76 voters

The Best Gary Cole Movies

Updated September 23, 2019 721 votes 76 voters 7.4k views48 items

List RulesVote 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?"
  • 1

    Office Space

    Jennifer Aniston, John C. McGinley
    Office Space is a 1999 American comedy film written and directed by Mike Judge. The film...  more

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  • 2

    DodgeBall: A True Underdog Story

    Ben Stiller, Chuck Norris
    DodgeBall: A True Underdog Story, commonly referred to as DodgeBall, is a 2004 American sports...  more

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    #10 of 16 Movies That Completely Changed Their Endings After Everyone Freaked Out#53 of 456 The Most Quotable Movies Of All Time

  • 3
    Talladega Nights: The Ballad of Ricky Bobby is a 2006 American sports comedy film directed by...  more

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    #245 of 306 The Best Ensemble Movies#561 of 1,506 The Most Rewatchable Movies

  • 4

    Pineapple Express

    Seth Rogen, James Franco
    Pineapple Express is a 2008 American buddy stoner action comedy film directed by David Gordon...  more

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    Behind-The-Scenes Stories From The Set Of 'Pineapple Express'#144 of 1,139 The Absolute Funniest Movies Of All Time

  • 5

    A Simple Plan

    Billy Bob Thornton, Bill Paxton
    A Simple Plan is a 1998 American neo-noir thriller film, and an adaptation of the 1993 novel...  more

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  • 6

    The Brady Bunch Movie

    RuPaul, Christine Taylor
    The Brady Bunch Movie is a 1995 American comedy film based on the 1969–1974 television series...  more

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    #146 of 252 The Funniest '90s Movies#84 of 117 The Best Movies Based on TV Shows

  • 7

    In the Line of Fire

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

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    #123 of 230 The Best Psychological Thrillers of All Time#377 of 549 The Greatest Epic Movies Ever Made

  • 8


    Charlie Sheen, Winona Ryder
    Lucas is a 1986 American teen tragicomedy film directed by David Seltzer and starring Corey...  more

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    #257 of 512 The Greatest Movies Of The 1980s, Ranked#236 of 305 The Funniest '80s Movies

  • 9


    Ryan Phillippe, Laura Linney
    Breach is a 2007 American historical and political thriller film directed by Billy Ray. The...  more

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    #37 of 90 The Greatest Movies About CIA Agents & Operatives#88 of 170 The Best Spy Movies

  • 10


    Kaley Cuoco, Russell Brand
    Hop is a 2011 3D live-action/computer-animated fantasy comedy film directed by Tim Hill and...  more

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    #24 of 41 The Best Children's and Kids' Movies on Netflix#3 of 15 The Best Russell Brand Movies

  • 11

    A Very Brady Sequel

    Rosie O'Donnell, David Spade
    A Very Brady Sequel is a 1996 comedy film and sequel to 1995's The Brady Bunch Movie. Both...  more

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    #53 of 68 The Best Comedy Movie Sequels#26 of 71 The Dumbest Movie Sequel Titles

  • 12

    Win a Date with Tad Hamilton!

    Paris Hilton, Kate Bosworth
    Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and...  more


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  • 13

    I Spy

    Eddie Murphy, Famke Janssen
    I Spy is a 2002 American spy comedy film starring Eddie Murphy and Owen Wilson. The film was...  more

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    #91 of 145 The Funniest Black Movies Ever Made#19 of 44 The Greatest Spy Comedy Movies Ever Made

  • 14

    Batman: Under the Red Hood

    Neil Patrick Harris, Jensen Ackles
    Batman: Under the Red Hood is a 2010 American superhero film produced by Warner Bros....  more

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    #54 of 156 The Best Superhero Movies Ever Made#472 of 534 The Best Animated Films Ever

  • 15

    Son of the Morning Star

    Rosanna Arquette, David Strathairn
    Son of the Morning Star is a two-part TV miniseries released by Chrysalis based on Evan S....  more
  • 16

    The Gift

    Katie Holmes, Cate Blanchett
    The Gift is a 2000 American supernatural thriller film directed by Sam Raimi, written by Billy...  more

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    #531 of 782 The Greatest Chick Flicks Ever Made#68 of 92 The Best Mindf*ck Movies

  • 17

    Cadet Kelly

    Hilary Duff, Sarah Gadon
    Cadet Kelly is a 2002 Disney Channel Original Movie starring Hilary Duff. The film premiered...  more

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    #92 of 109 The Best Disney Live-Action Movies#225 of 324 The Best Teen Movies Of All Time

  • 18

    The Ring Two

    Naomi Watts, Emily VanCamp
    The Ring Two is a 2005 American psychological horror film, and a sequel to the 2002 film The...  more

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    #90 of 225 The Worst Sequels Of All Time#420 of 719 The Best Horror Movies Of All Time

  • 19

    Kim Possible Movie: So the Drama

    Raven-Symoné, Jean Smart
    Dr. Drakken has an evil new plot for world domination, but his ultimate success depends upon...  more
  • 20

    Cry Wolf

    Jon Bon Jovi, Jared Padalecki
    Cry Wolf a 2005 American horror/slasher mystery directed by Jeff Wadlow after he won...  more
  • 21

    DC Showcase: The Spectre

    Alyssa Milano, Gary Cole
    DC Showcase: The Spectre is a 2010 short animated film, directed by Joaquim Dos Santos and...  more
  • 22

    For My Daughter's Honor

    Alyson Hannigan, Sara Rue
    For My Daughter's Honor, also released as Indecent Seduction, is a 1996 American television...  more
  • 23

    Lies He Told

    Gary Cole, Wendy Makkena
    Lies He Told is a 1997 drama film directed by Larry Elikann....  more
  • 24

    I'll Be Home for Christmas

    Jessica Biel, Jonathan Taylor Thomas
    I'll Be Home for Christmas is a 1998 Christmas family comedy film. It stars Jonathan Taylor...  more
  • 25

    Forever Strong

    Sean Astin, Arielle Kebbel
    Forever Strong is a sports film directed by Ryan Little and written by David Pliler and...  more