Rumors of a Zoolander sequel have circulated off and on for years, but yesterday sh*t got real when Deadline published a report that Penelope Cruz has signed onto the movie, with Justin Theroux writing the script and Ben Stiller directing. Originally, Deadline said Theroux would direct, but his commitment to The Leftovers season 2 won’t leave him enough time, so Stiller is helming. This is the world we live in—Justin Theroux, most famous for being Jennifer Aniston’s significant other, has too many projects to direct the sequel to an iconic comedy.
That’s a bit unfair of me. Theroux had a successful career as a screenwriter before he met Aniston and he’s tight with Stiller and that comedy crew. He co-wrote Tropic Thunder, which is a lifetime achievement as far as I’m concerned. That movie is f*cking brilliant. There’s no denying that Aniston has made Theroux into a household name, but he’s always been part of Stiller’s group, so it’s really not that surprising that he’d be tapped for Zoolander 2, though ultimately he can’t follow through on it.
I’m nervous about a Zoolander sequel regardless of who’s directing. Comedy sequels rarely work out, and Zoolander is such a high bar to clear. Part of me wants to revisit Zoolander, but then I remember Anchorman 2 and Dumb and Dumber To. Great comedy is lightning in a bottle, it depends so much on timing and chemistry and it’s so hard to capture it twice. So another part of me would be just as happy to see the Zoolander band get back together and make something new instead. But we’re rolling the dice on the sequel. Here’s hoping Stiller, Theroux & Co. can recreate the magic.