On David Duchovny’s Fail Better podcast in 2024, Ben Stiller admitted he went into Zoolander 2 thinking “everybody wanted this.” So when the movie flopped, it rattled him to his ridiculously good-looking core. The high-energy performer behind 2000s comedy classics like Dodgeball, Meet the Parents, Tropic Thunder, and the original Zoolander suddenly wondered if he’d lost his sense of what was funny. It’s a doubt that’s clearly stuck with Stiller as he’s transitioned into a new era of his career as the director behind critically acclaimed dramatic series like Escape at Dannemora and Severance.
But the widely known lesson of Zoolander 2’s failure should have already clear long before its release in February 2016: Sequels are tough. Especially in the 2010s, when Hollywood kept dusting off classics like Anchorman, Dumb and Dumber, and The Hangover for lackluster follow-ups. As Netflix began to kill off theatrical comedy as a reliable box-office hit, Hollywood pivoted to nostalgia and bloated casts as a quick fix. The only problem? No one stopped to ask what made the original movies work in the first place. A decade after its release, Zoolander 2 is an example of why 2010s comedy sequels tanked so hard, and why the genre is still struggling today.
Directed by and starring Stiller, Zoolander 2 brought the actor’s dimwitted supermodel Derek Zoolander back to the runway 15 years after the original became a cult comedy hit. Directed by and starring Stiller alongside Owen Wilson as rival model Hansel, the sequel follows the duo as they’re pulled into an Interpol conspiracy tied to the assassinations of the world’s most beautiful people. The film leans heavily on celebrity cameos and fashion-world satire in an attempt to recapture the original’s absurd magic.
Zoolander 2 kicks off with Justin Bieber getting gunned down, instantly tying the film to a very specific era of the mid-2010s. Right out of the gate, Stiller signals he’s not leaning on the same intentionally dumb comedy that made the original a hit. Instead, he tries to update the formula, clearly aiming to realign itself with what Hollywood thought was funny at the time: callbacks and cameos.
Even though the first Zoolander had big-name cameos like Billy Zane and David Bowie, they felt woven into the story, getting moments that mattered rather than just popping up for applause. In Zoolander 2, it’s more about the callback than the contribution. Zane’s back, the foam latte assistant returns, even the Evil DJ shows up, but it all feels thinner this time, more like cheap fan service than anything substantial.
What made the original Zoolander work is that Derek and Hansel played complete idiots in a mostly normal world. They felt like the extreme end of fashion’s nonsense. In the sequel, the whole world is just as ridiculous as they are, so the joke flattens out. Add in all the celebrity faces, and it stops feeling like a parody of reality and starts feeling like a parody of itself.
You could say the same thing about 2013’s Anchorman 2, which crams Kanye West, Liam Neeson, Harrison Ford, and Will Smith into its bloated, 2-hour runtime. A year later, Dumb and Dumber To forgot that Lloyd and Harry worked because they were clueless, not cruel, and leaned more into them being jerks than being dumb. A lot of comedies from that era either turned into something like the famously terrible Movie 43, throwing more celebrity faces at the screen than actual jokes.
Zoolander 2 ended up being part of the slow collapse of theatrical comedies. It’s a movie that chose to play it safe and lean on brand recognition instead of taking a real swing. Like many of its peers, it defaulted to the same overloaded cameo formula that had already begun to wear thin earlier in the decade. In the process, it lost sight of what made the original so sharp and specific. Rather than building the best sequel, Hollywood chased familiarity and assumed nostalgia alone would be enough.
Today, comedy is less universal than it was back then, and a theatrical comedy is harder to pull off than ever before. Audiences were so starved for laughs that some people found the new Naked Gun reboot “life-affirming,” while producers believed they would initially have to teach audiences how to watch parodies again. Nobody really has the cure for what’s hurting comedies right now, but if history’s any guide, the fix probably starts with getting back to basics — which is what Zoolander 2 should have done.
