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1* AdaptationDisplacement: Even fans who can quote the movie backwards and forwards aren't likely to be familiar with the two ''[=VH1=] Fashion Awards'' skits which the character of Derek Zoolander originated from.
2* CrossesTheLineTwice
3** Brint, Meekus, and Rufus's [[Website/DarwinAwards Darwin]]-worthy deaths in a [[TooDumbToLive "freak gasoline fight accident."]] It's probably the most voluntarily idiotic thing you'll ever see, and they just look so ''happy'' to be doing it!
4** Derek's heartfelt ambition to teach children to "read good" and "do other stuff good too" summed up oh-so-elequently by Maury.
5--> "He says he wants to teach underprivileged retards or some shit."
6** Matilda opens up to Derek and Hansel about why she doesn't like models... and the sentiment is brought to a screeching halt the second Derek says "Ew!" when she tells them that she used to be fat (though he apologizes immediately).
7** Later, Maury gets an entire classroom of children under 10 to shout, in unison, "Screw him! Hold out for more!" Profanity has never been so cute!
8* FashionVictimVillain: Mugatu looks like an unholy mixture of Satan, Cruella [=DeVille=], and a poodle. He also inexplicably dresses up as a young German boy during the brainwashing scene.
9** Katinka is only slightly better; she wears a business suit made of plastic, a very angular nurse's outfit and a lot of other weird things.
10* FountainOfMemes: Let's just say this movie is "very quotable" and leave it at that.
11** "I feel like I'm taking crazy pills!"
12** "What is this? A center for ANTS?!"
13** "I guess you can dere-LICT my balls, cap-i-tan!"
14** "Cool story, Hansel!"
15** "Orange mocha Frappucino!"
16** "You think I don't know what a eugoogoly is?"
17** "Hansel. He's so hot right now!"
18*** "Hansel. So hot right now. Hansel."
19** "Mer-MAN!"
20** " But why male models?"
21** " Listen to your friend Billy Zane. He's a cool dude!"
22*** "Put a cork in it, Zane!"
23** "They're [the files] ''in'' the computer?!''
24* FridgeBrilliance:
25** Zoolander's breathless accent probably sounds strangely familiar. It is: Ben Stiller is impersonating Creator/MarilynMonroe.
26** Derek is from New Jersey and can't turn left. Anyone who has driven in New Jersey would find this alternately funny and infuriating - [[http://en.wikipedia.org/wiki/Jughandle they use Jughandles]].
27* FridgeHorror: How many gas station employees were killed during the gasoline fight?
28* HilariousInHindsight:
29** Mugatu's defense of child labor sounds patently absurd, but [[https://www.youtube.com/watch?v=gR83FSRTPB4 Newt Gingrich seriously used that as an argument]].
30** Looks like someone is taking Mugatu's "Derelicte" idea [[http://www.newyorkfirst.com/gifts/lucky-beggar-walletcoin-purse-99/ seriously]]...
31** Derek's 'Blue Steel' look is essentially the same as the notorious duckface, which slowly took over young girls' social network profiles a few years after the film.
32** Derek famously dismisses a scale model of a building as "a center for ants." Fourteen years later, Film/AntMan1 would find himself running through a scale model of a building while under attack (even funnier, the trailer for ''Film/Zoolander2'' was run with that movie in theaters).
33* HollywoodHomely: Matilda. (Probably a deliberate joke; the DVD Menu has Derek refer to her as one of the "good-looking" ones)
34* MemeticMutation:
35** "Blue Steel", the signature modeling pose Zoolander strikes, has probably gotten more pop-culture nods than any other joke in the movie.
36** "What is this? A center for ANTS?!"[[note]]{{Snowclone}}d into describing anything the speaker considers too small.[[/note]]
37** "Doesn't anyone else notice this?! I feel like I'm taking ''crazy pills!''"
38** The scene of Derek [[https://www.youtube.com/watch?v=Tsvcey0bcgw dramatically walking through the mines]] is rather famous online, often being posted in response to situations involving overconfidence or miners themselves.
39** Since late 2022, [[https://www.youtube.com/watch?v=lCy04DTYTmA the scene of Zoolander and Hansel staring each other down]] is often used for comparison memes, set to a remix of “Who Is She”.
40*** In general comparing the rivalry between Hansel and Zoolander to any intense rivalry between a blonde man and a black-haired man. Especially so if the series they are being compared too is dark and serious, leading up to edits portraying them as Guts and Griffith from Berserk, or Solid Snake and Liquid Snake from ''VideoGame/MetalGearSolid''.
41** Also in 2022, the [[https://www.youtube.com/shorts/cxtSotESjEM "'scuse me, brah"/"You're excused... and I'm not your ''brah''"]] scene [[https://www.youtube.com/watch?v=5pvDtQXIvCQ took off like a rocket]] on social media, usually set to a [[https://youtu.be/Kf_Q8Mp9Jy4 remix]] of yally's "Party Party".
42* MexicansLoveSpeedyGonzales: Ask anyone in the fashion industry, they'll tell you that this movie is not only hilarious, but 100% accurate in its depiction of male models.
43* OneSceneWonder: Music/DavidBowie is the judge during the walk-off, and the movie even takes a moment to [[BossSubtitles put his name on the screen]]. Befitting the trope, Bowie's one scene is awesome.
44** [[TooDumbToLive Don't forget Brint, Meekus, and Rufus. Particularly Brint.]]
45** Creator/DavidDuchovny's brief cameo as a hand-model/informant was pretty remarkable as well.
46* RetroactiveRecognition: Creator/AlexanderSkarsgard makes his US film debut as one of Derek's model roommates who is killed in the gasoline explosion.
47* SignatureScene: Mugatu's [[VillainousBreakdown furious rant]] after Derek is snapped out of his mind control.
48* SpiritualSuccessor: Its plot, about a vapid male model who gets sucked into international espionage, was similar enough to Creator/BretEastonEllis' ''Literature/{{Glamorama}}'' (albeit [[PlayedForLaughs done as a comedic farce]] as opposed to a dark {{satire}}) that Ellis considered suing Ben Stiller over it, the two of them eventually reaching an out-of-court settlement.
49* UnintentionalPeriodPiece: A deluge of early-'00s or late-'90s cameos and pop music? Old-fashioned computer monitors and large translucent-orange Mac computer? Record players? Derek's tiny cell phone representing his privilege? It sure feels like the TurnOfTheMillennium.
50** In a more tragic note, it was one of the first films that aired after 9/11 that was set in New York, and as such edited out a shot of the Twin Towers. Ironically, moviegoers complained of this deletion, while other movies around the time such as ''Film/{{Glitter}}'' and ''Film/VanillaSky'' kept the shots in the film (and were applauded by audiences for doing so).
51* ValuesResonance: Although this movie is far from politically correct, the villains being white Westerners who want to kill the new Malaysian prime minister so that they can continue working Southeast Asian children for slave labor holds up pretty well, decades later. That's definitely evil and the kind of social issue that newer movies would want to satirize.
52* VindicatedByHistory: The film disappointed in theaters, having the misfortune to come out a few weekends after 9/11. Over the years, however, it became a hit on home video, with enough of a following to justify making [[Film/Zoolander2 a theatrical sequel]] nearly 15 years later.
53%%* TheWoobie: Derek.
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