Last Updated on November 23, 2021
Ben Stiller is known for his comedic flair but he also has a surprising talent for drama. We scoured his large repertoire of movies to find the most memorable and entertaining roles Stiller has ever brought to the big screen.
1. The Secret Life of Walter Mitty (2013)
Walter Mitty feels stuck. He works as a negative assets manager at Life magazine, has a crush on a co-worker, lives alone and chronically daydreams about adventure.
His life takes a drastic turn when the iconic photojournalist Sean O’Connell sends him a roll of negatives and claims that #25 is so amazing that it should go on the cover of the magazine. After discovering that the negative in question is missing, Walter embarks on a wild trip to find the photographer before his boss finds out that he lost the magazine’s best cover yet.
2. The Meyerowitz Stories (2017)
This movie follows the artistic, if not slightly dysfunctional, Meyerowitz family. After a separation from his wife, unemployment forces Danny to move back in with his father and his hippy stepmother.
Danny and his younger brother, Matthew, have to deal with their father’s habit of running away in public and his failing health, which brings several uncomfortable issues about past resentments to the table.
3. Meet The Parents (2000)
Greg Focker is excited to meet his girlfriend‘s parents and plans to propose to her in front of her entire family. But Pam’s father is a retired CIA operative who is paranoid about Greg’s every move and makes Greg so nervous that he botches every attempt to impress her parents.
After Pam’s weed-smoking brother frames Greg as a pothead and Greg’s klutzy behavior threatens to ruin an upcoming family wedding, the family banishes him. But Pam’s love finally convinces her father that Greg is not the loser they make him out to be.
4. While We’re Young (2014)
Stuck in middle-age, a stale marriage and getting no appreciation from a father-in-law who’s an accomplished film maker, Josh Srebnick struggles to complete his own documentary film.
When he and his wife meet a younger, more bohemian couple who are also interested in film production, the Srebnick couple’s life takes a refreshing turn. However, as Josh competes with them he realizes that they are deceptive and the ever-complicating relationship, which includes his father-in-law, threatens to ruin his marriage.
5. Tropic Thunder (2008)
In this unique comedy, Stiller teams up with great actors like Jack Black and Robert Downey Jr. Stiller plays a fading action star named Tugg Speedman who is cast in a movie that is based on a war hero’s life.
But when Speedman and his fellow actors keep messing up the director’s orders, the latter decides to film them in a jungle with hidden cameras to get more natural sequences. Unbeknownst to Speedman and his fellow actors, who believe everything around them is staged, they are dropped off in a jungle riddled with real mines and drug dealers, with hilarious results.
6. Brad’s Status (2017)
By most measurements, Brad Sloan should have a happy life. He’s got a good marriage, lives comfortably and runs a non-profit organization. But Brad is feeling increasingly insecure about his life choices after he realizes that all of his friends are super-wealthy.
When he has to rely on their influence to get his own son into Harvard, Brad can take it no more and regrets that he chose to start a non-profit and not a money-making business. But Brad soon discovers that no one’s life, not even his rich friends’, is without sorrow and he learns to appreciate the blessings he already has.
7. Greenberg (2010)
After a nervous breakdown, Roger Greenberg is released from the hospital and he returns to his brother’s house in Hollywood Hills to rest. During his stay, he meets several old faces from his past as well as Florence, who works for the Greenberg family.
But not all of his friends are happy to see Roger and his attempts to romance Florence and his ex-girlfriend do not go according to plan. As he bumbles to find his feet, Roger learns that he has to fix his mistakes that ruined his friendships and which woman owns his heart.
8. Zoolander (2001)
In this hilarious comedy, Stiller portrays top male model Derek Zoolander who hits a low point when he is overtaken as the best by a newcomer model named Hansel. So when fashion mogul Jacobin Mugatu offers Zoolander the star position in his next runway show, Derek jumps at the chance.
However, a conspiracy-loving ex-model warns Zoolander that the show is being used to brainwash him to assassinate the Prime Minister of Malaysia. Zoolander has to form an unlikely partnership with his rival Hansel to stop the plot.
9. The Royal Tenenbaums (2001)
In this comedy, Chas, Richie and their adopted sister Margo are child geniuses. After achieving the highest honors in sport, business and literature, the three adolescents are told by their father, Royal Tenenbaum, that he’s getting a divorce.
Years later, the now-grown Tenenbaum children have achieved little with their lives and return to their father’s mansion to receive some bad news. The movie follows their hilariously dysfunctional road towards healing as a family.
10. There’s Something About Mary (1998)
Theodore “Ted” Stroehmann is 16 and he is getting ready to go to the prom with the girl of his dreams, Mary Jensen. But an unfortunate zipper accident cancels the date and Ted loses contact with Mary for years.
Unable to forget about her, Ted hires a private investigator to track down Mary. However, her natural charm and beauty give Ted a lot of neurotic male competition including the private eye, a stalker, Mary’s neighbor and one of her patients.