Ben Stiller Directed Movies Ranked

For as much of an international star as Ben Stiller has become, the role of director is one he’s not often associated with despite releasing six feature films across three different decades since his debut in 1994. The actor, best known for his star turns in There’s Something About Mary, Meet the Parents, Starsky & Hutch and Night At the Museum, has arguably made his most valuable contributions to cinema through his own self-directed work, the likes of Derek Zoolander and Tugg Speedman born of his pen and directorial stewardship, his unique blend of different comedic styles making for some of the best comedies in recent memory.

In this edition of Ranked, we’re going to spotlight his work behind the camera, delving deep into his repertoire as a filmmaker to judge which of his six feature releases are the worst and which, of course, are the best, all the while acknowledging how “there’s way more to life than being really, really, ridiculously good looking”.

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6. Zoolander 2 (2016)

Fifteen years too late and lacking in inspiration or even a reason for being, Zoolander 2 felt like Ben Stiller being contractually forced to resurrect a much beloved IP for the good of a studio’s profit margins, and it told – the screenwriter, director, producer and star couldn’t even be bothered to maintain his iconic Derek Zoolander voice half the time.

The opening moments of Zoolander 2 act as a warning shot, the overly long prologue writing an entirely new movie in of itself to flesh out the reasons why half of the beloved cast won’t be returning, Stiller creating reasons for the character to dive back into the world of super model espionage that are more wafer thin than the reasons Stiller himself found for returning to the project at all – and not in an intelligent fourth-wall breaking way, but through such uninspired means that the lack of creativity simply radiates from each scene.



With much less super-modeling and a new specificity to parodying Daniel Craig era James Bond and recent Mission: Impossible movies, Zoolander 2 felt like a below average action-comedy of the Men in Black: International variety, only with less aliens and more cameos. The aesthetics were bland, the script so generic that the film could have been about anybody, the dialogue utterly trash (in stark contrast to the original), and the cameos felt forced and opportunistic rather than a part of the fabric of what Stiller was trying to say.

While the first Zoolander was sharp as a tack with regard to its parody of super model culture and wider consumerism, and was genuinely offering something worthwhile as both a throwaway comedy and something distinctly more intellectual, Zoolander only earned meaning through its relation to those wonderful aspects of the first movie and was, overall, absolute garbage; by far the worst film of Stiller’s directorial career.

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