Ben Stiller’s 6 Funniest Movies Ranked

Ben Stiller was born on November 30, 1965, in New York City to comedians and actors Jerry Stiller and Anne Meara. His parents frequently took him on the sets of their appearances, including The Mike Douglas Show when he was a kid. His older sister, Amy Stiller, has appeared in many of his productions, including Highway to Hell, Reality Bites, DodgeBall: A True Underdog Story, and Zoolander. Growing up, Ben showed an early interest in filmmaking and made Super 8 movies with his sister and friends. By nine years old, Stiller made his acting debut on his mother’s short-lived television series, Kate McShane.

Stiller’s Early Life and Career

In the late ’70s, Stiller performed with the New York City troupe NYC’s First All Children’s Theater. After being inspired by the television show Second City Television in high school, Stiller realized that he wanted to get involved with sketch comedy. As a teenager, Stiller dabbled in music and was even the drummer of the post-punk band Capital Punishment. The band released the studio album Roadkill in 1982. Stiller briefly enrolled as a film student at the University of California before leaving school to move back to NYC. In 1986, Stiller was cast in the Tony Award-winning Broadway revival of John Guare’s The House of Blue Leaves.

After Stiller created a parody of Martin Scorsese’s The Color of Money with a 10-minute short titled The Hustler of Money, his work got the attention of Saturday Night Live, which aired it in 1987. Two years later, SNL offered Stiller a spot as a writer. However, since the comedy sketch show didn’t want him to make more short films, he left after four episodes. Despite things not working out long-term at SNL, Stiller had his own show titled The Ben Stiller Show, which went from MTV to Fox to Comedy Central. Among the principal writers on the show were Stiller and Judd Apatow, with the show featuring the ensemble cast of Stiller, Janeane Garofalo, Andy Dick, and Bob Odenkirk.

With an impressive 135 acting credits beneath his belt, Stiller also produced 51 projects for film and television and directed 20 projects. Take a look below at our ranking of Ben Stiller’s six funniest movies:

• 6. Meet the Fockers

  In this 2004 sequel to Meet the Parents, Ben Stiller’s Gaylord “Greg” Focker’s eccentric parents are played by Barbra Streisand and Dustin Hoffman. In the beginning of the film, we are left in stitches by his parents’ answering machine that is utter chaos as Hoffman’s Bernie can’t figure out how to stop the recording. On top of that he is obsessed with chimichangas, even though it gives him horrible gas.

• 5. There's Something About Mary

  The 1998 comedy was a surprise hit at the time, gaining a cult following. Before taking on the role as magazine writer Ted Stroehmann in the Farrelly Brothers’ movie, Stiller was trying to focus on directing. It is always so cringe and hilarious watching the scene where Stiller’s pubescent character gets his scrotum stuck in his zipper on his ill-fated prom night with Cameron Diaz’s Mary.

• 4. Meet the Parents

  2000’s Meet the Parents was supposed to star Jim Carrey as the lead. He even contributed jokes to the screenplay, including the main character being named “Focker.” The Motion Picture Association (MPAA) wouldn’t allow the use of the name “Focker” until the filmmakers could find an actual person with that surname. This film has the iconic scene of Stiller’s Greg lying about pumping milk on a farm. When he says, “Oh yeah, you can milk anything with nipples,” De Niro replies, “I have nipples, Greg. Could you milk me?”

• 3. Starsky & Hutch

  Ben Stiller + Owen Wilson is comedy magic. Throw in Snoop Dogg, Vince Vaughn, Jason Bateman, Juliette Lewis, and Will Ferrell, and this remains one of our favorite Stiller flicks of all time. Our favorite scene of the 2004 comedy film is when Stiller’s Starsky unknowingly uses cocaine as sugar and has a wild dance-off at the disco against Dancing Rick.

• 2. Tropic Thunder

  The controversial movie that would never be made today, this 2008 Stiller production was a wild ride. The film stars Stiller, Jack Black, Robert Downey Jr., Jay Baruchel, and Brandon T. Jackson as a group of prima donna actors making a Vietnam War film, not knowing that they are really in danger. When RDJ’s Kirk Lazarus is questioned about who he is by Stiller’s Tugg Speedman, he says, “Me? I know who I am! I’m the dude playin’ the dude, disguised as another dude!”

• 1. Dodgeball: A True Underdog Story

  Stiller’s character had some of the most iconic lines in this classic comedy. 2004 was a great year for Stiller, as many of the films on our list came out that year. He plays the antagonist, White Goodman, a pretentious corporate gym owner who says the hilarious line, “Nobody makes me bleed my own blood.”