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The Best Tobey Maguire Movies

Updated January 8, 2020 1.7k votes 303 voters 18.9k views31 items

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

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

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

This list contains films like Deconstructing Harry and The Cider House Rules.

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

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  • 1
    Brothers is listed (or ranked) 1 on the list The Best Tobey Maguire Movies
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    Brothers

    Natalie Portman, Jake Gyllenhaal

    Released2009

    Directed byJim Sheridan

    Brothers is a 2009 American psychological drama war film directed by Jim Sheridan, and a... more on Wikipedia

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  • 2
    Spider-Man is listed (or ranked) 2 on the list The Best Tobey Maguire Movies
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    Spider-Man

    Tobey Maguire, Willem Dafoe

    Released2002

    Directed bySam Raimi

    Spider-Man is a 2002 American superhero film directed by Sam Raimi, based on the Marvel Comics... more on Wikipedia

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  • 3
    Spider-Man 2 is listed (or ranked) 3 on the list The Best Tobey Maguire Movies
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    Spider-Man 2

    Tobey Maguire, Kirsten Dunst

    Released2004

    Directed bySam Raimi

    Spider-Man 2 is a 2004 American superhero film directed by Sam Raimi, based on the Marvel... more on Wikipedia

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  • 4
    Ride with the Devil is listed (or ranked) 4 on the list The Best Tobey Maguire Movies
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    Ride with the Devil

    Mark Ruffalo, Tobey Maguire

    Released1999

    Directed byAng Lee

    Ride with the Devil is a 1999 American film directed by Ang Lee. The storyline was conceived... more on Wikipedia

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  • 5
    The Ice Storm is listed (or ranked) 5 on the list The Best Tobey Maguire Movies
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    The Ice Storm

    Katie Holmes, Christina Ricci

    Released1997

    Directed byAng Lee

    The Ice Storm is a 1997 American drama film directed by Ang Lee, based on the 1994 novel of... more on Wikipedia
  • 6
    Pleasantville is listed (or ranked) 6 on the list The Best Tobey Maguire Movies
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    Pleasantville

    Reese Witherspoon, Paul Walker

    Released1998

    Directed byGary Ross

    Pleasantville is a 1998 American fantasy comedy-drama film written, produced, and directed by... more on Wikipedia

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  • 7
    The Cider House Rules is listed (or ranked) 7 on the list The Best Tobey Maguire Movies
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    The Cider House Rules

    Charlize Theron, Michael Caine

    Released1999

    Directed byLasse Hallström

    The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John... more on Wikipedia

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  • 8
    Cats & Dogs is listed (or ranked) 8 on the list The Best Tobey Maguire Movies
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    Cats & Dogs

    Alec Baldwin, Susan Sarandon

    Released2001

    Directed byLawrence Guterman

    Cats & Dogs is a 2001 American-Australian action-comedy film, directed by Lawrence Guterman.... more on Wikipedia

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  • 9
    Spider-Man 3 is listed (or ranked) 9 on the list The Best Tobey Maguire Movies
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    Spider-Man 3

    Tobey Maguire, Kirsten Dunst

    Released2007

    Directed bySam Raimi

    Spider-Man 3 is a 2007 American superhero film directed by Sam Raimi, based on the Marvel... more on Wikipedia

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  • 10
    This Boy's Life is listed (or ranked) 10 on the list The Best Tobey Maguire Movies
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    This Boy's Life

    Leonardo DiCaprio, Robert De Niro

    Released1993

    Directed byMichael Caton-Jones

    This Boy's Life is a 1993 film adaptation of the memoir of the same name by American author... more on Wikipedia

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  • 11
    The Great Gatsby is listed (or ranked) 11 on the list The Best Tobey Maguire Movies
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    The Great Gatsby

    Leonardo DiCaprio, Tobey Maguire

    Released2013

    Directed byBaz Luhrmann

    The Great Gatsby is a 2013 romantic drama film directed by Baz Luhrmann, based on the 1925... more on Wikipedia
  • 12
    Life of Pi is listed (or ranked) 12 on the list The Best Tobey Maguire Movies
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    Life of Pi

    Gérard Depardieu, Irrfan Khan

    Released2012

    Directed byAng Lee

    Life of Pi is a 2012 American historical drama film directed by Ang Lee, based on the novel of... more on Wikipedia

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  • 13
    Fear and Loathing in Las Vegas is listed (or ranked) 13 on the list The Best Tobey Maguire Movies
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    Fear and Loathing in Las Vegas

    Johnny Depp, Cameron Diaz

    Released1998

    Directed byTerry Gilliam

    Fear and Loathing in Las Vegas is a 1998 American dark comedy film co-written and directed by... more on Wikipedia
  • 14
    Seabiscuit is listed (or ranked) 14 on the list The Best Tobey Maguire Movies
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    Seabiscuit

    Elizabeth Banks, Jeff Bridges

    Released2003

    Directed byGary Ross

    Seabiscuit is a 2003 American biographical sports psychological-drama thriller film based on... more on Wikipedia

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  • 15
    Don's Plum is listed (or ranked) 15 on the list The Best Tobey Maguire Movies
    21
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    Don's Plum

    Leonardo DiCaprio, Tobey Maguire

    Released2001

    Directed byR.D. Robb

    Don's Plum is a 2001 low-budget black and white drama film directed by R. D. Robb. Robb... more on Wikipedia
  • 16
    Joyride is listed (or ranked) 16 on the list The Best Tobey Maguire Movies
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    Joyride

    Tobey Maguire, Benicio del Toro

    Released1996

    Directed byQuinton Peeples

    Joyride is a 1996 American film directed by Quinton Peeples.
  • 17
    Wonder Boys is listed (or ranked) 17 on the list The Best Tobey Maguire Movies
    19
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    Wonder Boys

    Robert Downey Jr., Katie Holmes

    Released2000

    Directed byCurtis Hanson

    Wonder Boys is a 2000 Romantic comedy film directed by Curtis Hanson and written by Steve... more on Wikipedia

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  • 18
    The Details is listed (or ranked) 18 on the list The Best Tobey Maguire Movies
    18
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    The Details

    Elizabeth Banks, Kerry Washington

    Released2011

    Directed byJacob Aaron Estes

    The Details is a 2011 film directed by Jacob Aaron Estes. When a family of raccoons discover... more on Wikipedia
  • 19
    Empire Records is listed (or ranked) 19 on the list The Best Tobey Maguire Movies
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    Empire Records

    Liv Tyler, Renée Zellweger

    Released1995

    Directed byAllan Moyle

    Empire Records is a 1995 American coming-of-age film that follows a group of record store... more on Wikipedia

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  • 20
    Quiet Type is listed (or ranked) 20 on the list The Best Tobey Maguire Movies
    14
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    Quiet Type

    Tobey Maguire
    amazon_watch buy button
  • 21
    Revenge of the Red Baron is listed (or ranked) 21 on the list The Best Tobey Maguire Movies
    12
    10

    Revenge of the Red Baron

    Mickey Rooney, Tobey Maguire

    Released1994

    Directed byRobert Gordon

    Revenge of the Red Baron is a 1994 American film starring Mickey Rooney, Tobey Maguire,... more on Wikipediaamazon_watch buy button
  • 22
    Healer is listed (or ranked) 22 on the list The Best Tobey Maguire Movies
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    Healer

    Tobey Maguire, David McCallum

    Released1994

    Directed byJohn G. Thomas

    Healer is a 1994 American dramatic film starring Tyrone Power Jr., Tobey Maguire, David... more on Wikipediaamazon_watch buy button
  • 23
    Beyond All Boundaries is listed (or ranked) 23 on the list The Best Tobey Maguire Movies
    12
    13

    Beyond All Boundaries

    Brad Pitt, Tom Hanks

    Released2009

    Directed byDavid Briggs

    Beyond All Boundaries is a 2009 short film directed David Briggs and written by Chris Ellis.amazon_watch buy button
  • 24
    In Spite of Love is listed (or ranked) 24 on the list The Best Tobey Maguire Movies
    10
    11

    In Spite of Love

    Tobey Maguire, Andrea Roth

    Released1994

    Directed byDavid Greene

    In Spite of Love is a film directed by David Greene released on Apr 9, 1994.amazon_watch buy button
  • 25
    S.F.W. is listed (or ranked) 25 on the list The Best Tobey Maguire Movies
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    S.F.W.

    Reese Witherspoon, Tobey Maguire

    Released1994

    Directed byJefery Levy

    S.F.W. is a 1994 film directed by Jefery Levy. It is based on a novel by Andrew Wellman, and... more on Wikipedia
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