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Ben Stiller is known chiefly for his comedic movies and romantic comedies, but throughout his career, he has either created or been involved in various genres. Many of his films focus on a specific theme, usually critiquing a particular period in a person’s life, such as in Reality Bites or the new Amazon original, Brad’s Status.
With such an extensive catalog of films to choose from and because the idea of a “best” movie is more subjective, it is difficult to whittle it down. However, some movies are so integrated into popular culture or movies with an impactful theme or narrative that giving it the title of being one of the “best” Ben Stiller movies makes sense.
10 Heavyweights: Get Ready For The Best Summer
Heavyweights is a 90s classic, and Ben Stiller’s performance as Tony Perkins is often quoted 20-plus years later. The plot is relatively simple, a young boy, Gerry Garner, is sent to a fat camp by his parents. The movie starts with everything pointing to Gerry and his friends having a fantastic summer until it is revealed that the original owners of Camp Hope have had to sell their camp to Tony Perkins.
The movie’s lighthearted underdog story is like many children’s movies of the 90s. But the wild instability of Tony Perkins causes the film to be so beloved. Stiller is excellent at showing a steady decline in a character in a humorous way.
9 Dodgeball: Another Underdog Tale
Dodgeball, much like Heavyweights, follows unlikely heroes as they go up against a fitness entrepreneur, White Goodman. Although Dodgeball follows a similar arch seen in Heavyweights, Dodgeball is less of a feel-good movie. In the movie’s original ending, the members of Average Joe’s were supposed to lose the dodgeball tournament. The story still sets itself up for the actual end with the defeat of the Average Joes.
Ben Stiller’s performance in Dodgeball is very similar to his Tony Perkins. The difference is in how Goodman’s character is cockier and more dimwitted than Perkins. Stiller’s portrayal of Goodman created another very quotable character of the early aughts.
8 Duplex: Rent Stabilization
Duplex (2003) follows a New York City couple, Alex Rose and Nancy Kendricks, in their attempt to find their dream home. They eventually find a brownstone in Brooklyn that seemingly checks their wishlist, except for their new rent-stabilized tenant, Mrs. Connelly. The movie is a black comedy, as the couple concludes that the only way to get Mrs. Connelly out of the apartment is to kill her.
Duplex has been given an inadequate rating, according to critics. Still, despite the critics finding the characters of Alex and Nancy not relatable, there is a charm in the movie. Alex and Nancy are relatable for anyone who has had the experience of unruly tenants in an absurdist manner.
7 Keeping The Faith: A Priest And A Rabbi
In Keeping the Faith (2000), best friends Brian Finn and Jake Schram found the calling in their religions, becoming a priest and rabbi, respectively. Their old friend Anna Reilly comes back into their lives. Anna and Jake enter into a secret relationship at first because the relationship is meant to be a fling.
As a romantic comedy, Keeping the Faith also poses questions about bucking against tradition and accepting that their antiquated areas need to meet the modern world. The movie also expresses the idea that even priests can fall in love, but they continue to choose to commit to their vows, just as someone who commits to their relationships.
6 Meet The Parents: Look Who’s Coming To Dinner
Nurse Greg Focker has planned to propose to his girlfriend, Pam Byrnes, but the proposal is ruined when Pam receives a call from her sister, revealing that she was purposed. The rest of the movie occurs at the Brynes family home during the wedding weekend, where unfortunate events continue to happen to Greg.
Meet the Parents (2000) is relatable for anyone who has met their significant other’s parent(s) and felt the need to portray a better version of themselves to impress the family. The feeling of wanting desperately to impress someone close to a loved one to the point where someone, at the very least, puts their foot in their mouth is a standard emotion.
5 Tropic Thunder: Parodying Filmmaking and Hollywood
2008’s Tropic Thunder is a hilarious satire of Hollywood and the making of an action movie. The meta-movie “Tropic Thunder” is an adaptation of Vietnam veteran John “Four Leaf” Tayback’s memoir of the same title. Because of the diva attitudes of four of the cast, the production is threatened to be shut down unless the director can get control of the cast. The actors are brought to Vietnam to be immersed in the project, where they face the dangers of the Vietnam jungle.
The cast alone is spectacular, and the performances are some of the funniest of their careers. The movie has had its share of criticism, mainly from Robert Downey Jr.’s character, but it still holds up.
4 Zoolander: Being Ridiculously Good Looking Is Hard
Derek Zoolander is at a low point in his New York City male model career when the up-and-coming Hansel usurps him. Zoolander is sought out by a journalist, Matilda Jeffries, who becomes suspicious of Jacobim Mugatu’s offer to Zoolander. The duo uncovers that Mugatu has been using male models as assassins, and Zoolander is the newest recruit. With the help of Hansel, Zoolander and Matilda foil Mugatu’s plan.
Zoolander (2001) is a classic with its absurd plot and characters. It’s a satire on the fashion world, and male models still produce genuine laughs. There are many memorable scenes and quotes from the movie, even twenty years later.
3 Tower Heist: Ocean’s Eleven in New York
Ben Stiller stars as John Kovaks, a disciplined building manager of “The Tower,” a luxury apartment building in Manhattan. Billionaire resident Arthur Shaw is arrested and charged with embezzling $2 billion in a Ponzi scheme. Kovaks realizes that, if the charges are true, he invested the pensions of all “The Tower” employees with Shaw. On top of this revelation, one of the employees invested his entire life savings with Shaw as he was about to retire.
The movie follows the basic formula of a heist movie. However, what makes Tower Heist (2011) pop are the performances by many characters, particularly Stiller, Matthew Broderick, and Eddie Murphy. The chemistry and comedic timing with these three actors make the movie fun.
2 The Secret Life Of Walter Mitty: Day-Dreaming To Reality
Walter Mitty is an employee with Life magazine, which another company has just acquired, and suffers from chronic daydreams, mainly about his coworker, Cheryl Melhoff. In his job, Walter worked closely with a nomad photographer, Sean O’Connell; although the men had never met, because of their relationship, Sean left Walter a specific photo to be used for Life’s final print issue.
Walter uses his daydreams as a way to escape the mundane routine of his life. Walter daydreamed because he had forced himself to become something he wasn’t after his father’s death. Only when he was forced onto the path of adventure that the daydreams end, and he was living life.
1 Along Came Polly: The Risk Of A New Relationship
2004’s Along Came Polly is a romantic comedy that follows Risk Assessment Analyst Reuben Feffer, who married his girlfriend of four years. When Reuben finds his wife sleeping with the scuba instructor on their honeymoon, he returns to New York City, where he runs into Polly, an old friend from middle school.
Along Came Polly is a great romantic comedy in its simplicity. Unlike, There’s Something About Mary, the characters Reuben and Polly are created to balance each other out. It is apparent in the setup how extreme they are in their opposites, but it makes for a cute story.
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