Derek Zoolander was born into the very world that he’d so deliciously send up: the 1996 VH1 Fashion Awards. The character made his first appearance in a short film written by a surrealist comedian named Drake Sather, starring Ben Stiller. At the time, our obsession with the fashion world was reaching new heights. Supermodels were household names, and kids longing to be models were as commonplace as children aspiring to be doctors and lawyers. But nobody was really pointing out the industry’s more absurdist qualities. It was as if it had a giant “Kick Me” sign on its back, waiting for someone to do the honors.
After the success of the short—as well as a four-minute follow-up in 1997—Sather and Stiller began tossing around ideas about what a Derek Zoolander movie might look like. They went on to corral an all-star cast that included Stiller, Owen Wilson, Will Ferrell, Christine Taylor, Milla Jovovich, Jerry Stiller, David Duchovny, and Jon Voight, as well as a bevy of cameos from everyone from Vince Vaughn to Fabio to David Bowie to—yes—even Donald Trump. The film was set for a September 28 release in the year 2001. Likely because of the horrific events of 9/11, it didn’t get the attention (or box office success) it deserved. But in the following years, the film became a cult classic, inspiring countless people to bust out their best Blue Steel in their bathroom mirrors.
Zoolander has long been miscategorized as just another traditional early-2000s comedy. Obviously, the humor takes pride of place, but the movie actually has layers. The plot—which revolves around a male model being brainwashed into killing the Malaysian prime minister—is a commentary on child labor laws and their relationship to the clothing and fashion industry. And of course the movie is a giddy parody of the oddities and self-seriousness of a very rarified world. Stiller often pointed to The Manchurian Candidate as an inspiration. But regardless of intent, it’s one of those rare films that manages to unite all kinds of audiences for the simplest and best reason: Zoolander sends everyone home happy.
In honor of the film’s 20th anniversary, V.F. looks back and asks the cast and crew of Zoolander the most important question of all: Why male models?
JOEL GALLEN (PRODUCER): I was the executive producer of the 1996 VH1 Fashion Awards. It was the first year I was doing the show. I had been doing the MTV Movie Awards for a few years, and they had just started this VH1 Fashion Awards thing, and they were not happy with it. Obviously I like to inject irreverence into all the shows I do. And looking at the fashion industry, I thought, “This is an industry that takes itself really seriously with a lot of pompous people.” And that’s me being generous. So I came up with the idea of, “Let’s take different roles in the fashion industry and do little short films. We’ll make fun of, obviously, the model, the model’s agent, and the photographer. And we’ll try to cast them with well-known celebrity types.”
LAUREN ZALAZNICK (PRODUCER): Joel was known for producing these comedic roll-ins—short films. There was the Kathy Griffin Ugly Model School, the David Cross perfumers, the Nose film. There were these parodies of these very famous, at the time, Gap commercials.
BEN STILLER (“DEREK ZOOLANDER”/COWRITER/DIRECTOR): It was Drake Sather—the writer and comedian—who came up with the character Derek Zoolander for the shorts.
GALLEN: We made the model a male model, because we thought that would be much funnier. And Drake came up with the name Derek Zoolander.
GABÉ DOPPELT (FASHION STILLS PRODUCER): Joel would come to me to say, “Who’s a famous male model?” And I said, “Mark Vanderloo is probably the most famous male model right now.” And they thought that was funny and named him Derek Zoolander based on Mark Vanderloo’s name.
GALLEN: Ben Stiller was still sort of a rising comedic star. He took to it really well, and said he would do it. But I remember getting on the phone with Ben a few days before the show, and he was having second thoughts. He was concerned maybe it wasn’t funny enough. I told him, “Look, this [Fashion Awards broadcast] is not going out for another few days. Let me put it on the big screens tonight and let’s see what kind of reaction we get. If it doesn’t get a great reaction, only a couple thousand people will see it. That’s it. It won’t air.” And he liked that. That way he’s sort of protected. “If it doesn’t work, then it won’t air. If it works, it airs.” And it killed. (Laughs.)
ZALAZNICK: Ben was—and is—a fan darling and everyone loved the character right away. That’s why we brought it back!
GALLEN: For a second short [in 1997], we came up with the idea of the Zoolander School of Male Modeling, as if he was the biggest male model on the planet. It was almost like an infomercial. And shortly after the second short film, Drake and I were starting to think Maybe this thing could be a movie. So I met with Ben and told him that Drake had a take on the film, and did he think this is something that he’d be interested in?
STILLER: Honestly for me, it was watching what Mike Myers did with Austin Powers. I was a big fan of that movie, and seeing how he created this really over-the-top character that is sustained for a whole movie made me think that it could be a movie.
I was talking to Mike De Luca, who was a producer, and he was actually at New Line at that time. We were having a meeting and he said, “Oh, that Derek Zoolander character is really, really funny. I’d make a movie about that character.” And I was like “Oh wow. That would be really cool. That could be really fun.”
Stiller had an overall deal with Fox, which was also excited about the idea. But ultimately, Stiller says, “the character appeared on the VH1 Fashion Awards and VH1 was part of the Viacom world, so it would have to go to Paramount.”
SHERRY LANSING (FORMER PRESIDENT OF PARAMOUNT PICTURES): I knew right away that I wanted to be involved, because I loved the idea. I just thought it was really smart. And it’s one thing to be funny, and then there’s funny and smart, and then there’s funny and culturally relevant. And it was all those things. And it was really touching, too. So that wasn’t a hard decision.
Once the film was greenlighted, the screenplay would go through many drafts between Stiller and Sather. At one point, neither Stiller nor Sather was involved, and Paramount assigned someone else to take a stab at it. To this day, Stiller has never read that draft, so he can’t comment on how good—or bad—it is. But eventually, he and Sather were back on board.
STILLER: There was a long time before the movie actually got made. We worked on drafts. There was this early stage where Derek had a twin brother who was a Bruce Springsteen impersonator. In my limited repertoire of characters I did semi-okay was a Bruce Springsteen impression that we thought, Oh, okay. Derek could have a brother who’s a Bruce Springsteen impersonator and I would play both parts. (Laughs).
It was sort of an Island of Dr. Morreau story where Mugatu was involved in breeding models and kind of doing experiments on them. So there was like a half man, half donkey, half model character. And then it came around to the idea of doing much more of a Manchurian Candidate-style movie.
JOHN HAMBURG (COWRITER): I first met Ben at the Nantucket Film Festival. We started talking about working on stuff together, and they invited me to a reading of Zoolander in L.A. And I flew out and heard an early draft that they had written.
STILLER: We had these meetings, John, me and Stuart Cornfeld. Stuart was my producing partner at the time, who passed away last year. Stuart was a really amazing producer, and was a great writer, too. And we were throwing around ideas and talking about the script we had written that John was going to rewrite.
In one early version of the film, the ending took an absurdist turn in which Derek wound up in a subway station. He finally did the big reveal of the Magnum look in an attempt to stop an oncoming train—which didn’t work. Derek wound up going to heaven, where the film ended with a big musical number.
STILLER: That might have been like, the first thing that John Hamburg said has got to go. (Laughs). To me, it sounds like a very Drake Sather idea, who had a really dark sense of humor. I don’t remember much about it, but the idea was that he was so stupid that that would happen to him at the end.
HAMBURG: You want a feel-good ending, because you’re emotionally invested, but you also want to laugh at what an idiot he is. Which is why the Center for Kids Who Can’t Read Good is ultimately the right ending.
STILLER: When John wrote his draft, that was sort of what crystalized it. Like, Oh yeah. Now the movie actually works. He gave it this emotional heart in terms of really caring about Derek.
HAMBURG: We tried, even though he was so ridiculous, to take him really seriously from an emotional standpoint. To treat his issues seriously. That’s why there’s the coal miner and that angst with his father and that kind of stuff. Try to make it almost like this kitchen-sink drama.
CHRISTINE TAYLOR (“MATILDA”): I think, for Ben, it was important in trying to transcribe it into a feature film that there be a character that was grounded in reality that could be the voice of the audience, almost as their reaction to these crazy people. Somebody who’s not in the modeling world. So that Matilda character, on the page, reads as sort of the straight man to the hijinks going on around her. It needed that foundation in reality that could allow the audience to react to the absurdity in the same way she was.
HAMBURG: At one point, Ben wanted to star in it and write it and produce it, but didn’t initially want to direct it.
STILLER: At one point, I was talking to Adam McKay about directing it. And then I talked to John about it.
HAMBURG: I didn’t feel like I was meant to be the director. And I think Ben realized that. Everyone was like Ben, you know this character inside and out. You’re really a great visual filmmaker. You should direct this movie.
STILLER: We wrote Hansel for Owen Wilson. But at a certain point, there was a question of whether or not he was going to do it. And I don’t know if it was whether or not Owen wanted to do it, or if he was going to be available to do it. Because I definitely remember us doing readings for Hansel. And the one reading I remember being really funny—and he came in with like, a whole character—was Jake Gyllenhaal. But then Owen wound up doing it.
And then Andy Dick was supposed to be Mugatu. But Andy wasn’t available, because he had a series called Go Fish and they couldn’t work out the dates.
ANDY DICK (“OLGA”): Ben Stiller is my savior. He gave me my first job. He put me on The Ben Stiller Show. He’s, like, my god. I actually have an altar to him. I kneel down facing North East. I have a little carpet and I bow down and do my little prayers. He really is a godsend. God bless him.
So he came to me and said, “I have this movie.” At the time, I was on a show called Go Fish with Kieran Culkin. My lawyer, Jared Levine, literally said, “Andy. You signed on to do this Kieran Culkin show, Go Fish.” And I was like, “Yeah, but this is my friend. It’s Ben Stiller!” And my lawyer said “You can’t mess with this right now. You can’t do the movie.” And Ben kept calling me saying, “Andy, I walk away from things all the time.” And I’m like, “You know what? I don’t want to walk away from money and make people mad.” I was naïve and scared and my lawyer was saying, “Don’t do this.”
STILLER: For many, many years after, I heard from Andy Dick how upset he was that he was not Mugatu.
DICK: I’m so mad at myself that I stupidly did that. I should’ve listened to goddamn Ben. He said, “Just walk away from Go Fish.” And I should’ve. It got cancelled after five episodes. Go Fish can go fuck itself.
STILLER: He would’ve been amazing. I think Will Ferrell and Andy Dick are two of the funniest people ever. But now, it’s impossible for me to imagine anybody but Will as Mugatu.
Also at one point, I was [also] going to play Maury and the twin brother. As we started to go along, it was like “Oh, this is way too much.” (Laughs). The budget was going to be too much for me to play three characters. So we cut the brother.
MONICA LEVINSON (PRODUCER): About two weeks before the shoot, I believe it was [Zoolander producers] Scott [Rudin] and Stuart [Cornfeld] who said, “Why don’t you have your dad [Jerry Stiller] play Maury?” And he was like. “Oh, thank God! That would be amazing.”
STILLER: I’m so happy, because it’s impossible to imagine anybody but my dad playing Maury. I was so happy when that happened.
TAYLOR: The script had been written well before I met Ben. We had gotten married in May of 2000. And when Zoolander came up, it became clear that I probably would be sent out or submitted to audition for it. We had a conversation about it: “Let’s not go through that thing where I audition for the studio. If the studio is looking for a big name, let’s not put me through that.” And as the cast started coming together, maybe two or three had gotten offered it and for various reasons couldn’t do it. My joke is that I was fourth choice and cheap.
And I remember Ben calling me and saying, “Hey, I know we said we wouldn’t do this. But the studio knows you”—because I had done The Brady Bunch movies with Paramount—“and they love the idea.” So I didn’t have to jump through hoops.
JON VOIGHT (“LARRY ZOOLANDER”): I’m a fan of Ben’s. I think he was a very talented guy. When he called me for this thing, I said, “Well, I’d be interested, sure. Let me take a look at it.” I did, and I thought it was a very good script. And I thought the character was an interesting character for me to play. I thought I could make it work.
DAVID DUCHOVNY (“J.P. PREWITT”): I think the script came to Téa [Leoni], my wife at the time. I saw it in the house and I was like, “What’s this?” She said it was Ben’s movie. And I’m like, “How come I don’t have a part in it? I should have a part in it.” She said, “Look at it.” And I think I called my agent and said, “Call Ben and say I want to be in this film.” And then Ben got back to my agent and said, “Ask him to choose one of these three parts.” Prewitt, the hand model, was one, and I think his brother was another. And there was another part at some point. I thought the hand model was the most fun for me to try.
NATHAN LEE GRAHAM (“TODD”): Ben came to see the final performance of The Wild Party. And I believe Paramount and Scott Rudin were one of the main producers of the show. So Paramount and Ben called my agents the very next day. We set up a meeting, and I was just told to wear something sort of fashionable and that this project was based upon a character he played on VH1 called Derek Zoolander, which I had no idea about at the time. I went in, and we just talked. He asked me some questions. And I was, of course, delighted and excited to meet him. We talked a little bit about The Wild Party. And for the life of me, I have no idea how he watched that show—which was about a 1928 jazz poem—and thought that I should be a part of Zoolander. I don’t know how he made the connection, but thank goodness he did.
TAYLOR: Obviously I was married to Ben and I knew Owen, because they were friends. So going into it, I already knew the people I’d be working with a lot. Will, I didn’t know. I had met him a couple of times. And a lot of the supporting cast that Ben filled in and sprinkled in throughout the film are really dear friends of ours—some of them who had acted before, some of them who had never acted before. His parents are both in it, his sister is in it. My brother, who is not an actor, has a part at the end. It felt like this sort of family affair.
JUSTIN THEROUX (“EVIL DJ”): Ben and I were friends at the time. We had met a little bit before that. And I think he just said, “Oh, would you do this small part in this Zoolander movie.” And I said “Sure.” I think the character was only in the spa scene originally, but then it sort of expanded.
BILLY ZANE (“BILLY ZANE”): I was living in Manhattan from ’99 until a bit after 9/11, right next door to the Mercer Hotel. I was frequenting quite a few fashion shows and gallery openings and enjoying my Manhattan minute. And in the process, I kept running into Ben, who was doing research for the film at some Hugo Boss shows, among others. And he asked me to show up to this one sequence that had quite a few cameos in it of people playing themselves, with a nod to self-parody. And I said, “Of course. I’m there in a heartbeat.”
PATTON OSWALT (“MONKEY PHOTOGRAPHER”): I knew Ben. We had been friends for a while. And he just called and said, “Hey, do you want to go to New York and do this scene in this movie?” And I said “Oh yeah. Absolutely. That sounds really fun.” We had the basic idea of what the scene was, which was me yelling at him and calling him a monkey. And then we just went with it.
FABIO (“FABIO”): First of all, I always loved Ben Stiller, and his humor. I always loved his movies. So when he reached out and asked me to be in this movie, it was a thrill. I really had a good time. And it was a brilliant idea. Because there was never a movie about making fun of the model industry, especially back then.
With the cast and cameos in place, Ben and the team he assembled—which included cinematographer Barry Peterson, production designer Robin Standefer, composer David Arnold, and costume designer David C. Robinson—began figuring out what the film would look like aesthetically.
STILLER: I think the only other movie that had been done around that time [in the world of fashion] was Prêt–à–Porter, which was a different kind of movie. I always looked at [Zoolander] like a Mel Brooks movie or something like that. That was what I was aspiring to, because he would create this sort of heightened reality.
BARRY PETERSON (CINEMATOGRAPHER): It was my first studio movie. I think Ben’s directive was We want a young director who is shooting commercials and hip-looking stuff. I was shooting Super Bowl commercials and shooting cool fashion at that stage. So it felt like the perfect fit.
The first thing he said to me was he didn’t want it to be an out-and-out ‘comedy.’ He wanted people for a moment to believe that they’re watching The Manchurian Candidate. And then within it was the comedy—within it was the simplicity of these models.
DAVID C. ROBINSON (COSTUME DESIGNER): I started five weeks out because I was the second designer. They had fired the first designer, and so I had five weeks, and that included getting a crew and finding a space, because there was no space. So that was a little scary. (Laughs)
ROBIN STANDEFER (PRODUCTION DESIGNER): Ben was working with a production designer and they didn’t really gel. So [art director] Stephen Alesch and I got this sort of clandestine call. And I went and met Ben one night in his office. We just talked about the narrative, the script, and the whole concept of the film. And Stephen and I agreed to take it over. We brought in a whole new crew. A normal prep is maybe three to four months. They were about to start in a month, so we had to really rethink a lot of significant sets. We just worked 24/7.
ROBINSON: The first concept I pitched to him was to have each scene be a different fashion editorial style. So the funeral would be Helmut [Lang] and all low angles, black and white, with sexy blonde girls. And Hansel’s loft would be Mario Testino. There’s all these saturated colors and textures. And Ben was like, “Kids don’t know that. Nobody’s going to get any of those things.” And I think he was right. So then I thought, Okay. The clothes really have to be funny based on the context that they’re in. Like Derek wearing all white to the funeral, or wearing a python suit with matching luggage at the coal mine. That became more of the M.O., which made a lot more sense.
LEVINSON: Gabé was brought in as a consultant, and she and I worked very closely together, because she had a line on every designer and was able to reach out to everybody and get what we needed from the designers.
DOPPELT: My job was kind of—for lack of a better word—to create the wallpaper behind the movie, to really make Ben and Owen into as legitimate as we could male models. This included every billboard, every bus, every magazine cover in their portfolios. I called everybody that I knew would give me permission to parody them. For instance, Herb Ritts, with the famous photograph of a male model holding these huge tires. It was a very famous Herb picture, and I asked him if I could parody the picture and not have him sue us. And he said it was funny and let us do it.
FABIO: At that time, most people were infatuated with the fashion world. They love the fashion world, they want to know more about it. I worked with all of the guys and girls [in the industry], and I remember most of them taking themselves so seriously. It’s like, “Come on! You’re just a mannequin. You’re just posing in front of a camera. It’s no big deal! It’s not like you’re working in a mine or you’re doing a major contribution to the world.” This movie was really showing how some of the models take themselves so seriously.
THEROUX: The fashion scene of New York took itself incredibly seriously, as it still sort of does. But it was more modular. I don’t think people thought about the Paris fashion week or the Milan fashion week. It was at the beginning of the explosion of the internet, so things weren’t linked in the same exact way. It was more sort of in-house, so to speak, in Manhattan. The Met Ball was still a pretty quiet affair, which is evidenced by the fact that it isn’t even in the movie. If the Met Ball was as big as it is now, then it probably would’ve been front and center. It probably would’ve been set at the Met Ball.
DOPPELT: I remember my first bad experience was early on when I got a call from one of the producers, Stuart Cornfeld. And he said, “I need to talk to you. We think you’re not funny.” And my heart dropped, because it’s not something that you want to hear when you’re working on a film that is meant to be a parody and your job is to be funny. I’m not a comedy writer or anything. So I sat down with him and he was trying to articulate how I had to be funny. I don’t know how it all came together, but probably in about two days, it clicked how to be funny.
ROBINSON: I recall that the people in the fashion world wanted nothing to do with us. The VH1 short was apparently not well liked in the fashion world. We went to designers to try to get clothes and they were not interested at all in working with us.
DOPPELT: I actually recall that it was well received and kind of embraced. And it didn’t harm that Anna Wintour was giving us as much support as she could behind the scenes as well. If anybody called her up and asked her what she thought, she would tell them to go for it.
STILLER: Anna Wintour really loved the character and was really, really supportive. I think, for whatever reason, at that time people were very into the idea—because it was a time when fashion was starting to become so much a part of the pop culture world.
We knew we had to shoot the sequence that happened at the Fashion Awards [at the beginning of the film] at the real Fashion Awards. We didn’t have a choice. We couldn’t recreate it.
LEVINSON: VH1 was involved as an executive producer. So we said, “What we really want to get is the big crowd. We can’t replicate that on our budget. Can we shoot live there?” And they said, “Only during the commercial breaks.”
GALLEN: I helped coordinate, orchestrate, and oversee that part of the shoot, because I knew all the players and had produced that show for three years.
ZALAZNICK: It was a live-to-tape show with hundreds and hundreds and hundreds of people in an audience, with the precision and kind of high-stakes poker it always feels like when you’re shooting a film in the middle of a video production. It was loads of extra money, and we had to figure out what the TV production was going to absorb and what the film cost was going to absorb.
LEVINSON: We ended up shooting during three commercial breaks of the first four commercial breaks. Each break was about three-and-a-half minutes. And we had to change the podium onstage, put our own prop up there. And we had to film Ben walking down the aisle and up onto the stage. So we had three shots at it in those two-minute breaks. It was a pretty exciting event.
GALLEN: The show itself was not live. It was a taped show. So if a commercial break ran a little bit longer, it wasn’t going to kill anybody.
PETERSON: We grabbed a Steadicam and pulled Ben up onto the stage. It was totally stressful. You had to get it and get out of the way so they could continue the show.
DOPPELT: I just remember the show’s producer in my ear—and anybody else’s ears who was involved—saying “One minute to go. One minute to live. 60 seconds.” And these guys just basically took their time. We cut it so damn close to the show going live with Derek Zoolander on the stage.
CELIA COSTAS (PRODUCER): We asked the audience during the breaks not to get up and leave and just stay in their seats.
FABIO: It was a lot of fun. He directed me to improvise. “Just say whatever.” In one of the scenes, I kind of made fun of Donatella [Versace], but they didn’t use it.
DOPPELT: Jennifer Lopez was meant to be in that scene, but she dropped out at the last minute. So we had to have somebody recognizable fill in for the character sitting next to Ben when they actually call Owen’s name and [Derek] loses the award. So I asked Donatella Versace if she would do it, and she agreed. It was just such a funny moment. And I think Ben just leans over and kisses her, with Donatella just thinking, “Oh my God.”
LEVINSON: We also really wanted to take advantage of the amazing look of that red carpet and the crowds that were coming in and all of the photographers. So I said to the team of photographers standing there, “Okay, I’m going to bring Ben Stiller out. But I can’t bring him out unless you call him Derek. If you call him Derek, I’ll bring him out.” And they all said “Sure, sure.” So I brought him out, and they all yelled “Derek!” And we got the shot.
LEVINSON: We knew certain celebrities were showing up at the awards. So we reached out to some of them in advance, and some people we were just pulling [others] aside and saying, “Would you mind doing this?”
PETERSON: “We’re doing a movie. Ben Stiller is Derek Zoolander doing this thing. We just want to ask you a couple questions. Talk about how incredible he is, how he’s really good looking.” They fed them a bit, and because they’re all great actors, everyone nailed it.
Following an embarrassing mishap at the VH1 Fashion Awards and the death of his model roommates in a gas station explosion, Derek returns home to the coal mine where his father, Larry Zoolander, and his brothers work. John Hamburg says that Derek’s icy relationship with his father was added to give Zoolander an emotional arc that had been missing in earlier drafts of the script. They cast Jon Voight and gave him the world’s most ridiculous wig.
VOIGHT: I remember for my scene, I thought, How am I going to look more like him? I thought about doing prosthetics or something like that. And he said, “No, we’ve got these great wigs.” They handed me this wig. I put the wig on and said, “Holy shit. That’s great.”
PETERSON: John’s scenes were a super quick, half day shoot. He came in and played it, and you believed he’s Derek’s dad. He just nailed that part and gave it credibility, even though they all had Zoolander hair. He’s giving his Oscar performance from one of his Oscar-winning movies, playing the father of an idiot son.
VOIGHT: We were doing the scene at the bar, and I was working on it with Ben. He was really good as a guide through it and all of that. But I remember him thinking of me as a serious actor. He probably was working with one of the old thoroughbreds. And he didn’t think of me as one of his comic chums. (Laughs). But there was a little more respect or a different tone with me. And that was nice, in a certain way. All I was trying to do was fill in and be the right guy for it, and be funny. And I was. I didn’t fail him. I didn’t fail Ben.
To make the world of Zoolander believable, fake print ads, billboards, and artwork had to be created featuring Ben Stiller and Owen Wilson as Derek and Hansel.
LEVINSON: We would just sit on the floor and go through fashion magazines, trying to figure out some pictures where we could just photoshop Ben and Owen’s heads onto the pictures. And some things where we could do it in a funnier version in our own photo shoot.
DOPPELT: I remember how incredibly committed Ben was. [We wanted to] do a parody of a Shape magazine cover. Because I needed a serious kind of male body, I planned to chop Ben’s head off of the photograph and put it on a sort of muscle-y man’s body. But in fact we didn’t need to, because Ben really committed to the idea of transforming himself into this male model, and his body was just perfect.
Many scenes have become fan favorites over the years. One of them is the foamy latte scene between Will Ferrell and Nathan Lee Graham, where Ferrell winds up getting incensed over Graham getting his drink order wrong and spits it all over Graham’s face and shirt. .
GRAHAM: The famous foamy latte scene—we did it like 14 times in a row. I remember Ben getting frustrated because he couldn’t see the imprint of the latte clearly on my 2(x)ist white V-neck T-shirt. Ben was just like, “Why can’t we see the imprint of the foamy latte? The shirt’s not tight enough!” So they kept stretching it, and they kept putting clamps on my back. So eventually, they had to cut the T-shirt on the sides and sew me into it so that it stretched tall enough against my chest so that you could see the imprint of the latte on my shirt. That’s just how much detail Ben had.
Despite Andy Dick having to turn down the role that eventually went to Will Ferrell, Ben Stiller still wanted to include his old friend in the film in some way. So Dick wound up playing the part of Olga, a grotesque masseuse who manages to give Derek a ridiculous-looking erection under the covers.
DICK: After I turned down Mugatu, he said “Why don’t you come in? I’ll give you a hundie grand for a day.” And I was like, “Thank you. I’ll do it.” I had to come in at 6 a.m. and do five hours of makeup prosthetics. And I remember saying, “Why are we doing this?” And he said “Well, I want to change your look, but I want them to still know it’s you.” I felt like he really was just punishing me. I was already punished enough that I said “No”. I’m basically an extra that spent five hours in makeup to say no lines and slap a dick around.
Even with all the stellar cameos in the film, there is one particularly epic one during the runway walk-off scene that never fails to catch first-time viewers by surprise.
STILLER: To this day, I don’t know how we landed David Bowie. First of all, he was an incredible gentleman when he came to film. Everybody was in awe of him, the fact that he was there. I mean, it was very surreal to me that he was actually there.
PETERSON: Meeting David Bowie was one of the only starstruck moments I’ve had in my 30 years doing this stuff. I walked in and went, “Oh, my God. That’s David Bowie.”
STILLER: I think he had a good sense of humor and thought, Oh, this could be fun! And then he and I were talking about possibly putting some music into the movie that I don’t think ended up in the movie. But I’m sure that’s why he was considering it also. Like, Hey, maybe we could talk about putting some of this music in the film. Other than that, I don’t know why he was there. (Laughs) He was incredibly gracious when we filmed. He gave us this air of credibility that made that sequence especially work so well.
ZANE: My scene [leading up to the walk-off] was pretty much entirely improvised. And that’s what was really so fun about it. Derek was challenging Hansel and he had his whole crew behind him. And Ben said “Billy, why don’t you back me up?” And I said “I love it! I’ve got Derek’s back. Sure, no problem.” At which point, the dialogue between him and Owen just kept going into more and more wonderful and bizarre places.
Owen’s line “Listen to your friend Billy Zane. He’s a cool dude”—I don’t remember being scripted at all. That was just Owen in his mad genius just creating this funny meme in the making. I just thought it was humorous on the day. I had no idea that it was going to evolve into something that people quote more than any other line from my other films.
THEROUX: In the Zoolander world, Billy Zane is God.
The person that actually helps set the plot of the film in motion is David Duchovny. Duchovny, completely unrecognizable as hand model J.P. Prewitt, summons Derek and Matilda to a graveyard made up of former models turned assassins, where he reveals Mugatu’s plan to brainwash Derek into killing the Malaysian prime minister.
STANDEFER: The model cemetery was one of the first things we had to shoot. There were literally a hundred painters and carpenters sculpting and building these hedge stones. Like Adonis with a penis. They were so insane. And at that moment, there was some foreshadowing that this was an incredible and funny and ironic send-up of fashion. And it was so timely. I had these flashes of, I think this is going to be epic and an archetype on some level.
DUCHOVNY: I think I said I wanted to be balding or bald. And we had this whole wig setup. I think I was wearing padding too. And I just realized the straighter I could be, the funnier I could be. So I just committed to the reality. Almost like, this guy’s in a different movie. This is Gene Hackman in some other movie.
DAVID ARNOLD (COMPOSER): He wanted the scene with David Duchovny to be kind of suspenseful and highlight the dramatic reveals and consequences of male model assassins over the years.
DUCHOVNY: I remember we ran the scene a lot. It was a real long walk-and-talk, and I had the bulk of the dialogue. It was very exposition-heavy. And I remember after a number of takes, I fucked it up. And both Ben and Christine go, “Finally!” I was coming from X-Files world, where you gotta know that shit backwards and forwards. I was like, “I’m not gonna make a mistake!” They were happy when I finally did.
Also, I think we laughed a lot at that moment where I explain everything, I give him all the answers, and then he asks the same question. I think we improvised where I said, “You serious? I just told you.”
Almost immediately following the sequence in the cemetery, Derek and Matilda hide out in Hansel’s loft, where the three—and many others—engage in a hilariously over-the-top orgy scene.
TAYLOR: For the orgy scene, I can almost viscerally remember how nervous everybody was. It was up in that set in Hansel’s loft. Everybody was around and was going to have their moment in this crazy shot that they had designed of the camera going around in circles. Everybody was hanging out, wondering, when they got called into the room, how awkward, uncomfortable, or silly it was going to be. We knew it was going to be comedic. It wasn’t going to be sexual. But for me, I’m with Ben and Owen, who is one of Ben’s closest friends. And they’re both kissing my shoulder. It was so awkward. It was all of these people I knew who I never thought in a million years I’d be snuggled up together with, being just absurd.
They kept giving it an R rating because of that scene. And Ben really went to bat and said, “Listen, would I ever put my wife in a scene that would be compromising or anything worse than PG-esque?” (Laughs)
Despite not being able to set up their own awards show, the production did construct its own runway show for the film’s big climax, Derelicte, which consisted of turning literal garbage into fashion.
ROBINSON: The fashion show was really fun. Of course we wanted to end it with a wedding dress, so we did the refrigerator box that turns into a wedding dress. And I gotta say, that fashion model really gained my trust because here she is, inside this box, four rods holding it in place. She has to drop the rods, pick up her bouquet, and then walk down the runway with a 40 pound winch on her back while her dress is being drawn in by the winch in high heels on a plexiglass runway. So I suddenly realized why models make so much. I was like, “That is a tall order.” And she did it flawlessly.
STILLER: Derelicte was always a pretty out-there idea. But to me, in retrospect, it now seems kind of tame in terms of what actually has been done. And, you know, that was us trying to figure out, All right, what’s going to keep this in some sort of world that’s sort of believable but it’s ridiculous?
ROBINSON: I was at Parsons-Meares, who did all the stuff for the fashion show. And I loved, for one thing, watching the girls in the shop blow up those condoms for the boa that’s made up of inflated condoms. They were all looking at me like they were going to kill me. (Laughs) While I was in the fitting room stapling garbage onto the cape Ben wears with the tagger gun, Bette Midler walked in. She was at Parsons, I guess, getting fitted for something. And her thing is collecting garbage on the West Side Highway. And Bette looked at the costume and said, “This has to be my Halloween costume.” I said, “I’m sorry, sweetie, but no. It’s already taken.”
PETERSON: [The show was shot] in Brooklyn in, I think, a power plant. I think it’s since been knocked down and condemned. It was like The Walking Dead. We’d show up to the place at night and had all these ghoulish people in their plastic bags and everything walking around. It was surreal.
THEROUX: I think I “broke-danced” at Ben’s wedding. And then he was like, “Wait, we should do this break dance thing.” And I said, “Why don’t we do a breakdance battle, like between me and Hansel?” So we ended up doing that. And it just became Hansel’s battle sequence at the end. It wasn’t a breakdance fight that had to look fantastic, necessarily. In fact, the more absurd the better.
I think Owen had a stunt double for the head spins and things like that. (Laughs) I did all my own moves. We did have a fight coordinator, because we had to actually make punches happen during the breakdancing. Like, him doing a head spin and whacking me repeatedly in the face. That sort of thing. And it was very kind of run-and-done indie style. It wasn’t exactly like we were doing a fight sequence from Mission: Impossible.
ZALAZNICK: It was so hard to get everyone to be available in New York on the same day. It was wildly difficult. And we didn’t have the money to move shoot days around or fill [the crowd] in with CGI. And that really is a testament to Ben picking up the phone and saying, “Hey, this is going to be really cool. Can you do this?” Those folks were all there for Ben.
For each scene, Stiller had to serve not just as the star and the director, but as a writer and a producer. The herculean juggling of tasks did not go unnoticed, especially by his wife.
TAYLOR: I remember having this sort of out-of-body experience. I watched Ben and Owen playing these absurd characters, but was sort of in awe of the technicians they were as actors To watch them go in and out of it—especially Ben, who had to snap in and out of being the director and going to see the scene and then sitting down, getting into position, and then turning on the character, knowing where the camera was and the angles—I felt like I was in this master class. I remember feeling this insecurity of, Am I holding a candle to what these guys are doing?
ZALAZNICK: It was a real tough shoot. Ben was directing, and he was key talent, and took a lot of hair and makeup in the morning to transform into Derek. And it’s a rip-roaring comedy with a lot of heart and soul. It was probably under-budgeted for what it needed to be, to be a little more comfortable. So you’re running and gunning. You’ve got to make your days. We’re not going to get into a lot of overages.
COSTAS: We thought we were making a nice little small movie in New York. And it just got bigger and bigger. They very much wanted to do it in New York, and they felt that the quality of everything would be better. We’d have better actors, the clothes would be better, the extras would look better. And that was all true.
VOIGHT: I remember talking to Ben and he was going through some tough times, I guess with finances—how much they were giving him to shoot this or that. And he wasn’t getting that much support or extra time.
DOPPELT: There were a lot of challenges. I think the studio was pretty tough on Ben. I wasn’t involved in any of those logistics, but I could just feel the tension a bit. And he was, to be completely honest, working overtime in multiple jobs. It just seemed strange to me that Ben wasn’t getting the support that he should’ve gotten as the director-producer-writer-star of the movie.
COSTAS: We did a lot of stuff at the last minute. Things were ready at the last minute. And it was also a very busy time in New York. So there were challenges in terms of crew, in terms of time, in terms of locations. Everything worked out. But it [was] always nerve-racking. It was really fast and furious. Just people flying in and out, figuring things out. Ben was very much still creating the movie when we filmed it. But in the best possible way.
LEVINSON: Will had to schedule around his SNL schedule. And that was his real hair! I gotta tell you, I’m sure SNL and Lorne [Michaels] weren’t thrilled that he dyed his hair and let it grow to that length. But he did it for the movie, which is amazing.
PETERSON: [Even] Will’s dog had a little white wig. For some reason, I just remember it being the sleepiest poodle I’ve ever seen in my life. It may have been 102, I don’t have a clue. But it seemed to be the most un-high-strung poodle ever. I think it was just old and didn’t care. As long as Will had him in his arms, he was happy to sleep.
Zoolander was poised to have a big opening weekend, with the studio expecting $20 million.
LANSING: The director usually shows myself, as well as the senior executives who worked on the picture, the first cut. And usually—I would say 99 and 9/10’s of the time—I’d have notes. Well, why did you do this? Why did you do this? What about this? And the movie started and I just was riveted and started to laugh. I couldn’t stop laughing and was moved and touched and all the wonderful things. And by the time the movie was over, I turned to Ben and I said, “Here are my notes.” And it was a blank page. And I don’t know when that has ever happened. But let’s just say 99.%t of the time I had a full, several pages of notes. I said, “I just think it’s brilliant. I have nothing to add.”
The week before its wide opening on September 28, there was supposed to be a big New York premiere for the film. But on Tuesday, September 11, 2001, a TV spot for the movie on WNYW was interrupted by television’s first breaking news report that a plane had crashed into one of the Twin Towers.
STILLER: It was such a surreal experience to even be sort of considering what to do. Everybody was so thrown off by 9/11 and so affected by it, that there was no context for it. There was no context for how to react to it. I remember a certain person at the studio not really getting the importance of what had happened and sort of insinuating like, Oh, this will blow over. Don’t worry about it.
ZALAZNICK: Within a couple of days, your work is your work, and I’m like “So when are we going to push the release date to? Has that been discussed? Am I out of the loop?” Because I’ve got to pull the promos from VH1. And Joel and Ben’s team and agents and Paramount are all telling me the same thing: “Paramount’s not pushing the date.” … I was like, “You cannot release Zoolander a week from Friday. Have you noticed that comedy has been put on hold? That entertainment has been put on hold? David Letterman has decreed no late night. Lorne Michaels is not premiering Saturday Night Live. There is no baseball. What do you mean you’re putting it out?” And they were like, “It’s been marketed. We’ve spent the money that we are going to spend. And maybe it’s a good antidote.”
LANSING: We were concerned, but we must have felt the public would respond and that Ben and all the talent associated were big enough stars to get an audience in and that people were ready to go to the movies.
THEROUX: I remember having long conversations with [Ben] about it. Look, obviously nobody wants to promote a comedy the weekend of 9/11. But it was important I think for people, if they wanted to, to go to a movie theater and have a giggle and get their mind off it.
GRAHAM: They changed the premiere to the Paramount lot in Los Angeles. They moved everything from New York to Los Angeles, and they scaled everything down.
PETERSON: And it was a premiere where you drive in in your vehicle and they put the mirrors under the car to make sure there were no explosives under your car. It wasn’t at a normal theater. It was at the lot on their property. And it was a very scary time.
STILLER: There was that question that came up during the press junkets and going and doing interviews of, “Was it in good taste to release the movie this soon after 9/11?” And at that time—and I still do feel—that it was important to let people have an opportunity to go out and escape for a couple of hours from the events that were happening and have a chance to laugh if they wanted to.
TAYLOR: Nobody knew. Nobody knew if anybody was going to go out to the movies to see it. And I think ultimately when you look back, people weren’t going to the movies. With the timing of it, it was a lose-lose situation. But Ben stood behind the movie he made. And I think everybody in it stood behind the movie. We were all really proud of it.
STILLER: Looking back on it, it was just one of those moments in time where you go, Okay. This is much less important than anything else that’s going on in the world, whether or not people go see Zoolander.
PETERSON: I remember totally trying to frame in the Twin Towers [for a shot]. We were running on a camera car, and I was like “Left, left, left. Perfect. They’re centered!” And then we had to get rid of them. That was iconic for the time, and we did our best to show it and wanted it to be part of the city. Obviously it’s a super-ugly thing that happened. But to try to hide it was a bit weird.
STILLER: We did take the World Trade Center out of the skyline, which I really regretted and made sure it was in for the DVD release. That was the one thing that I really felt bad about. But it was also a decision I made at that moment in time because I felt that was the right thing to do. And in retrospect, I feel like it wasn’t the right thing to do. So I changed it.
COSTAS: Certainly, because it was released shortly after, it didn’t do the business it would’ve done normally. I think it would’ve been a hit if it had been released in normal times. But it’s really gratifying to see something build over the years and become an iconic film.
The film, which had a $28 million budget, wound up taking in $60.8 million. So while it wasn’t necessarily a flop, it didn’t quite do the business it was expected to. Because of its plot, the film also wound up being banned in Malaysia, which is still the case today.
STILLER: I was just surprised that the movie was even released in Malaysia. I was like, Wow. We even got there. Like, they were actually even needing to ban us because they released it.
HAMBURG: Maybe with 20 years of maturity, I would’ve thought about the sensitivity towards Malaysia differently? I guess it does make sense. But we weren’t poking fun at Malaysia. It was just sort of the MacGuffin for the story.
STILLER: Roger Ebert killed the movie. He hated the movie. And he literally said it’s, like, one of the reasons why people don’t like America in the world. So it relates to the Malaysia thing. There was this reaction from certain people where I was like, Oh, my God. I had no idea that we were going to a place that was affecting people like this. We just thought it was a stupid comedy.
The movie would of course inspire a delighted cult following over the years, one noteworthy fan being the legendary director Terrence Malick.
HAMBURG: I experienced it as a slow build. Sometimes when a movie gets mixed reviews and doesn’t do great, you’re like, Well, it wasn’t that good. I always felt like Zoolander was special in some way. I was proud of it. I thought it was really funny. Ben did an amazing job directing it. And then slowly, people would find out I was involved and start quoting lines.
STILLER: I started to get feedback like people dressing up like Derek and Hansel or Mugatu for Halloween. And then I started to hear “I feel like I’m taking crazy pills” as a saying that people were using when something crazy was happening.
THEROUX: Most people didn’t know I had anything to do with it. And I would just hear people quote it over and over again. It just sort of seeped into pop culture.
STANDEFER: I thought it was this super cool but weird, off-color movie that we did with Ben. It felt almost private somehow, like an inside joke. And then, I was at a dinner, and someone made a Blue Steel face.
GRAHAM: I was taking the shuttle from Times Square to Grand Central Station. When I got on the train, I get in my car, sit down, and put my head down. Let’s say I was reading Vanity Fair, because 9 times out of 10, that’s what it was. Two jocks—I’m not going to stereotype or generalize, but that’s what it was—get on and stand above me with their arms stretched, looking at each other. And they are acting out the foamy latte scene as they walk on the train. And that’s when I knew that it reached cult status for real.
HAMBURG: I remember working on a movie I was directing, and one of the production assistants was saying, “Well, you know about the Zoolander drinking game.” I was like, “No, of course not.” This was three or four years after the movie was released. He was like, “We watch the movie and every time Mugatu says, ‘Hansel’s so hot right now,’ you have to chug a beer.”
TAYLOR: I can say it because I’m not Ben, but I sometimes think that he can be a little bit ahead of his time when it comes to comedically putting something out there.
DUCHOVNY: Tonally, it was a wee bit ahead of its time. It was just a little too absurd right at that moment. And a few years later, for a while, it became like a dominant tone in American comedy. In the end, I think it’s just wonderful the way it has really found its place.
OSWALT: It was one of those things like Office Space or Donnie Darko or even the first Austin Powers, which apparently didn’t do great in the theaters but caught on. It really holds up after repeated viewings because it’s so its own level of silliness and it just kind of draws you in.
LANSING: This is an iconic film and it has stood the test of time. And I think Ben Stiller did an extraordinary job of—not only being in it—but his directing was extraordinary. It’s satirical, it’s funny, it’s kind-hearted, there’s nothing mean spirited about it. And yet, it’s very observant of our culture as well. That is a really, really difficult thing to balance. And if you say Blue Steel today or you say Zoolander, people automatically take that pose. I’ve seen people do that.