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The Best Gary Cole Movies 

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Updated September 23, 2019 360 votes 75 voters 7.2k views 48 items

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

List of the best Gary Cole movies, ranked best to worst with movie trailers when available. Gary Cole'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 Gary Cole movies is decided by how many votes they receive, so only highly rated Gary Cole movies will be at the top of the list. Gary Cole has been in a lot of films, so people often debate each other over what the greatest Gary Cole movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Gary Cole films to end the squabble once and for all.

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

List films include The Rising Place, Pineapple Express and more.

"This list answers the questions, "What are the best Gary Cole movies?" and "What are the greatest Gary Cole roles of all time?"
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Jennifer Aniston, John C. McGinley, Mike Judge

Released: 1999

Directed by: Mike Judge

Office Space is a 1999 American comedy film written and directed by Mike Judge. The film satirizes the everyday work life of a typical mid-to-late-1990s software company, it focuses on a handful ...more

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#124 of 350 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #347 of 410 The Best Rainy Day Movieslisted on The Very Best Movies About Hackers

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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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#46 of 1,027 The All-Time Greatest Comedy Films #261 of 1,699 The Most Rewatchable Movies #51 of 1,211 The Absolute Funniest Movies Of All Time

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Will Ferrell, John C. Reilly, Amy Adams

Released: 2006

Directed by: Adam McKay

Talladega Nights: The Ballad of Ricky Bobby is a 2006 American sports comedy film directed by Adam McKay. Number one NASCAR driver Ricky Bobby (Will Ferrell) stays atop the heap thanks to a pact ...more

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#63 of 1,027 The All-Time Greatest Comedy Films #392 of 1,699 The Most Rewatchable Movies #65 of 1,211 The Absolute Funniest Movies Of All Time

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Seth Rogen, James Franco, Gary Cole

Released: 2008

Directed by: David Gordon Green

Pineapple Express is a 2008 American buddy stoner action comedy film directed by David Gordon Green. A process server (Seth Rogen) and his marijuana dealer (James Franco) are forced to flee from ...more

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Behind-The-Scenes Stories From The Set Of 'Pineapple Express' #229 of 1,027 The All-Time Greatest Comedy Films #1,402 of 1,699 The Most Rewatchable Movies

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Billy Bob Thornton, Bill Paxton, Bridget Fonda

Released: 1998

Directed by: Sam Raimi

A Simple Plan is a 1998 American neo-noir thriller film, and an adaptation of the 1993 novel of the same name by Scott B. Smith, who also wrote the screenplay. Directed by Sam Raimi, the film ...more

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#19 of 35 The Best Snowy Thriller Movies, Ranked #27 of 59 The Very Best New Noir Movies #108 of 173 The Best Film Noir Movies

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RuPaul, Christine Taylor, Shelley Long

Released: 1995

Directed by: Betty Thomas

The Brady Bunch Movie is a 1995 American comedy film based on the 1969–1974 television series The Brady Bunch. The film features all the original regular characters, all played by new actors. It ...more

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#255 of 624 The Greatest Guilty Pleasure Movies #193 of 493 The Funniest '90s Movies #267 of 1,027 The All-Time Greatest Comedy Films

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Clint Eastwood, John Malkovich, Rene Russo

Released: 1993

Directed by: Wolfgang Petersen

In the Line of Fire is a 1993 American action thriller film directed by Wolfgang Petersen, and starring Clint Eastwood and John Malkovich. Written by Jeff Maguire, the film is about a ...more

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#127 of 253 The Best Psychological Thrillers of All Time #194 of 624 The Greatest Guilty Pleasure Movies #358 of 599 The Greatest Epic Movies Ever Made

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Ryan Phillippe, Laura Linney, Chris Cooper

Released: 2007

Directed by: Billy Ray

Breach is a 2007 American historical and political thriller film directed by Billy Ray. The screenplay by Ray, Adam Mazer and William Rotko is based on the true story of Robert Hanssen, an FBI ...more

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#35 of 75 The Greatest Movies About CIA Agents & Operatives #100 of 163 The Best Spy Movies #40 of 99 The Best Docudrama Movies

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Charlie Sheen, Winona Ryder, Corey Haim

Released: 1986

Directed by: David Seltzer

Lucas is a 1986 American teen tragicomedy film directed by David Seltzer and starring Corey Haim, Kerri Green, Charlie Sheen and Courtney Thorne-Smith. The film was Winona Ryder's screen debut.

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#260 of 571 The Greatest Movies Of The 1980s, Ranked #376 of 710 The Best Movies Roger Ebert Gave Four Stars #263 of 439 The Funniest '80s Movies

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Kaley Cuoco, Russell Brand, Hugh Laurie

Released: 2011

Directed by: Tim Hill

Hop is a 2011 3D live-action/computer-animated fantasy comedy film directed by Tim Hill and staring Russell Brand, Hugh Laurie, and James Marsden. On Easter Island, an optimistic young talking ...more

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#552 of 601 The Best Animated Films Ever #6 of 15 The Best Russell Brand Movies #2 of 22 The Best Easter Movies Are A Hoppin' Good Time

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Rosie O'Donnell, David Spade, Barbara Eden

Released: 1996

Directed by: Arlene Sanford

A Very Brady Sequel is a 1996 comedy film and sequel to 1995's The Brady Bunch Movie. Both films are Spoofss to the classic 1969–1974 television sitcom The Brady Bunch. The film was directed by ...more

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#326 of 1,027 The All-Time Greatest Comedy Films #10 of 12 12 Comedy Sequels That Might Actually Be Better Than The Originals #54 of 68 The Best Comedy Movie Sequels

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Eddie Murphy, Famke Janssen, Owen Wilson

Released: 2002

Directed by: Betty Thomas

I Spy is a 2002 American spy comedy film starring Eddie Murphy and Owen Wilson. The film was directed by Betty Thomas, and based on the television series of the same name that aired in the 1960s ...more

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Win a Date with Tad Hamilton! Paris Hilton, Kate Bosworth, Ginnifer Goodwin

Released: 2004

Directed by: Robert Luketic

Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and starring Kate Bosworth, Topher Grace, and Josh Duhamel.

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#257 of 802 The Greatest Chick Flicks Ever Made #44 of 94 The Worst January Movie Releases #17 of 29 Great Movies About Male-Female Friendships

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Robin Williams, Connie Nielsen, Clark Gregg

Released: 2002

Directed by: Mark Romanek

One Hour Photo is a 2002 American psychological thriller film written and directed by Mark Romanek and starring Robin Williams, Connie Nielsen, Michael Vartan, Gary Cole, and Eriq La Salle. ...more

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#109 of 253 The Best Psychological Thrillers of All Time #26 of 157 The Best Movies You Never Want to Watch Again #34 of 149 The Best and Scariest Psychological Thrillers of All Time

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Neil Patrick Harris, Jensen Ackles, Kelly Hu

Released: 2010

Directed by: Brandon Vietti

Batman: Under the Red Hood is a 2010 American superhero film produced by Warner Bros. Animation and released by Warner Home Video. It is the eighth animated feature in the DC Universe Animated ...more

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#492 of 601 The Best Animated Films Ever #48 of 188 The Best Superhero Movies Ever Made #62 of 186 The Greatest Comic Book Movies of All Time

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Hilary Duff, Sarah Gadon, Aimee Garcia

Released: 2002

Directed by: Larry Shaw

Cadet Kelly is a 2002 Disney Channel Original Movie starring Hilary Duff. The film premiered with 7.8 million viewers. It is Duff's second starring film role, her first being Casper Meets Wendy. ...more

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#172 of 195 The Best G-Rated Comedies #122 of 238 The Best G-Rated Children's Movies #6 of 26 The Best G-Rated Teen Movies

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Katie Holmes, Cate Blanchett, Keanu Reeves

Released: 2000

Directed by: Sam Raimi

The Gift is a 2000 American supernatural thriller film directed by Sam Raimi, written by Billy Bob Thornton and Tom Epperson and based on the alleged psychic experiences of Thornton's mother. ...more

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#505 of 802 The Greatest Chick Flicks Ever Made #60 of 102 The Best Movies Directed by the Star #53 of 70 The Best Mindf*ck Movies

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Naomi Watts, Emily VanCamp, Mary Elizabeth Winstead

Released: 2005

Directed by: Hideo Nakata

The Ring Two is a 2005 American psychological horror film, and a sequel to the 2002 film The Ring, which was a remake of the 1998 Japanese film Ringu. Hideo Nakata, director of the original ...more

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#83 of 233 The Worst Sequels Of All Time #379 of 853 The Best Horror Movies Of All Time #60 of 101 The Worst Part II Movie Sequels

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Son of the Morning Star Rosanna Arquette, David Strathairn, Dean Stockwell

Released: 1991

Directed by: Mike Robe

Son of the Morning Star is a two-part TV miniseries released by Chrysalis based on Evan S. Connell's best-selling book of the same name. It starred Gary Cole and featured Dean Stockwell, Rosanna ...more
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Jon Bon Jovi, Jared Padalecki, Lindy Booth

Released: 2005

Directed by: Jeff Wadlow

Cry Wolf a 2005 American horror/slasher mystery directed by Jeff Wadlow after he won $1,000,000 at the 2002 Chrysler Million Dollar Film Festival.
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Raven-Symoné, Jean Smart, Gary Cole

Released: 2005

Directed by: Steve Loter

Dr. Drakken has an evil new plot for world domination, but his ultimate success depends upon finding out KP's weakness which may involve a new hottie at Middleton High School named Eric, who ...more
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Gary Cole, Wendy Makkena, Ron Lea

Released: 1997

Directed by: Larry Elikann

Lies He Told is a 1997 drama film directed by Larry Elikann.
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Jessica Biel, Jonathan Taylor Thomas, Gary Cole

Released: 1998

Directed by: Arlene Sanford

I'll Be Home for Christmas is a 1998 Christmas family comedy film. It stars Jonathan Taylor Thomas, Jessica Biel, Adam LaVorgna, Gary Cole, Eve Gordon, Sean O'Bryan, and Andrew Lauer.

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#108 of 143 The Best Disney Live-Action Movies #72 of 109 The Best Christmas Movies of All Time #20 of 30 The Best '90s Christmas Movies

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For My Daughter's Honor Alyson Hannigan, Sara Rue, Mary Kay Place

Released: 1996

Directed by: Alan Metzger

For My Daughter's Honor, also released as Indecent Seduction, is a 1996 American television film directed by Alan Metzger.
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DC Showcase: The Spectre... is listed (or ranked) 25 on the list The Best Gary Cole Movies
DC Showcase: The Spectre Alyssa Milano, Gary Cole

Released: 2010

Directed by: Joaquim Dos Santos

DC Showcase: The Spectre is a 2010 short animated film, directed by Joaquim Dos Santos and written by Steve Niles, featuring Gary Cole as Detective Jim Corrigan, whose suspects are brought to ...more