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The Best Gary Cole Movies

Updated September 23, 2019 692 votes 75 voters 7.3k 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?"
...more
  • 1
    Office Space is listed (or ranked) 1 on the list The Best Gary Cole Movies
    67
    4

    Office Space

    Jennifer Aniston, John C. McGinley

    Released1999

    Directed byMike Judge

    Office Space is a 1999 American comedy film written and directed by Mike Judge. The film... more on Wikipedia

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    #7 of 49 The Very Best Movies About Hackers#101 of 149 Movies That Should Never Be Remade

  • 2
    DodgeBall: A True Underdog Sto is listed (or ranked) 2 on the list The Best Gary Cole Movies
    37
    8

    DodgeBall: A True Underdog Story

    Ben Stiller, Chuck Norris

    Released2004

    Directed byRawson Marshall Thurber

    DodgeBall: A True Underdog Story, commonly referred to as DodgeBall, is a 2004 American sports... more on Wikipedia
  • 3
    Talladega Nights: The Ballad o is listed (or ranked) 3 on the list The Best Gary Cole Movies
    36
    8

    Released2006

    Directed byAdam McKay

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

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    #497 of 1,647 The Most Rewatchable Movies#70 of 1,137 The Absolute Funniest Movies Of All Time

  • 4
    Pineapple Express is listed (or ranked) 4 on the list The Best Gary Cole Movies
    34
    8

    Pineapple Express

    Seth Rogen, James Franco

    Released2008

    Directed byDavid Gordon Green

    Pineapple Express is a 2008 American buddy stoner action comedy film directed by David Gordon... more on Wikipedia
  • 5
    A Simple Plan is listed (or ranked) 5 on the list The Best Gary Cole Movies
    27
    10

    A Simple Plan

    Billy Bob Thornton, Bill Paxton

    Released1998

    Directed bySam Raimi

    A Simple Plan is a 1998 American neo-noir thriller film, and an adaptation of the 1993 novel... more on Wikipedia

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    #20 of 37 The Best Snowy Thriller Movies, Ranked#36 of 59 The Very Best New Noir Movies

  • 6
    The Brady Bunch Movie is listed (or ranked) 6 on the list The Best Gary Cole Movies
    23
    7

    The Brady Bunch Movie

    RuPaul, Christine Taylor

    Released1995

    Directed byBetty Thomas

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

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    #138 of 252 The Funniest '90s Movies#298 of 560 The Greatest Guilty Pleasure Movies

  • 7
    In the Line of Fire is listed (or ranked) 7 on the list The Best Gary Cole Movies
    20
    4

    In the Line of Fire

    Clint Eastwood, John Malkovich

    Released1993

    Directed byWolfgang Petersen

    In the Line of Fire is a 1993 American action thriller film directed by Wolfgang Petersen, and... more on Wikipedia

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    #123 of 242 The Best Psychological Thrillers of All Time#354 of 553 The Greatest Epic Movies Ever Made

  • 8
    Lucas is listed (or ranked) 8 on the list The Best Gary Cole Movies
    16
    2

    Lucas

    Charlie Sheen, Winona Ryder

    Released1986

    Directed byDavid Seltzer

    Lucas is a 1986 American teen tragicomedy film directed by David Seltzer and starring Corey... more on Wikipedia

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    #238 of 314 The Funniest '80s Movies#266 of 522 The Greatest Movies Of The 1980s, Ranked

  • 9
    Breach is listed (or ranked) 9 on the list The Best Gary Cole Movies
    16
    2

    Breach

    Ryan Phillippe, Laura Linney

    Released2007

    Directed byBilly Ray

    Breach is a 2007 American historical and political thriller film directed by Billy Ray. The... more on Wikipedia

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    #38 of 74 The Greatest Movies About CIA Agents & Operatives#91 of 155 The Best Spy Movies

  • 10
    Hop is listed (or ranked) 10 on the list The Best Gary Cole Movies
    20
    8

    Hop

    Kaley Cuoco, Russell Brand

    Released2011

    Directed byTim Hill

    Hop is a 2011 3D live-action/computer-animated fantasy comedy film directed by Tim Hill and... more on Wikipedia

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    #8 of 15 The Best Russell Brand Movies#1 of 22 The Best Easter Movies Are A Hoppin' Good Time

  • 11
    A Very Brady Sequel is listed (or ranked) 11 on the list The Best Gary Cole Movies
    16
    4

    A Very Brady Sequel

    Rosie O'Donnell, David Spade

    Released1996

    Directed byArlene Sanford

    A Very Brady Sequel is a 1996 comedy film and sequel to 1995's The Brady Bunch Movie. Both... more on Wikipedia

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    #24 of 70 The Dumbest Movie Sequel Titles#55 of 68 The Best Comedy Movie Sequels

  • 12
    Win a Date with Tad Hamilton! is listed (or ranked) 12 on the list The Best Gary Cole Movies
    12
    0

    Win a Date with Tad Hamilton!

    Paris Hilton, Kate Bosworth

    Released2004

    Directed byRobert Luketic

    Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and... more on Wikipedia

    More 

    #35 of 94 The Worst January Movie Releases#18 of 29 Great Movies About Male-Female Friendships

  • 13
    I Spy is listed (or ranked) 13 on the list The Best Gary Cole Movies
    16
    4

    I Spy

    Eddie Murphy, Famke Janssen

    Released2002

    Directed byBetty Thomas

    I Spy is a 2002 American spy comedy film starring Eddie Murphy and Owen Wilson. The film was... more on Wikipedia

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    #74 of 87 The Funniest Black Movies Ever Made#21 of 27 The Greatest Spy Comedy Movies Ever Made

  • 14
    The Gift is listed (or ranked) 14 on the list The Best Gary Cole Movies
    12
    4

    The Gift

    Katie Holmes, Cate Blanchett

    Released2000

    Directed bySam Raimi

    The Gift is a 2000 American supernatural thriller film directed by Sam Raimi, written by Billy... more on Wikipedia

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    #699 of 836 The Greatest Chick Flicks Ever Made#72 of 92 The Best Movies Directed by the Star

  • 15
    Cadet Kelly is listed (or ranked) 15 on the list The Best Gary Cole Movies
    12
    4

    Cadet Kelly

    Hilary Duff, Sarah Gadon

    Released2002

    Directed byLarry Shaw

    Cadet Kelly is a 2002 Disney Channel Original Movie starring Hilary Duff. The film premiered... more on Wikipedia

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    #91 of 238 The Best G-Rated Children's Movies#163 of 195 The Best G-Rated Comedies

  • 16
    The Ring Two is listed (or ranked) 16 on the list The Best Gary Cole Movies
    10
    2

    The Ring Two

    Naomi Watts, Emily VanCamp

    Released2005

    Directed byHideo Nakata

    The Ring Two is a 2005 American psychological horror film, and a sequel to the 2002 film The... more on Wikipedia

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    #401 of 714 The Best Horror Movies Of All Time#90 of 225 The Worst Sequels Of All Time

  • 17
    Cry Wolf is listed (or ranked) 17 on the list The Best Gary Cole Movies
    14
    8

    Cry Wolf

    Jon Bon Jovi, Jared Padalecki

    Released2005

    Directed byJeff Wadlow

    Cry Wolf a 2005 American horror/slasher mystery directed by Jeff Wadlow after he won... more on Wikipediaamazon_watch buy button
  • 18
    For My Daughter's Honor is listed (or ranked) 18 on the list The Best Gary Cole Movies
    8
    2

    For My Daughter's Honor

    Alyson Hannigan, Sara Rue

    Released1996

    Directed byAlan Metzger

    For My Daughter's Honor, also released as Indecent Seduction, is a 1996 American television... more on Wikipediaamazon_watch buy button
  • 19
    I'll Be Home for Christmas is listed (or ranked) 19 on the list The Best Gary Cole Movies
    8
    2

    I'll Be Home for Christmas

    Jessica Biel, Jonathan Taylor Thomas

    Released1998

    Directed byArlene Sanford

    I'll Be Home for Christmas is a 1998 Christmas family comedy film. It stars Jonathan Taylor... more on Wikipedia

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    #73 of 101 The Best Christmas Movies of All Time#21 of 30 The Best '90s Christmas Movies

  • 20
    The Dukes of Hazzard: The Begi is listed (or ranked) 20 on the list The Best Gary Cole Movies
    11
    6

    The Dukes of Hazzard: The Beginning

    Willie Nelson, Sherilyn Fenn

    Released2007

    Directed byRobert Berlinger

    The Dukes of Hazzard: The Beginning is a 2007 American television film. The film is a prequel... more on Wikipediaamazon_watch buy button
  • 21
    Mozart and the Whale is listed (or ranked) 21 on the list The Best Gary Cole Movies
    8
    4

    Mozart and the Whale

    Josh Hartnett, Radha Mitchell

    Released2005

    Directed byPetter Næss

    Mozart and the Whale is a 2005 romantic comedy-drama film starring Josh Hartnett and Radha... more on Wikipedia
  • 22
    Gang Related is listed (or ranked) 22 on the list The Best Gary Cole Movies
    8
    4

    Gang Related

    Tupac Shakur, James Earl Jones

    Released1997

    Directed byJim Kouf

    Gang Related is a 1997 American crime thriller film written and directed by Jim Kouf starring... more on Wikipedia
  • 23
    Lies He Told is listed (or ranked) 23 on the list The Best Gary Cole Movies
    8
    0

    Lies He Told

    Gary Cole, Wendy Makkena

    Released1997

    Directed byLarry Elikann

    Lies He Told is a 1997 drama film directed by Larry Elikann.amazon_watch buy button
  • 24
    The Joneses is listed (or ranked) 24 on the list The Best Gary Cole Movies
    6
    3

    The Joneses

    Demi Moore, Amber Heard

    Released2009

    Directed byDerrick Borte

    The Joneses is a 2009 American film written and directed by Derrick Borte. It stars Demi... more on Wikipedia
  • 25
    Forever Strong is listed (or ranked) 25 on the list The Best Gary Cole Movies
    8
    0

    Forever Strong

    Sean Astin, Arielle Kebbel

    Released2008

    Directed byRyan Little

    Forever Strong is a sports film directed by Ryan Little and written by David Pliler and... more on Wikipedia
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