What Are The 7 Best Ben Stiller Movies Of All Time?

Ben Stiller has worn many hats throughout his career: actor, filmmaker, comedian, voice actor, screenwriter, movie director, and producer. Luckily, we have been privy to all of his accomplishments. From making us laugh out loud to leaving us in awe, the list of Stiller’s film accomplishments is endless. That’ why we at StudyFinds read through eight expert sources to come away with the top seven best Ben Stiller movies of all time. Let us know if we missed your favorite flick in the comments below!

The List: Best Ben Stiller Movies, According to Fans

1. “There’s Something About Mary” (1998)

"There's Something About Mary" (1998)
“There’s Something About Mary” (1998)

“There’s Something About Mary” was the first of its kind. The Farrelly brothers directed this unpredictable rom com that brought both the shock and the laugh factor. Ranker calls it a “timeless comedy that captures Stiller’s undeniable charm and comedic prowess.”

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We don’t want to say that this movie put Stiller on the map, but it kind of did. After this it was a waterfall of comedies like “Meet the Parents” and “Zoolander.” However, for the Farrelly Brothers, Rolling Stone says that they struggled to regain that magic.

Stiller plays Ted Stroehmann, a former gawky high schooler who tries to redeem himself with his high school crush, Mary. As an adult, he tries to win her over with the competition of other weirdos. Movie Web calls it “raunchy, slopstick and disgusting.”

2. “Tropic Thunder” (2008)

"Tropic Thunder" (2008)
“Tropic Thunder” (2008)

Stiller offers one of the best performances in this film as both actor and director. He plays Tugg Speedman, a misguided actor. Ranker calls it an “uproarious comedy” that mocks Hollywood’s odd obsession with war movies. Plus, the cast is full of stars, making it an even more appealing watch.

Slash Film hails “Tropic Thunder” as one of the funniest films of the 21st century, probably due to its jokes on Hollywood film. Coming from Stiller, who is in the business, makes it even more interesting and funny.

I think it’s safe to say that as the director, Stiller had some convincing pull on what he had the actors do (and wear) in the film. While some of the scenes could’ve gotten him canceled today, “Tropic Thunder” was too hilarious that not many people criticized those details, according to Rolling Stone.

3. “Meet The Parents” (2000)

"Meet The Parents" (2000)
“Meet The Parents” (2000)

In this film, Stiller plays the loveable Greg Focker who tries to win over his fiance’s tricky dad. Not a regularly easy feat, Jack (Robert DeNiro) poses an extraordinary challenge supplemented by his former CIA-agent skills. While butting heads, Ranker admits you can’t deny the on-screen chemistry of the pair.

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Stiller connects with audiences as he portrays a man desperate for acceptance of his fiancé’s family. If you have ever had an uncomfortable family dinner or holiday, you can attest. Slash Film says things get so awkward, that they compare it to a horror movie.

Different from his normally goofy characters, Stiller plays a rather normal guy. As normal as Focker may be, he isn’t lacking in awkward situations. Rolling Stone calls it a surprise comic masterpiece.

4. “Zoolander” (2001)

"Zoolander" (2001)
“Zoolander” (2001)

Ranker admits that many look to Derek Zoolander as Stiller’s most iconic role. Zoolander is a conceded male model who is ridiculously funny. As the director, Stiller offers the audience a glimpse into the exaggerated world of fashion industry.

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Let’s not forget that “Zoolander” bolsters a talented supporting cast, including Owen Wilson and Will Ferrell. You can’t go wrong with that crew. As idiotic as the storyline is, it’s a popular one. Slash Film describes the plot: “As Derek attempts to relaunch his career, the fashion influencer Jacobim Mugatu (Will Ferrell) brainwashes him to assassinate the Prime Minister of Malaysia.”

Derek Zoolander was a character that actually first hit the screen during a skit on the VH1 Fashion Awards. It clearly hit, resulting in a blockbuster. Premiering weeks after 9/11, “Zoolander” managed to gross over $60 million. Rolling Stone says people must have been desperate for a comedic distraction.

5. “Dodgeball” (2004)

"Dodgeball" (2004)
“Dodgeball” (2004)

Picture an egotistical guru on steroids, and you just nailed Stiller’s character, White Goodman. Goodman takes his elite dodgeball team and challenges Vince Vaughn’s character, Peter LaFleur, in an intense competition. According to Ranker, “The film’s emphasis on camaraderie and perseverance elevates it beyond standard slapstick fare.”

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“Dodgeball” offers a slew of supporting characters that complement Stiller’s comedic genius, making it one of his most memorable films. Vaughn’s character needs to earn $50,000 to save his gym. It’s up to the dodgeball competition to save his tail. Rolling Stone calls his team a “group of weak misfits.”

Although it is not the first time we’ve seen it, it’s particularly funny to watch Stiller’s character be rejected by his love interest. Movie Web thinks it is almost as funny as the mustache he dons.

6. “Flirting With Disaster” (1996)

"Flirting With Disaster" (1996)
“Flirting With Disaster” (1996)

Another example of a regular Joe put in silly situations, “Flirting With Disaster” brings its characters into dark situations. Stiller and his wife played by Patricia Arquette are a married couple who just have a baby with whom Stiller won’t name until he finds his biological parents. Slash Film says Stiller does a great job showing his character’s “insecurity, terrified of disappointing his child and confronting the issues in his upbringing.”

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This is one of Stiller’s earliest roles and one of Director David O. Russell’s best films. Movie Web explains the plot as Stiller’s character and his family embarking on a hilarious journey.

Stiller is perfect in this very underrated film that not many people have had the chance of seeing. Gold Derby says that the director’s “at-times quirky dialogue proved to be a great match to Stiller’s sensibility.”

7. “The Royal Tenenbaums” (2001)

"The Royal Tenenbaums" (2001)
“The Royal Tenenbaums” (2001)

Another star-studded movie, “The Royal Tenenbaums” is a quirky comedy-drama that follows the lives of three estranged genius siblings – a former tennis prodigy, a financial whiz kid, and a playwright – who reunite under one roof with their eccentric parents. After years of personal failures, their father attempts to reconnect with his family by feigning a terminal illness. Slash Film claims that you may have to “adjust to Wes Anderson‘s artful style of filmmaking.”

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Royal Tenenbaum (Gene Hackman) pushed all of his children to find success during their youth, but they each have grown up dealing with mental health issues. It’s hilarious, weird, and certainly is some of Stiller’s best work.

A Breakdown of Ben Stiller’s Career:

Early Life and Influences:

  • Son of Comedy Legends: Stiller comes from comedic royalty. His parents, Jerry Stiller and Anne Meara, were a renowned comedy team who influenced his early interest in humor.
  • Exploring Comedy: Even as a child, Stiller’s comedic side emerged. He made his own Super-8 parody films, mimicking popular movies of the time.
  • Stepping into Acting: Stiller dropped out of UCLA after nine months to pursue acting full-time. He landed roles in stage productions and television commercials.

Rise to Stardom:

  • Sketch Comedy Breakthrough: Stiller’s big break came in the late 1980s with his short-lived sketch comedy show, “The Ben Stiller Show.” While the show itself didn’t last long, it garnered him recognition and launched his comedic career.
  • Early Film Roles: Stiller transitioned to film in the late 1980s and early 1990s, appearing in movies like “Empire of the Sun” and “The Thin Line Between Love and Hate.”
  • Directing Debut and Collaboration: In 1994, Stiller both directed and starred in the Gen X comedy “Reality Bites,” establishing himself as a filmmaker with a distinct voice.

Comedy Icon Status:

  • Box Office Success: The late 1990s and early 2000s saw Stiller become a box office magnet. Movies like “There’s Something About Mary,” “Meet the Parents” (and its sequels), and “Zoolander” cemented his comedic acting prowess.
  • “Frat Pack” Member: Stiller became associated with a group of comedic actors like Owen Wilson and Will Ferrell, often referred to as the “Frat Pack.” These actors frequently collaborated on successful comedies.
  • Genre Exploration: While known for comedies, Stiller also ventured into other genres, including action-comedy (“DodgeBall: A True Underdog Story”) and voice acting (“Madagascar” franchise).

Continued Success and Recognition:

  • Award Recognition: Stiller’s work has been recognized by awards like MTV Movie Awards and Primetime Emmy Awards.
  • Diverse Projects: Stiller continues to act, direct, and produce across various genres. He’s tackled dramatic roles (“The Meyerowitz Stories”) and darker comedic themes (“Tropic Thunder”).


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