The hilarious and brilliantBen Stilleris 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 comedyHot 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 seriesThe Ben Stiller Show,the actor slowly but surely began to take Hollywood by storm, beginning with his directorial debut with 1994’sReality 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 likeZoolander, There’s Something About Mary, Meet the Parents,andDodgeball,having most recently directed episodes for theApple TV+ workplace thrillerSeverance.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 ofSeverance, Stiller stayed busy between directing jobs withBig Man, London,andSuper Sad Love Story, as well as developing and producingDodgeball 2. These are the best Ben Stiller movies.
11Greenberg
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 dramedyGreenberg, 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 ofdirector Noah Baumbachand 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 attempt 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 asThe Meyerowitz StoriesandWhile We’re Young.
10The Secret Life of Walter Mitty
A remake of the 1947 film and adaptation of James Thurber’s short story, the 2013 adventure dramedyThe Secret Life of Walter Mittywas 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 ofRolling StonecommendedThe Secret Life of Walter Mitty,writing, “In his uniquely funny and unexpectedly tender movie, Stiller takes us on a personal journey of lingering resonance.”
9Starsky & Hutch
Stiller teamed up with pal and frequent collaborator Owen Wilson for the 2004 buddy cop action comedyStarsky & 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 theTodd 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 attempt to be like that.”
8Reality Bites
Ben Stiller made his directorial debut with the 1994 romantic dramedyReality Bites,in which he appears alongside thelovely Winona Ryderand 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 seriesThe 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 Bitesdebuted 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.
7Zoolander
Some of Hollywood’s most adored funnymen, Ben Stiller, Owen Wilson and Will Ferrell, joined comedic forces for the hilarious 2001 fashion industry satireZoolander,which centers on the titular dim-witted fashion model who becomes brainwashed to assassinate the Prime Minister of Malaysia. Stiller firstcreated the character for a skitat 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.
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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.Zoolanderwas 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.
6Night at the Museum
Shawn Levy’s 2006 fantasy comedyNight at the Museumis 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 Museumwas 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.
5The Royal Tenenbaums
From the minds ofthe talented Wes Andersonand Owen Wilson comes the 2001 dramedyThe 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 thewriting of J.D. Salinger,with the characters in the bookFranny and Zooeyinspiring a great deal of the child prodigy material included.
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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 inThe Royal Tenenbaumshas 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’sThe Grand Budapest Hotel.
4Dodgeball: A True Underdog Story
2004’s uproarious sports comedy flickDodgeball: A True Underdog Storycenters 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 & Roepercommended the amusing farce, callingDodgeballa “hilariously worthy successor to the great goofball comedies of the late Seventies and early Eighties, movies likeCaddyshackandMeatballs.”Though there have been talks of a sequel, nothing has come to fruition, but the cast didbriefly reunite in 2017to help raise funds for the Stiller Foundation.
3Tropic Thunder
Ben Stiller’s 2008 big screen action-comedy extravaganzaTropic Thunderis a star-studded flick featuring some of the entertainment industry’s finest including anexcellent 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 onactors he knewwho 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 likeApocalypse Now, RamboandPlatoon,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.”
2There’s Something About Mary
The adored 1998 Farrelly Brothers romantic comedyThere’s Something About Maryfamously stars Cameron Diazas 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 actuallyinspired 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 Marywas a knockout with both audiences and critics, garnering numerous accolades and widespread praise and becoming a surprise hit with a long-lasting cult following.
