3.5 out of 5 stars

Ben Stiller’s world was turned upside down by one man and five syllables: Der-ek-Zoo-lan-der. Everything was starting to click for Stiller back in 2001. There’s Something About Mary (1998) and Meet the Parents (2000) had been huge hits at the box office. In 1993, Stiller won an Emmy for writing on his short-lived TV series The Ben Stiller Show (1990-93), then followed it up by directing the modestly received Reality Bites (1994), which he also starred in. From there, Stiller directed The Cable Guy (1996), which did well financially but was less beloved by critics due to its dark humour. Stiller went on to star in other films, but Zoolander proved to be the perfect palette cleanse. 

The lovable dimwit’s origins stem back to the mid-1990s, where he contributed shorts to VH1’s Fashion Awards in consecutive years. Both “Derek Zoolander: Male Model” and “Derek Zoolander University” contained the seeds (and even some of the jokes) that bloomed into Stiller’s 2001 feature film. So what better setting to open the movie than at the VH1 Fashion Awards? Zoolander (Stiller) has his sights set on a fourth consecutive ‘Best Male Model of the Year’ award but a rising star and natural foe called Hansel (Owen Wilson) stands in his way. When Hansel upsets and wins the award, Zoolander is sent into an existential crisis. Making matters worse, when his three model roommates (one of whom is played by True Blood’s Alexander Skarsgård?!) die tragically after a playful gasoline fight, Zoolander contemplates giving up the catwalk entirely.

Meanwhile, one of the hottest designers, Jacobin Mugatu (Will Ferrell), has been tasked by the most powerful executives in the fashion industry to assassinate the Prime Minister of Malaysia. The new child labour laws would significantly increase the costs of production, reducing profits for those at the top. Mugatu decides to blackmail Zoolander’s agent Maury Ballstein (Ben’s father Jerry Stiller), who convinces Derek to be the face of Mugatu’s new campaign, knowing full-well the designer plans to brainwash Zoolander to carry out the assassination.

This movie is flushed with cameos of celebrities from the early-2000s. On the red carpet, there’s Cuba Gooding Jr., Natalie Portman, Christian Slater, Tom Ford, and a former POTUS all appearing as themselves and sharing their admiration for Zoolander’s achievements. That list alone would be impressive for an entire movie, but it’s only the tip of the iceberg. Zoolander also finds time to spend with Winona Ryder, Billy Zane, Paris Hilton, David Bowie, Justin Theroux, Gary Shandling, and Fred Durst, to name just a few.

Narratively, the film relies on the notion that male models are easy to brainwash because they’re already so vain, which feeds into the film’s sense of humour. Zoolander’s a character who’s so self-indulgent and vacuous that he has absolutely no comprehension for anything that exists around him. And while those may be unfavourable traits, Stiller makes the character likable because of how genuine and sincere he comes across. He’s not ignorant, he’s just completely oblivious while navigating an assassination scheme, humanitarianism, labour exploitation, and conspiracy theories, through the lens of someone who can’t turn left. It’s a rich comedic playground for Stiller. 

Mirroring him along the way is Owen Wilson as Hansel. The two models are presented as polar opposites, but in truth they’re very similar. Hansel tries to present himself as a spiritual being, who has the propensity for coming off pretentious to others in the industry, but he’s just as clueless as Zoolander. He appreciates Sting’s music, but he’s never listened to him (he just respects the fact that he’s making it). He felt like an outsider as a kid because he didn’t have dreams of being an astronaut, but was instead more interested in what bark was made of. Both Hansel and Zoolander are empty vessels that corporations manipulate to advertise whatever product they’re trying to sell. Or in this case, whichever world leader they’re trying to have killed. 

Stiller leans on the lack of awareness in his main characters to critique ideas of a problematic industry that has only lingered with the rise of social media. When Zoolander is about to retire, his roommates explain that models help people because “they make people feel good about themselves” and “teach them how to wear their hair in interesting ways.” Hairstyles are one thing, but Stiller is certainly tongue in cheek here by recognising the unrealistic standards of beauty represented in advertisements, perpetuated by these models. 

Later in the film, journalist Matilda Jeffries (Stiller’s partner Christine Taylor) vulnerably explains to Zoolander and Hansel that she became bulimic in her teens because she didn’t look like the women in her mom’s catalogues. After shaking off some confusion (Zoolander thinks she can read minds), they both tell her not to worry about it and it’s not a big deal. “We throw up after lots of meals.”—“Yeah, it’s a great way to lose a few pounds before a show.” Again, neither has any understanding of the weight of Matilda’s words and can only understand how it relates to them. But these lofty expectations of beauty still linger today, with more ways to consume media than ever before. 

On top of the social critiques, there are so many jokes crammed into this movie that, even when one fails, another one will land moments later. There are incredible sight gags, like Zoolander’s calendar that ‘demonstrates his range’, but just features the same photo of him every month, only he’s wearing a different coloured shirt. For some reason, Hansel is really into yo-yo’s and even uses one to disarm one of Mugatu’s cronies towards the end of the movie. And of course, Mugatu’s invention—the piano key necktie–is referenced throughout and he’s sure to remind everyone of its cultural impact. 

Though Zoolander’s impact was relatively modest at the box office (grossing $60M), there was enough of a cult following to revisit the characters in a sequel. Zoolander 2 (2016) unfortunately didn’t live up to expectations and was a massive flop, with the gross barely surpassing the budget (grossing $56M but costing $55). As with many comedy sequels, there were too many callbacks and recycled jokes, making the effort feel redundant. Zoolander 2 also came with some controversy, due to the transphobic nature of Benedict Cumberbatch’s character “All”, who’s the butt of a couple of jokes for being androgynous. The jokes felt lazy and out of place for characters who had been beloved otherwise. 

But where the sequel failed, the original excelled. The male models and fashion industry were always the targets, and that self-deprecation is part of what made those idiots so endearing. Stiller’s appreciation for the character is reflected in the casting decisions. His entire family is in the movie! In addition to both Christine Taylor and Jerry Stiller in larger roles, his mother makes a brief cameo as an angry protester who eggs Mugatu on the red carpet. Even his son gets a cameo of his own at the end of the film as Derek Jr., and manages to pull off a ‘Blue Steel’ look just like his dad. 

Though the stain of the sequel lingers, the original still holds up decades later. Yes, some of the gags do fall flat, but the volume is there and Zoolander provides so many quotable moments. It remains as funny as it was all those years ago, even if Hansel isn’t as hot as he once was. 


frame rated divider retrospective

Cast & Crew

director: Ben Stiller.
writers: Drake Sather, Ben Stiller & John Hamburg (story by Drake Sather & Ben Stiller).
starring: Ben Stiller, Owen Wilson, Will Ferrell, Christine Taylor, Milla Jovovich, Jerry Stiller & Jon Voight.