Zoolander: The Best Comedy of the Early 2000’s?

We revisit one of the most influential comedies of the early 2000’s, Zoolander, with Ben Stiller starring as the iconic male model.

Last Updated on May 31, 2023

Clear the runway! It’s time to revisit Zoolander… Directed and co-written by Ben Stiller, the film focuses on Derek Zoolander, a slow-witted supermodel, who becomes embroiled in an international conspiracy to assassinate the Prime Minister of Malaysia by the top people in the fashion industry, namely Jacobim Mugatu and Derek’s agent Maury Ballstein, before he can pass progressive labor laws in his country that would harm their businesses. Zoolander is recruited as a pawn and brainwashed into killing him during a fashion show. If that wasn’t enough, Derek faces an identity crisis due to his declining popularity, his family’s embarrassment of his occupation, and his search for a higher calling in life besides being ridiculously good looking. Thanks to his friend and eventual love interest, journalist Matilda Jeffries, Derek becomes aware of the planned assassination plot. Once Derek squashes his beef with competing male model Hansel, the three try to stop the assassination. The character of Derek Zoolander originated from a pair of VH1 sketches for the VH1 Fashion Awards in 1996 and ’97. The name was inspired by the names of two real-life male models: Dutchman Mark Vanderloo and American Johnny Zander.


Ben Stiller headlines the cast as the eponymous Derek Zoolander. Owen Wilson co-stars as Hansel, a rising star taking the fashion world by storm. Wilson was Stiller’s first choice for the role. However, he was uncertain if Owen would be available and auditions were held with even Jake Gyllenhaal reading for the role. That said, Stiller really only considered Wilson for the part and didn’t think the movie could have been made if the actor wasn’t involved. Christine Taylor plays Matilda Jeffries, a smart yet somewhat repressed journalist. Will Ferrell relishes in the role of villainous Mugatu. Comedian Andy Dick was actually set to play Mugatu, but was unavailable due to a previous commitment for the TV show Go Fish. Instead Andy would don a fat suit to become Olga the Masseuse who memorably has a fight with Derek’s dick. Milla Jovovich as Katina, Mugatu’s wicked henchman (er henchwoman… henchperson? whatever). The actor based her performance on her mother, Galina Jovovich. Jerry Stiller, Ben’s real-life father, plays Maury Ballstein, which was a role that Ben Stiller originally intend to play, but changed his mind after already deciding to play the lead as well as direct the film. Must’ve been weird for Ben to direct his dear ol’ dad to do this. Fun fact: that off-screen voice heard saying, “Ooo, Maury!” after the tushy squeeze, is actually the voice of Christine Taylor, Ben’s real-life wife! 

David Duchovny has a steal-scening role as J.P. Prewett, a washed-up hand model who reveals the dark underbelly of male modeling to Derek and Matilda. Duchovny was also offered the role of Derek’s brother, Luke, played by Vince Vaughn, but opted for J.P instead. Jon Voight has a great turn as Larry Zoolander, Derek’s disappointed father. To round out the Zoolander clan, comedian Judah Friedlander appears as Scrappy Zoolander. Alexander Skarsgard makes his American film debut as Meekus, one of Derek’s three roommates who suffers an untimely death due to a freak gasoline fight accident. The criminally-underrated Nathan Lee Graham plays Mugatu’s long-suffering number two, Todd. Justin Theroux has an excellent minor role as the Evil DJ, who’s appearance was inspired by Gary Oldman’s character in True Romance. Theroux had breakdanced at Stiller’s wedding to Christine Taylor in 2000, so Stiller asked if he’d show off his skills in the film. Practically everyone was anyone in the early aughts had a cameo in this… Patton Oswalt, David Bowie, Billy Zane, Lance Bass, Victoria Beckham, Stephen Dorff, Fred Durst, Tom Ford, Cuba Gooding Jr., Fabio, Lukas Haas, Tommy Hilfiger, Paris Hilton, Heidi Klum, Lenny Kravitz, Lil’ Kim, James Marsden, Natalie Portman, Mark Ronson, Winona Ryder, Garry Handling, Christian Slater, Gwen Stefani, Donatella Versace, Owen Wilson’s older brother Andrew, and yep, even Donald Trump. Also was that a blink-and-miss-it cameo from the legendary Jennifer Coolidge on the fashion Illuminati Board? Can’t believe the filmmakers did this to my girl, J.Cool.


Staying true to its VH1 roots, the opening scenes were filmed at the real life VH1/Vogue Fashion Awards in 2000 during commercial breaks. Derek Zoolander’s signature “Blue Steel” look stemmed from Ben’s wife Christine ribbing him about the way he looks when he combs his hair in front of a mirror in real life. Since he was also busy filming Behind Enemy Lines at the time and had a short haircut for that role, Owen Wilson was required to wear a wig for this entire movie. However, he wasn’t required to master a yo-yo, as those shots were performed by professional yo-yo stunt performer, Steve Brown. Without knowing if he would agree to it, Ben Stiller wrote David Bowie into the script as the  judge of Derek and Hansel’s walk-off. Thankfully, David agreed because he found the script too funny to turn down. His role is perfect for this oddball movie since David Bowie is the ULTIMATE judge of what’s “cool.”

Of course, there’s the infamous ad-lib during the scene where Duchovny’s J.P. Prewett explains the entire conspiracy to Derek. As he finishes answering Derek’s original question of (edit: “Why male models?”), Stiller has forgotten his next line and improvised this line in-character (edit: “But why male models?”). Duchovny played along and replied in character: (edit: You serious? I just… I just told you that a moment ago.”) Speaking of J.P. Prewett, looks like there was another scene with him appearing in the final scene at the Derek Zoolander Center for Kids Who Can’t Read Good and Who Wanna Learn to Do Other Stuff Good Too. The admittedly tame orgy sequence was initially longer and earned the movie an R-rating. After recutting the scene multiple times, getting rid of the inclusion of a goat, and convincing the MPAA’s board that the sequence was “more silly than sexy,” Stiller achieved in getting his desired rating of PG-13. And the silver lining is that the goat can still be seen briefly the morning after. In the original ending, Derek would’ve been fatally struck by a train and ascend to heaven, but the idea was scrapped as the producers feared they could not fit it into the film’s budget. 


Released on September 28th, 2001, the film received pretty positive reviews overall and became a minor box-office success, grossing almost $61 million dollars worldwide on a budget of $28 million. Although the studio was expecting it to perform better in theaters, the lackluster returns were cited as a consequence of releasing the film so soon after the September 11th terrorist attacks. Stiller made the decision to digitally remove any backgrounds that originally contained the Twin Towers in the city skyline, editing them out of one shot and obscuring them in another. People have questioned this move, but Stiller defended his decision to erase images of the Twin Towers, saying he did what he thought was appropriate at the time. Additionally, Zoolander was never shown in Malaysia as Malaysia’s censorship board deemed it “definitely unsuitable” for obvious reasons. They should have just done what they did for the Asian market release, with all references to Malaysia being changed to Micronesia, and just have Hansel mistake Micronesia for Malaysia later on. The film was also banned in neighboring Singapore due to its bilateral sensitivities and the movie’s depiction of using the drug peyote. However, the country eventually came around in 2006, releasing it with an NC-16 rating. There’s also an interesting legal case involving a 1998 satirical novel by Bret Easton Ellis, Glamorama, which tells the story of a slow male model who becomes involved in a plot formulated by international terrorists who recruit from within the fashion industry. With the noted similarities, the author attempted to take legal action, but the case was settled out-of-court.


After many years of waiting, fans finally heard traction on a sequel to the cult classic. In 2008, Stiller said he intended to make a sequel, by January 2011, a script had been completed, and filming commenced in Rome in early 2015. In March of that year, Stiller and Wilson appeared at the Paris Fashion Week in character for the film. On February 12th, 2016, Zoolander 2 was released to both harsh critical and fan reception before becoming a box office bomb with it barely recouping its production budget of $55 million dollars. Look, let’s put it this way. If the first Zoolander was ahead of its time, then the second one was WAY behind. Stiller was glad the film flopped because it would’ve prevented him from pursuing more serious, non-comedic work like Escape at Dannemora and Severance. In 2012, stars Ben Stiller and Owen Wilson met the actual Malaysian Prime Minister (with zero incidents). I thought that was it until I discovered there’s an animated movie called Zoolander: Super Model. It was produced in 2011 as a series of shorts with the intent of releasing it as a web series, but instead the episodes were loosely packaged together as a film and released on Netflix UK in 2016. It wouldn’t be released worldwide until May 2020. The film parodies ‘80s Saturday morning cartoons, depicting Derek and Hansel as superheroes.


Since its initial release, Zoolander has only increased in popularity thanks to its high rewatch-ability, hilarious characters, and endlessly quotable dialogue. Stiller and Co. included some amazing homages and nods to titles like 2001: A Space Odyssey and Star Trek, with Mugatu’s name being inspired by an albino ape creature known as “The Mugato.” Mugatu’s appearance was even modeled after the Star Trek character. See the resemblance? Not to mention that Stiller’s production company is called Red Hour Films, which is a reference to another episode of Star Trek. This movie truly succeeds at lampooning celebrity and high fashion culture and feels oddly prescient in a way. Such as Derek Zoolander’s “Blue Steel” being the harbinger of the subsequent social media selfie. Zoolander shows us that by accepting ourselves for who we are, and with a little help from our friends, we too can make the world a better place for super models and kids who wanna read good. Oh, and also discover our inner power to turn left… On that note, I give Zoolander 4 out of 5 orange mocha Frappuccinos.

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