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. 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.

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. Whether you're attending a Halloween party, a themed event, or simply want to have some fun, our Zoolander costumes are the perfect choice. Embrace your inner fashionista and make a statement that will have everyone saying, "That's so Zoolander!"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. 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. 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. 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. If you're more of a Mugatu fan, we've got you covered too. Transform into the eccentric fashion designer with our Mugatu costumes. With his outrageous outfits and quirky personality, Mugatu is a Halloween costume that will definitely turn heads. Choose from his flamboyant leopard print suit or his iconic "M" sweater – just make sure to perfect your evil laugh and practice your villainous monologues.

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. Time to pull out your modeling moves and serious faces! Zoolander is no joke (well kind of) when it comes to modeling, and now if your chance to recreate his character with some flashy style and your best model impressions. Since Zoolanders outfits are pretty out there, his character makes for a fun costume on cosplay nights! 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: 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. 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?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. 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. No Zoolander costume is complete without the iconic red pants. These animal-printed red pants are the epitome of bold fashion choices. They are designed to make a statement and turn heads wherever you go. Get ready to strut your stuff and leave a lasting impression on everyone at the party. Signature Zoolander Wig 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.

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. This Derek Zoolander Costume is officially licensed, ensuring that you're getting the real deal. You can trust that every detail has been carefully crafted to capture the essence of Zoolander's unique style. Whether you're attending a Halloween party or a themed event, this officially licensed costume will make you the center of attention and the talk of the runway. 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. 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. 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.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. 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: 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. Attention all aspiring male models! Get ready to walk the runway of Halloween with the Derek Zoolander Costume. With its striking design and attention to detail, this costume is sure to make you feel like the world's most famous male model. Fashionably Fabulous Design

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. 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. 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?”Complete your Zoolander look with our selection of accessories. From Derek's signature hairstyle wig to Mugatu's eccentric eyewear, we have all the details covered. Add a touch of humor with our Zoolander-inspired props, such as the infamous "really, really ridiculously good-looking" mug or the "Zoolander for President" sash.