was, who couldn't we get?" says Justin Theroux. "This one was a joy because you just got to sit down and go, 'All right, let's have this person!' And nine times out of 10, if their schedule worked out, they said yes."

It's hardly a spoiler to say that Derek and Hansel are very much as you remember them. "They're essentially sexualised seven-year-olds living in an adult world," Theroux explains. "And they don't judge each other at all. I find that so funny because you can put them in these adult situations but you really are writing children. Also, one of my favourite things just in general, even in life, is seeing incredibly stupid people being incredibly confident."

"Derek and Hansel are very simple characters," Stiller adds. "I don't pretend to know what the secret is, why people connect with them. But I can guess at it; they are genuine and pretty innocent. It's always very clear, if the scene is written correctly, how Derek will react to a situation. The audience has a certain innate expectation of how they want to see him be and, if you go outside of that, it's pretty clear what areas Derek doesn't work in."

Unlike Stiller, Theroux did not find it too taxing to send up the fashion world. "Any industry that has really big personalities, I don't think it's that hard to satirise because their egos are so out of control," he says. "It's about — not being crass — you just scoop up a handful of them and make them all fuck each other and cram it into one character, then you have something that resembles the truth and is also satire."

Stiller is proud of the new film, but experience has taught him not to predict how it will be received. "Overall, I'm excited about it," he says. "I personally always just love Owen in the movie, he makes me laugh all the time, and Mugatu for me, I've always been a big Mugatu fan, I'm a big Will fan in general. His character is one of the funniest characters ever for me, just as an audience.

"The first scene we shot with Will is when he reunites with Todd, his assistant," Stiller continues. "And those two guys probably hadn't worked together or seen each other in 13 or 14 years and they just got in the helicopter and he gives him his latte and it's that moment again and they just went into it and it was so great."

So, Zoolander 2: some old jokes, some new ones. Stiller is older, wiser and more realistic. Has he stuck to the budget this time? "Better," he replies. Is that a yes or no? "Close," he smiles. "Very close."

"Do I feel confident?" Stiller goes on. "I feel confident that we made the movie we wanted to make. The same way we did with the first one. That's what I feel good about. But I don't know if I ever feel super-confident when I put a movie out there. I wish I could be that guy who's like, 'This is going to change the world! Wait till they get a load of this!'"

Stiller laughs heartily but with an edge. Momentarily he breaks eye contact and appears to consider a prawn on his plate. "You know, what happened first time round gives you hope for all your movies: maybe in another 15 years they'll get that one…"

Buy the March issue of Esquire for the Derek Zoolander Spring Style Special and other exclusive content.

Zoolander 2 is out on 12 February

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