Ben Stiller Says the Failure of ‘Zoolander 2’ Haunted Him for Years

The ‘Zoolander’ sequel was a cigarette in the gas-fight of Stiller’s filmography
Ben Stiller Says the Failure of ‘Zoolander 2’ Haunted Him for Years

While making Zoolander 2Ben Stiller thought that the sequel to his 2001 smash hit would add another instant classic comedy film to his already impressive filmography. Then, following the film’s release, Stiller’s career took a left turn. 

The mid-2010s was a weird time for the comedy film industry. Following the conclusion of the Hangover trilogy in 2013 and with the mid-budget movie itself quickly falling out of fashion among studio financiers, some comedy directors turned to the properties of the past in search of sure things that would revitalize the genre — 21 Jump Street and 22 Jump Street rebooted an antiquated drama series for film success. Adam McKay returned to his roots with Anchorman 2: The Legend Continues. And, in the riveting world of fashion, Derek Zoolander mounted a comeback fifteen years after his first film had theatergoers across the country asking, “But why male models?”

However, despite the significant investment made by Stiller and Paramount Pictures into picking up where the first Zoolander film left off, 2016’s Zoolander 2 was a critically panned commercial failure that stopped the non-franchise in its tracks. In an upcoming episode of David Duchovny’s podcast Fail Better, Stiller explained how the crushing failure of Zoolander 2 changed the course of his career for years to come, lamenting of the sequel, “I thought everybody wanted this.” 

And here I thought male models didn’t think for themselves.

Stiller recalled his thoughts following the release of Zoolander 2 as, “Wow, I must have really fucked this up. Everybody didnt go to it. And its gotten these horrible reviews. The writer, director and star of the film told Duchovny, to whom Stiller grew close following Duchovnys brief but hilarious appearance in the original Zoolander, “It really freaked me out because I was like, ‘I didnt know was that bad?’”

“What scared me the most on that one was, lm losing what I think whats funny, the questioning yourself,” Stiller explained of how the flop impacted his career trajectory and creative life, “On Zoolander 2, it was definitely blindsiding to me. And it definitely affected me for a long time.

However, Stiller found failure to be the best teacher, saying of the silver lining from Zoolander 2s disappointing performance, “The wonderful thing that came out of that for me was just having space where, if that had been a hit, and they said, 'Make Zoolander 3 right now, or offered some other movie, I would have just probably jumped in and done that.” 

The failure of Zoolander 2 forced Stiller to re-evaluate his artistry, he followed a different path that led to massive success. Stiller explained, “I had this space to kind of sit with myself and have to deal with it and other projects that I had been working on — not comedies, some of them — I have the time to actually just work on and develop.

Those other projects included the 2018 crime drama limited series Escape at Dannemora, which landed Stiller on the nominations list of most major industry accolades and a win for Outstanding Directing — Miniseries or TV Film at the DGA Awards, and his ongoing AppleTV+ psychological thriller Severance, which just recently wrapped filming on its highly anticipated second season. 

Its fair to say that, following the collapse of the Zoolander franchise, Stiller rebuilt his aspirations at least three times bigger.


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