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The Best Ryan Phillippe Movies 

Ranker Film
Updated September 21, 2019 1.3k votes 244 voters 23.1k views

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

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

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

Examples include By Virtue Fall and Cruel Intentions.

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

Robert Altman and Ridley Scott are among those who have directed Ryan Phillippe at one point or another during their careers in the film industry. If Ryan Phillippe movies are your thing, then check out the greatest movies by Ryan Gosling and Rodrigo Santoro too.

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1
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Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

Released: 1999

Directed by: Roger Kumble

Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of Les Liaisons dangereuses, written ...more

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Matthew McConaughey, Marisa Tomei, Bryan Cranston

Released: 2011

Directed by: Brad Furman

The Lincoln Lawyer is a 2011 American thriller film adapted from the novel of the same name by Michael Connelly, starring Matthew McConaughey, Ryan Phillippe, William H. Macy and Marisa Tomei. ...more

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3
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Sandra Bullock, Brendan Fraser, Ludacris

Released: 2004

Directed by: Paul Haggis

This movie is a 2004 ensemble drama film co-written, produced, and directed by Paul Haggis. The film is about racial and social tensions in Los Angeles, California. A self-described ...more

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4
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Jennifer Love Hewitt, Sarah Michelle Gellar, Anne Heche

Released: 1997

Directed by: Jim Gillespie

I Know What You Did Last Summer is a 1997 American slasher film based on the 1973 novel of the same name by Lois Duncan. The film changes many aspects of the book, which was not a slasher novel. ...more

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5
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Paul Walker, Ryan Phillippe, Jamie Bell

Released: 2006

Directed by: Clint Eastwood

Flags of Our Fathers is a 2006 American film directed, co-produced and scored by Clint Eastwood and written by William Broyles, Jr. and Paul Haggis. It is based on the book of the same name ...more

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6
Straight A's is listed (or ranked) 6 on the list The Best Ryan Phillippe Movies
Anna Paquin, Ryan Phillippe, Luke Wilson

Released: 2013

Directed by: James Cox

Straight A's is a 2012 comedy/drama film written by David Cole and directed by James Cox.
7
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Salma Hayek, Heidi Klum, Donald Trump

Released: 1998

Directed by: Mark Christopher

54 is a 1998 American drama film written and directed by Mark Christopher, about Studio 54, a world-famous New York City disco club, the main setting of the film. It stars Ryan Phillippe, Salma ...more

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8
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Ryan Phillippe, Nastassja Kinski, Jenny Lewis

Released: 1998

Directed by: Antonio Tibaldi

Little Boy Blue is a 1997 film directed by Antonio Tibaldi. The screenplay was by Michael Boston.
9
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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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10
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Channing Tatum, Joseph Gordon-Levitt, Ryan Phillippe

Released: 2008

Directed by: Kimberly Peirce

Stop-Loss is a 2008 American drama film directed by Kimberly Peirce and starring Ryan Phillippe, Channing Tatum, Abbie Cornish and Joseph Gordon-Levitt. It was distributed by Paramount Pictures ...more
11
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Angelina Jolie, Hilary Duff, Sean Connery

Released: 1998

Directed by: Willard Carroll

Playing by Heart is a 1998 American comedy-drama film, which tells the story of several seemingly unconnected characters. It was entered into the 49th Berlin International Film Festival.
12
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Sarah Silverman, Juliette Lewis, James Caan

Released: 2000

Directed by: Christopher McQuarrie

The Way of the Gun is a 2000 American action film written and directed by Christopher McQuarrie and starring Ryan Phillippe, Benicio del Toro, Juliette Lewis, Taye Diggs, Nicky Katt, and James ...more

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13
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Ryan Phillippe, Laurence Fishburne, Gina Torres

Released: 2006

Directed by: Laurence Malkin

Five Fingers is a 2006 drama/thriller film directed by Laurence Malkin, and written by Chad Thumann and Malkin. The film had ten producers, including actor Laurence Fishburne, who stars ...more
14
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Helen Mirren, Clive Owen, Maggie Smith

Released: 2001

Directed by: Robert Altman

Gosford Park is a 2001 British mystery film directed by Robert Altman and written by Julian Fellowes. The film stars an ensemble cast, which includes Helen Mirren, Maggie Smith, Michael Gambon, ...more
15
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Malin Åkerman, Ryan Phillippe, Taylor Kitsch

Released: 2010

Directed by: Steven Silver

"The Bang Bang Club was the name given to four young photographers, Greg Marinovich, Kevin Carter, Ken Oosterbroek and Joao Silva, whose photographs captured the final bloody days of white ...more
16
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Tim Robbins, Ryan Phillippe, Claire Forlani

Released: 2001

Directed by: Peter Howitt

Antitrust is a 2001 thriller film written by Howard Franklin and directed by Peter Howitt. Antitrust portrays young idealistic programmers and a large corporation that offers significant money, ...more

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17
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Jason Statham, Ryan Phillippe, Wesley Snipes

Released: 2005

Directed by: Tony Giglio

Chaos is a 2005 Canadian-British thriller film directed by Tony Giglio, and starring Jason Statham, Ryan Phillippe and Wesley Snipes. The film was released on direct-to-DVD in the United States ...more
18
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Jeff Bridges, Ryan Phillippe, Željko Ivanek

Released: 1996

Directed by: Ridley Scott

White Squall is a 1996 American drama feature film, directed by Ridley Scott.

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19
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Ewan McGregor, Eva Green, John Hurt

Released: 2009

Directed by: Gerald McMorrow

Franklyn is a 2008 British film written and directed by Gerald McMorrow as his debut feature. Produced by Jeremy Thomas, it stars Ryan Phillippe, Eva Green and Sam Riley. Shooting took place in ...more
20
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Claire Danes, Susan Sarandon, Amanda Peet

Released: 2002

Directed by: Burr Steers

Igby Goes Down is a 2002 comedy-drama film that follows the life of Igby Slocumb, a rebellious and sardonic New York City teenager who attempts to break free of his familial ties and wealthy, ...more

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21
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Jake Gyllenhaal, Jamie Lee Curtis, Steve Carell

Released: 1998

Directed by: Stephen Gyllenhaal

When a Pot Baron (Lithgown) is killed in a remote field in Northern California and his three farm hands (Phillippe, Thornton and Azaria) are the only witnesses, an odd comedy ensues as they try ...more

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22
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Setup Bruce Willis, 50 Cent, Ryan Phillippe

Released: 2011

Directed by: Mike Gunther

Setup is an action thriller heist film directed by Mike Gunther and written by Gunther and Mike Behrman. It stars 50 Cent, Bruce Willis and Ryan Phillippe. It was released straight to DVD and ...more
23
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Piper Perabo, Ryan Phillippe, Sarah Polley

Released: 2004

Directed by: Roland Suso Richter

The I Inside is a 2003 psychological thriller directed by Roland Suso Richter. It was written by Michael Cooney based on his own play Point of Death. This film has no connection with the ...more
24
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Dane DeHaan, Alex Russell, Michael B. Jordan

Released: 2012

Directed by: Josh Trank

Chronicle is a 2012 American found footage science-fiction thriller film directed by Josh Trank. After gaining telekinetic powers from an unknown object, three teenagers use their abilities for ...more

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25
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Ryan Phillippe, Tony Curtis, James Brolin

Released: 1994

Directed by: Max Tash