
How a blindsided Ben Stiller was left questioning his future: “I must have really fucked up”
Second-generation star Ben Stiller has been at the top of his game for decades now and seems to go from strength to strength every single year, with the list of great movies he’s starred in being ridiculously long, but even if he’d stopped 20 years ago, his career would still be hall-of-fame worthy.
In 2001, Stiller starred in and directed the fashion-centric farce, Zoolander, as the titular supermodel Derek Zoolander, ‘blue steel-ing’ his way through a scheme by an evil fashion designer, played by Will Ferrell, to assassinate the prime minister of Malaysia. The film was a massive success, both critically and financially, and still holds up as one of the greatest comedies of its time, and a sequel seemed like a slam dunk. However, despite rampant fan speculation, a follow-up never came…until 2016.
Stiller returned to direct Zoolander No 2 alongside much of the original cast. This time, Derek and his enemy-turned-friend Hansel, played by Owen Wilson, would have to join forces to navigate a return to the fashion industry and to take down a mysterious killer.
Legacy sequels can be big business, and this one had 15 years’ worth of hype on its side, but alas, that wasn’t enough, and Zoolander No 2 made less than its predecessor and ended up losing the studio money. To make matters worse, it was slated by reviewers, with the decision to cast Benedict Cumberbatch as a non-binary character receiving particular criticism.
All of this bad press naturally got to Stiller. On an episode of his former co-star David Duchovny’s podcast Fail Better (everyone has a podcast these days), the iconic funnyman revealed that he was caught completely off-guard by the negative press surrounding the long-anticipated sequel.
“I thought everybody wanted this,” he lamented (via People), “Then it’s like, ‘Wow, I must have really fucked this up. Everybody didn’t go to it. And it’s gotten these horrible reviews’. It really freaked me out because I was like, ‘I didn’t know, was it that bad?’ What scared me the most on that one was, l’m losing what I think what’s funny, the questioning yourself…on Zoolander 2, it was definitely blindsiding to me. And it definitely affected me for a long time.”
While it might have been hard to swallow at the time, the failure of Zoolander 2 might have actually benefited Stiller in the long run. If it had been a success, then that would have locked the actor into making nothing but comedy for the next several years, but instead, he was free to explore other options.
In the decade since the ill-fated sequel, he has expanded his portfolio to include some very highly-rated dramas, including Escape at Dannemora and Severance. Would he have had the freedom to make those shows if he’d been stuck making Zoolander 3? Almost certainly not.
This whole incident proves a number of things. Not only does it show that you can turn any bad situation into a positive, but it also demonstrates just how much tastes change over the course of less than two decades.


