The Five Absolutely Essential Ben Stiller Movies

Whether he’s working with arthouse auteurs or Robert De Niro, the actor-director brings an intense likability to every role he plays. No one rocks Blue Steel the way he does
The Five Absolutely Essential Ben Stiller Movies

Welcome to “Five Absolutely Essentials,” an overview of the greatest comedians’ most memorable moments. Mind you, these aren’t necessarily their “best” movies — rather, these are the five films that best represent different aspects of their talent, their ambition, their persona and the artistic risks they’ve taken along the way. If you’re looking for a sense of a comic in all his or her complexity, here’s where to start. 

Even when Ben Stiller makes silly comedies, he has a seriousness of purpose. Where other funny people relish being clowns, the 57-year-old writer, director, actor and producer has carried himself differently, his brainy approach always evident — and sometimes drawing criticism from colleagues. In an infamous 2012 New Yorker profile, an unidentified marketer who had worked with Stiller complained, “A lot of what he asks for is some variation of ‘Take me seriously.’ And he believes you’ll only take him seriously if he’s overbearing, prickly and rude.”

Perhaps part of that self-consciousness stems from growing up in a show-business family: His parents were beloved comedians Jerry Stiller and Anne Meara. Regardless, from a young age Stiller has tried to prove himself, making short films as a boy and even being cast on Broadway, seemingly constantly jumping from one project to the next, his ambitions always evident. Eventually, he worked on Saturday Night Live and then got his own sketch show, The Ben Stiller Show, which aired briefly in the early 1990s, earning rave reviews but failing to find an audience. Undeterred, he directed his first feature, Reality Bites, setting in motion a film career that’s now been rolling along for more than 30 years. (You have to wonder how much different his trajectory would have been if he’d been cast in Encino Man.)

Selecting Stiller’s five essential movies is challenging since he’s straddled different worlds. There’s a whole group of fans who know him from family films like Night at the Museum, while a different contingent think of him as the thoughtful, neurotic guy in melancholy comedy-dramas from indie auteurs like Noah Baumbach and Wes Anderson. (And then there are the movies he’s directed, such as The Cable Guy.) An actor this versatile is hard to encapsulate, but I took this assignment as seriously as the man himself. 

Flirting With Disaster (1996)

When Stiller read the script for Flirting With Disaster, writer-director David O. Russell’s screwball comedy, he was struggling to establish himself as a viable big-screen presence. He thought the movie, about an insecure married man trying to track down his long-lost birth parents, could reverse his fortunes. “I really want this part,” Stiller supposedly told Russell. “Please don’t make me audition, because I’ll screw it up.”

Whereas 1994’s Reality Bites, his feature directorial debut in which he also starred, cast him as a slightly anonymous, uptight guy, Flirting With Disaster harnessed Stiller’s ability to wring comedy out of slow-burn exasperation. His character Mel is someone who’s never felt entirely whole, and the birth of his first child sets him on an odyssey to find out why his biological mother gave him up for adoption as a baby. Part sex comedy, part road-trip saga, Flirting With Disaster let Stiller be funny but also a credible romantic lead. (Mel is married to Patricia Arquette but finds himself attracted to Téa Leoni’s bumbling adoption agent.) The crazier things become, the more hilarious Stiller gets. Suddenly, the future looked really bright for him. 

There’s Something About Mary (1998)

In 1998, Stiller was flexing his dramatic muscles, starring in Neil LaBute’s caustic Your Friends & Neighbors and playing an addict in the big-screen adaptation of Permanent Midnight. But those indie films were overshadowed by his first huge commercial hit, There’s Something About Mary, in which a lovelorn writer named Ted is still hung up on his high-school crush, Mary (Cameron Diaz). The comedy, directed by the Farrelly brothers, contains perhaps the most iconic scene of Stiller’s career. Of course, I’m talking about the moment of utter pain and humiliation when an adolescent Ted, getting ready for prom with Mary, catches his scrotum in his zipper.

“He makes a joke funnier by his reaction to it,” Peter Farrelly once explained of his star, adding, “But he’s still got the likability factor.” Indeed, Mary was as outrageous as the brothers’ earlier raunchy comedies, but the gross-out gags were mitigated by the sweet love story at the center. Stiller helped sell the movie’s rom-com element, exuding an adorkable rapport with Diaz. Soon, he became the secret weapon for several mainstream comedies, becoming a household name in the process. 

Meet the Parents (2000)

Stiller’s nice-guy persona was never put on better display than in this crowd-pleasing comedy in which he plays Greg, a nurse who meets his girlfriend’s family, immediately feeling judged by Jack (Robert De Niro), an unsmiling former CIA agent who doesn’t like the idea of this wimp dating his daughter. Greg squirms delightfully as Jack slowly eviscerates his masculinity, and it wasn’t hard for Stiller to convey his character’s meekness: He was intimidated by De Niro in real life.

“I remember the first day that we shot together. I think it was the scene where we meet for the first time at the doorstep,” Stiller recalled years later, noting that he accidentally cracked up at something during filming, fearful that he’d offended this consummate actor’s actor. “I started sweating because I’m like, ‘I can't believe I’m breaking character on the first scene, the first line. He’s going to think I’m the worst.’ But then there was a moment where he smiled and I then felt, ‘Okay, it’s all right.’ But from then on, I never felt any more comfortable, actually.”

In Meet the Parents, Stiller was an exquisite everyman, Greg’s self-consciousness around Jack expressing a universal anxiety that men feel when they know they don’t measure up to their girlfriend’s dad. Stiller nailed the film’s comedy of embarrassment, and his interactions with De Niro were constantly funny, especially once Greg finally snaps. Meet the Parents’ success launched a lucrative franchise, and while the sequels weren’t nearly as good, Stiller understood why audiences kept showing up for more installments: “They love watching the screws being put into Greg.”

Zoolander (2001)

Audiences had seen Derek Zoolander before his 2001 film. The character had been the brainchild of Saturday Night Live writer Drake Sather, who conceived the clueless diva for a short film that aired during the 1996 VH1 Fashion Awards. “Derek came out of Drake saying, ‘Hey, I want you to be a male model in this little sketch that we’re doing,’” said Stiller. “And I go, ‘Well, that’s ridiculous.’ And he says, ‘Yeah, that’s why it’ll be funny. It’s you doing it.’”

Directed and co-written by Stiller, Zoolander notoriously flopped due to its release shortly after 9/11, but it’s since gone on to become a beloved cult classic. The same part of Stiller that was capable of creating outlandish characters on The Ben Stiller Show was expertly utilized for his portrayal of Zoolander, a vain, shallow dummy who, despite it all, actually has a good heart. 

“It’s really hard to satirize the fashion world,” Stiller once said. “It’s hard to figure out how to top what’s going on in reality. Everything is so out-of-control.” And yet, whether it was the supermodel’s ridiculous looks or Stiller’s inspired decision to turn the story into an action-comedy that spoofed spy films, Zoolander found ways to make outlandish stupidity very, very funny. A few years later, Stiller would be just as audacious satirizing Hollywood ego with Tropic Thunder.

Greenberg (2010)

As he’s gotten older, Stiller has migrated to more serious fare, directing the acclaimed drama series Escape at Dannemora and Severance. And he’s been equally unafraid to tackle roles that are light on laughs, like 2017’s underrated Brad’s Status. But perhaps his best onscreen mixture of comedy and drama was in this 2010 Noah Baumbach film. He’s excellent as Roger, a bitter middle-aged man who suffers from mental-health issues, falling into a seemingly unworkable romantic relationship with Greta Gerwig’s directionless personal assistant Florence. Greenberg had plenty of funny moments, but the comedy stemmed from the realness of Roger’s discontent and regret.

“This is really the first movie for me that there was no improvisation,” Stiller said at the time, later adding, “It made me realize as an actor how lazy you can be in terms of trying to change dialogue to be more comfortable for you to say as a person, as opposed to trying to understand what the character is saying.” 

For those who were only familiar with Stiller from Meet the Parents or Night at the Museum, Greenberg was probably a shock. But Stiller’s collaboration with Baumbach — which has continued with While We’re Young and The Meyerowitz Stories — allowed him to stretch as an actor in rewarding ways. For someone with such intense likability, Stiller seemed energized playing a character so prickly and off-putting. And yet, you couldn’t help but end up feeling sorry for poor Roger. The frazzled comic desperation that Stiller always brings to his roles was, here, used to portray someone far more pathetic and beaten-down. 

Who said he had to play someone who gets his junk stuck in his fly to convey real pain?

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