The hilarious and brilliant Ben Stiller is an esteemed comedian, actor, and filmmaker who has been a constant comedic force for over 30 years. The dynamic performer has crafted a colorful and remarkable resume for himself since making his big-screen debut in the 1987 action comedy Hot Pursuit, appearing in both beloved TV and cinematic hits that have given immense laughter and joy to viewers across the world.
After making a name for himself with his 1990 sketch comedy series The Ben Stiller Show, the actor slowly but surely began to take Hollywood by storm, beginning with his directorial debut with 1994’s Reality Bites. From that moment forth, Stiller would go on to direct, write and star in a myriad of beloved comedy staples.
Throughout his impressive career, Stiller has creatively contributed to over 50 films, directing and starring in smash hits like Zoolander, There’s Something About Mary, Meet the Parents, and Dodgeball, having most recently directed episodes for the Apple TV+ workplace thriller Severance. He is a member of a comedic group of actors colloquially known as the Frat Pack, consisting of fellow A-listers such as Vince Vaughn, Owen Wilson, and Will Ferrell; he has been acknowledged as the leader of the group because of his frequent collaborations with the other members in his projects.
Updated February 1st, 2023: If you're a fan of the talented Ben Stiller, you'll be happy to know this article has been updated with additional content and films.
Stiller’s flicks have collectively grossed over $2.6 billion in the United States and Canada, making him one of comedy’s most bankable stars. After the incredible season finale of Severance, Stiller stayed busy between directing jobs with Big Man, London, and Super Sad Love Story, as well as developing and producing Dodgeball 2. These are the best Ben Stiller movies.
11 Greenberg
Ben Stiller showcased his dramatic side when he appeared as a struggling musician-turned-carpenter in search of his life's purpose in the 2010 dramedy Greenberg, which follows Roger Greenberg as he house-sits for his brother and develops an unexpected bond with his sibling's soul-searching assistant Florence (Greta Gerwig). Stiller had been a big fan of director Noah Baumbach and jumped at the chance to portray a multi-layered character working through his issues.
On working with the director, Stiller once expressed, "Noah’s work is very detailed and goes into specifics on the characters; it’s all written on the page. We rehearsed a lot; it really has to be said as written. So there was hardly any improvisation on the shoot and that was exciting – not having the burden of having to come up with something to try to make it better." The picture marked the first of multiple collaborations between Stiller and Baumbach, with the pair going on to work together in projects such as The Meyerowitz Stories and While We're Young.
10 The Secret Life of Walter Mitty
A remake of the 1947 film and adaptation of James Thurber’s short story, the 2013 adventure dramedy The Secret Life of Walter Mitty was directed by and stars Ben Stiller in the eponymous role, and follows the daydreaming Life magazine photo editor as he escapes his monotonous existence through vivid fantasies, embarking on a real-life extraordinary adventure he’ll never forget. Featuring the additional talent of Kristen Wiig and Shirley MacLaine, the whimsical picture allowed Stiller to shine in a more earnest role while beautifully weaving together humor and self-examination; his gifts both in front and behind the camera are on full display in the dramedy.
Despite opening to a mixed bag response, critics agreed that Stiller crafted a thought-provoking and entertaining film that, like its predecessor, inspires moviegoers to dream big. Peter Travers of Rolling Stone commended The Secret Life of Walter Mitty, writing, “In his uniquely funny and unexpectedly tender movie, Stiller takes us on a personal journey of lingering resonance.”
9 Starsky & Hutch
Stiller teamed up with pal and frequent collaborator Owen Wilson for the 2004 buddy cop action comedy Starsky & Hutch, an adaptation of the popular '70s television series that centers on the titular Bay City Police detectives as they attempt to take down a notorious drug trafficker. Stiller is hilarious as the high-strung and macho David Starsky and Wilson as the easy-going lothario Ken "Hutch" Hutchinson, with the charming duo sharing the screen with fellow stars like Vince Vaughn, Snoop Dogg and Jason Bateman in the big-screen extravaganza.
Original series stars Paul Michael Glaser and David Soul also make cameos in the Todd Phillips flick, with the comedy serving as a prequel to the fan favorite TV show that showcases the crime-fighting pair's initially rocky relationship. Stiller enjoyed the playful nature of the adaptation, revealing in an interview, "I think it was fun, the not politically correct attitude those guys had back then. You could just be a cop and be a tough guy, and not worry about offending anybody. That's kind of who they were. It's fun to try to be like that."
8 Reality Bites
Ben Stiller made his directorial debut with the 1994 romantic dramedy Reality Bites, in which he appears alongside the lovely Winona Ryder and Ethan Hawke in a story that follows aspiring videographer Lelaina as she works on a documentary about the disenchanted lives of her fellow Generation X friends and roommates. After watching the pilot episode of Stiller’s sketch comedy series The Ben Stiller Show, producers approached the star to direct the dramedy and not act in it; after having issues coming up with a credible character to complete the love triangle, Stiller suggested he be the third person and subsequently appeared alongside Ryder and Hawke.
Upon initial release, Reality Bites debuted to mainly positive responses but in the years since has achieved a cult status and has been singled out for capturing the spirit of the early 1990s grunge scene among young adults while depicting the issues that plagued them during that period of their lives.
7 Zoolander
Some of Hollywood’s most adored funnymen, Ben Stiller, Owen Wilson and Will Ferrell, joined comedic forces for the hilarious 2001 fashion industry satire Zoolander, which centers on the titular dim-witted fashion model who becomes brainwashed to assassinate the Prime Minister of Malaysia. Stiller first created the character for a skit at the 1996 VH1 Fashion Awards, with the name being inspired by two male models who both worked for Calvin Klein: American Johnny Zander and Dutchman Mark Vanderloo.
A slew of famous faces made cameos in the zany and over-the-top flick, such as David Bowie, Lenny Kravitz, Heidi Klum, and Donatella Versace, while Stiller showed off his directing chops once again by helming the picture. Zoolander was a box office success, earning over $60 million with reviewers praising it for its upbeat, escapist approach to New York fashion and the dynamite cast’s hilarious performances. A sequel, Zoolander 2, was released in 2016 with many of the original’s stars returning.
6 Night at the Museum
Shawn Levy’s 2006 fantasy comedy Night at the Museum is based on the Milan Trenc children’s book, and tells the wondrous story of a divorced father who becomes the night watchman at New York City’s American Museum of Natural History and makes the startling discovery that the exhibits come to life at night. A myriad of dazzling performers star in the picture, portraying some of history’s most admired and famous figures; the late and great Robin Williams appears as Theodore Roosevelt while Oscar-winner Rami Malek is a pharaoh and the mummy of Ahkmenrah.
Levy credited lead Ben Stiller for landing such an elite ensemble cast, having once said, “When actors hear that Ben Stiller is in a movie, they want to work with him. It’s a high-water mark and it absolutely draws actors in and I’m convinced that’s a big part of why we got this cast.” Night at the Museum was a blockbuster hit, grossing over $570 million while kicking off the fantasy series that would spawn two lucrative sequels; an animated sequel for Disney+ was released in 2022.
5 The Royal Tenenbaums
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From the minds of the talented Wes Anderson and Owen Wilson comes the 2001 dramedy The Royal Tenenbaums, which follows the eccentric members of the dysfunctional Tenenbaum family as the three gifted siblings experience immense success in their youth but failure and crippling disappointment in their adulthood. The film’s narrative was greatly influenced by the writing of J.D. Salinger, with the characters in the book Franny and Zooey inspiring a great deal of the child prodigy material included.
Gene Hackman appears as Royal Tenenbaum, with Angelica Huston as his ex-wife and Ben Stiller, Owen Wilson, and Gwyneth Paltrow as their uniquely gifted grown prodigies. Stiller is hilarious as the overprotective, jumpsuit-wearing son obsessed with his children's safety. The storytelling in The Royal Tenenbaums has been described as having an absurdist and whimsical sense of humor, with literature helping shape the narrative through its use of book chapters and narration. The dramedy earned Anderson and Wilson an Oscar nomination for Best Screenplay and became the director’s most successful film until 2014’s The Grand Budapest Hotel.
4 Dodgeball: A True Underdog Story
2004’s uproarious sports comedy flick Dodgeball: A True Underdog Story centers on a group of misfits who decide to enter a Las Vegas dodgeball tournament in order to save their beloved local gym from the onslaught of a corporate health fitness chain. Vince Vaughn and Ben Stiller stars as adversaries Peter LaFleur and White Goodman, with the latter appearing as the ruthlessly hilarious owner of Globo Gym, the corporate chain that is threatening LaFluer’s small and dilapidated Average Joe’s gym.
The scene-stealing Stiller is in peak comedic form in the entertaining film, memorably sporting tight spandex shorts, a handlebar mustache and an over-the-top cocky attitude with sidesplitting zingers and sass. Ebert & Roeper commended the amusing farce, calling Dodgeball a “hilariously worthy successor to the great goofball comedies of the late Seventies and early Eighties, movies like Caddyshack and Meatballs.” Though there have been talks of a sequel, nothing has come to fruition, but the cast did briefly reunite in 2017 to help raise funds for the Stiller Foundation.
3 Tropic Thunder
Ben Stiller’s 2008 big screen action-comedy extravaganza Tropic Thunder is a star-studded flick featuring some of the entertainment industry’s finest including an excellent Robert Downey Jr. performance, Jack Black, Nick Nolte, and Stiller himself, and follows a group of prima donna actors making a Vietnam War film. When their exasperated director drops them in the middle of the jungle, they are forced to rely on their acting skills to survive the real life action and danger around them.
Stiller also co-wrote the screenplay, basing the premise on actors he knew who became “self-important” and “self-involved” and believing they had been part of a real military unit after attending boot camps for war films. The comedy was developed to satirize Vietnam War pictures like Apocalypse Now, Rambo and Platoon, and notoriously featured Downey Jr. appearing in blackface, a choice Stiller made earnestly to poke fun at actors; he later expressed, “When people see the movie–in the context of the film, he’s playing a method actor who’s gone to great lengths to play a black guy. The movie is skewering actors and how they take themselves so seriously.”
2 There’s Something About Mary
The adored 1998 Farrelly Brothers romantic comedy There’s Something About Mary famously stars Cameron Diaz as the aforementioned Mary, and depicts the various men in her life that are in love with her and are desperately vying for her affections. Ben Stiller portrays Ted Stroehmann, a man who gets his chance to meet up with his dream girl from high school even though his first date with her thirteen years prior was an utter disaster.
According to Bobby Farrelly, the iconic scene in which Ted gets his scrotum stuck in his pants fly was actually inspired by a real event, when their sister was listening to some records with some eighth grade students in the basement of their house: “One of the kids went up to the bathroom and zipped himself up. He was in there for a long time. My dad, who was a doctor, actually had to go in and say, ‘Hey, kid. You alright?’” There’s Something About Mary was a knockout with both audiences and critics, garnering numerous accolades and widespread praise and becoming a surprise hit with a long-lasting cult following.
1 Meet the Parents
Jay Roach’s beloved 2000 comedy Meet the Parents hilariously chronicles a series of disastrous events that befall the kind-hearted but hapless nurse Greg Focker (Ben Stiller) while visiting his girlfriend’s parents. In the treasured flick, Robert De Niro and Blythe Danner portray Jack and Dina Byrnes, with the former striking fear and intimidation in Focker due to his background as a retired CIA operative.
Roach wanted an opportunity to “do character-driven comedy” and “to create realistic characters, but heighten the comedic situations and predicaments.” He chose to cast De Nero as the overprotective Jack Brynes due to the actor’s comedy work in Analyze This while selecting Stiller because “I saw Meet the Parents as an anxiety dream, and in my view nobody plays that kind of material better than Ben… He has lots of great ideas, and he’s very skilled at loose improvisation.” The film has one of the best De Niro movie performances, transplanting his tough-guy gangster person into domestic comedy. Meet the Parents was one of the highest-grossing films of 2000 and earned Stiller an American Comedy Award, and its success led to the hit sequels Meet the Fockers and Little Fockers.