Ever since Justin Theroux brainwashed Ben Stiller’s Derek Zoolander as an evil DJ in the cult comedy Zoolander, fans have been waiting for a sequel. 15 years later, they’re finally getting one, and this time around Theroux went all in and co-wrote the script for Zoolander 2 alongside the franchise’s star and creator, Ben Stiller. The highly-anticipated (and heavily marketed) sequel sees the return of Derek Zoolander and his former rival Hansel (Owen Wilson), as they seek their place in a fashion world that has long forgotten them. Expect more of what made the first Zoolander a surprise hit, including shock humor (orgies), a sea of celebrity cameos (Justin Bieber), and a relentless mocking of their heroes’ utter cluelessness.
It was that ethos that got Zoolander 2 in hot water last year, after the first trailer revealed a scene featuring an androgynous model named “All,” played by Benedict Cumberbatch. Almost immediately, the movie was accused of transphobia and threatened by a boycott, an unexpected backlash that deeply affected Theroux. He has since addressed the controversy, but when we spoke to him on the phone last week, he had much more to say on the topic, along with revealing the process of booking all those celebrity cameos, why his wife Jennifer Aniston wasn’t one of them, and what we can expect from a couple of his highly anticipated future projects.
How much pressure was involved in writing this sequel? Zoolander fans have been waiting for this film for 15 years.
I know! I’m one of those fans that has been waiting. It was pressure of course, but I think one of the reasons why I think it took so long is we weren’t feeling so much pressure that we wanted to put down the first idea that came into our heads. We really wanted to make sure that it made sense, that there was a good story in it, and that we could make it as good as possible. So we really ground out the pages for a long time and kept adding and adding and subtracting and just really worked the script as much as possible. And then once we had a couple of set key scenes and the idea to go to Rome and make it international, I think that’s when we started to get really exited to write.
What were those writing sessions with Ben like? Were the two of you just on the floor laughing the whole time?
The first couple of meetings were like, “What would be the ideal thing?” So we kind of struck on this idea of this sort of Da Vinci Code-esque storyline. This historical, scrolling back through history and the genesis of male models and Adam and Eve. And then once we had that idea, we thought that it was a solid sort of thing to hang it on. And then running at the fact that at the time, 10 years later, they are irrelevant and washed up and don’t even know who they are. And Mugatu’s plan to get them back into the industry. The way that me and Ben work historically is it’s a very low-pressure thing where we get together and have a coffee and start chatting about stuff. There were a million ideas that we threw at the wall and then the best idea, the funniest idea, hopefully wins.
You went to Paris Fashion Week to learn more about fashion. What has working on Zoolander taught you about fashion? You were already pretty fashionable going into this. Have you since upped your game?
I don’t think I’ve upped my game. The truth is, I actually knew quite a bit about fashion in general. I’ve been going to fashion shows for a while. But what was fun was just sort of meeting some of the characters. The reason for doing that trip was to inhale a lot of the personalities that surround fashion and to try and create these amalgam characters and construct them. We wanted to create a few new characters so it wasn’t just Derek, Hansel, and Mugatu. The personalities in fashion are so big. And so squishing a couple of them together to create these other characters was fun.
Was there anything you picked up at fashion week and you were like, “I could never be caught dead in this?”
Oh tons of stuff! The fashion shows are meant to be these sort of heightened things. We would joke that I’ll wear like a Dior jacket and a pair of Saint Laurent boots or something. The funny thing about Derek and Hansel is that they wear all designers, all at once. Their clothes are just cramped on them in such terrible ways.
You’ve already addressed the controversy behind Benedict Cumberbatch’s transgender model. But what do you think about modern society’s culture of outrage in general? The idea that everything nowadays is considered offensive, even blatant comedies and satires like Zoolander 2? People still will find something to freak out about.
Well they even freak out about it prior to investigation. That character is the most famous in our world, at least the most famous model going in. The joke is sort of squarely aimed at some middle-aged models who don’t understand the world they’ve come back to. And satirically speaking, that was the world we wanted to run in. Look, people like to be outraged, but I think we had the same thing with Robert Downey in Tropic Thunder, where just prior to that people were like, “Oh my God! Robert Downey is in blackface.” But once they see the actual movie, they go, “Oh no. This is about a douchey actor that takes himself too seriously and completely crosses the line.” So obviously, it’s not making fun of black people, it’s making fun of big Hollywood egos. And I think the same is sort of true here. A good satire hopefully makes people understand that we’re firmly on the side of them. So when I heard this I was kind of like, “Wait what? What is everybody talking about? This is actually written to be on your side, not to be attacking you or marginalizing you.” We’re not trying to stick a finger in the eye of anyone, except for Derek and Hansel.
When writing the jokes surrounding All’s scenes, did you ever expect that there would be some controversy once the trailer hit and people saw the film? Or were you shocked that that was the reaction?
I was shocked that was the reaction. But again, I’ll defend it all day long. Once you start apologizing for it or kind of going, “Oh shit. I won’t do that again,” I think you do a disservice to comedy. Many comedians have gone off the record—Chris Rock or Seinfeld go, “Eh, I’m so sick of it.” Understand the joke. Then it sounds even worse when you have to explain a joke. It’s like, “Oh good God.” The minute you start describing what’s funny about a joke, you really start to really be a boring person.
I love how people are more offended by All than Hansel’s orgy.
I know! Exactly! It’s worth pointing out that Hansel’s also deeply bisexual—or omnisexual—but no one is going “He’s bisexual and biface” or whatever. But I think if people understand his character and understand the jokes, they don’t gravitate towards criticizing him.
Well it sounds like if you had Hansel and All hook up, then it would have solved all your problems.
That’s entirely possible! I’m sure they probably did at some point!
Speaking of Hansel’s orgy, how did you rope Kiefer Sutherland into that?
That was all Ben, the cameos and all that. It was a catch-as-catch-can kind of situation. Some were obviously scripted and some were like, “Oh my God. We’re gonna get Kiefer Sutherland. It’s going to be amazing!” A lot of those cameos, we just couldn’t believe that we were going to get them!
Is it true that nobody said no and that you guys actually had a ton of A-listers calling you to try to squeeze their way into the film? Was there a point where you had to say, “Okay, no more celebs can fit into this movie”?
There were a lot of incoming calls. It wasn’t like we were being bombarded, but you bump into someone and they go, “Hey! I hear you’re working on Zoolander. If there’s anything, I’m around.” But with the practicalities of “We’re shooting in Rome, we have to fly you out,” then people, just because they are busy people, have a hard time getting out there. So the ones we got, we got. The others we couldn’t work out, we couldn’t work out. But if they had the time, most of them came.
So you had all these amazing A-listers appear in the film but didn’t your wife want in on that action? You couldn’t find a spot for her?
Her agent just shot me right down! I sent the script to her. No. I’m joking. I think she would have wanted to do it. She was busy working too, so obviously it became a scheduling thing there too as well.
Yeah, yeah. They probably wanted her in the orgy scene and you instantly put the kibosh on that.
[Laughs] No! We would have loved to have had her. I couldn’t get her on the phone!
What are our chances of ever seeing a Zoolander 3?
I don’t know. I mean what would that look like? In another 15 years? If there was an appetite for it and there was a really good idea for it, I think we would do it. But it’s also one of those things where you don’t want to make it less special by trying to turn it into a franchise. It’s never going to be Star Wars. You want to do something that people will like. If there was a reason to do it and people wanted it, I’m sure we could find the time to do it.
Well you could totally make geriatric versions of Hansel and Derek.
Oh yeah I know! Two models in wheelchairs being pushed around.
Next up for you is Girl on The Train, which is currently in post-production. What can you tell us about the film and what attracted you to the role of Tom?
We just wrapped it. It’s hard to talk about the part but I also loved the book. It was just one of those things where it was a lucky thing. I’m good, old friends with Emily Blunt. So it’s rare when you get a job and you get to goof around. And I love the director and the director of photography and I thought, “This is going to be a fun thing to do.” It was not a hard sell.
Did you read the book prior to getting asked to do the role?
No, I hadn’t. I read it after I had heard about it. Actually, Jen had read the book. She had it so I took a look at it and loved it. And I had never really done that kind of thriller-mystery thing, so that was fun, too. Reading it and turning the pages, I was like, “I get to do that? Oh!”
The Leftovers is coming back for its third and final season. Is that bittersweet? Are you sad to see that character go?
I’ll definitely be sad to see that character go. I wouldn’t say it’s bittersweet. I talked with Damon [Lindelof] before we even started shooting, when I was thinking about doing it and he assured me, “Look, we’re not going to try and milk this for nine seasons. This is probably like a two or three or four season show.” He didn’t really think there was a reason for it to exist longer than that, even though I think it’s a really good show. So it’s both. It’s bittersweet because I love everyone I work with and I love that character. But it’s also nice to know that there’s some punctuation at the end of it and there’s a period, a full stop, and it will have an end date.
Damon recently mentioned in an interview that the storyline is going to move away from questions of Kevin’s sanity. Are you excited to take that character into new ground?
Oh, you know more than me! I don’t know what’s going to happen. I know he’s working and he’s trying to figure out what the next season will be. He always plays a little dumb but I think he has a good idea of what it looks like. And I think he’s smart and he doesn’t tell his actors that because then they start working in other directions. Every script that he produces is always a surprise to me, a magic trick. I have no opinion one way or another on what should happen with Kevin. I just have complete faith that it will be good. He can never not challenge me with that character.
Any fun bloopers on set?
On Leftovers? Sure! No. Every day was funny working on Zoolander 2; getting those guys all together and those girls playing ball. It’s a really fun set. So many deep belly laughs have happened with filming that. And normally we dread the press tour, but we had so many good laughs on this one. Because now the pressure is off a little bit, and we were just laughing our asses off the whole way.
Are you nervous for audiences to see the film?
Yeah. Of course you get nervous. You want people to like it. It’s like sending your kid off to school on the first day. You don’t want them to come back with black eyes. So we hope people enjoy it.
I’m rooting for the geriatric version. Zoolander 3!
I’ll put it on the calendar for 15 years from now.