The Evolution of Ben Stiller's Career

By Peter Martin

Ben Stiller delivers a performance that is uniquely his own in The Secret Life of Walter Mitty, which he also directed with his signature comedic and dramatic flourishes. We take a closer look at the twists and turns of the actor-director's career.

The Ben Stiller Show (1992)

Stiller, who began making movie parodies at the age of 10 after his father gave him a Super-8 camera, scored with a short spoof of Martin Scorsese's The Color of Money that was picked up by Saturday Night Live. He continued to refine his sense of comic absurdity with a brief stint on SNL and more short films, which led to his own show on MTV and Fox in the early '90s. Though short-lived, it won an Emmy for Outstanding Writing by Stiller and cowriter Judd Apatow.

Reality Bites (1994)

For his feature directorial debut, Stiller cast himself as a cable TV executive who crashes into a relationship with aspiring filmmaker Winona Ryder, with Ethan Hawke in the mix as a romantic rival. Reflecting the fears and concerns of Generation X, the movie demonstrated Stiller's abilities as a director to get the most out of his cast and the script.

Flirting with Disaster (1996)

Stiller came into his own as a leading man in this early film by David O. Russell (American Hustle). As Mel Coplin, a neurotic New Yorker on a road trip in search of his biological parents, Stiller works through thorny issues with his wife, an inappropriate attraction to an adoption agency employee, and multiple mixed-up parental units, all with a zany, grounded sense of humor.

The Cable Guy (1996)

For his second directorial effort, Stiller worked with producer Judd Apatow and star Jim Carrey to create a very dark comedy that is both insanely funny and quite disturbing in its implications. Though it received a mixed reaction from critics and audiences at the time, it holds up as a bold and daring, nay, even visionary movie.

The Zero Effect (1998)

The film dials down the comic madness that often surrounds Stiller in other starring roles, allowing him to emerge as a stable force in the life of his employer, "the world's greatest detective" (Bill Pullman). As a voice of sanity and an almost-conventional straight man, Stiller still earns plenty of laughs from his underplayed performance in an undervalued mystery.

There's Something About Mary (1998)

The flip side of Zero Effect finds Stiller riding a wave of slapstick gags and pratfalls, somehow imbuing his hapless character with what The Guardian described as "lovable discomfort." Here, Stiller is an everyman with a crush on an unobtainable beauty who is far more kooky than he can imagine, and he wins our sympathy with every desperate stab at romance.

Permanent Midnight (1998)

Stiller demonstrated his dramatic range in the acerbic Your Friends & Neighbors and, even more resoundingly, in this movie, inspired by the real-life experiences of a drug-addicted TV writer. Although often painful to watch, Stiller taps a deep reservoir of emotion as his character struggles to survive.

Mystery Men (1999)

Way ahead of its time, the movie allowed Stiller and company to mercilessly mock superhero stereotypes, with Stiller a highlight as the ironically named Mr. Furious. The movie remains a hidden gem. On a personal note, while making his television pilot Heat Vision and Jack, Stiller met actress Christina Taylor; they later married and now have two children.

Keeping the Faith (2000)

Here Edward Norton made his directorial debut and stars as a priest who must deal with romantic feelings he develops for childhood friend Jenna Elfman--who happens to be dating his best friend, a rabbi (Stiller). It's a bright and adult-skewing film, and Stiller expertly blended his comic and dramatic talents.

Meet the Parents (2000)

Again showing his mastery of "loving discomfort," Stiller played things more broadly. He's an everyman character again, a boyfriend going home to meet his girlfriend's parents, only in this case he must go mano-a-mano with the intimidating, overly protective Robert De Niro. Stiller is hilarious as he attempts to do the right thing, only to be foiled at every turn.

Zoolander (2001)

Anarchy reigns in this colorful and riotous comedy. As a director, Stiller excels in maximizing the laugh potential of even the smallest moments, what some might call "the throwaway bits." But in Stiller's hands, those bits are knitted together into a tapestry that brings everything together. His comic timing is precise and always on the money, even as the world's dimmest male model.

The Royal Tenenbaums (2001)

Once again plumbing the depths of a character at the intersection where hilarity collides with tragedy, Stiller embodies a financial genius with all the neuroses of an incredibly anxious, overly protective father to his twin sons. His anxiety has a basis in grief -- his wife died in a plane crash -- and Stiller subtly reveals his character's all-too-human vulnerability.

Dodgeball: A True Underdog Story (2004)

In a busy year when Stiller appeared in no less than six movies, including star turns in Along Came Polly, Starsky & Hutch, Envy and Meet the Fockers, it's his portrayal of the villainous White Goodman in this silly sports comedy that stands out. Stiller makes for a surprisingly nasty, unethical businessman.

Night at the Museum (2006)

Stiller invaded the family market by voicing Alex the lion in 2005's Madagascar and then appeared as a ne'er do well security guard in this fantasy adventure. Stiller is an unusually modest and self-effacing action star. He adjusts his behavior and reactions on the fly so that we never doubt either his sincerity or the reality of museum exhibits coming to rip-roaring life.

Tropic Thunder (2008)

A high-water mark for Stiller's brand of parody, the movie goes far beyond simple spoofs of well-known war and action movie tropes, daringly making place for Robert Downey Jr.'s method actor in blackface as well as Tom Cruise's oily movie studio executive. Stiller and his collaborators gleefully pushed the boundaries for "acceptable" content in mainstream movies.

Greenberg (2010)

Once again, Stiller touched base with his darker side, essaying the role of a prickly middle-aged man who is adrift in life. Often hostile and unpleasant, he does not have complete control of his emotions, and Stiller actively avoids doing anything "cute" to make his character more likable, instead striving for an honest portrayal of a complex personality. It's a devastating performance.

Watch as Ben Stiller tells us more on our original series, "FrontRunners."