Ben Stiller is a man of many talents. While we all know he's one of the funniest actors in the industry, he's also a noted screenwriter, director and producer. He got his on-screen big break in 1986 on an episode of the family comedy "Kate & Allie," which he followed up with a brief run on "Saturday Night Live" in 1987. Since then, Ben's risen through the ranks to become a heavy hitter in Hollywood, turning out hit film after hit film, many of which have gone on to become cult favorites. One such movie? "Zoolander." To celebrate the 20th anniversary of the release of "Zoolander" on Sept. 28, 2021, Wonderwall.com is taking a look at Ben's best movies to stream…
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"Zoolander" on Amazon Prime Video
The 2001 comedy "Zoolander" allowed Ben Stiller — who wrote the screenplay, directed the film and played the title role — to embrace his inner dumb supermodel, and we couldn't love it more. The film follows Derek Zoolander, a really, really, ridiculously good-looking male model who's fallen from grace and is so desperate to climb back to the top that he unwittingly allows himself to be brainwashed into killing the prime minister of Malaysia. The ridiculous plot coupled with Zoolander's amazing, superpower-like "blue steel" duck face made for a weirdly enjoyable film. The 2016 sequel was just as funny (and just as duck-lippy).
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"Meet the Parents" on Peacock, YouTube & Amazon Prime Video
We're not sure if we loved Ben Stiller's character Gaylord "Greg" Focker in "Meet the Parents" as much as we loved the comedic interplay between him and Jack Byrnes (played by Robert De Niro). But it doesn't matter, because both had us laughing hard. Jack is a retired CIA operative who isn't impressed with Greg — the boyfriend of his daughter, Pam (played by Teri Polo). As Greg tries to win Pam's family over in hopes of getting their permission to propose, he manages to do just about everything wrong, leading to some of the funniest moments in movie history.
"There's Something About Mary" on Amazon Prime Video
There is no Ben Stiller movie funnier than the 1998 romantic comedy "There's Something About Mary" in which he plays Ted, the high school nerd who lands a date to the prom with his much more popular crush, Mary (played by Cameron Diaz). Unfortunately, Ted has a minor accident in the bathroom involving a zipper and his male anatomy, ruining the date and his chance with Mary. Fast-forward to 13 years later when Ted attempts to rekindle their romance but finds he first has to overcome a jealous ex-boyfriend, a stalker private detective and his own insecurities about falling in love with the most beautiful girl in the world.
"Dodgeball: A True Underdog Story" on Amazon Prime Video
In the 2004 sports comedy "Dodgeball: A True Underdog Story," Ben Stiller plays White Goodman, which is a funny play on words because White is actually one very bad man. Not only is he a juiced-up personal trainer in love with his body and his gym — he's also a ruthless dodgeball competitor who isn't afraid to play dirty. We love Ben as the bad guy, even more when he's a bad guy who's totally full of himself.
"The Secret Life of Walter Mitty" on Hulu, YouTube & Amazon Prime Video
In the 2013 adventure dramedy "The Secret Life of Walter Mitty," Ben Stiller tackles one of his most challenging roles to date — a film negatives manager for Life magazine who has an unhealthy habit of zoning out and imagining himself as a hero in life-or-death scenarios. The fantasies are Walter's coping mechanism, helping him compensate for his boring, adventure-less life. When a missing film negative forces Walter to go out into the world to find it, he learns that a life full of adventure was always at his fingertips.
"The Royal Tenenbaums" on YouTube & Amazon Prime Video
In the 2001 dramedy "The Royal Tenenbaums," Ben Stiller plays Chas, a former child prodigy who made real estate deals worth millions when he was only a teenager. As an adult with two sons of his own, Chas is compulsively overprotective as he tries to keep his sons from having the kind of dysfunctional life he knew, thanks to his underhanded dad, Royal Tenenbaum. There's a dark, disturbed beauty to Chas, which makes us adore him all the more.
"Reality Bites" on Apple TV, YouTube & Amazon Prime Video
The 1994 romantic comedy "Reality Bites" was actually Ben Stiller's directorial debut. In the film, he stars as Michael Grates, an executive for a TV network whose name fits his personality because he seriously grates on our nerves. Again, this is a moment where Ben's ability to act is front and center because even though Michael's girlfriend Lelaina (played by Winona Ryder) cheats on him and (presumably) dumps him for her roommate Troy (played by Ethan Hawke), we sort of don't feel bad because Michael's annoying and overly intense and just needs to go away.
"Tropic Thunder" on Amazon Prime Video
The war comedy "Tropic Thunder" (which starred and was co-written, directed and produced by Ben Stiller) was offensive to many, based on its depictions of disabled and mentally handicapped people and the choice to have Robert Downey Jr. perform in blackface, but this isn't a review of the film — we're just talking about Ben's character, Tugg Speedman. Tugg is a Hollywood action star who's past his prime (perhaps an homage to Tom Cruise?) when he's hired as the lead in a war movie that turns into a real-life battle for survival. What made Tugg hilarious was his eternal optimism and inability to realize that he was in real danger (especially when he was kidnapped by drug lords in the jungle).
"Night at the Museum" (and its sequels) on Amazon Prime Video
Who didn't love Ben Stiller's character Larry Daley, the security guard in "Night at the Museum" and the sequels "Night at the Museum: Battle of the Smithsonian" and "Night at the Museum: Secret of the Tomb"? He's just a dad trying to do right by his son — who later discovers an entire world of history and magic when the wax figures and displays at the museum come to life at night. While Larry survives each new adventure (including warring soldiers, attacking dinosaurs and naughty monkeys), he also serves up a dose of humor and lovableness we deeply enjoyed.
"The Meyerowitz Stories (New and Selected)" on Netflix
If you've yet to catch Ben Stiller as Matthew Meyerowitz in "The Meyerowitz Stories (New and Selected)" on Netflix, you're missing out. The dramedy is about a strong-willed artistic father (played by Dustin Hoffman) and how his domineering nature created ripples in the lives of his now-adult children (including Adam Sandler as Danny Meyerowitz). It's a funny film overall, but Ben really shines in the role of Matt — a seemingly confident professional who's quietly aching for his dad to acknowledge his accomplishments.
"Along Came Polly" on Hulu & Peacock
There's a lot to love about Ben Stiller's sweet, affable character Reuben Feffer in "Along Came Polly." He's a nerdy insurance underwriter who judges everything and everyone based on how much risk they pose. After he catches his wife cheating on him, he's trapped in a joyless existence of risk analysis, unable to open his heart to anyone new. Enter the familiar trope of a beautiful, free-spirited woman (Polly, played by Jennifer Aniston) who introduces him to new experiences (like salsa dancing and eating foreign food, which gives him a hilarious bout of gastric distress). It's a ridiculous, overplayed storyline but still, we can't help but root for Reuben and his wildflower Polly every step of the way.
"The Heartbreak Kid" on Netflix
In the 2007 romantic comedy remake "The Heartbreak Kid" (based on the 1972 movie of the same name), Ben Stiller plays Eddie, a jerk of a single guy who just can't commit. Enter Lila (played by Malin Akerman), a beautiful, smart and successful woman who totally throws Eddie for a loop and manages to change his mind about settling down. After dating for just a few weeks, he marries Lila, only to discover she's not exactly the image of female perfection he imagined. Of course, while on their honeymoon (and while Eddie's questioning his marriage), he meets another beautiful, accomplished woman and falls for her. The storyline makes us all kinds of annoyed, but that's because Ben did such a good job of convincing us Eddie was a total womanizer.
"Greenberg" on Amazon Prime Video
In the romantic dramedy "Greenberg," Ben Stiller plays Roger, a grumpy man with little happening in his life after he suffers a nervous breakdown. As he house-sits for his brother Phil (played by Chris Messina), Roger develops a romantic connection with his brother's dog walker, Florence (played by Greta Gerwig). The film is kind of rambling at times, but there's a genuine heart to Roger that endears him to us, even when he's kind of being a jerk.
"Flirting with Disaster" on Pluto TV & Paramount+
In the 1996 dark comedy "Flirting with Disaster," Ben Stiller plays Mel Coplin, a man who ventures across the country to meet his birth parents for the first time. Having recently welcomed his first child with his wife, Nancy (Patricia Arquette), Mel declares that he needs to meet his parents before he can decide on a name for their newborn son. The film sees Mel in all sorts of fun, strangely hilarious and at times emotional situations as he embarks on a wild goose chase for the parents he never knew.
"Black & White" on Amazon Prime Video
In the 1999 crime drama "Black & White," Ben Stiller plays a shady cop named Mark who wants to pay a college basketball star to throw games so he can win a bet. The movie, which boasts a stellar cast of actors including Robert Downey Jr., Jared Leto, Elijah Wood, Gaby Hoffman and supermodel Claudia Schiffer (seen here), should have been good, but in reality, it was a hot mess. The role was an early indicator that while Ben is a great actor, drama without humor is definitely not his forte.
"Madagascar" (and its sequels) on Amazon Prime Video
You don't have to be a kid to fall in love with Ben Stiller's animated character, Alex the lion, in "Madagascar" (or the two sequels that followed). Alex is, in many ways, a typical New Yorker who loves the comforts of home (which happens to be the New York Zoo). When he accidentally gets shipped to Madagascar with several of his zoo pals, sending his neurosis into overdrive, Alex proves you can take the lion out of the city, but you can never take the city out of the lion.
"Brad's Status" on Amazon Prime Video
In this coming-of-age story, Ben Stiller plays Brad, who is accompanying his young adult son on a tour of universities on the East Coast. While Brad comes to grips with the fact that his son is ready to spread his wings, he's also stuck with the nagging doubt that his own life wasn't everything it should have (and could have) been, especially in comparison to his much more successful friends. In the film, Brad is an emotional, fallible being who frustrates us, makes us laugh and manages to warm our hearts.
"Envy" on Hulu, HBO Max & YouTube
What could go wrong when you put two noted comedic actors like Ben Stiller and Jack Black together in a comedy that involves a dead horse and vaporizing poo? Apparently, everything. In "Envy," Ben plays Tim Dingman, the jealous co-worker/neighbor/friend of Jack's character, Nick Vanderpark (who created Vapoorize, a product that vaporizes feces). If the concept hasn't already bored you, then perhaps you're one of the three people who claimed to enjoy the movie. Poop jokes are so 1990s.
"Mystery Men" on Amazon Prime Video
There are few things as entertaining as seeing a motley crew of superheroes band together to save the world from total destruction. In 1999's "Mystery Men," Ben Stiller plays Mr. Furious/Roy, a superhero who relies exclusively on rage as his power. Admittedly, while the role isn't necessarily one of Ben's strongest, there's something incredibly enjoyable about seeing him portray such an atypical character. As to be expected, Ben brings all the charm and charisma to a seriously angry performance.
"Duplex" on Amazon Prime Video
The movie "Duplex" starring Ben Stiller as Alex Rose, Drew Barrymore as his wife, Nancy, and Eileen Essell as their intolerable upstairs neighbor, Mrs. Connelly, was actually kind of cute as far as comedies go. The reason Ben's character landed so low on our list is because he only had one real mode in the film: angry and annoyed. Ben's a decent actor, so seeing him relegated to a near-constant frown is a waste of his talent.
"Keeping the Faith" on Hulu, HBO Max & YouTube
In Edward Norton's directorial debut, "Keeping the Faith," Ben Stiller stars as Rabbi Jake Schram, a single Jewish man who's having a secret love affair with his childhood friend Anna (played by Jenna Elfman). The twist in this romantic dramedy is that Jake's best friend, a Catholic priest named Brian (played by Edward), is secretly in love with Anna and considering leaving the faith to pursue a relationship with her. We didn't hate the movie, but we didn't like how Jake acted like such a hypocrite, engaging in the affair with Anna while rebuffing her when she wanted to take their relationship to the next level. Make up your mind, Rabbi, and stop being a player!
"Tower Heist" on Peacock & Amazon Prime Video
The 2007 crime comedy "Tower Heist" taught us that we really love Ben Stiller when he's playing an angry good guy who's out for revenge. He stars as Josh Kovaks, a building manager who mistakenly trusts a wealthy (and criminal) investment broker with his and his employees' pensions — leaving them with nothing. When he realizes the man who stole from them doesn't care about the devastation he's caused, Josh devises a plan to rob him and steal back their money. Of course, not being a criminal himself, he's forced to reach out to his old friend Slide (played by Eddie Murphy), a petty thief who becomes his Mr. Miyagi of breaking and entering.
"Starsky & Hutch" on Tubi, YouTube & Apple TV
One of the early major motion pictures based on a dated TV series was 2004's "Starsky & Hutch," which starred Ben Stiller as police detective David Starsky (opposite Owen Wilson's Ken Hutchinson). David's one of those obnoxious macho men who has an unnatural love for his car (and likes shoving his authority down everyone's throat). It's not that the acting was bad, it's that Ben was so good at making David seem like a jerk we actually hated him in real life.
"While We're Young" on Amazon Prime Video
Anyone over 30 can totally relate to Ben Stiller's character, Josh, in the dramatic comedy "While We're Young." As a man who's settled into comfortable "old person" normalcy with his wife (played by Naomi Watts), a new friendship with a 20-something couple reinvigorates them and reminds them what it's like to be young again. All that changes when Josh realizes their fun new friendship may just be a scam, but hey, you're only young once, er, twice, or something.
"Permanent Midnight" on Amazon Prime Video
In 1998's "Permanent Midnight," Ben Stiller takes on the starring role of real-life screenwriter Jerry Stahl. The film charts Jerry's rise to stardom as he transitions from little-known television writer to mega-successful comedy writer whose credits include "thirtysomething" and "ALF." While the film was criticized for its unclear intention and meandering storytelling, Ben still expertly embodied a man whose personal addictions posed a risk to his professional success.
"The Watch" on Hulu, HBO Max & Apple TV
We know "The Watch" had terrible reviews, but there's something to be said about Ben Stiller's character, Evan. In the comedy, which, surprisingly, wasn't about a wristwatch but rather a vigilante group of men who form a neighborhood watch on their block to fight crime and solve a murder, Evan is a type-A kind of guy who's convinced aliens have invaded his hometown of Glenview, Ohio. He approaches the neighborhood watch like he approaches life: hardcore, while looking like a total doofus (which is part of the magic).
"Zero Effect" on YouTube & Amazon Prime Video
In the 1998 dramatic comedy "Zero Effect," Ben Stiller plays Steve Arlo, the assistant detective (and official behind-kisser) of Daryl Zero (played by Bill Pullman). Steve is annoyingly by-the-book and lacks any real humor, but at least he had a few good scenes that made us think twice — like when he gets wasted and goes on a rant about how annoying Daryl actually is.
"Your Friends and Neighbors" on Amazon Prime Video
In the 1998 dark comedy "Your Friends and Neighbors," Ben Stiller plays Jerry, an unhappy theater instructor who pursues a woman despite being married himself. Truthfully, this isn't one of Ben's most likable roles, but he convincingly plays an unfaithful, misogynistic and selfish middle-aged man. In a film that capitalizes on infidelity as a solution to marital dissatisfaction, Ben shows off his acting prowess.