The Box Office Flop That Had Ben Stiller Questioning His Career

"Zoolander 2" didn't have the best debut back in 2016. The sequel to Ben Stiller's 2001 comedy classic made just $55 million worldwide on a $50 million budget. Considering movies generally need to double their budget in order for the studio to start seeing a return on investment, that isn't all that great. Such a poor box office showing was made worse by the critical response, with the film currently sitting at a dismal 22% on Rotten Tomatoes. Indeed, /Film's review criticized "Zoolander 2" for being as stupid and out of touch as Derek Zoolander himself.

There was no reason why "Zoolander 2" needed to be as bad as it was, though. The sequel reassembled the stars of the original, with Stiller joined by Owen Wilson and Will Ferrell. Like its predecessor, the film also featured multiple celebrity cameos, including one particularly distasteful turn from Benedict Cumberbatch as a non-binary character. Okay, maybe there was a reason why the sequel bombed.

Anyway, all of this, it seems, upset Stiller. The star of both films co-wrote, produced, and directed the sequel and was apparently blindsided by its critical and commercial failure. Still, Stiller previously spoke about having made peace with the failure of "Zoolander 2" and had seemingly moved on from the whole debacle. Now, however, he's revisited this particularly dark chapter in his career in an interview where he elaborated on his struggles with the film's reception.

Speaking to David Duchovny on the debut episode of Duchovny's upcoming "Fail Better" podcast (via People), Ben Stiller explained how, going into the "Zoolander 2," he thought "everybody wanted this," adding, "And then it's like, 'Wow, I must have really f****d this up. Everybody didn't go to it. And it's gotten these horrible reviews.'" According to the "Meet the Parents" star, the whole experience "really freaked [him] out," with Stiller claiming he didn't know the film was as bad as it was before it came out. He continued:

"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."

Duchovny featured in the original 2001 film as J. P. Prewitt, the world's greatest hand model who explains to Zoolander that the fashion industry has been behind "every major political assassination over the last 200 years." The "X-Files" actor previously explained to Vanity Fair how he asked his agent to reach out to Stiller about appearing in the film, and knew exactly what kind of character his cameo should be. Perhaps, then, Stiller's familiarity with Duchovny is what allowed the actor to open up more about his struggles following "Zoolander 2." Whatever the reason, the actor was willing to explain how the whole experience is what led him to become involved in Showtime's crime drama "Escape at Dannemora" and the mind-blowing, must-watch Apple TV+ series "Severance."

In recent years, Ben Stiller has turned towards drama, demonstrating his directing talents on "Escape at Dannemora" and earning a Directors Guild of America Award and two Emmy nominations as a result. He then turned his attention to "Severance," directing multiple episodes of the acclaimed first season and serving as executive producer. Without "Zoolander 2," it seems unlikely any of this would have happened. As Stiller went on to tell David Duchovny:

"The wonderful thing that came out of [the response to 'Zoolander 2'] 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. But 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."

Asked why he specifically didn't want to pursue more comedy after the failure of "Zoolander 2," Stiller claimed, "It was just hurt," and explained that he'd always loved directing. "I always loved making movies," the 58-year-old said. "I always, in my mind, loved the idea of just directing movies ... since I was a kid, and not necessarily comedies. And so, over the course of like the next like, nine or 10 months, I was able to develop these limited series." Though it's far from one of the best Ben Stiller movies, in a way, we should all be grateful for "Zoolander 2" for pushing Stiller towards better projects that have defined his late-career success.

Stiller's episode of "Fail Better" premieres May 7.