311 voters

The Best Tobey Maguire Movies

Updated January 8, 2020 1.7k votes 311 voters 19.3k 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?"


  • 1

    Spider-Man 2

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

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  • 2


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

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  • 3


    Elizabeth Banks, Jeff Bridges
    Seabiscuit is a 2003 American biographical sports psychological-drama thriller film based on...  more

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  • 4


    Reese Witherspoon, Paul Walker
    Pleasantville is a 1998 American fantasy comedy-drama film written, produced, and directed by...  more

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  • 5

    Spider-Man 3

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

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  • 6

    Wonder Boys

    Robert Downey Jr., Katie Holmes
    Wonder Boys is a 2000 Romantic comedy film directed by Curtis Hanson and written by Steve...  more

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  • 7

    Tropic Thunder

    Ben Stiller, Jack Black
    Tropic Thunder is a 2008 American action satire comedy film directed by Ben Stiller. Through a...  more

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  • 8

    The Great Gatsby

    Leonardo DiCaprio, Tobey Maguire
    The Great Gatsby is a 2013 romantic drama film directed by Baz Luhrmann, based on the 1925...  more

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  • 9

    The Cider House Rules

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

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  • 10

    Fear and Loathing in Las Vegas

    Johnny Depp, Cameron Diaz
    Fear and Loathing in Las Vegas is a 1998 American dark comedy film co-written and directed by...  more

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  • 11


    Natalie Portman, Jake Gyllenhaal
    Brothers is a 2009 American psychological drama war film directed by Jim Sheridan, and a...  more

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  • 12

    The Good German

    George Clooney, Cate Blanchett
    The Good German is a 2006 film adaptation of the novel by Joseph Kanon. It was directed by...  more
  • 13

    Deconstructing Harry

    Demi Moore, Jennifer Garner
    Deconstructing Harry is a comedy film written and directed by Woody Allen and released in...  more

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  • 14

    Cats & Dogs

    Alec Baldwin, Susan Sarandon
    Cats & Dogs is a 2001 American-Australian action-comedy film, directed by Lawrence Guterman....  more

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  • 15

    Don's Plum

    Leonardo DiCaprio, Tobey Maguire
    Don's Plum is a 2001 low-budget black and white drama film directed by R. D. Robb. Robb...  more
  • 16

    The Wizard

    Tobey Maguire, Christian Slater
    The Wizard is a 1989 adventure comedy-drama film starring Fred Savage, Christian Slater, Jenny...  more

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  • 17


    Tobey Maguire, Benicio del Toro
    Joyride is a 1996 American film directed by Quinton Peeples....  more
  • 18

    Ride with the Devil

    Mark Ruffalo, Tobey Maguire
    Ride with the Devil is a 1999 American film directed by Ang Lee. The storyline was conceived...  more

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  • 19

    The Details

    Elizabeth Banks, Kerry Washington
    The Details is a 2011 film directed by Jacob Aaron Estes. When a family of raccoons discover...  more
  • 20

    Empire Records

    Liv Tyler, Renée Zellweger
    Empire Records is a 1995 American coming-of-age film that follows a group of record store...  more

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  • 21

    Quiet Type

    Tobey Maguire
  • 22

    Duke of Groove

    Uma Thurman, Kiefer Sutherland
    Duke of Groove is a 1996 short film directed by Griffin Dunne....
  • 23

    Life of Pi

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

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  • 24

    This Boy's Life

    Leonardo DiCaprio, Robert De Niro
    This Boy's Life is a 1993 film adaptation of the memoir of the same name by American author...  more

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  • 25

    The Ice Storm

    Katie Holmes, Christina Ricci
    The Ice Storm is a 1997 American drama film directed by Ang Lee, based on the 1994 novel of...  more