Ben Stiller used to just be known as the son of Jerry Stiller and Anne Meara. Now that he has more than 25 years in the film industry as an actor, director, and producer, Ben is arguably the most known figure from the family. While he usually focuses his talents on comedy, he’s started to explore more deep, genre-rich work behind the camera. Most recently, he became one of the main creative forces backing the Apple TV+ hit Severance.
Today, we’ll go into the time machine and celebrate movies with Ben Stiller and his best of the best as an actor. From laugh-out-loud comedy to indie films with great directors, here are the best Ben Stiller movies to stream and enjoy with friends, family, or by yourself!
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12. Reality Bites (1994)
99m
Genre
Drama, Romance
Stars
Winona Ryder, Ethan Hawke, Janeane Garofalo
Directed by
Ben Stiller
Watch on Amazon
Reality Bites is a coming-of-age story that follows a group of recent college graduates in Houston navigating life after school. Lelaina, played by Winona Ryder, aspires to be a documentary filmmaker and chronicles the experiences of her friends, who are all struggling to find their footing in the face of a recession. Lelaina herself is stuck in a dead-end job and caught in a love triangle between her slacker best friend Troy (Ethan Hawke) and a successful but uptight TV executive (Ben Stiller). The film explores the anxieties and disillusionment of Generation X, grappling with issues like unemployment, dead-end jobs, and the search for meaning in a world that seems to have passed them by. It’s a comedic look at their struggles, but it also examines their hopes and dreams.
11. DodgeBall: A True Underdog Story (2004)
92m
Genre
Comedy
Stars
Vince Vaughn, Christine Taylor, Ben Stiller
Directed by
Rawson Marshall Thurber
Watch on Hulu
Dodgeball: A True Underdog Story follows the misadventures of a recreational dodgeball team. This exaggerated take on sports films allows Ben Stiller and Vince Vaughn to show off everything they’ve got in their comedic toolboxes, although some viewers and critics took umbrage with the over-the-top storytelling. If you like seeing Stiller at his goofiest, this is a pretty good place to start in his catalog.
10. The Secret Life of Walter Mitty (2013)
114m
Genre
Adventure, Comedy, Drama, Fantasy
Stars
Ben Stiller, Kristen Wiig, Sean Penn
Directed by
Ben Stiller
Watch on Apple TV+
The Secret Life of Walter Mitty tells the story of the titular character, played by Stiller, who travels the world in pursuit of a purpose. Along the way, he discovers the love and life he’s always daydreamed of, a perfect and relatable analogy for so many of the viewers watching from home. Stiller also directed this movie, a decision some critics felt led to uneven storytelling. I appreciate the feel-good arc of the main character and the change of pace Stiller accepted in this film compared to his other roles.
9. Zoolander (2001)
90m
Genre
Comedy
Stars
Ben Stiller, Owen Wilson, Christine Taylor
Directed by
Ben Stiller
Watch on Amazon
Not many characters Stiller plays are more famous than the fashion model Derek Zoolander. This movie with Ben Stiller follows the trials and troubles of Zoolander as he comes to grips with his place in the fashion industry after losing an award to Owen Wilson’s character, Hansel. The movie uses a lot of stereotypes and outlandish assumptions about people who work in the modeling industry, but it’s certainly good for many memorable laughs. An ill-received sequel was finally released in 2016, but we’d rather just remember the first movie here.
8. Flirting with Disaster (1996)
92m
Genre
Comedy
Stars
Ben Stiller, Patricia Arquette, Téa Leoni
Directed by
David O. Russell
Watch on Amazon
Flirting with Disaster is one of the earliest hits of Ben Stiller’s career, and it still presents plenty of laughs more than 25 years later. Stiller plays a man in search of his biological parents, and he forces his wife to travel the country with him to track them down. The journey is as offbeat as can be expected, and the results of the search are equally wacky. This black comedy was one of the films that proved Stiller could carry a production as the lead man. Other actors include Alan Alda and Mary Tyler Moore.
7. The Meyerowitz Stories (New and Selected) (2017)
112m
Genre
Comedy, Drama
Stars
Adam Sandler, Ben Stiller, Dustin Hoffman
Directed by
Noah Baumbach
Watch on Netflix
Stiller is just one part of The Meyerowitz Stories, but he’s excellent in it. The film tells the story of three children of two eccentric parents who are still struggling to reckon with their childhood even as adults. As is often the case, Stiller plays the most straight-laced of the siblings, but even he comes unhinged as he comes face to face with both his parents, and in particular, his brother. Stiller, Adam Sandler, Dustin Hoffman, and Elizabeth Marvel are all excellent in this movie. Noah Baumbach is one of the best directors of interesting character studies, and The Meyerowitz Stories is one of his most underrated.
6. Tropic Thunder (2008)
107m
Genre
Action, Comedy, Adventure, War
Stars
Ben Stiller, Jack Black, Robert Downey Jr.
Directed by
Ben Stiller
Watch on Amazon
When it comes to movies that probably would be controversial if they were made today, Tropic Thunder is certainly on the top of the list. The satirical war film pokes fun at a myriad of Hollywood tropes, sometimes using outdated avenues like brown face to illicit laughs. Stiller portrays has-been actor Tugg Speedman, a former movie star who has to figure out how to get through the dangers of a real jungle with the help of his co-stars. Other big names in this one include Robert Downey Jr., Jack Black, and Tom Cruise.
5. There's Something About Mary (1998)
119m
Genre
Romance, Comedy
Stars
Cameron Diaz, Ben Stiller, Matt Dillon
Directed by
Bobby Farrelly, Peter Farrelly
Watch on Hulu
4. Greenberg (2010)
107m
Genre
Comedy, Drama, Romance
Stars
Ben Stiller, Greta Gerwig, Rhys Ifans
Directed by
Noah Baumbach
Watch on Amazon
In what might be one of Stiller’s best dramatic performances, Greenberg sees Stiller playing one of the least likable protagonists imaginable. The most remarkable thing about the movie, though, is how much you come to feel for Stiller’s central character, a lost soul yearning for connection. He’s perfectly paired with Greta Gerwig, and the movie is really just about the two of them trying to find a way to come together. Another collaboration with Baumbach, Greenberg is a reminder that Stiller can do straight drama laced with a little bit of dark comedy.
3. Night at the Museum (2006)
108m
Genre
Action, Adventure, Comedy, Family, Fantasy
Stars
Ben Stiller, Carla Gugino, Dick Van Dyke
Directed by
Shawn Levy
Watch on Disney+
2. The Royal Tenenbaums (2001)
110m
Genre
Comedy, Drama
Stars
Gene Hackman, Anjelica Huston, Ben Stiller
Directed by
Wes Anderson
Watch on Amazon
Although not one of Wes Anderson’s typically used actors, Ben Stiller really nails his role as Chas Tenenbaum, the son of a father who leaves during adolescence only to reappear later on in his children’s adult years to zany and absurdist results. Gwyneth Paltrow, Bill Murray, and Owen Wilson are some of the other names you’ll be excited to see in this comedy-drama film from the early 2000s. The film remains of Stiller and Anderson’s best projects due to its indie feel and unique humor surrounding family issues.
1. Meet the Parents (2000)
108m
Genre
Comedy, Romance
Stars
Ben Stiller, Robert De Niro, Teri Polo
Directed by
Jay Roach
Watch on Amazon
Ben Stiller is already a big star on his own. Add Robert De Niro to the mix and you have a legendary pairing that was sure to be a hit the second they were cast together. The best comedy pokes fun at the most relatable moments in our lives, and the plot of this classic 2000s family flick definitely has an innate understanding of the awkward reality of in-law relationships. Stiller and De Niro possess a golden chemistry as Stiller’s character tries to impress De Niro’s, enough to continue pursuing a relationship with his daughter. This movie spawned two sequels across more than a decade with Meet the Fockers and Little Fockers. These films never were able to quite capture the comedic magic of the original Meet the Parents, but this is often a regular occurrence when making follow-ups.
