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The Best Ryan Phillippe Movies

Updated September 21, 2019 2.0k votes 250 voters 23.4k views

List RulesVote 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?"

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  • Cruel Intentions1
    91
    11

    Cruel Intentions

    Reese Witherspoon, Sarah Michelle Gellar

    Released1999

    Directed byRoger Kumble

    Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,... more on Wikipedia

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  • Stop-Loss2
    82
    12

    Stop-Loss

    Channing Tatum, Joseph Gordon-Levitt

    Released2008

    Directed byKimberly Peirce

    Stop-Loss is a 2008 American drama film directed by Kimberly Peirce and starring Ryan... more on Wikipedia
  • Five Fingers3
    67
    18

    Five Fingers

    Ryan Phillippe, Laurence Fishburne

    Released2006

    Directed byLaurence Malkin

    Five Fingers is a 2006 drama/thriller film directed by Laurence Malkin, and written by Chad... more on Wikipedia
  • Playing by Heart4
    80
    31

    Playing by Heart

    Angelina Jolie, Hilary Duff

    Released1998

    Directed byWillard Carroll

    Playing by Heart is a 1998 American comedy-drama film, which tells the story of several... more on Wikipedia
  • Gosford Park5
    67
    19

    Gosford Park

    Helen Mirren, Clive Owen

    Released2002

    Directed byRobert Altman

    Gosford Park is a 2002 British mystery film directed by Robert Altman and written by Julian... more on Wikipedia
  • The Bang Bang Club6
    59
    16

    The Bang Bang Club

    Malin Åkerman, Ryan Phillippe

    Released2010

    Directed bySteven Silver

    "The Bang Bang Club was the name given to four young photographers, Greg Marinovich, Kevin... more on Wikipedia
  • White Squall7
    53
    16

    White Squall

    Jeff Bridges, Ryan Phillippe

    Released1996

    Directed byRidley Scott

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

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  • The Lincoln Lawyer8
    48
    13

    The Lincoln Lawyer

    Matthew McConaughey, Marisa Tomei

    Released2011

    Directed byBrad Furman

    The Lincoln Lawyer is a 2011 American thriller film adapted from the novel of the same name by... more on Wikipedia
  • Crash9
    40
    8

    Crash

    Sandra Bullock, Brendan Fraser

    Released2004

    Directed byPaul Haggis

    This movie is a 2004 ensemble drama film co-written, produced, and directed by Paul Haggis.... more on Wikipedia

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  • I Know What You Did Last Summer10
    47
    16

    I Know What You Did Last Summer

    Jennifer Love Hewitt, Sarah Michelle Gellar

    Released1997

    Directed byJim Gillespie

    I Know What You Did Last Summer is a 1997 American slasher film based on the 1973 novel of the... more on Wikipedia

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  • Antitrust11
    80
    50

    Antitrust

    Tim Robbins, Ryan Phillippe

    Released2001

    Directed byPeter Howitt

    Antitrust is a 2001 thriller film written by Howard Franklin and directed by Peter... more on Wikipedia

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  • Franklyn12
    43
    18

    Franklyn

    Ewan McGregor, Eva Green

    Released2009

    Directed byGerald McMorrow

    Franklyn is a 2008 British film written and directed by Gerald McMorrow as his debut feature.... more on Wikipedia
  • Igby Goes Down13
    48
    25

    Igby Goes Down

    Claire Danes, Susan Sarandon

    Released2002

    Directed byBurr Steers

    Igby Goes Down is a 2002 comedy-drama film that follows the life of Igby Slocumb, a rebellious... more on Wikipedia

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  • Little Boy Blue14
    32
    8

    Little Boy Blue

    Ryan Phillippe, Nastassja Kinski

    Released1998

    Directed byAntonio Tibaldi

    Little Boy Blue is a 1997 film directed by Antonio Tibaldi. The screenplay was by Michael... more on WikipediaAmazon_watch buy button
  • Straight A's15
    33
    13

    Straight A's

    Anna Paquin, Ryan Phillippe

    Released2013

    Directed byJames Cox

    Straight A's is a 2012 comedy/drama film written by David Cole and directed by James Cox.
  • Setup16
    34
    18

    Setup

    Bruce Willis, 50 Cent

    Released2011

    Directed byMike Gunther

    Setup is an action thriller heist film directed by Mike Gunther and written by Gunther and... more on Wikipedia
  • Homegrown17
    33
    17

    Homegrown

    Jake Gyllenhaal, Jamie Lee Curtis

    Released1998

    Directed byStephen Gyllenhaal

    When a Pot Baron (Lithgown) is killed in a remote field in Northern California and his three... more on Wikipedia

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  • Flags of Our Fathers18
    33
    22

    Flags of Our Fathers

    Paul Walker, Ryan Phillippe

    Released2006

    Directed byClint Eastwood

    Flags of Our Fathers is a 2006 American film directed, co-produced and scored by Clint... more on Wikipedia

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  • Chronicle19
    23
    11

    Chronicle

    Dane DeHaan, Alex Russell

    Released2012

    Directed byJosh Trank

    Chronicle is a 2012 American found footage science-fiction thriller film directed by Josh... more on Wikipedia

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  • The I Inside20
    46
    40

    The I Inside

    Piper Perabo, Ryan Phillippe

    Released2004

    Directed byRoland Suso Richter

    The I Inside is a 2003 psychological thriller directed by Roland Suso Richter. It was written... more on Wikipedia
  • A Perry Mason Mystery: The Case of the Grimacing Governor21

    Released1994

    Directed byMax Tash

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  • 5422
    32
    26

    54

    Salma Hayek, Heidi Klum

    Released1998

    Directed byMark Christopher

    54 is a 1998 American drama film written and directed by Mark Christopher, about Studio 54, a... more on Wikipedia

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  • The Way of the Gun23
    25
    21

    The Way of the Gun

    Sarah Silverman, Juliette Lewis

    Released2000

    Directed byChristopher McQuarrie

    The Way of the Gun is a 2000 American action film written and directed by Christopher... more on Wikipedia

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  • Tlatelolco6824
    21
    15

    Tlatelolco68

    Ryan Phillippe, John Leguizamo

    Released2011

    Directed byCarlos Bolado

    Tlatelolco68 (original title: Tlatelolco: Mexico68) is a 2011 historical drama film written by...Amazon_watch buy button
  • MacGruber25
    23
    21

    MacGruber

    Val Kilmer, Kristen Wiig

    Released2010

    Directed byJorma Taccone

    MacGruber is a 2010 American action comedy film based on the Saturday Night Live sketch of the... more on Wikipedia

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