It’s been 15 years since Derek Zoolander graced the runways of New York and stopped a Chinese throwing star in its tracks with just a look. There had been many rumours about whether the beautiful but dim-witted male supermodel would ever return, but it was eventually confirmed that Zoolander No. 2 would be out this month. Naturally, everyone’s favourite male models announced the sequel in flamboyant style: during the Valentino show at Paris Fashion Week, two Hollywood titans stormed the catwalk – Owen Wilson (reprising his role of the inimitable Hansel) and of course, star Ben Stiller.

Director and co-writer of the long-awaited sequel, Stiller certainly approved of the stunt: “That was really exciting and scary because it was a big surprise – you can’t trip and it was a big thing we worked on for about a year to get to that point and keep it a secret... Anna [Wintour, Vogue editor-in-chief] was a big part of making that happen, too,” he says. “The lead up to it was pretty wild because we were waiting and hiding for three hours backstage; the models didn’t even know…”.

We worked on the Valentino catwalk set-up for a year in secret... Anna Wintour helped

For Stiller it was vital that the film felt right and he reveals that he began planning a sequel as far back as 2005 but that it simply didn’t ‘come together’ at that point. Then, in 2010 he and actor Justin Theroux (Mulholland Drive, Iron Man 2) wrote a script but again the elements weren’t there and rather than make something just for the sake of it, Zoolander 2.0 was shelved – until now, that is.

“It’s hard to make movies,” Stiller admits. “They come together very specifically. This movie, I thought, all the cast was really important in it, I wanted to bring it all together and so we let it go again and then, it just wouldn’t go away. Back in 2013-ish we started to really look at it once more.”

It’s odd to some, Stiller included, that Zoolander became such a cult hit following what was a disappointingly slow start. He insists that no one was interested in the film on its initial release and that its popularity and cult status has grown slowly over the years to the point where it was just impossible to ignore. The hope is, naturally, that this time around the opposite will happen.

The one obvious drawback of making a film about models a decade and a half on is that they will inevitably be past their shelf life in such a fickle industry, or as Stiller eloquently puts it, “it’s like they are ancient relics” so this became a key part of the storyline. During an early scene, set during a fashion show, Derek and Hansel burst out of coffins wearing stickers that say ‘I am old’ and ‘I am lame’ respectively. The pair are mocked by the crowd and the realisation dawns that they are no longer the handsome young stars they used to be. Cue an orchestra of tiny violins…

Mario Testino captured Derek Zoolander for CÎROC Ultra-Premium Vodka in New York in celebration of its limited edition Derek Zoolander Blue Steel bottle

For funny guy Stiller, age is a poignant factor; having recently turned 50 he knows too well the constant pressure to stay youthful in Hollywood. “Being able to finally make this movie now I’m this age, I had to understand how I could feel like it made sense for the movie,” he says. “But in Derek and Hansel’s minds, they are still models and how do models think of themselves at this age? In a weird way, all these movies have always had very personal, real things you connect with, even if they are the most fraudster things, because I feel it’s how you make them relevant to the people watching them. So for me, that thing of Derek and Hansel trying to figure out how they belong in this new world is something I could really connect with.”

Unlike his blue-steeling and strutting alter ego, Stiller is far from washed-up. In his 28-year career, the native New Yorker has written, starred in, directed and/or produced more than 50 films. From playing hapless nurse Gaylord ‘Greg’ Focker in Meet The Parents to pantomime villain White Goodman in Dodgeball: A True Underdog Story, Stiller is a versatile, comedic powerhouse whose films have collectively grossed over $2.6bn in just Canada and the United States alone.

It’s not surprising then that acting is in Stiller’s blood. His parents were both performers – during the 1960s and 1970s they were a successful comedy duo going under the name ‘Stiller and Meara’. His mother Anne passed away last year, but his father Jerry is still a working actor. In fact, he plays dastardly model agent Maury Ballstein in Zoolander but it is yet to be confirmed whether or not he will be reprising the role.

One character guaranteed to return is the beautiful investigative journalist Matilda Jeffries, played by Stiller’s real-life spouse Christine Taylor. The pair have been married since 2000 and have two children together – daughter Ella, 13, and son Quinlan, 10. They have appeared on screen together in several of Stiller’s films but Zoolander is probably the most surreal, thanks to that narcotics-induced group-sex scene which included Owen Wilson, some Finnish dwarves and a couple of Maori tribesmen. Naturally, though, when two comedians come together part of the joy is being able to work on each other’s films and the couple have spoken in the past about memorable times they have had on set, most notably during the filming of Dodgeball where Stiller accidentally hit his wife in the face with a ball several times. We can only imagine how long he spent in the doghouse after that.

Ben Stiller and co-star Owen Wilson ‘announced’ the Zoolander sequel by taking a turn on the catwalk at Valentino’s Paris Fashion Week show last year

One of the more surprising Zoolander megafans is the impossible-to-please, Vogue editrix Anna Wintour, who Stiller admits was instrumental in making the second film happen – her seal of approval opened up so many doors to the rest of the fashion world. “She just really loved the first movie and when I told her what I was doing in the next one she was immediately like, ‘Please let me help in any way possible’,” Stiller smiles.

“In the first movie, we didn’t have anybody from the fashion world in it really, although we had the VH1 Fashion Awards in the beginning. There were some interviews with Tom Ford and Tommy Hilfiger, but people in the movie weren’t really from the fashion world. Now, over the last 15 years, they have really embraced the movie, so in the new one we have a lot of people from the industry –and Anna has been a really great partner in enabling that to happen.”

Though press and audiences have seen no more than a trailer for Zoolander 2, there is already controversy swirling around Benedict Cumberbatch’s character All, who is a ‘non-binary supermodel’. In an introductory scene, Hansel and Derek attempt to understand whether All is a male or female model: ‘Do you have a bun or hotdog?’ Cumberbatch, unrecognisable in a long black wig and Lady Gaga-style bleached eyebrows, simply replies ‘All is all’. Some have argued that this is offensive to the transgender community and an online petition against the movie recently reached more than 21,000 supporters. But for
co-writer Justin Theroux, the protestors missed the point. He told The Wrap: “I don’t even know what to make of it, because it hurts my feelings in a way. I take great care in the jokes I write, and the umbrage being taken is out of the context of the scene. I wish people would see the movie first.”

Naturally, this isn’t the first time Stiller and Theroux have come under fire for being politically incorrect. In their 2008 hit comedy Tropic Thunder, Robert Downey Jr essentially ‘blacked up’ to portray Kirk Lazarus, an Australian method actor who famously advised Ben Stiller’s character Tugg Speedman to never go ‘full retard’ in an acting role.

“Satire is a thing that points out the idiots, and we went through it on Tropic Thunder with the ‘R’ word,” Theroux continued. “The goal was not to mock or be cruel to the mentally challenged, but exalt in the stupidity of people who use that word. I’m all for letting words be ugly when the target is correct.”

Despite the controversy, Stiller insists the greatest side effect coming off the back of such a popular original in Zoolander meant they were able to secure a slew of celebrity cameos for the sequel including Justin Bieber, Kim Kardashian and Ariana Grande. “Benedict is great – he was so game and so excited,” Stiller says. “I felt really fortunate that people who were fans of the first movie wanted to come on board and be a part of the second one. There are definitely a few surprises in there.”

Benedict Cumberbatch is great. I felt fortunate fans of the first movie wanted to get on board

He does, however, cite frustration at having to reveal so much before the film’s release. “It’s always that thing with the trailer of how much you put out there. For me, I wish everything could be a surprise, but you also want people to come to the movie and see what it is. I think we saved a few good ones, some just really funny, sort of odd ones, too. There’s a bunch of people from the fashion world in the movie as well – people you’d think wouldn’t be in the movie, but they are in there…”.

Spurred on by Stiller’s new-found fascination with fashion, the Zoolander sequel is set in Rome; having met Mr Valentino a few times over the years – and seeing the documentary Valentino: The Last Emperor – he felt inspired and saw a “complement in Italian movies and the fashion world”.

“It’s a much more personal experience, making a movie over there,” he says. “I found that all the creative people really take pride in their work; they care about it and that makes a difference. Not that we don’t here [in Hollywood] but it’s a different thing. Learning that rhythm for me was a big part of it and being able to shoot at Cinecittà Studios in Rome [where Fellini’s Casanova was filmed, among many other notable Italian productions] was something that I was really looking forward to – just the history there. So it’s a different way of approaching it.”
Stiller picked up another quintessentially Italian skill during filming too. “I learned to smoke,” he laughs. “But I have quit now. However, by the end of filming I was rolling my own cigarettes, just for a second.” One would think that after such a prolific career, Stiller would be more jaded – or at least a little fatigued by film-making. The opposite appears to be true; he is as curious and fascinated by the process as ever. That doesn’t mean to say his life has always been straightforward – although he has managed to maintain a consistent comedic Hollywood persona, he has been incredibly open and honest about his battle with depression, and has suffered several manic episodes.

These days, though, it seems he has finally found the balance: “I think as you get older, you just want to feel good about yourself. For me, as I get older, I think about my life and I feel it gets much simpler. I just want to be healthy and happy. I just want to be around because I think that’s the reality of life – you start to see all sort of things happening to people and those realities that we live with.”

However, the slightly less existential question remains: after delving so deep into the fashion world for his return as Derek Zoolander, has Stiller found himself wearing anything more daring or ‘on-trend’ in real life? “The first thing I think of is the Saturday Night Live sketch a few years ago where I wore a deep V-sweater. I wore that giant V-neck sweater and had nothing else on,” he winces. “I’m still not able to watch the sketch because it’s such a ridiculous outfit and in movies, I also wore ridiculous things. In life, this is about as daring as I get – all in black!”

Zoolander 2 is in cinemas from 12 February.