Zoolander movies in order
Zoolander Marathon

Zoolander (2001)

Ben Stiller directed the original Zoolander, which introduces us to Derek Zoolander, a legendary male supermodel with a heart of gold and a brain... well, not so much. In a world filled with glitter, poses, and absurd fashion trends, Derek is at the peak of his career until his world crumbles after losing the Male Model of the Year award for the fourth time in a row. What follows is a wild mix of fashion industry satire, brainwashing plots, and an over-the-top villain: Mugatu, played by Will Ferrell in one of his most iconic roles, is the star of this film. With Owen Wilson as Hansel ("so hot right now"), Christine Taylor as Matilda Jeffries, and Milla Jovovich as the dangerous Katinka, this film is a parade of absurd humor, celebrity cameos, and the most ridiculous fashion clichés ever put on film. The Blue Steel pose, the "center for ants" scene, and the Derelicte fashion show are now part of mainstream culture. With its blend of slapstick comedy, modeling world humor, and a dash of action, Zoolander is the perfect start to your marathon. And yes, we know: it's impossible to watch this film without trying a new pose every fifteen minutes.

Zoolander 2 (2016)

Fast forward fifteen years, and we're back in the crazy world of international fashion, but now with even more glitz, glamour, and total absurdity. Zoolander 2 is set in Rome's fashion scene, years after the first film. Derek and Hansel have been out of the spotlight, but they're thrown back into chaos when a mysterious plot involving the biggest stars in pop culture comes to light. The sequel takes the fashion conspiracy storyline to a new level, with Penélope Cruz as agent Valentina Valencia, Kristen Wiig as the alien-like Alexanya Atoz, and Justin Theroux returning as the Evil DJ. And, of course, Mugatu is back. This time, he's even more eccentric, with a revenge plan that only a Zoolander film could come up with. The movie makes constant nods to the first one with Magnum-pose callbacks, new ridiculous facial expressions, and a ton of celebrity cameos (count them as a drinking game, seriously). Though Zoolander 2 received mixed reviews when it was first released, it's a must-watch for anyone wanting to fully experience the world of Derek and Hansel. The sequel is a tribute to the fans, full of inside jokes, over-the-top slapstick comedy, and a storyline as ridiculous as you'd hope. It's great for a late-night binge or a themed fashion party with friends. Pro tip: Put on your most impractical outfit and host a runway catwalk in your living room.

Why This Order Works

The Zoolander franchise is relatively straightforward in terms of timeline. There aren't any spin-offs, prequels, or secret side-stories yet. But it's worth watching the films in release order. The first Zoolander movie sets up the characters, world, and absurd logic that the sequel plays with. Zoolander 2 is full of references and inside jokes that you'd probably miss if you didn't already know about them. Also, Derek and Hansel's development as characters, weird as it is, is straightforward and based on what happened in the first film. In terms of how funny it is, this order works best. Zoolander (2001) is a fresh, original satire on the New York fashion scene, while Zoolander 2 is a hyper-stylized, international overdrive version of it. The first movie sets the foundation, and the second just cranks up the volume. And honestly, that's exactly what you want when diving into a world full of glitter, absurd outfits, and overacting for an evening.

Extra Viewing Pleasure: Trivia and Fun Facts

Did you know that Ben Stiller not only plays Derek Zoolander, but he also directed both films? Did you know the first Zoolander actually came from a sketch at the VH1 Fashion Awards? The movies are full of Easter eggs. For example, the "walk-off" concept keeps showing up in both movies, and minor roles from before are making a comeback (keep an eye on Justin Theroux). And of course, the poses have changed from Blue Steel to Magnum to... well, you'll have to see for yourself. Also fun: Mugatu's character is based on a Star Trek villain you probably haven't heard of, and the whole Derelicte fashion show is a pretty funny parody of how fashion can sometimes be totally out of touch with reality. The franchise is a nod to celebrity culture, fashion, and how seriously people sometimes take themselves. All with a perfectly timed soundbite or silly look from Stiller in between.

Set Up Your Marathon in Style

For the ultimate Zoolander movie marathon, we recommend watching it all in one evening. It's just two movies, so it's perfect for a Friday night with friends. Dress in your most over-the-top outfit, make a playlist of early 2000s fashion beats, and serve snacks that look like they belong on a catwalk (but are still edible). And remember, whenever someone says "Blue Steel," strike a pose! Best of luck with the facial muscle soreness. So whether you're revisiting the films for nostalgia or diving into the world of male model comedy for the first time, the Zoolander films are the perfect mix of absurdist comedy and iconic pop culture moments. Believe us, this is a franchise you really can't take too seriously. If you don't know how to watch, how can you expect to participate?