Ben Stiller Directed Movies Ranked

2. Tropic Thunder (2008)

For everything that Zoolander offered in terms of comedy, parody, wit and charm, Tropic Thunder offered with a more distinct understanding of the form, Stiller never seeming like a more in touch and openly self-critical filmmaker than in this 2008 Oscar-nominated release.

Tropic Thunder felt like every bit the Hollywood exorcism it aimed for, parodying the industry’s on-screen tropes, behind the scenes insanity, endless pursuit of a golden cash cow and history with terrible representation. From the opening spoof trailers that immaculately parodied real-life action, drama and comedy trailers of the time, Tropic Thunder set course for a charismatic takedown of the Hollywood way, all made in the Hollywood way of course.

What was so unique about Tropic Thunder was how it did all of this while also offering an endlessly quotable, laugh-a-minute comedy with laughs for fans of physical humour, referential humour and wordplay alike, bending its deep-cuts around a narrative that was genuinely worth investing in.

Like the work of his early career, Tropic Thunder felt like a film from a man on a mission, and just as was the case with The Secret Life of Walter Mitty, it also looked like a big budget Hollywood film. Starring an ensemble of names including Stiller himself, Jack Black, How To Train Your Dragon star Jay Baruchel, Steve Coogan, Nick Nolte, Danny McBride, Matthew McConaughey, Tom Cruise in an almost unrecognisable role and Robert Downey Jr in an Oscar-nominated turn, Tropic Thunder truly had a bit of everything for everyone, and while time has been less kind regarding readings of some of its most controversial commentaries/parodies, Tropic Thunder remains one of the best out and out studio comedies of the 21st century and a release almost insurmountable in terms of Stiller’s own directorial career.

1. Reality Bites (1994)

When it comes to purpose, meaning and inspiration, nothing in the Stiller catalogue touches his 1994 debut feature Reality Bites, a film that oozes an understanding for what it feels like to try and make your way in the world post-college/university.

Starring Ethan Hawke as a gloriously attractive but distinctly pretentious would-be philosopher, Janeane Garofalo as an independent and progressive yet quietly trepidatious best friend, Stiller himself as a relatively up-tight but infinitely more successful business man boyfriend, and Winona Ryder at the centre of it all as the morally strong, lovable, always self-doubting protagonist, Reality Bites seems to immaculately capture the anxieties and hope of an age group that has so much yet to experience but always feels like their time is running out. While Tropic Thunder and Zoolander were immensely funny and intelligent takedowns, Reality Bites is a much more honest and touching representation of Stiller’s talents.

Shot by the would-be three-time Oscar winning Director of Photography Emmanuel Lubezki, Reality Bites is a film that can’t even be criticised for looking less cinematic than Stiller’s later work despite his relative lack of experience, the cinematography of one of the world’s greats elevating everything Stiller constructs to forge an almost anti-authoritarian piece of young person culture as much through the way it looks as the way it’s constructed. To this day, Reality Bites is arguably Stiller’s most traditionally beautiful film.

There’s something about Reality Bites that screams early Richard Linklater or Cameron Crowe, the 1994 release sitting comfortably alongside the likes of Dazed and Confused (1993) and Singles (1992) as a very of-its-time yet somehow timeless ensemble drama of issues in young adulthood.

While traditionally minds may not reach to this film while thinking of Stiller as a star persona or filmmaker, there is so much that can be said of the overwhelming quality of this fantastic debut feature, Reality Bites being a criminally under-seen but ever extraordinary inclusion in the Stiller filmography and an underrated gem of its era.

But what do you think? Would you have ordered things differently? Let us know in the comments below, and while you’re there feel free to share this article with your friends.

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