Having not seen this movie since I was 12, but seeing it pop up here and there in my youtube recommendations I was curious to see if it held up. Comedy usually doesn't age well, and the early 00s in particular were rife with a certain style of comedy that definitely wouldn't fly today. So I was positively surprised to find out that not only does it hold up, it feels well ahead of its time in a lot of respects. It's a perfect example of how to use comedy derived from stupidity: Derek Zoolander and all of his compatriots are dumb as bricks, and it leads to some outlandishly absurd scenes and jokes which I don't want to spoil, because they're so ludicrous. If I were any kind of anthropologist, I'd even venture a guess that this feels very in line with the chaos and absurdity of meme humor.
Considering this came out in 2001, the same year as Freddy Got Fingered, it's genuinely remarkable just how wholesome and progressive this film feels. A movie depicting male modeling could easily be rife with homophobic jokes, but they're completely absent. Matilda brings up her history with bulimia and it's both treated seriously as well as used to deliver a pretty caustic punchline at the fashion industry. There's a really wholesome scene between Derek and Hansel where they settle their differences, and it isn't one where the female lead has to talk them through it, she doesn't say a word. Outside of that it's just consistently funny: almost every scene has quotable lines and good jokes that are all derived from the characters and not just non-sequiturs. Almost a joke of its own is the just insane amount of cameos, among which are Donald Trump, Fred Durst, David Bowie, Billy Zane, Tom Ford, Cuba Gooding Jr, Natalie Portman, Patton Oswalt, Christian Slater and I don't think I've covered even half of it.
It's not anything too remarkable visually, though it does replicate that hectic 00s MTV style quite accurately in certain scenes. But beyond that it's pretty basic and kind of flat. Not that much to say about it to be honest. A good time and holds up.