Entertainment

The Best Ben Stiller Movies 

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Updated June 14, 2019 4.7k votes 658 voters 45.7k views 76 items

List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Ben Stiller movies, ranked best to worst with movie trailers when available. Ben Stiller's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Ben Stiller movies is decided by how many votes they receive, so only highly rated Ben Stiller movies will be at the top of the list. What is the greatest Ben Stiller movie of all time? What are the most entertaining Ben Stiller films?

If you think the best Ben Stiller role isn't at the top, then upvote it so it has the chance to become number one. The greatest Ben Stiller performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

List features movies from the Ben Stiller filmography like Zero Effect, Zoolander, and more.

"This list answers the questions, "What are the best Ben Stiller movies?" and "What are the greatest Ben Stiller roles of all time?"

Ben Stiller is no stranger to working with popular directors, including Steven Spielberg, Brett Ratner and Steven Soderbergh. If you're a fan of Ben Stiller, then check out our lists of the best Joseph Gordon-Levitt and Ryan Gosling movies as well.

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1
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Natalie Portman, Paris Hilton, Heidi Klum

Released: 2001

Directed by: Ben Stiller

Zoolander is a 2001 American comedy film directed by Ben Stiller and, starring Stiller and Owen Wilson. The film contains elements from a pair of short films directed by Russell Bates and ...more

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#543 of 1,699 The Most Rewatchable Movies #238 of 803 The Greatest Chick Flicks Ever Made #86 of 1,196 The Absolute Funniest Movies Of All Time

2
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Robert De Niro, Ben Stiller, Owen Wilson

Released: 2000

Directed by: Jay Roach

Meet the Parents is a 2000 American comedy film directed by Jay Roach. Male nurse Greg Focker (Ben Stiller) meets his girlfriend's parents before proposing, but her suspicious father (robert De ...more

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#333 of 1,699 The Most Rewatchable Movies #125 of 803 The Greatest Chick Flicks Ever Made #30 of 1,196 The Absolute Funniest Movies Of All Time

3
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Ben Stiller, Jack Black, Robert Downey Jr.

Released: 2008

Directed by: Ben Stiller

Tropic Thunder is a 2008 American action satire comedy film directed by Ben Stiller. Through a series of freak occurrences, a group of actors shooting a big-budget war movie are forced to become ...more

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#844 of 1,699 The Most Rewatchable Movies #65 of 1,009 The All-Time Greatest Comedy Films #57 of 1,196 The Absolute Funniest Movies Of All Time

4
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Cameron Diaz, Sarah Silverman, Ben Stiller

Released: 1998

Directed by: Peter Farrelly, Bobby Farrelly

There's Something About Mary is a 1998 comedy film, directed by the Farrelly brothers, Bobby and Peter. It stars Cameron Diaz, Matt Dillon and Ben Stiller, and it is a combination of romantic ...more

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#360 of 1,699 The Most Rewatchable Movies Behind-The-Scenes Stories From The Making Of ‘There’s Something About Mary’listed on The Highest Grossing 90s Movies

5
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Ben Stiller, Chuck Norris, Vince Vaughn

Released: 2004

Directed by: Rawson Marshall Thurber

DodgeBall: A True Underdog Story, commonly referred to as DodgeBall, is a 2004 American sports comedy film produced by 20th Century Fox and Red Hour Productions, written and directed by Rawson ...more

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#48 of 1,009 The All-Time Greatest Comedy Films #54 of 1,196 The Absolute Funniest Movies Of All Time

6
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Robin Williams, Ben Stiller, Carla Gugino

Released: 2006

Directed by: Shawn Levy

Night at the Museum is a 2006 American fantasy adventure-comedy film based on the 1993 children's book of the same name by Milan Trenc. It follows a divorced father trying to settle down, ...more

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#166 of 1,009 The All-Time Greatest Comedy Films #107 of 116 The Best Native American Movies

7
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Chris Rock, Ben Stiller, Jada Pinkett Smith

Released: 2005

Directed by: Eric Darnell, Tom McGrath

Madagascar is a 2005 American computer-animated comedy film produced by DreamWorks Animation, and released in movie theaters on May 27, 2005. The film tells the story of four Central Park Zoo ...more

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#400 of 1,699 The Most Rewatchable Movies #315 of 1,196 The Absolute Funniest Movies Of All Time

8
Happy Gilmore is listed (or ranked) 8 on the list The Best Ben Stiller Movies
Adam Sandler, Ben Stiller, Julie Bowen

Released: 1996

Directed by: Dennis Dugan

Happy Gilmore is a 1996 sports comedy film directed by Dennis Dugan and produced by Robert Simonds. It stars Adam Sandler as the title character, an unsuccessful ice hockey player who discovers ...more

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#101 of 1,699 The Most Rewatchable Movies #11 of 1,009 The All-Time Greatest Comedy Films The Best Quotes From 'Happy Gilmore' Are A Hole In One

9
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Jennifer Aniston, Alec Baldwin, Ben Stiller

Released: 2004

Directed by: John Hamburg

Along Came Polly is a 2004 American romantic comedy film written and directed by John Hamburg, starring Ben Stiller and Jennifer Aniston in the lead roles.

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#1,199 of 1,699 The Most Rewatchable Movies #10 of 66 The Best Movies About Getting Dumped

10
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Robert De Niro, Barbra Streisand, Dustin Hoffman

Released: 2004

Directed by: Jay Roach

Meet the Fockers is a 2004 American comedy film directed by Jay Roach and the sequel to Meet the Parents. The film stars Robert De Niro, Ben Stiller, Dustin Hoffman, Barbra Streisand, Blythe ...more

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#527 of 1,699 The Most Rewatchable Movies #190 of 803 The Greatest Chick Flicks Ever Made

11
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Snoop Dogg, Carmen Electra, Will Ferrell

Released: 2004

Directed by: Todd Phillips

Starsky & Hutch is a 2004 American action comedy film directed by Todd Phillips. The film stars Ben Stiller as David Starsky and Owen Wilson as Ken "Hutch" Hutchinson and is a film ...more

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#1,051 of 1,196 The Absolute Funniest Movies Of All Time #81 of 114 The Best Movies Based on TV Shows

12
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The Secret Life of Walter Mitty

Released: 1947

"The Secret Life of Walter Mitty" is a short story by James Thurber. The most famous of Thurber's stories, it first appeared in The New Yorker on March 18, 1939, and was first ...more
13
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Amy Adams, Robin Williams, Ben Stiller

Released: 2009

Directed by: Shawn Levy

Night at the Museum: Battle of the Smithsonian is a 2009 American adventure comedy film directed by Shawn Levy, and starring Ben Stiller, Amy Adams, Owen Wilson, Hank Azaria, Christopher Guest ...more

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#501 of 1,009 The All-Time Greatest Comedy Films #182 of 317 The Best Movies for Kids

14
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Christina Applegate, Will Ferrell, Ben Stiller

Released: 2004

Directed by: Adam McKay

Anchorman: The Legend of Ron Burgundy, or simply Anchorman, is a 2004 comedy film directed by Adam McKay, produced by Judd Apatow, starring Will Ferrell, and written by McKay and Ferrell. The ...more

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#213 of 1,699 The Most Rewatchable Movies #5 of 1,009 The All-Time Greatest Comedy Films

15
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Eva Longoria, Ben Stiller, Malin Åkerman

Released: 2007

Directed by: Peter Farrelly, Bobby Farrelly

The Heartbreak Kid is a 2007 romantic comedy film directed by the Farrelly brothers. Starring Ben Stiller, The Heartbreak Kid is a remake of the 1972 film of the same name. The film was ...more
16
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Ben Stiller, Willam Belli, Vince Vaughn

Released: 2012

Directed by: Akiva Schaffer

Neighborhood Watch is a 2013 comedy science fiction film directed by Akiva Schaffer

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#170 of 191 The Best Alien Movies Ever Made #24 of 31 The Funniest Comedy Movies About Aliens

17
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Alec Baldwin, Fergie, Chris Rock

Released: 2008

Directed by: Eric Darnell, Tom McGrath

Madagascar: Escape 2 Africa is a 2008 American computer-animated comedy film written by Etan Cohen, and directed by Eric Darnell and Tom McGrath. This sequel to the 2005 film Madagascar ...more

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#132 of 590 The Best Animated Films Ever #630 of 1,699 The Most Rewatchable Movies

18
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Gwyneth Paltrow, Alec Baldwin, Bill Murray

Released: 2001

Directed by: Wes Anderson

The Royal Tenenbaums is a 2001 American comedy-drama film directed by Wes Anderson and co-written with Owen Wilson. The film stars Gene Hackman, Anjelica Huston, Bill Murray, Gwyneth Paltrow, ...more

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#731 of 1,699 The Most Rewatchable Movies #426 of 1,196 The Absolute Funniest Movies Of All Time #251 of 292 The Top Tearjerker Movies That Make Men Cry

19
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Ben Stiller, Jerry Stiller, Judd Apatow

Released: 1995

Directed by: Steven Brill

Heavyweights is a 1995 comedy film directed by Steven Brill and co-written by Brill with Judd Apatow. Heavyweights is about a fat camp for kids that is taken over by a fitness guru named Tony

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20
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Jim Carrey, Ben Stiller, Jack Black

Released: 1996

Directed by: Ben Stiller

The Cable Guy is a 1996 American thriller dark comedy film directed by Ben Stiller, who also co-stars in the film, and starring Jim Carrey and Matthew Broderick. The film was released in the ...more

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#289 of 1,196 The Absolute Funniest Movies Of All Time #57 of 493 The Funniest '90s Movies #228 of 302 The Greatest Soundtracks of All Time

21
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Kate Upton, Eddie Murphy, Joan Rivers

Released: 2011

Directed by: Brett Ratner

This film is a 2011 American comedy film directed by Brett Ratner. The plot follows Josh Kovaks (Ben Stiller), Charlie Gibbs (Casey Affleck) and Enrique Dev'reaux (Michael Peña), ...more
22
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Brad Pitt, Tina Fey, Will Ferrell

Released: 2010

Directed by: Tom McGrath

Megamind is a 2010 American 3D computer-animated superhero comedy film directed by Tom McGrath. It was produced by DreamWorks Animation and distributed by Paramount Pictures. The film premiered ...more

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#86 of 590 The Best Animated Films Ever #59 of 184 The Best Superhero Movies Ever Made #8 of 99 The Greatest Kids Sci-Fi Movies

23
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Winona Ryder, Renée Zellweger, Ben Stiller

Released: 1994

Directed by: Ben Stiller

Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by Ben Stiller. It stars Winona Ryder, Ethan Hawke and Stiller, with supporting roles by Janeane ...more

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#386 of 460 The Most Quotable Movies of All Time #174 of 493 The Funniest '90s Movies

24
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Ben Stiller, Tom Waits, Hank Azaria

Released: 1999

Directed by: Kinka Usher

Mystery Men is a 1999 American superhero comedy film directed by Kinka Usher and written by Neil Cuthbert and Bob Burden, loosely based on Burden's Flaming Carrot Comics, and starring Hank ...more

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#756 of 1,699 The Most Rewatchable Movies #70 of 165 The Greatest Comic Book Movies of All Time

25
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Jessica Chastain, Chris Rock, Ben Stiller

Released: 2012

Directed by: Eric Darnell, Tom McGrath, Conrad Vernon

Madagascar 3: Europe's Most Wanted is a 2012 American 3D computer-animated comedy film, produced by DreamWorks Animation and distributed by Paramount Pictures. It is the third installment of the ...more

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#155 of 590 The Best Animated Films Ever #60 of 72 The Best CGI Animated Films Ever Made