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The Best Maggie Gyllenhaal Movies

Updated September 23, 2019 1.1k votes 140 voters 20.2k views34 items

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

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

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

Away We Go and The Patron Saint of Liars are included on this list.

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

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  • 1
    The Kindergarten Teacher
    70
    6

    The Kindergarten Teacher

    Maggie Gyllenhaal, Parker Sevak

    Released2018

    Directed bySara Colangelo

    The Kindergarten Teacher is a 2018 American drama film directed by Sara Colangelo, based on... more on Wikipedia
  • 2
    Mona Lisa Smile
    50
    9

    Mona Lisa Smile

    Julia Roberts, Kirsten Dunst

    Released2003

    Directed byMike Newell

    Mona Lisa Smile is a 2003 drama film produced by Revolution Studios and Columbia Pictures in... more on Wikipedia

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  • 3
    Crazy Heart
    43
    8

    Crazy Heart

    Colin Farrell, Jeff Bridges

    Released2009

    Directed byScott Cooper

    "Crazy Heart stars Jeff Bridges as an aging country music legend wrestling with his loss of... more on Wikipedia

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  • 4
    A Dangerous Woman
    33
    7

    A Dangerous Woman

    Jake Gyllenhaal, Maggie Gyllenhaal

    Released1993

    Directed byStephen Gyllenhaal

    A Dangerous Woman is a 1993 film directed by Stephen Gyllenhaal. The screenplay was written by... more on Wikipedia
  • 5
    World Trade Center
    34
    8

    World Trade Center

    Nicolas Cage, Maggie Gyllenhaal

    Released2006

    Directed byOliver Stone

    World Trade Center is a 2006 disaster drama film directed by Oliver Stone and based on the... more on Wikipedia

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  • 6
    Nanny McPhee and the Big Bang
    29
    6

    Nanny McPhee and the Big Bang

    Ewan McGregor, Ralph Fiennes

    Released2010

    Directed bySusanna White

    Nanny McPhee and the Big Bang is a 2010 British family film. It is a sequel to the 2005 film... more on Wikipedia
  • 7
    The Dark Knight
    31
    9

    The Dark Knight

    Christian Bale, Michael Caine

    Released2008

    Directed byChristopher Nolan

    The Dark Knight is a 2008 superhero film directed by Christopher Nolan, based on the DC Comics... more on Wikipedia

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  • 8
    Adaptation
    30
    8

    Adaptation

    Nicolas Cage, Meryl Streep

    Released2002

    Directed bySpike Jonze

    Adaptation is a 2002 American comedy-drama metafilm directed by Spike Jonze and written by... more on Wikipedia

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  • 9
    Trust the Man
    29
    8

    Trust the Man

    Eva Mendes, Julianne Moore

    Released2005

    Directed byBart Freundlich

    Trust the Man is a 2005 romantic comedy film starring David Duchovny, Billy Crudup, Julianne... more on Wikipedia

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  • 10
    Sherrybaby
    36
    22

    Sherrybaby

    Maggie Gyllenhaal, Danny Trejo

    Released2006

    Directed byLaurie Collyer

    Sherrybaby is a 2006 American drama film written and directed by Laurie Collyer. Screened at... more on Wikipedia
  • 11
    40 Days and 40 Nights
    23
    10

    40 Days and 40 Nights

    Maggie Gyllenhaal, Josh Hartnett

    Released2002

    Directed byMichael Lehmann

    40 Days and 40 Nights is a 2002 romantic comedy film directed by Michael Lehmann, written by... more on Wikipedia

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  • 12
    Stranger than Fiction
    31
    19

    Stranger than Fiction

    Will Ferrell, Dustin Hoffman

    Released2006

    Directed byMarc Forster

    Stranger than Fiction is a 2006 American comedy-drama-fantasy film directed by Marc Forster,... more on Wikipedia

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  • 13
    Won’t Back Down
    26
    15

    Won’t Back Down

    Maggie Gyllenhaal, Holly Hunter

    Released2012

    Directed byDaniel Barnz

    Won't Back Down is a drama film directed by Daniel Barnz starring Maggie Gyllenhaal, Viola... more on Wikipedia
  • 14
    Riding in Cars with Boys
    21
    13

    Riding in Cars with Boys

    Drew Barrymore, Maggie Gyllenhaal

    Released2001

    Directed byPenny Marshall

    Riding in Cars with Boys is a 2001 film based on the autobiography of the same name by Beverly... more on Wikipedia

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  • 15
    Paris, je t'aime
    24
    18

    Paris, je t'aime

    Natalie Portman, Willem Dafoe

    Released2006

    Directed byTom Tykwer, Gus Van Sant, Olivier Assayas, Christopher Doyle, Ethan Coen

    Paris, je t'aime is a 2006 anthology film starring an ensemble cast of actors of various... more on Wikipedia

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  • 16
    Confessions of a Dangerous Mind
    18
    13

    Confessions of a Dangerous Mind

    Brad Pitt, Julia Roberts

    Released2002

    Directed byGeorge Clooney

    Confessions of a Dangerous Mind is a 2002 biographical spy comedy film depicting the life of... more on Wikipedia

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  • 17
    Cecil B. Demented
    20
    17

    Cecil B. Demented

    Maggie Gyllenhaal, Melanie Griffith

    Released2000

    Directed byJohn Waters

    Cecil B. Demented is a 2000 American black comedy film written and directed by John Waters.... more on Wikipedia
  • 18
    Hysteria
    16
    13

    Hysteria

    Maggie Gyllenhaal, Felicity Jones

    Released2011

    Directed byTanya Wexler

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  • 19
    Innocence
    14
    11

    Innocence

    Liya Kebede, Kelly Reilly

    Released2013

    Directed byHilary Brougher

    Innocence is a 2012 drama film directed by Hilary Brougher based on a novel by Jane Mendelson.
  • 20
    Criminal
    16
    15

    Criminal

    Maggie Gyllenhaal, Michael Shannon

    Released2004

    Directed byGregory Jacobs

    Criminal is a 2004 US film based upon the Argentine film Nine Queens. Directed by Gregory... more on Wikipedia
  • 21
    Strip Search
    15
    14

    Strip Search

    Kerry Washington, Rashida Jones

    Released2004

    Directed bySidney Lumet

    Strip Search is a drama film made for the HBO network, first aired on April 27, 2004. The film... more on Wikipedia
  • 22
    Donnie Darko
    22
    26

    Donnie Darko

    Drew Barrymore, Ashley Tisdale

    Released2001

    Directed byRichard Kelly

    Donnie Darko is a 2001 American supernatural drama film written and directed by Richard Kelly... more on Wikipedia

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  • 23
    Happy Endings
    14
    15

    Happy Endings

    Lisa Kudrow, Laura Dern

    Released2005

    Directed byDon Roos

    Happy Endings is a 2005 American film written and directed by Don Roos and starring Tom... more on Wikipedia
  • 24
    Voice from the Stone
    6
    6

    Voice from the Stone

    Emilia Clarke, Maggie Gyllenhaal

    Released2012

    Directed byEric D. Howell

    Voice from the Stone is a 2012 drama mystery, thriller film directed by Eric D. Howell based...
  • 25
    Homegrown
    12
    15

    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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