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Ben Stiller Explains Why Zoolander 2 Flopping Was Actually A Good Thing

Ben Stiller and Penelope Cruz as Derek Zoolander and Valentina Valencia in Zoolander 2
(Image credit: Paramount Pictures)

In a world where sequels and reboots seem to be the name of the game, not every one of them is going to be a winner. 2016’s Zoolander 2 certainly wasn’t. The comedy bombed at the box office, disappointed critics and audiences alike and offended the transgender community. Six years later, Ben Stiller, who starred n and directed the sequel, is sharing why he’s actually a-OK with Zoolander’s success not striking twice. 

Zoolander 2 opened in theaters this time years ago to disappointing results. Ben Stiller admits it was “not a great experience” to watch a movie he helmed and led to fail all over the world. Here’s why he’s made peace with it: 

If Zoolander 2 had been a huge hit, and then people were saying ‘Zoolander 3!’ ’Do this movie! That movie!’—that might have taken me off the road of having the space to work on developing Dannemora.

Since Zoolander 2, Ben Stiller has made a very sharp turn from comedies to more gritty dramas, including Escape At Dannemora, a critically-acclaimed miniseries he made after returning for another Blue Steel. While speaking to Esquire, Stiller shared that if Zoolander was a big hit, he isn’t sure he would have had time to make the shift he has since in his career. He continued:  

I might have gotten distracted by other bright shiny objects, but instead it opened a path where I could just do what I’d honestly wanted to do for years and years, which was: just direct something! To say, I’m just going to work on this project that I want to work on, because it takes a little time to get these things going, and if you don’t stick with it you don’t get there.

Perhaps Zoolander 2 gave Ben Stiller the kick in the butt he needed to go after different kinds of opportunities that are less commercial than the star-studded and cameo-filled comedy was in 2016. Escape At Dannemora is a biographical crime drama about a female prison employee in upstate New York (played by Patricia Arquette) who becomes romantically involved with two inmates (Benicio Del Toro and Paul Dano) and hatches a plan with them to help them escape. 

Prior to Zoolander 2, Ben Stiller had directed another great project that skewed more on the dramatic side with The Secret Life of Walter Mitty, and the failure of his comedy allowed him to branch out to that side of his interests. His latest project is a thriller series called Severance, starring an impressive cast that includes Adam Scott, John Turturro, Christopher Walken and Patricia Arquette. 

Severance centers on Scott’s Mark, an employee of a company called Lumon Industries, who agrees to their “severance” program, which separates his non-work and work memories from each other. The show, which can be streamed with an AppleTV+ subscription, has been receiving great praise. While we don’t expect another Zoolander movie anytime soon, if at all, Ben Stiller has found a really intriguing new avenue for himself as a director these days. 

YA genre tribute. Horror May Queen. Word webslinger. All her writing should be read in Sarah Connor’s Terminator 2 voice over.