Ben Stiller has a made a name for himself as an actor, writer, and director of original and thought provoking fare at the multiplex. Both a comic and deeply dramatic big screen performer, Stiller’s work as both a genuinely entertaining studio comedy filmmaker and provocative thespian in his own right is a talent not to be dismissed. While films like Zoolander and its forthcoming sequel may be on the forefront of most viewer’s minds at the present moment, Stiller’s larger body of work is indicative of far deeper thought and consideration than the former property’s lazily misconstrued assimilation of the disparate elements of a very specific facet of the entertainment industry. With the celebrated performer’s fiftieth birthday upon us, we here at AE would like to extend our fondest regards to Stiller as he reaches out across the temporal expanse of a half-decade, and consider five of his greatest cinematic achievements:

Reality Bites

Universal Pictures

Reality Bites (1994)

Serving as his directorial debut, Stiller shines throughout this honest portrayal of mid-1990s angst and desperation as the straight man to Ethan Hawke’s wounded artist. With fellow and former The Ben Stiller Show alum Janeane Garofalo rounding out an all star cast including the formerly cited Stiller and Hawke, Winona Ryder, and Steve Zahn, the celebrated comic performer here gives his first glimpse of the kind of earnest, hard-hitting dramatic material that he would return to throughout his career, though this might be his most winning and pure example of the former.

Flirting With Disaster

Miramax Films

Flirting With Disaster (1996)

Alongside his equally thrilling co-star Patricia Arquette, Stiller’s turn in this early David O. Russell film is perhaps one of the performer’s most overlooked roles. As new father Mel Coplin comes to grips with his own status as the adopted son of two overbearing foster parents, he takes his young wife and newborn child on a cross-country road trip to find his birth parents. A comedy of errors ensues that is equal parts Howard Hawks, screwball silliness, and subtle character study. Much of Stiller’s capacity as a tragicomic performer is on display here in a film that’s not only one of the actor’s most memorable roles, but is also a production that seemingly lays the way for the kinds of films and performances soon to come.

The Royal Tenenbaums

Buena Vista Pictures

The Royal Tenenbaums (2001)

Stiller’s appearance in one of Wes Anderson’s seminal works is among his very best onscreen roles. As Chas Tenenbaum, Stiller exudes a certain hysterical mania that has lent well to some of his bigger studio comedy roles; only under Anderson’s direction his frenzied mental state is lent more melancholy than levity. As a part of an ensemble cast of equally dynamic and indispensable lead actors, Stiller can become overshadowed in the production as a whole, though it would be hard to imagine the movie without Stiller and his two motherless sons in matching, red track suits.

Tropic Thunder

DreamWorks Pictures

Tropic Thunder (2008)

In a manner altogether more even-handed and well-researched through hard-earned, real life experience, Stiller’s return to social satire in 2008 is probably his funniest film to date. Playing off of many of the hubristic follies and atonal melodramatics that so afflicts the dregs of Hollywood super-talents, Stiller’s ode to the industry that made him a household name abandons the hyperbole of Zoolander for intelligence and nuance in structure, execution, and overall performance. While there’s still plenty of room for bad taste throughout, this particularly sophomoric take on the mythology of high-minded, middle-brow Best Picture wannabe pretenders is startling in its criticisms and profound through its insights.

Greenberg

Focus Features

Greenberg (2010)

While he has time and time again proven himself to be a comic actor willing to go the extra mile that at times borders on tragic, Stiller’s first creative partnership with writer and director Noah Baumbach is probably the first instance of his emergence as a full-fledged dramatic actor. Shirking all of the supposed idiosyncrasies that previously set him apart as a studio comedy icon, Stiller turns all of those self-same quirks and anxieties into a character as afflicted and neurotic as the very best Woody Allen originals, but with the added sophistication and laissez-faire attitude of the former stand-up’s successors. It’s hard to pick one role that serves to define a given talent’s entire career, but Stiller may have trouble surpassing the level of emotional maturity and attendant onscreen anguish so perfected here.