"C'mon, it'll be fun!"
Think of the times this phrase has talked you in to doing things. For better or worse, a situation arose that felt like it would be too much of a good time to turn down. At its essence, that phrase has to be why Ben Stiller decided to return for Zoolander 2. It must have been fun to write (along with Justin Theroux, John Hamburg and Nick Stoller), to direct mostly the same ensemble again, and to act as the self-centered and vapid supermodel Derek Zoolander one more time. Whether it was fun to watch is another story.
Back when 2001's Zoolander first came out, Stiller was enjoying the success of There's Something About Mary. He already had an Emmy for his prematurely canceled sketch show, The Ben Stiller Show, and had directed two feature films. So while turning a sketch character that had originated on a VH1 Fashion Awards show seemed like a gamble, Stiller had more than enough goodwill and cache to pull it off. But here's why I bring that up: it's been awhile since Stiller was that Ben Stiller. Ben Stiller is now the star of the Night at the Museum movies. He's Gaylord Focker. The closest he's come to his sketch comedy roots was 2008's Tropic Thunder, but 2013's The Secret Life of Walter Mitty seemed to herald that Stiller was ready to move on to more mature themes as a director, while occasionally paying the bills as a voice actor in a Madagascar movie and then prove he's still a legit actor in a Noah Baumbach joint. That's Stiller's career now, so heading back into something as silly and over-the-top as Zoolander seems like a step backward for Stiller at this point. Sadly, the sequel proves that it was.
Uber-fans of the original movie will be happy to know that Zoolander No. 2 starts off (after an initial chase scene which seems to exist only to kick-start the litany of Macguffins included in the movie) with an explanation of what happened to Derek Zoolander in the intervening years that includes every detail of the ending of the original, even The Derek Zoolander Center for Kids Who Can't Read Good and Who Wanna Learn to Do Other Stuff Good Too. In fact, what happens to the building is a major catalyst for what Zoolander's life has become (though it might have been smart to date the "archival footage" of the building's demise to a later date to avoid some unnecessary allusions to the disaster that happened only weeks before the original movie opened in 2001), as the building's collapse leaves him widowed and ruins his friendship with Hansel (Owen Wilson). Eventually stripped of his son by Child Protective Services, Zoolander lives in seclusion until he is asked to come out of retirement to model in Rome at the request of Alexanya Atoz (an almost-unrecognizable Kristen Wiig). Zoolander only agrees in an attempt to prove he is a responsible father and get his son back.
Meanwhile, Hansel, who has been living in his own retired seclusion, is also requested to come to Rome, because of course he would be, so, pretty quickly, Derek and Hansel are forcibly reunited. With both characters struggling with fatherhood - Zooolander wants to prove he can be one and Hansel is struggling with not knowing his father while facing imminent fatherhood himself - the two eventually team up with Interpol Fashion Agent Melanie Valentina (Penelope Cruz), who is investigating the deaths of several pop stars who strike a Zoolander pose in their final moments.
And here's where Zoolander No. 2 was poised to potentially rise above the recent spate of late sequels to popular comedy films (Anchorman 2, Dumb and Dumber To). At this point, the sequel could have gone several different routes which may have been more appealing than the final result. One route would have been teaming a tough, intelligent Interpol agent with two idiot models (Cruz is only exasperated by Zoolander for a single exchange and is ultimately revealed as being a huge Zoolander fan), which would have been similar to the original but with more of an action-movie vibe. Another route could have been having Derek and Hansel fumble their way back into the modern fashion world (they do participate in a humbling fashion show that reveals what the sequel might have been). Another route would be about two vain models trying to be fathers (Hansel and Derek do have a fairly funny exchange about the personalities of fat kids, but once Derek reunites with Derek Jr. it abruptly ends in a sequence that tries but fails to capture a moment like the "gas fight" sequence from the original). Instead, Zoolander No. 2 skips over all of these possibilities to pursue an unnecessarily complicated and silly mythical plot point that only serves to set up the return of Mugatu (Will Ferrell).
That said, Ferrell's arrival adds a pulse to a movie that was quickly fading, especially since Wiig is grossly underused, as is SNL's Kyle Mooney as fashion designer Don Atari. Even Cruz could have been better served, as she is given the thinnest of characters and isn't ever tasked with playing foil to the idiocy of Derek and Hansel, like Christine Taylor did in the original. So, as welcome as Ferrell's late, second-half appearance is, it's too late to save the sequel, even as Ferrell's Mugatu hilariously makes fun of the film's silly mythical plot point in a moment that should have happened earlier.
Of course, Zoolander No. 2 was supposed to be made years ago but never did earlier, and that might ultimately be it's undoing. It seems in the intervening years, Stiller and his three other writers (THREE!) have forgotten that what made Derek Zoolander tolerable in the original was having Taylor act as a proxy for the audience, someone who was reticent to like him but is eventually won over. Without that device, it's merely nostalgia and cameos that push along the sequel's narrative, and while there are a handful of funny moments along the way, it isn't enough.
Admittedly, I'm not a huge fan of the original, but I was ready to embrace Zoolander No. 2. Like many, I'd love to see Stiller recapture some of his Ben Stiller Show days, but, the fact is, he's too far removed from it. In terms of career trajectory, Stiller's moved beyond this, and that's okay. However, it makes Zoolander No. 2 an undeniable step backward at a time when Stiller is better served moving ahead with fresh ideas. At the very least, the original Zoolander was satire, while the sequel is a lifeless rehashing which sort of proves my point: this is something Stiller did back in the early 2000s and it isn't what he does anymore.
Still, it's hard to blame Stiller. After all, it was probably a lot of fun to step back into the Zoolander world, and he's far from the last person touched by nostalgia. Hell, Kevin Smith will probably make Clerks 11 at some point in the next thirty years (coincidentally, that's a sketch idea that The Ben Stiller Show would have destroyed). Perhaps, like Wet Hot American Summer, Stiller would have done better exploring all the different plot threads he introduced (and subsequently dropped) in a Netflix series (who, by the way, are one of the sequel's many, many corporate sponsors). However, even at 102 minutes, Zoolander No. 2 can't capture its former glory. It seems Derek Zoolander has taken his final stroll down the catwalk, and that's for the best.