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Watching ‘Zoolander’ With My Teenage Brother, 20 Years After Its Release

The idea that Zoolander premiered on this day 20 years ago is a notion that causes my millennial brain to short circuit a bit. Time! What a crazy, sometimes horrifying construct!

I will be the first to admit that I was a pre-teen disciple of this film and I have seen it more times than I care to admit. My mom and I watched the Zoolander DVD so frequently that we wore it out and had to buy a second copy. Yet, somewhere between high school and my early 20’s, my strange devotion to Zoolander fell by the wayside.

Fast forward to 2021. I now have a 13-year-old brother who, bless his heart, was born 7 years after Zoolander’s release. When it recently came to my attention that he had never had the pleasure of viewing this piece of early-2000s cinema, I went on about it and quoted the best one-liners to such great lengths that he insisted we watch it together while I was visiting home recently.

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Who was I to say no? In fact, I realized that I haven’t seen it in well over a decade and so I was thrilled to watch it with him and our mom. Considering Zoolander was my favorite movie when I was his age, I was curious to see if my brother would love it as much as I did.

For those of you who have never had the pleasure of watching this satirical action-comedy, here’s the gist: Derek Zoolander (Ben Stiller) is a former A-list male supermodel who has recently become disgraced and obsolete in favor of newer, sexier male models, namely, Owen Wilson’s character, Hansel.

Hansel. So hot right now.

However, due to his narcissism and dim-wittedness, Derek is unknowingly recruited by a group of global fashion designers, led by Will Ferrell’s character, Jacobim Mugatu, to assassinate the Prime Minister of Malaysia.

Why the Prime Minister of Malaysia, you might ask? Because he is in favor of prohibiting child labor in sweatshops, which would upend the entire fashion industry, according to the cadre of shady fashion overlords at the center of the film’s plot. Derek does his absolute best to triumph in an industry that has (quite literally) brainwashed him to be a killing machine and “Relax” by Frankie Goes to Hollywood is featured prominently throughout the film as the song that triggers Derek’s brainwashing. What could go wrong, am I right?

My little bro’s favorite part: 

Let it be known that my teenage brother loved Zoolander as much as I hoped he would! (Hooray!) We had to keep rewinding because we were both laughing so hard. (And so was our mom!)

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So, what part did he like the most? I asked him after viewing and he immediately started quoting, “I’ve got the black lung, pa!”

This now-iconic scene where Derek Zoolander is in a coal-miner bar with his father (Jon Voight) and brothers (Vince Vaughn and Judah Friedlander), after 1 short day of working in the mines causes Derek to develop an adorable little cough, which Derek asserts is the result of a respiratory issue that only affects lifelong miners. (Note: This scene takes place in Southern New Jersey, which is deemed “coal mining country” in the film. If you’ve never been to New Jersey, I can confirm there are ZERO active coal mines there, which makes this part even funnier.)

My favorite part:

I was curious to see if my old favorite scene in Zoolander would still be as funny as I’d remembered. And luckily, for the sentimental sake of my nostalgia, it was! I’m talking about the walk-off scene in which Derek and Hansel compete in front of a large crowd of celebrities and fashionistas to see who is the more superior male model. In the style of a high-profile boxing match, Hansel is hyped up by his posse while Derek is nursed in the corner of “the ring” by model Tyson Beckford, who mists his face with Evian and reminds him “You’re not a kid anymore, Derek!”

The walk-off culminates in a gag that was practically written for 13-year-old boys, with both men attempting to pull their undies out of their pants… with varying levels of success. I think this is the part where my brother laughed the hardest. And I must say, the walk-off scene made me appreciate that unique feeling of joy when you see someone you love very much laugh incessantly at something you found equally as hilarious years before they were even born. After this particular viewing of Zoolander, the walk-off scene has a new level of sentimentality for me.

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Some of the bit-part actors are now A-list celebrities

Talk about curveballs, you guys! There were several occasions where I insisted we pause and rewind, exclaiming, “Wait, isn’t that so&so?!?” Here were 2 such occasions that really threw me for a loop:

Alexander Skarsgård makes an appearance in the beginning of the film as Meekus, one of Derek’s 3 supermodel roommates. Sadly, all of Derek’s roommates perish in a freak gasoline fight accident upon getting orange mocha frappuccinos and joy-riding through Manhattan to “Wake Me Up Before You Go-Go” by Wham!. (Sorry for the spoiler alerts but you’ve officially had 20 years to watch this movie so… I’m not actually that sorry!)

How have I seen this movie a bajillion times and never realized that Justin Theroux plays the DJ?! Yes, Justin Theroux from Mulholland Drive, The Girl on the Train, and HBO’s The Leftovers plays a neanderthal-chic DJ who helps to brainwash Derek to kill the prime minister of Malaysia. And I had to wait 20 years after the film was released to realize that fact.

The amount of celebrity cameos in this film is actually insane 

The best cameo this time around, IMO, was Patton Oswalt as the bespectacled photographer who screams “dance monkey, dance!” when Derek is dressed in full circus monkey costume. This was another instance where my poor mother and brother were forced to rewind and listen to me expound about how I had never noticed this before.

In addition to Patton Oswalt, Paris Hilton, Lance Bass, Sting, 2 of the 5 Spice Girls (Victoria Beckham and Emma Bunton), Jennifer Coolidge, Lenny Kravitz, Natalie Portman, Gwen Stefani, Billy Zane, and Donald and Melania Trump all make appearances throughout the film. (In fact, the next time you watch Zoolander, see if you can cross off every celeb on this list. It’ll be fun, I promise!)

Among the extensive list of celebrity cameo appearances, there is 1 instance that shocked me to my core. Here’s the situation: Derek Zoolander is sitting in a private room in the back of a swanky nightclub, flirting with a Hollywood ingenue that people in my generation know for a variety of roles. But, the generation gap between my brother and I really made itself known in this scene when my little bro cocked his head and pointed to the TV, saying:

“Wait, isn’t that the Mom from Stranger Things?” 

Whaaaat?! Oh my gosh. Is this how teenagers identify Winona Ryder these days? The short answer, I informed him, is, “Yes, yes it is.” The long answer is, “Wait, have you never seen Beetlejuice? Or Edward Scissorhands? Or Reality Bites? Heathers? Not even The Crucible?! Of course not, you’re 13! You have some serious catching up to do, young grasshopper.”

There *were* a few cringe-worthy moments that definitely did not age well…

In addition to the Donald and Melania Trump cameo (which aged way more than Melania has), there was also a notoriously off-color joke about Bulimia (“You can read minds?”) that induced a present-day cringe, and 2 instances of Derek sporting blackface in the film. But fans (and also the media) still have a lot to say about Ben Stiller’s directorial choices when it came to depicting blackface in the film.

RIP Jerry Stiller (and also David Bowie)

Seeing as Ben Stiller starred in, directed, produced, and co-wrote Zoolander, he had carte blanche to make the film a family affair. Not only does his wife, Christine Taylor, star as Matilda Jeffries, the Newsweek reporter who becomes Derek’s central love interest, but Ben’s own father, Jerry Stiller (who you may remember as Frank Costanza from Seinfeld) was cast by his son to play the role of Maury Ballstein, Derek’s agent. Rewatching this film tugged at my heart a bit knowing that Jerry Stiller is no longer with us, having passed away last May. In my humble opinion, his performance as Maury Ballstein remains unprecedented in many ways.

Also, I hate to even admit this on the internet but, shamefully, this movie was how I first learned who David Bowie was… And, for that reason, whenever I hear a David Bowie song, I always instinctively think of Zoolander. (If you’re outraged at the fact that I just said that, know that I became a David Bowie fan later in life, and “Young Americans” is the best album ever so you can go be mad at me about that instead.)

Since I’ve previously explained that the walk-off scene in which David Bowie appears is my favorite scene in the movie, watching that part this time around made me a bit heartsore for the rock & roll legend. But you can rest assured that I can still sometimes be found dramatically removing my sunglasses and saying, “I believe I might be of service” to absolutely no one.

“Wait, do you think this movie was banned in Malaysia?”

My little bro was on to something with this astute question. Upon further investigation (ie: a Google search), I learned that the film was deemed “definitely unsuitable” by the Malaysian Home Affairs Ministry Film Censorship Board in 2001, and Zoolander has never been released in the country. Bonus censorship fact: Zoolander was also banned in neighboring Singapore but not for its plot to assassinate Malaysia’s Prime Minister. Surprisingly, the film was censored in Singapore for a scene depicting the use of peyote. (The more you know, right?)


Ethical clothing manufacturing and child labor exploitation are still completely relevant issues

Who would’ve guessed that the ideological crux of this film would still hold such weight in the year 2021? I mean, not that the primary purpose of Zoolander was to spread awareness of child labor exploitation in Malaysia but… it’s not not about that.

But what about Zoolander 2?

Not that anyone asked but no, I ha