Ben Stiller Directed Movies Ranked

5. The Secret Life of Walter Mitty (2013)

The Secret Life of Walter Mitty looked and felt like every bit of a passion project for Ben Stiller, and the story of a so-called “every man” doing extraordinary things in pursuit of a picture for the final cover of LIFE Magazine offered a plethora of unique situations and locations that brought joy and beauty to the film. Otherwise, it was a bit of a mess.

Tonally, The Secret Life of Walter Mitty tried to alternate between fantastical drama and out-and-out comedy, the film at times feeling like a more laid back and less pretentious Into the Wild and at others like a less endearing Pee-wee’s Big Adventure. One moment there was a Shark attack played for laughs and the other there was an energising downhill free-skate in Iceland, and while the intention was clearly to separate these moments as reality versus fantasy, the result was tricky to navigate and removed a lot of the tension and investment that Stiller sought from each of us as his audience.

The Secret Life of Walter Mitty also suffered from a rare case of asking you to care about a pursuit that you don’t really believe to be the right course of action. We are suitably informed that the character’s adventure will be good for him, that it will connect him spiritually with the world around him, but the film oddly focuses its emotional levity on the character’s sense of duty to fulfill a promise to his photographer and magazine, one that will see “Picture 25” on the final ever cover. The issue is that the magazine has been bought out by an unnamed entity represented by Adam Scott’s cartoonish villain Ted Hendricks, that Hendricks is to shut down the magazine, and that after constantly berating Walter, Hendricks fires him (before he gets the chance to finish his job). It leaves you wondering: why should he get the picture to help the guy who bullied and then fired him? Unfortunately, the sense of the magazine’s workforce togetherness and identity, as well as Walter’s own duty, are not defined well enough for his choice to be unquestioned.

There is genuinely the skeleton of a special movie within The Secret Life of Walter Mitty, but for all of its moving parts it is nothing more than a distinctly average offering, even in spite of its truly mesmerising locations.

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4. The Cable Guy (1996)

Stiller followed up his indie-feeling feature debut with the star-driven studio comedy The Cable Guy in 1996, a film that took its place in the video collections of many a millennial over the years and still, likely, reminds 90s kids of a “simpler, happier time”.

Featuring Jim Carrey at arguably the peak of his comedic powers – Ace Ventura 1 & 2, Batman Forever, Dumb & Dumber and The Mask were each released in the 2 years prior – The Cable Guy takes on a life of its own as a Carrey project, the star’s overwhelming gravitas sucking in almost all of the film’s Stillerisms recognisable from Reality Bites and molding them into the image of a Carrey movie.

The result is a fun, albeit not a classic, Carrey entry, and an early career lesson for Stiller who would move from bit-parts and cameos in his early movies to lead roles in every picture he’d direct from this point on. It seems like the way control was plucked from him here was not to his liking.

What sits The Cable Guy at this point on the list is the way that the back and forth between Stiller and Carrey worked for some, but stopped either man from having their cake and eating it, and arguably stopped us from something altogether more appealing. In watching this film back-to-back with the films released before and after, Reality Bites and Zoolander respectively, it also becomes clear that this is the most uninspired, dated and uncool of the trio, making it not only a project less Stiller than the rest, but one that is also not to the standards of the rest of his work from this fantastic period in his career.

3. Zoolander (2001)

Certainly the most iconic film of Stiller’s directorial filmography and the movie offering arguably the most iconic role of his long and distinguished acting career, Zoolander was and remains a must-see comedy for the ages.

Starring the likes of Owen Wilson, Milla Jovovich, David Duchovny and Will Ferrell, Zoolander did something on the big screen that hadn’t been seen before, merging popular culture and television culture to offer one of the sharpest and most quotable comedies of the era – “what is this, a centre for ants?”

Inspired in every sense of the word, and featuring Stiller in the lead role when his popularity as a lead actor was arguably never higher, Zoolander tapped into the zeitgeist of the time to offer something truly unique and special, a moment in time that few filmmakers ever capture. To look back at the film two decades later is to shine it in a different light, but one that showcases how timeless so many of its laughs were and how talented of a filmmaker Stiller can be. Since the passing of Ben’s father Jerry Stiller in 2020, the moments featuring his lovable character also seem to have taken on a new meaning, Ben’s fondness for his father and his father’s impeccable comedic timing being present in each and every scene the pair share.

Zoolander is more than a few steps up the ladder from The Cable Guy in terms of comedic chops, but it sits at number 3 owing to how the work to come is more refined and/or personal.

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