In addition to acting, producing, and writing for film and television, Ben Stiller is also a director. He was in the director’s seat for many episodes of Dan Erickson’s hit television seriesSeverance, but also has a resume dating back to roughly 1990.
Beyond his other television directing work such asThe Ben Stiller Show,Escape at Dannemora, and the unaired sci-fi comedy pilotHeat Vision and Jack, Stiller has directed a handful of movies which often also tend to feature him as the star. Here are the best movies in which Ben Stiller plays the important role of the director.
5The Cable Guy
A Black Comedy Thriller
The Cable GuystarsJim Carreyas a lisping employee of the cable company named Ernie “Chip” Douglas who befriends a man named Steven Kovacs (Matthew Broderick) who recently broke up with his girlfriend, Robin Harris (Leslie Mann), after a failed marriage proposal. When Steven bribes Chip to upgrade his cable, the titular cable guy ends up becoming something of a nuisance in his life, continually stalking him and even manipulating Robin into giving him a second chance. It is later discovered that he is not in fact named Ernie Douglas or even a current employee of the cable company at all, and has had a history of stalking and harassing customers. When Steven ends their friendship, the cable guy becomes more vindictive, culminating in the kidnapping of Robin, which Steven must resolve.
Despite starring the immensely bankable Jim Carrey, the film was one of his less successful ventures, grossing around only $100 Million. The film had a mixed reception, likely due to it being something of a departure from Carrey’s typically more lighthearted fare. Yet this very same fact has caused people to view it more favorably in retrospect, with it now being considered a cult classic. Carrey himself has spoken positively of his titular role, and fans marked it as the beginning of a series of more dramatic roles Carrey would perform in later movies. Ben Stiller identified the film’s relative failure as “educational and spirit-building” in an interview with Quartz. “When I did something well received after that, it was always tempered by the knowledge that it didn’t mean that the project itself was better or worse.”
Stiller plays a minor role as a pair of ex-child star twins, Sam and Stan Sweet, the latter of whom is accused of murdering the former. The resulting trial is a major media event that ends with an unseen outcome, as the cable guy cuts the city’s television signal when the verdict is given.
4Reality Bites
A Gen-X Dramedy
One of Ben Stiller’s earlier directorial efforts,Reality Bitesstars Winona Ryder as a college graduate named Lelaina Pierce, attempting to put together a documentary detailing herself and her friends - namely Vickie Miner (Janeane Garofalo), Sammy Gray (Steve Zahn), and Troy Dyer (Ethan Hawke). Lelaina and her friends deal with various struggles associated with young adults, including difficulty finding work and navigating relationships.
Lelaina has trouble holding down a job, and reconciles her boundless expectations after graduating with the disappointing reality of her life. It is this fact, along with the documentary’s vignettes, that grant the film its title. Beyond her struggles with work, Lelaina is torn between her mutual attraction to Troy, a jaded yet poetic musician who seems apathetic to life, and her blossoming relationship with Michael Grates (Ben Stiller), a stodgy yet successful VP for a television channel who offers to air her documentary.
Ultimately, Lelaina finds disappointment in both relationships, with Troy’s initial desire for romance replaced with hesitance once she properly entertains it, and Michael’s handling of the documentary and similar merely surface-level appreciation of her causing friction between the couple. Lelaina ultimately chooses Troy after he reconciles with her. Despite losing his girlfriend, Michael finds a silver lining to Lelaina and Troy’s relationship, as it becomes fodder for a show he produces.
The film is tonally different from certain other films directed by Ben Stiller, as the comedy is more slice-of-life rather than absurdist. That said, its sincere edge and raw emotion make it a more than worthy watch.
3Zoolander
A Satire of the Fashion Industry
Zoolanderfeatures the titular male modelDerek Zoolander(Ben Stiller) coping with his declining career next to the sudden loss of his entourage and the growing career of a rival male model named Hansel MacDonald (Owen Wilson). He is unknowingly recruited into a conspiracy by his agent, Maury Ballstein (Jerry Stiller) and fashion mogul, Jacobim Mugatu (Will Ferrell), to assassinate Malaysia’s Prime Minister. This is accomplished by transforming him into a sleeper agent who will be activated when he hears the song,Relaxby Frankie Goes To Hollywood. With the aid of journalist, Matilda Jeffries (Christine Taylor, Stiller’s wife), and Hansel, Zoolander is ultimately able to foil the plan.
Despite, or even perhaps because Derek doesn’t have two brain cells to rub together, the film is a singular hilarious experience with its absurd plot points and infectious energy. Although it had a mixed reception at the time, the film has proven to be immensely quotable in retrospect, with lines such as “I feel like I’m taking crazy pills!” and “Put a cork in it, Zane!” still being frequently thrown around by fans. Less enduring was its sequel,Zoolander No. 2, which was also directed and co-written by Stiller, but far more negatively received.
2The Secret Life of Walter Mitty
From Negatives to Positives
The Secret Life of Walter Mittywas originally a short story detailing a daydreamer, who imagines himself doing incredible things as influenced by the relatively mundane settings he finds himself present in. Both movie adaptations use this as a premise, from which Walter Mitty does eventually become a more assertive individual.
The 2013 remake, starring and directed by Ben Stiller, is set in the year 2000. Mitty works atLife Magazine, and is given a negative roll from traveling photojournalist Sean O’Connell (Sean Penn) for the magazine’s final physical issue. Unfortunately, Walter cannot find the specific negative O’Connell recommended he use, and is forced to spend most of the film retrieving it. He also has a crush on his co-worker, Cheryl Melhoff (Kristen Wiig), who encourages him to use the other negatives as clues to find the missing one. This results in Walter attempting an adventure to meet Sean in person, deducing his location with clues that take him to Greenland, Iceland, and the Himalayas. He eventually succeeds in retrieving the negative, and wins Cheryl’s admiration due to his adventures, with it being implied they will begin a relationship.
This is also an earlier collaboration betweenStiller andSeverancestar Adam Scott, playing the role of Ted Hendricks. Ted is the managing director of the magazine’s transition toLife Online, and regularly insults Walter and his colleagues. This culminates in a more confident Walter getting upset at him as he presents him with the negative, ultimately telling him off for his rudeness and reminding him to give the staff credit, as they were part of whyLifewas such a beloved magazine. The final issue is presented, giving thanks to the staff. The film is ultimately a wholesome story about a maladaptive daydreamer growing into a more confident individual whose life becomes far more interesting than he ever could have imagined.
1Tropic Thunder
A Classic Yet Controversial Hollywood Satire
Tropic Thunderwas the brainchild of Ben Stiller, having conceptualized it in the late 1980s around the time he filmed a minor role in Steven Spielberg’sEmpire of the Sun. The concept at the heart of the project was performers he knew who went into boot camp training for war movies, and emerged acting as if they actually participated in a war. Having been roughly 20 years in the making since it was originally thought of, the film featured an all-star cast and was released in 2008.
Tropic Thunderstars Stiller as a washed-up action star, Tugg Speedman, who notably lacks personal connections in his life. Speedman attempts to resurrect his flailing career by starring in a war movie sharing the film’s title. His co-stars are extreme method actor Kirk Lazarus (Robert Downey Jr.), drug-addicted comedic actor Jeff Portnoy (Jack Black), closeted macho rapper Alpa Chino (Brandon T. Jackson), and earnest newcomer Kevin Sandusky (Jay Baruchel).
With tensions running high and the budget running low, abusive studio executive Les Grossman (Tom Cruise) demands the director, Damien Cockburn (Steve Coogan) get the group under control. On advice from Four Leaf Tayback (Nick Nolte), the author of the film-within-a-film’s source material, the performers are dumped into a jungle where hidden cameras will track them as they act out the film. Unfortunately, it is also home to a violent gang who manufactures heroin. Although they fail in making the actual film, the attempt is recorded and the performers are given accolades for the newly retitledTropic Blunder. Grossman takes all the credit for its success.
The film is controversial because of the topics it chose to tackle. Robert Downey Jr.’s character, Kirk Lazarus, appears in blackface, a part of the actor’s ill-conceived attempt to portray a Black character. Alpa Chino, an African-American performer, criticizes Lazarus for his usage of the offensive practice, as well as his other attempts to become Black through method acting.
Similarly criticized wasSimple Jack, Speedman’s previous foray into dramatic acting, which finds him portraying a farm boy with a mental disability. The film is partially credited with the decline of his career, with its only known fans being the Flaming Dragon Gang. This is a riff on dramatic Oscar-bait movies such asRain ManorI Am Sam, which star neurotypical actors as characters with intellectual disabilities. Despite some backlash from advocacy groups, the creators of the film defend the inclusion of these jokes, claiming they are meant to satirize the performers who earnestly partake in such films in a negative light, rather than target the marginalized individuals used as fodder. As recently as 2023,Ben Stiller said he is still proud of the filmand the effort everyone involved put into it.
