Zoolander

For the last decade, male modelling has been dominated by one name, and five syllables: Der! Ek! Zoo! Lan! DER!

Derek Zoolander is a really, really, ridiculously good-looking (but incredibly shallow) male model who suffers both a professional and personal setback when he loses the Male Model of the Year crown to Hansel ("he's so hot right now") and his friends to a tragic gasoline-fight accident. His manager sends him to a day spa, but it turns out to be a brainwashing center, where Derek becomes a sleeper agent programmed to assassinate the prime minister of Malaysia (an obstacle to the fashion industry's continued use of cheap Malaysian labor). It's up to Derek, his love interest Matilda, and his rival-turned-friend Hansel ("he's so hot right now") to foil this plot and help Derek live past thirty.

A sequel, Zoolander 2, was released in 2016.

Tropes used in Zoolander include:

Actor Allusion: Jon Voight as Derek's father.

"Damn it Derek, I'm a coal miner, not a professional film or television actor."

- David Duchovny as a conspiracy theorist.
- Ben Stiller's character's manager is played by his father, and his love interest is played by his wife.
Arson, Murder, and Jaywalking: After giving Derek a long list of what he's supposed to do as an assassin, Mugatu adds: "Obey my dog!"
Also Sprach Zarathustra: Part of a Shout-Out to 2001: A Space Odyssey.
Babies Ever After: The ending. Derek's son even adopts his first look: a pout reminiscent of his daddy's.
Backhanded Apology: The Jerkass version gets used twice.
Banned in Malaysia: Probably due to the perceived implication that all of its citizens are sweatshop workers and that its prime minister was Zoolander's assassination target. Also banned in Singapore as a move of goodwill, but the Singaporean ban was later repealed.
The Baroness: Katinka.
Beethoven Was an Alien Spy: The fashion industry has been behind every major assassination for the past 200 years, using male models as assassins.
Berserk Button: "One look? ONE LOOK?!"
Big No: Derek's reaction (actually a "Brint!") when he realizes his friends are about to get burned to death by a carelessly lit cigarette.
Brainless Beauty: Male models. (Although according to David Duchovny's character, hand models "work differently"). Also, Fabio is apparently too smart for the job that Mugatu brainwashed Zoolander to do.
Buffy-Speak: The Derek Zoolander Center For Kids Who Can't Read Good And Wanna Learn To Do Other Stuff Good Too.
The Cameo: Lots, from the celebrities at the fashion show in the opening part of the film to Billy Zane's memetic role to David Bowie as the walkoff judge, and lots more where that came from. Also includes James Marsden in a blink-and-you'll-miss-it shot as John Wilkes Booth during the assassination exposition.
Captain Oblivious: The runway competition.
Casting Gag: David Duchovny as a former hand model and Conspiracy Theorist.
Catch Phrase: Mugatu's variations on Hansel being "so hot right now."
Cloudcuckoolander: Rhymes with "Derek Zoolander".
Chekhov's Gun: Magnum
Cooking Duel: The runway walk-off.
Competence Zone: None of the male models lives past thirty (except the precious few who wise up and retire beforehand), something that The Omniscient Council of Vagueness ruthlessly enforces.
Conspiracy Kitchen Sink: According to J.P. Prewett (David Duchovny's character), pretty much every assassination in history can be traced back to the international fashion industry.

Matilda: Wait a minute, Lee Harvey Oswald wasn't a male model.
Prewett: You're goddamn right he wasn't, but those two lookers on the Grassy Knoll sure as shit were!

Corrupt Corporate Executive: The fashion industry executives.
Comically Missing the Point: This exchange from the film's climax.

Matilda: Derek, you did it!
Derek: I know! I turned left!
Matilda: (beat) That too, but you also saved the Prime Minister of Malaysia!
Derek: Oh. Cool.

Cymbal-Banging Monkey: In a flashback, Derek is briefly shown dressed up as a Cymbal-Banging Monkey. "Dance, monkey, dance!"
Dance Battler: "They're breakdance fighting!"
Dark Action Girl: Katinka, who is also The Dragon.
Defictionalization: Orange Mocha Frappuccinos were sold at Starbucks for a limited time.
Department of Redundancy Department:

Hansel: "And I felt like this guy is really hurting me. And it hurt!"

Derek: Maybe you don't understand that the world doesn't revolve around you and your 'Do whatever it takes, ruin as many people's lives, just so long as you can make a name for yourself as an investigatory journalist, no matter how many friends you lose, or people you leave dead and bloodied along the way, just so long as you can make a name for yourself as an investigatory journalist, no matter how many friends you lose, or people you leave dead and bloodied and dying along the way?'

Dirty Old Man: Maury Ballstein.
Disney Acid Sequence: The drug-fueled orgy.
"Falling in Love" Montage: Parodied in the orgy scene, where Matilda begins by making out with Derek and Hansel, and then the partners get a little... weird.
Fashion Show
Fire-Forged Friends: Zoolander and Hansel started as the worst of enemies but when things get ugly they become the best of friends.
Genius Ditz: Zoolander (and most everyone associated with the fashion industry) is a complete moron, but when it comes to fashion, make-up and just improving one's physical appearance he is a genius.
Glowing Eyes of Doom: Mugatu's toy poodle; during the brainwashing sequence, its eyes flash bright green.
Idiot Ball: Played for Laughs of course. Seriously, Derek and Hansel in particular are dumber than a bag of hammers.
Informed Attractiveness: Ben Stiller as a model? Owen Wilson?! Consciously done, because, well...
Intrepid Reporter: Matilda, who has a special hatred for models.
Its Pronounced Tropay: Mugatu's new campaign, "deraleect" (derelict).
Janitor Impersonation Infiltration: Hansel and Derek.
Joisey: At one point Derek goes to work with his family in the coal mines of South Jersey. The real South Jersey is a coastal plain.
Karma Houdini: Maury Ballstein. At the end, he admits to having been in on the child labor conspiracy for almost all of his career. However, he does not seem to have been punished in any way.
- Presumably he would get immunity in exchange for his testimony.
Lampshade Hanging: see Only Sane Man below.
Laser Guided Tykebomb: Derek gets brainwashed into this.
Love Epiphany: Parodied.

Derek: There was a moment last night, when she was sandwiched between the two Finnish dwarfs and the Maori tribesmen, where I thought, "Wow, I could really spend the rest of my life with this woman."

Malaproper: Derek, of course.

Derek: Or are you here to tell me what a bad eugoogolizer I am?
Matilda: A what?
Derek: A eugoogolizer... one who speaks at funerals. [after a confused look from Matilda] Or did you think I was too stupid to know what a eugoogoly was?

Malaysia: Most famously, for the film being banned in the country. See Banned In Malaysia above.
The Man in the Mirror Talks Back
Missing Mom: Derek's mom is dead.
Musical Trigger: "Relax" is what turns Derek into a killing machine.
My Hovercraft Is Full of Eels: Derek's grasp of Malay leaves much to be desired.
- Given that he's "dumb as a stump," the fact that he speaks Malay at all is pretty impressive.
Nice Guy: Derek, in a subversion of the typical bitchy-superstar stereotype, is actually sweet-natured and generous.
No Celebrities Were Harmed: Averted; all of the cameo actors play themselves.
One-Scene Wonder: David Bowie is the judge during the walk-off, and the movie even takes a moment to put his name on the screen. Befitting the trope, Bowie's one scene is awesome.
- Don't forget Brint, Meekus, and Rufus. Particularly Brint.
The One Thing I Don't Hate About You: "It's that damned Hansel! He's so hot right now!"
Only Sane Man: Part of Mugatu's Motive Rant. It is unusual that the villain is the Only Sane Man.

"He only has one look! [...] Does nobody else notice? I feel like I'm taking crazy pills!"

- Matilda fits this role much better however.
Only Six Faces: All of Derek's so-called "looks" are ~~almost~~ identical. (However, his "Magnum" look stops a shuriken in mid-air. Even Mugatu is wowed: "Dear god, it's beautiful!")
- There is a difference between Magnum and all the rest: he turns left before delivering it.
  - Less mindblowing-ly, his head is also vertical, as opposed to the angle his other looks were at.
The Omniscient Council of Vagueness: The round table running the fashion industry.
Overly Long Gag: The participants during the orgy scene.
- In a deleted scene, Derek enters the club where Hansel is having an after-party, passing something like six or seven groups of people just to throw a lame one-liner back at Hansel for an earlier insult. (Part of this scene ends up in the Imagine Spot when the hand model discusses why male models make the perfect assassins.)
Outdated Outfit: Mugatu's "Little Cletus" disguise is of what a child in the early 1900's would probably wear. Ironic, considering Mugatu should be keeping up with the latest fashions.
- Maury says that he can take any piece of crap polish it a little and sell it to a queen, so maybe Mugatu decides what is hot and what is not?
A Party - Also Known as an Orgy
Perfectly Cromulent Word: Derek is not an ambiturner. He can't turn left.
Phrase Catcher: Hansel. "He's so hot right now." In particular from Mugatu.
Punctuated! For! Emphasis!: When introducing Derek as a nominee for Model of the Year, the announcer guy enunciates each syllable separately (see page quote). Derek silently counts along to make sure that his name is indeed five syllables.
Real Life Relative: Christine Taylor, who played Matilda, is Ben Stiller's wife.
Refuge in Audacity: The whole movie, pretty much, but the ones that definitely stand out are the assassination plot and Mugatu's new line that does a high fashion spin on what homeless people wear.
- The latter is pretty Hilarious in Hindsight: it's been done for real... thanks, Vivienne Westwood!
Running Gag: Every time someone mentions Hansel, Mugatu immediately adds "He's so hot right now."
Scale-Model Destruction: Mugatu shows off a model of a school he's planning to build in Derek Zoolander's honor. Derek gets ticked and destroys it, because he doesn't understand the concept of a model.

Derek Zoolander: What is this, a school for ants? How can the children learn anything if they can't fit in the building?!.

Serious Business: The fashion industry.
Shaggy Dog Story

Hansel: So I'm rappelling down Mount Vesuvius when suddenly I slip, and I start to fall. I mean, I'm about to die. Just falling, "Ahhh! Ahhh!" I'll never forget the terror. When suddenly I remember, "Holy shit, Hansel, haven't you been smoking Peyote for six straight days, and couldn't some of this maybe be in your mind?"
Derek: ...and?
Hansel: ...it was. I was totally fine. I've never even been to Mount Vesuvius.

She Cleans Up Nicely: Matilda, again.
Shout-Out: "Beat It" plays over the walk-off between Derek and Hansel; Derek's brainwashing sequence channels A Clockwork Orange; Derek and Hansel imitate the "Dawn of Man" sequence in 2001: A Space Odyssey, complete with the soundtrack playing Also Sprach Zarathustra; The confrontation between Derek and his manager before he walks for Mugatu refers to The Godfather Part II.
Spit Take: Hilariously overdone by Mugatu.

"Todd! Were you not aware that I get farty and bloated with a foamy latte?!"

Technology Marches On Derek's tiny cell phone was a hilarious reveal meant to display how privileged he was (this being 2001 before having a cell phone was highly commonplace), but by today's standards, it looks extremely out of date and low grade despite being still ridiculously tiny, largely because it failed to anticipate that the advent of smart phones would stop dead the trend they were exaggerating.
This Is What the Building Will Look Like: Even if they can't fit inside the building.
This Looks Like a Job For Aquaman: Only a male model has the skills to make a perfect assassin, and only Derek's "Magnum" look (or is it "Blue Steel"?) can stop them!
Throw It In: At the end of David Duchovny's long-explanation for why models make the perfect assassins, Ben Stiller forgot what the next line was, and tried to wordlessly re-do the take by repeating his earlier line, "But why male models?" Duchovny, not wanting to ruin the take, ad-libbed "...are you serious? I just told you that, a moment ago."
Too Dumb to Live: Derek and his friends.
Training Montage: Derek's training to be an assassin.
What Kind of Lame Power Is Heart, Anyway?? "Magnum."
Weaksauce Weakness: Derek can't turn left (until the climax).
"Well Done, Son" Guy: Derek temporarily retires from modeling and tries to join his dad and brother in the mining field. It doesn't go over well.
What Happened to the Mouse?: What happened to the shadowy evil council who have been killing world leaders for decades?
- Nothing. Mugatu takes the fall while they get to be Karma Houdini.
Who Shot JFK?: According to the hand model, it's two male models on the grassy knoll.
Whole-Plot Reference: The whole movie is clearly inspired by The Manchurian Candidate.