Derek Zoolander Lands His First Vogue Cover Alongside Zoolander 2 Costar Penélope Cruz

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He’s back! Ben Stiller, a.k.a. Derek Zoolander, and femme fatale Penélope Cruz lead a gang of fashion and Hollywood royalty in a (very) long-awaited sequel. Let the walk-offs begin.

Let’s start with the enduring mystery of the universe: Is there more to life than being really, really, really ridiculously good-looking?

Fair question, no? And urgent now that the legend is back: Derek Zoolander. Greatest male supermodel of his generation. Eponymous founder of the Derek Zoolander Center for Kids Who Can’t Read Good and Who Wanna Learn to Do Other Stuff Good Too. An irresistible dynamo of discipline, charm, and really, really, really good-lookingness.

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Derek Zoolander takes us inside his really, really ridiculously good-looking apartment:

He’s as recognizable as a head of state. As versed in world affairs as any common house cat. As handsome as Michelangelo’s David. Or Victoria Beckham’s David. Smells like—to tell the truth, Derek Zoolander smells like an orange mocha frappuccino.

Fifteen years have passed since Zoolander last captivated the fashion world, a darling to designers who cherished his beauty, his professionalism, his . . . OK, well that’s it. Remember what Tom Ford cooed in the original film? “I think about Derek every time I design a collection.”

When we last saw Derek, there wasn’t any Snapchat, Periscope, Yik Yak, or even Facebook. There was no Uber, no SoulCycle, no Juice Press, no Candy Crush, and certainly no “Netflix and chill.” People actually used their telephones—as telephones. Gluten was a thing. Life was primitive and raw.

Today he is at a Vogue photo shoot in a loft on the Brooklyn waterfront, and it’s as if he hasn’t aged a moment since George W. Bush’s first term. Sitting in a makeup chair, wrapped in a robe, black hair magnificent, he is surrounded by an awestruck new generation of supermodels: Jourdan Dunn, Gigi Hadid, and Joan Smalls. These women were barely out of their Chanel onesies when Zoolander dominated the scene with campaigns like the “Merman,” man mermaid for men’s moisturizer. You remember the Merman, yes?

Derek (swimming toward camera):

Moisture is the essence of wetness. And wetness is the essence of beauty.

Here in the loft, as the supermodels pose, as the photographer’s shutter starts to click, as the crew hushes, VH1’s three-time Male Model of the Year sucks in his cheekbones and unleashes the moneymakers:

Blue Steel.

Le Tigre.

Magnum.

It’s amazing to witness. Seeing Zoolander do Blue Steel is like watching a prima ballerina turning 32 perfect fouettés. Like watching Roger Federer hit his one-handed backhand. Like seeing Neil Armstrong step onto the moon in a Dior leather stocking boot.

Suddenly, Derek is seized by an old memory. A bit of Zoolander déjà vu.

“This is Hansel’s apartment,” he says.

And it is. As it turns out, this same airy redbrick loft served in the 2001 film as the apartment set for Hansel, Derek Zoolander’s rival turned frenemy turned pal. This very Brooklyn loft used to have a skateboard half-pipe, a communal table, a mud room, and a goat. There was an epic orgy here with Hansel. And Derek. And Derek’s Time magazine–reporter love interest. And a Maori tribesman. And a sherpa. And Finnish dwarfs.

It’s all rushing back, like a dream, a distant fantasy of long ago. For a long time, this style revival didn’t seem possible. But Zoolander has returned. This is actually happening.

We were on our own—both in the fashion world and with the studio, too. They were just like, ‘We don’t quite know what this is’

Ben Stiller on the first film

Karl Lagerfeld,” Ben Stiller says. “We didn’t get Karl Lagerfeld. I would have liked to get Karl. I came close.” It’s early fall, and Stiller, the co-writer, director, and star of Zoolander and Zoolander 2, is attempting to pause for a minute in an office inside an editing studio in Manhattan’s Tribeca neighborhood. He is dressed in a pair of Adidas sneakers, dark jeans, and a Cadet navy jacket. (“I sort of have my uniform,” Stiller admits. “I’ve become a person who wears the exact same thing.”)

Stiller is in a frantic final rush. A moment ago, he was in an editing suite putting final touches on the new film, including a scene involving a major star you will all recognize whom I’m not supposed to mention. There are a lot of scenes with major stars you will all recognize whom I’m not supposed to mention. That’s part of the Zoolander 2 fun, and Stiller got pretty much everyone he wanted.

“I was thrilled to say yes to Ben,” says Marc Jacobs, who appears as himself. “I thought the first one was hilarious.”

The only major holdout, it appears, was Karl L. “He’s iconic,” Stiller says. “It breaks my heart. Maybe if we ever do another. . . .” He smiles.

Any question about the fashion world’s reception of Zoo­lander 2 was settled last March when Stiller and costar Owen Wilson, who plays Hansel, surprise-crashed a Valentino show at Paris Fashion Week. An ordinarily jaded and exhausted audience lost its mind, springing from seats to take smart-phone photos of the two actors parading down the runway.

Derek Zoolander Takes Us Inside His Really, Really Ridiculously Good-Looking Apartment:

“I kept saying, ‘Why are we even being secretive? It’s not so big a deal . . . we’re going to walk out there to a smattering of applause,’ ” Wilson recalls. Instead, he says, the uproar at Paris Fashion Week was “the best reaction you could have imagined.”

The anticipation wasn’t like this at the century’s turn, when Stiller was making an odd film based on a series of VH1 shorts created with the late comedian Drake Sather. The plot was strikingly ridiculous: A male model from a New Jersey coal-mining town is hypnotized by the evil designer Mugatu (a Bozo-haired Will Ferrell) to assassinate the Malaysian prime minister, who is threatening a crackdown on sweatshops.

“It wasn’t like a slam-dunk movie idea,” Stiller says. “For the most part, we were on our own—both in the fashion world and with the studio, too. They were just like, ‘We don’t quite know what this is.’ ” He recalls an early test screening in New Jersey. “It wasn’t that they hated it,” he says. “They were just like, ‘Oh, OK.’ Honestly, that’s what it was like when the movie came out, too. Same thing. ‘Oh, OK.’ ”

Zoolander was not a runaway commercial success. It may have been too weird and released too soon after tragedy—less than three weeks after the September 11 attacks. While it eventually earned around $60 million worldwide and turned a profit, it did not rock the box office. “Underwhelming,” says Stiller now.

But over time, on DVD and cable, the film developed a rabid audience—its feverish fangirls and fanboys. Millennials who were grade-schoolers when it arrived in theaters now cling to it like a Caddyshack of their generation. Terms like Blue Steel and walk-off, snippets of dialogue—Derek’s “What is this? A center for ants?” and Mugatu’s “Hansel, s_o_ hot right now”—endure. Stiller has starred in billion-dollar franchises (he was Greg Focker in the Meet the Parents movies and security guard Larry Daley in the Night at the Museum films) but says Zoolander is probably the character fans ask him about the most. He does not mind this. “I’d much rather have somebody say, ‘Hey, Zoolander,’ than ‘Hey, Focker.’ ”

“It’s entered into people’s consciousness in a way that not many movies I’ve worked on have,” says Wilson. “Abroad in particular. I guess there’s something about the humor that translates—the sort of a cartoon element to it.”

Stiller says he considered a Zoolander sequel in the middle of the prior decade and came close in 2010. Says producer Scott Rudin: “Ben has carried the torch on this from what seems like the Paleozoic era. I’ve never seen somebody with the tenacity, wit, and first-rate business sense that he has.”

At first glance, it would seem very difficult to follow a film so thoroughly rooted in the Zeitgeist of a decade and a half ago. But a funny thing has happened: The fashion vanity that Zoolander spoofed went mainstream. Phones in pockets plus the proliferation of social media turned mugging for the camera into ordinary, everyday human behavior. It’s impossible to look at Stiller doing the pouty-serious Blue Steel or Magnum and not think of the bazillion Instagram selfies floating around the Internet. A lot of times, all of us are making the same exact face, without irony.

“That look came out of me in the mirror at home, when I brush my hair or whatever,” Stiller says of Blue Steel. “I guess with the selfie culture, it’s just a natural extension. Did I have any idea that it would live on? No.”

Now that Stiller’s back playing Zoolander, “it’s hard for me to not do it when somebody wants to take a picture with me. I just go into it, like a trained dog.”

He’d talk to me dressed in these absurd outfits, and that hair,” Cruz says of being on set with Stiller. “I couldn’t stop laughing in his face

When Zoolander 2 begins, we find our Derek shamed from fashion, living life as a recluse in the wintry hollows of New Jersey. Lured out of retirement to solve a European murder mystery involving celebrities and selfies—look, did anyone expect le Carré?—Zoolander reunites with Hansel and tangles again with Mugatu. There are turns from Kristen Wiig as a Donatella Versace–like mogul, Benedict Cumberbatch as the new model-of-the-moment, named All, and Justin Bieber does a sublime job as Justin Bieber.

Finally, there’s a seductive new character: Valentina Valencia, a motorcycle-riding Interpol special agent—fashion division—played by the one and only Penélope Cruz.

“I was in South Africa in a supermarket buying diapers, and my phone rang and it was Ben,” Cruz tells me over a late-afternoon drink (OK, I had the drink) at the Mandarin Oriental hotel overlooking Central Park. She is wearing a patterned dress from the Russian designer Ulyana Sergeenko.

“I’m one of those people who’s seen the first Zoolander four or five times,” she says. “I’ve done comedy in Spain, in my own language, but I’ve always said I want to do more comedies in English. I do all these intense dramas, and all my characters are always suffering. For many reasons I need to once in a while do a crazy comedy.” She laughs and leans back into the hotel sofa. “I said to Ben, ‘Count on me.’ ”

Filming took place over three-and-a-half months in early 2015 in Rome. Stiller calls the experience “both awesome and crazy,” recounting a scene in which he sped a tiny Fiat through narrow streets and kept getting interrupted by pedestrians. (“New Yorkers are kind of like that, too, but they take it to another level there.”) Much of the film was made at the city’s famous Cinecittà Studios, and a climactic scene was staged at the Terme di Caracalla, the ancient stone baths where Fellini shot part of La Dolce Vita. “We shot in the tunnels, at night, in these places where they don’t even do tours,” says Cruz, who will be seen again in May in Ma Ma, a personal project that she also produced.

The shoot was a family affair. Stiller brought his children to Rome, as did Wilson. Cruz brought hers as well—she and husband Javier Bardem are the parents of Leo, now four, and Luna, two. Cruz said she was impressed by Stiller’s ability to juggle his multiple roles on the set, but taking direction from Derek Zoolander was sometimes too much. “He’d talk to me really seriously, dressed in these absurd outfits, and that hair,” she says. “I couldn’t stop laughing in his face.” After the film wrapped, Cruz confesses to me, she caught herself doing her own pouty version of Blue Steel.

“It’s contagious,” she says, furrowing her brow and pursing her lips. “You start doing weird things with your face.”

Stiller believes that Zoolander is more about its characters than it is a satire of fashion, but the movie celebrates the industry’s absurd edges and comical self-regard as well as any film ever has. It also pulls off a neat trick, letting the fashion world in on the joke, which is one of the reasons those style mavens were leaping out of their chairs at Stiller and Wilson’s Valentino-show cameo. “It’s refreshing to see powerful people in the industry laughing at it,” says Cruz. “It’s good for the film, but it’s also very healthy.”

“People in fashion take themselves way too seriously most of the time,” says Alexander Wang. “That’s what they got right.”

“Narcissism isn’t an epithet in fashion,” says Justin The­roux, who plays a menacing deejay in both films, and with Nicholas Stoller and John Hamburg helped Stiller co-write number two. “It’s celebrated and encouraged. Writing about the fashion world is a lot like using Hollywood, or actors, as source material. They’re both showy professions that exist in front of cameras, so the narcissism bar is already pretty high.”

I was shown a close-to-finished version of Zoolander 2, and I am happy to report that obsessives of the original and merry newcomers will not be disappointed. Derek, Hansel, and Mugatu are in turn-of-the-century form, and Cruz gives the sequel global flair. Bieber’s great. Rome’s gorgeous. The Derek Zoolander Center for Kids Who Can’t Read Good and Who Wanna Learn to Do Other Stuff Good Too? Well, the building had some structural issues. I don’t want to add more for fear of spoiling the surprises, though it does appear to be the first comedy to feature performances by the winners of the CFDA Lifetime Achievement Award and the NASA Distinguished Public Service Medal.

“There’s that saying—‘They want a sequel until they get one,’ ” Stiller jokes. In many ways Zoolander 2, like its predecessor, resembles a fashion collection on the eve of its debut: a creative leap of faith, a little off the wall as a proposition, a lot of anticipation, and, welp, fingers crossed for the response. “Would a studio make Zoolander 1 today?” Stiller asks. “It’s hard to know. It’s a quirky, weird movie.”

Having a character like Zoolander back is good for the planet. Moviemaking has mostly become a cautious business driven by money, but many of the best people who do it, like fashion designers, love those fits of inspiration that cannot be dreamed up in a focus group or a boardroom. Sometimes the public’s taste truly can surprise. Sometimes people want to laugh with the world’s greatest male supermodel. There is more to life other than being really, really, really ridiculously good-looking. Barely, but there is.