Throughout the 2000s, Ben Stiller was one of the most bankable stars in the world, frequently starring in blockbuster comedies that kept him at the top of the Hollywood food chain. In more recent years, Stiller has stepped out of the spotlight in order to focus more on directing, but he still makes plenty of movies.
Even at the height of his fame, Stiller found time to make smaller, darker movies that explored material that mainstream Hollywood would usually shy away from. For every family movie that Stiller has made, he’s also made an edgier piece to balance it out.
10 Family-Friendly: Night At The Museum
The premise of Night at the Museum is a juicy one: Ben Stiller takes a job as a night watchman at New York’s Museum of Natural History and is shocked to discover that, when the sun goes down, all the exhibits come to life.
There are delightful supporting performances, like Robin Williams as Teddy Roosevelt and Owen Wilson as a miniature cowboy, while the story is surprisingly riveting.
9 Surprisingly Dark: Envy
This movie almost slipped through the cracks and went straight to video. Its lead actors, Ben Stiller and Jack Black, became huge stars at the perfect time, giving the producers enough faith to give it a theatrical release.
It received negative reviews, but there are fascinating ideas at play in Envy as a man becomes jealous of his friend’s increasing success.
8 Family-Friendly: Madagascar
Every movie star worth their salt has starred in a DreamWorks Animation production, from Mike Myers to Jack Black to Will Ferrell. Ben Stiller is no different, headlining one of the studio’s most lucrative franchises, Madagascar, alongside Chris Rock, Jada Pinkett Smith, and David Schwimmer.
The story of some New York zoo animals who fall off a ship mid-transportation and wash up on the titular island has some hilarious gags, as well as some engaging character development.
7 Surprisingly Dark: Duplex
Danny DeVito’s directorial efforts are known for their dark comic sensibility, like Throw Momma from the Train and The War of the Roses. In 2003, DeVito directed Ben Stiller and Drew Barrymore in the pitch-black comedy, Duplex.
The film centers on a young couple who find the perfect New York property to move into. The only hitch is that they have to kill the current tenant, a sweet old lady, to get it.
6 Family-Friendly: The Secret Life Of Walter Mitty
A re-adaptation of James Thurber’s short story “The Secret Life of Walter Mitty,” which was first translated to the screen in 1947, had been in development hell for years before Ben Stiller took a crack at it. He directed, co-produced, and starred in an adaptation of the story in 2013.
Walter Mitty is a character that everyone can relate to and aspire to be. Worried he’s about to lose his job, he embarks on an incredible adventure.
5 Surprisingly Dark: The Cable Guy
After making his directorial debut with the Gen. X classic Reality Bites, Stiller got back behind the camera to direct Jim Carrey in one of his all-time greatest performances in The Cable Guy, a darkly comic take on stalker movies.
Stiller himself appears as twins on trial for murder, at the center of a media frenzy as the story takes place. The news unfolds in the background as Carrey’s titular character stalks one of his customers, played by Matthew Broderick.
4 Family-Friendly: Heavyweights
Forgotten to the past as everyone involved has made bigger and better movies, Heavyweights is a family movie about a fat camp that gets a crash course from a fitness guru, played hysterically by Ben Stiller.
The movie was one of the earliest productions of Judd Apatow, who has since gone on to revolutionize the R-rated comedy.
3 Surprisingly Dark: Flirting With Disaster
The second movie by writer-director David O. Russell, Flirting with Disaster stars Ben Stiller as a father who decides to track down his own biological parents.
The premise could’ve been used for a sweet, sentimental drama, but Russell subverted expectations and made it as a dark comedy. Stiller is backed by an incredible supporting cast that includes Patricia Arquette, Téa Leoni, Alan Alda, Mary Tyler Moore, Lily Tomlin, and Richard Jenkins.
2 Family-Friendly: Little Fockers
As the Meet the Parents saga went on, each movie got more and more family-friendly. They’re all rated PG-13, but each one gradually phased out the risqué situational humor of the original and focused more on slapstick.
The only one that’s an out-and-out family movie is Little Fockers, which revolves more around Greg and Pam’s kids than the couple themselves. There’s even a scene near the end where Greg fights Jack in a ball pit.
1 Surprisingly Dark: Permanent Midnight
Adapted from Jerry Stahl’s memoir of the same name, Permanent Midnight stars Ben Stiller as Stahl as he struggled to make it as a writer while grappling with heroin addiction. It’s one of Stiller’s few wholly dramatic leading roles.
Owen Wilson co-stars as Stahl’s friend, a fellow addict, in one of his many collaborations with Stiller (and their only non-comedic one), while Elizabeth Hurley, Maria Bello, and fellow regular Stiller cohort Janeane Garofalo all provide strong support.
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