The original Zoolander was a cult success largely because those who bothered to watch it wound up finding themselves pleasantly surprised. It was spirited and quotable, absurd in a way that worked both as clever satire and dumb, belly-laugh comedy. Sequels rarely replicate the experience of watching that film for the first time for a couple reasons: the audience now has real expectations and well, the people involved are self-aware enough to try and make good on those. This is a problem with this type of comedy film, and one we've seen happen time and again in lackluster sequels like Anchorman 2 and The Hangover 2. More often than not, you can see the talent involved confuse what made the first outing work. Instead of an attitude or a spirit, we find a doubling down on repeated events, celebrity cameos, or supporting characters and the jokes come off as a desperate attempt to cash in. Zoolander 2 is guilty of a great many of these sins. It repeats and extends jokes, it becomes unclear about what makes its stupid characters funny and often makes them a little mean-spirited, it clunkily tries to adapt an idea for a different cultural moment, it has been embraced by exactly the thing the original criticized.
And yet, it feels like a mistake to bother with taking the film to task on these offenses for one reason and one reason only: it's still pretty damn entertaining.
Chances are, if you were a kid who rewatched Zoolander time and again, you're going to be amused by its sequel. While lacking in much of the wit that made the first film work, the type of over-the-top, posed idiocy offered up by Ben Stiller and Owen Wilson remains funny. There's a surreal level of impossibility in the world the film proposes. We must remember that the events we're seeing come in the wake of a supposedly great male model stopping a throwing star mid-air with a pout, and the sequel takes this as a kind of game-changer. After an extensive prologue involving the bullet-ridden death of Justin Bieber, we find Derek Zoolander (Ben Stiller) in hiding. His school for kids who can't read good collapsed and killed his wife, his son was taken from him, and only a mysterious message carried by Billy Zane can drag him to Italian fashion week. Hansel, too, is brought out of retirement by Zane in the midst of his own orgy-related crisis. When the two meet up, they are brought by an Interpol agent-slash-swimsuit model (Penelope Cruz) into another couture conspiracy, this time involving Derek's estranged son Derek Jr. (Cyrus Arnold).
The story is relatively slight, the details don't add up, and if you go looking for plot holes... I mean, you're going to build quite a list. What it lacks in narrative cohesion, though, it makes up for in a total commitment to the absurd. Zoolander 2 devolves ever-further into its own goofy weirdness, offering up island prisons for fashion criminals, exploding designers, genetic fountains of youth, a collectively pregnant poly-amorous orgy, a creepy child with Fred Armisen's CG-face, the assertion that swimsuit models can swim with a superhuman speed. It's palpably strange in ways that may not always work, but are almost always delightfully silly. The actors and various talents involved are running with the opportunity to get weird, and with all the added costuming and bright set pieces, the film creates an energy we don't see in many live action comedies. There's a strange dream-logic to the stupidity here, something that feels a little more like falling down an Adult Swim rabbit hole than stepping into a movie theater. It's zany, weird fun; a dumb kind of frothy. If you just go with it, the questions of why the film exists or whether or not its good are totally supplanted by the fact that it manages to make most of these over-the-top excursions at least passably entertaining.
Ultimately, this is really the only way of evaluating this type of film's success or failure. The question of whether or not you laughed is everything, and totally subjective. Zoolander 2 is stupid. Like, willfully, purposefully, really, really, ridiculously stupid. It stretches the bounds of its characters and conceits. It repeats and tries hard to expand on already off-kilter jokes. It knows it isn't necessary and knows it shouldn't be trying to surpass the first film. It just tries to be funny. And, yeah, I did laugh. I laughed kinda a lot. I smiled kinda a lot. In fact, I'd say I generally enjoyed myself. Rating it is arbitrary. The fact is: I'd sure as hell watch it again.