Born in New York City to parents/the legendary comedy duo of Jerry Stiller and Anne Meara, Ben Stiller has seemed to always have a place in show business. He made his acting debut at the age of nine, auditioned for Marty McFly, and after a stint on a soap opera, he fell into creating sketch comedy and short parodies. This led to the cult-classic sketch series, The Ben Stiller Show, which ran for a single season. But while it seemed like Stiller’s career path was set in sketch comedy, he made his feature directorial debut with Reality Bites, starring Ethan Hawke and Winona Ryder. Stiller’s entire filmography reflects this desire to grow and change, leading him to become one of Hollywood’s most underrated directors.
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Offbeat Approaches
Sony Pictures
While he may star in mainstream feature films, Ben Stiller’s own directorial work often veers away from a conventional angle or approach. A meta approach is taken to the opening of the very first episode of The Ben Stiller Show, as a writer came up to Stiller and pitched the very bit he was in the middle of, something fairly underutilized in the nineties. This type of humor was backed up by future masters of comedy like David Cross, Bob Odenkirk, Judd Apatow, and more, who all won an Emmy for their writing on the show.
Stiller’s particular brand of unconventional choices is perhaps best illustrated by his first major studio film, The Cable Guy. Often described as a “black comedy”, The Cable Guy features Jim Carrey as the titular cable guy, who becomes increasingly more obsessed with one of his clients, played by Matthew Broderick. The movie confounded people upon release due to its darker tone, which is matched by Stiller’s thriller-esque approach. Not only is Carrey’s character genuinely unnerving, a far-send from his string of lovable characters at the time of release, but Broderick’s character is brash and dismissive, adding up to a comedy that has more of a bite than an average ’90s movie. The film also aims to explore deeper themes, such as celebrity obsession and the antisocial effects of media, that most dramas even avoid.
Attempts to De-Center Himself
Paramount Pictures
Despite being featured, or even starring in most of his projects, Ben Stiller has noticeably tried to distance himself as the sole star of voice of his projects, which enhances the creative value of his films, and stands out as handily rare in Hollywood. In his first feature, Reality Bites, Stiller actually plays the pseudo-antagonist named Michael, a TV executive that meddles with the creative vision of Lelaina’s (Winona Ryder) documentary. In The Cable Guy, he’s even further removed, playing twin brothers Sam and Stan Sweet in an analogue to the Menedez Brothers case. In that movie, the televised murder trial of Sam is a thematic undercurrent, but one that only extends to a cameo role for Stiller. The Cable Guy uses Stiller’s fame to enhance the thematic content of the film.
After the tough reception to The Cable Guy, Stiller played the titular lead in Zoolander, but did so to elevate the broad comedy in the movie. Instead of being overly-protective of his own image, Ben Stiller uses the character of male model Derek Zoolander to debase himself in every way imaginable, and instead gives the more successful character, Hansel, to Owen Wilson. After Zoolander’s success, Stiller was able to open his next directed comedy into more of an ensemble, with Tropic Thunder. While Stiller does play a lead in the film, he still plays the most naive character who goes through the most physical turmoil.
A Dramatic Turn to Television
Apple TV+
Where most directors would see a commercial flop as a sign to recommit to what you’ve been successful for, Ben Stiller used the failure of Zoolander 2 as a springboard into more complex, dramatic television work. Released in 2016 after over a decade of fan requests, Zoolander 2 received criticism for its celebrity-laden runtime and unoriginal story, only barely recouping its production costs. After two years, Stiller returned with another directorial effort, this time a seven-episode miniseries titled Escape at Dannemora. A departure in format and genre for Stiller, the Showtime series follows a pair of prisoners played by Benicio Del Toro and Paul Dano, who escape from a New York prison with the help of a guard, played by Patricia Arquette in an Emmy-Winning role. Stiller approached the story with a deft realism that elicits flashbacks to the darker, cooler palette of The Cable Guy.
Stiller’s bet on television direction paid off with the release of the Apple+ series Severance, which premiered in 2021 to critical acclaim. The series follows a group of office employees who cannot remember their lives outside of work, and vice-versa. Stiller follows his interest in crushing realism even further with the sanitized aesthetic of Severance’s main location, and notably plays with different camera lenses to achieve different atmospheres between home and work for the characters. Stiller’s directorial work, as well as the entire show, to receive numerous Emmy nominations, and secure a second season.
While his work is not always universally-loved, Ben Stiller has used his success to direct movies and television that attempts to reach beyond something cliché or palatable. His gamble on prestige television arguably helped cement a new streamer. Even when he stars in his own projects, he tries to spotlight someone else, or at least make himself look like a fool. And if he’s in charge, he will absolutely attempt to buck the most popular, digestible trends in comedy and storytelling. Ben Stiller may be underrated as a director, but that lets him do his best, most innovative work.
