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?"

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Office Space
Jennifer Aniston, John C. McGinley
Released: 1999
Directed by: Mike Judge
Office Space is a 1999 American comedy film written and directed by Mike Judge. The film... more
2
37
8
DodgeBall: A True Underdog Story
Ben Stiller, Chuck Norris
Released: 2004
Directed by: Rawson Marshall Thurber
DodgeBall: A True Underdog Story, commonly referred to as DodgeBall, is a 2004 American sports... more
3
36
8
Talladega Nights: The Ballad of Ricky Bobby
Will Ferrell, John C. Reilly
Released: 2006
Directed by: Adam McKay
Talladega Nights: The Ballad of Ricky Bobby is a 2006 American sports comedy film directed by... more
More Talladega Nights: The Ballad of Ricky Bobby
#92 of 925 The All-Time Greatest Comedy Films#490 of 1,540 The Most Rewatchable Movies
4
34
8
Pineapple Express
Seth Rogen, James Franco
Released: 2008
Directed by: David Gordon Green
Pineapple Express is a 2008 American buddy stoner action comedy film directed by David Gordon... more
More Pineapple Express
Behind-The-Scenes Stories From The Set Of 'Pineapple Express'#39 of 97 The Best Movies to Watch on Mushrooms
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27
10
A Simple Plan
Billy Bob Thornton, Bill Paxton
Released: 1998
Directed by: Sam Raimi
A Simple Plan is a 1998 American neo-noir thriller film, and an adaptation of the 1993 novel... more
More A Simple Plan
#20 of 37 The Best Snowy Thriller Movies, Ranked#39 of 59 The Very Best New Noir Movies
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23
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The Brady Bunch Movie
RuPaul, Christine Taylor
Released: 1995
Directed by: Betty Thomas
The Brady Bunch Movie is a 1995 American comedy film based on the 1969–1974 television series... more
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#228 of 541 The Greatest Guilty Pleasure Movies#140 of 252 The Funniest '90s Movies
7
20
4
In the Line of Fire
Clint Eastwood, John Malkovich
Released: 1993
Directed by: Wolfgang Petersen
In the Line of Fire is a 1993 American action thriller film directed by Wolfgang Petersen, and... more
More In the Line of Fire
#124 of 244 The Best Psychological Thrillers of All Time#34 of 123 The Best Assassin Movies

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16
2
Lucas
Charlie Sheen, Winona Ryder
Released: 1986
Directed by: David Seltzer
Lucas is a 1986 American teen tragicomedy film directed by David Seltzer and starring Corey... more
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#244 of 314 The Funniest '80s Movies#267 of 522 The Greatest Movies Of The 1980s, Ranked
9
16
2
Breach
Ryan Phillippe, Laura Linney
Released: 2007
Directed by: Billy Ray
Breach is a 2007 American historical and political thriller film directed by Billy Ray. The... more
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#37 of 89 The Greatest Movies About CIA Agents & Operatives#9 of 99 The Best Docudrama Movies
10
20
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Hop
Kaley Cuoco, Russell Brand
Released: 2011
Directed by: Tim Hill
Hop is a 2011 3D live-action/computer-animated fantasy comedy film directed by Tim Hill and... more
More Hop
#8 of 15 The Best Russell Brand Movies#1 of 22 The Best Easter Movies Are A Hoppin' Good Time
11
16
4
A Very Brady Sequel
Rosie O'Donnell, David Spade
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... more
More A Very Brady Sequel
#111 of 117 The Best Movies Based on TV Shows#23 of 70 The Dumbest Movie Sequel Titles
12
12
0
Win a Date with Tad Hamilton!
Paris Hilton, Kate Bosworth
Released: 2004
Directed by: Robert Luketic
Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and... more
More
#42 of 61 The Best Movies with Rich People Spending Big#19 of 29 Great Movies About Male-Female Friendships
13
16
4
I Spy
Eddie Murphy, Famke Janssen
Released: 2002
Directed by: Betty Thomas
I Spy is a 2002 American spy comedy film starring Eddie Murphy and Owen Wilson. The film was... more
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#85 of 100 The Funniest Black Movies Ever Made#21 of 27 The Greatest Spy Comedy Movies Ever Made
14
12
4
The Gift
Katie Holmes, Cate Blanchett
Released: 2000
Directed by: Sam Raimi
The Gift is a 2000 American supernatural thriller film directed by Sam Raimi, written by Billy... more
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#683 of 836 The Greatest Chick Flicks Ever Made#69 of 92 The Best Movies Directed by the Star
15
12
4
Cadet Kelly
Hilary Duff, Sarah Gadon
Released: 2002
Directed by: Larry Shaw
Cadet Kelly is a 2002 Disney Channel Original Movie starring Hilary Duff. The film premiered... more
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#158 of 323 The Best Teen Movies Of All Time#92 of 238 The Best G-Rated Children's Movies
16
10
2
The Ring Two
Naomi Watts, Emily VanCamp
Released: 2005
Directed by: Hideo Nakata
The Ring Two is a 2005 American psychological horror film, and a sequel to the 2002 film The... more
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#409 of 722 The Best Horror Movies Of All Time#90 of 224 The Worst Sequels Of All Time
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14
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Cry Wolf
Jon Bon Jovi, Jared Padalecki
Released: 2005
Directed by: Jeff Wadlow
Cry Wolf a 2005 American horror/slasher mystery directed by Jeff Wadlow after he won... more
18
8
2
For My Daughter's Honor
Alyson Hannigan, Sara Rue
Released: 1996
Directed by: Alan Metzger
For My Daughter's Honor, also released as Indecent Seduction, is a 1996 American television... more
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8
2
I'll Be Home for Christmas
Jessica Biel, Jonathan Taylor Thomas
Released: 1998
Directed by: Arlene Sanford
I'll Be Home for Christmas is a 1998 Christmas family comedy film. It stars Jonathan Taylor... more
More I'll Be Home for Christmas
#70 of 127 The Best Christmas Movies of All Time#41 of 74 The Best '90s Christmas Movies
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The Dukes of Hazzard: The Beginning
Willie Nelson, Sherilyn Fenn
Released: 2007
Directed by: Robert Berlinger
The Dukes of Hazzard: The Beginning is a 2007 American television film. The film is a prequel... more
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8
4
Mozart and the Whale
Josh Hartnett, Radha Mitchell
Released: 2005
Directed by: Petter Næss
Mozart and the Whale is a 2005 romantic comedy-drama film starring Josh Hartnett and Radha... more
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8
4
Gang Related
Tupac Shakur, James Earl Jones
Released: 1997
Directed by: Jim Kouf
Gang Related is a 1997 American crime thriller film written and directed by Jim Kouf starring... more
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8
0
Lies He Told
Gary Cole, Wendy Makkena
Released: 1997
Directed by: Larry Elikann
Lies He Told is a 1997 drama film directed by Larry Elikann.... more
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6
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The Joneses
Demi Moore, Amber Heard
Released: 2009
Directed by: Derrick Borte
The Joneses is a 2009 American film written and directed by Derrick Borte. It stars Demi... more
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8
0
Forever Strong
Sean Astin, Arielle Kebbel
Released: 2008
Directed by: Ryan Little
Forever Strong is a sports film directed by Ryan Little and written by David Pliler and... more

Win a Date with Tad Hamilton!

For My Daughter's Honor