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The Greatest Man Child Movies

Updated June 14, 2019 1.6k votes 174 voters 18.7k views

List RulesUpvote and add the best movies featuring men who haven't grown up.

There something slightly off putting yet hilarious about men who refuse to grow up, and in these Peter Pan Syndrome movies, they make for great comedy fodder. These are the greatest arrested development movies, wherein the main character must grow up and come to terms with being an adult. Also known as most Adam Sandler movies. I've always found it interesting that most overage coming of age movies are also romantic comedies, signaling in some way that all a guy needs to want to grow up is a good woman. Hmmm. I left this list open, so feel free to add any I miss and vote up or down your favorites.
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  • 1
    The 40-Year-Old Virgin
    103
    17

    The 40-Year-Old Virgin

    Elizabeth Banks, Kat Dennings

    Released2005

    Directed byJudd Apatow

    The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed... more on Wikipedia
  • 2
    Tommy Boy
    89
    14

    Tommy Boy

    Dan Aykroyd, Rob Lowe

    Released1995

    Directed byPeter Segal

    Tommy Boy is a 1995 American road comedy film directed by Peter Segal, written by Bonnie and... more on Wikipedia
  • 3
    Mallrats
    83
    15

    Mallrats

    Ben Affleck, Shannen Doherty

    Released1995

    Directed byKevin Smith

    Mallrats is a 1995 American romantic comedy film written and directed by Kevin Smith. It is... more on Wikipedia
  • 4
    Old School
    76
    15

    Old School

    Elisha Cuthbert, Snoop Dogg

    Released2003

    Directed byTodd Phillips

    This movie is so funny. And all of the characters are either in states of regression or arrested development

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  • 5
    Knocked Up
    71
    20

    Knocked Up

    Jessica Alba, Eva Mendes

    Released2007

    Directed byJudd Apatow

    Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd... more on Wikipedia
  • 6
    Black Sheep
    53
    13

    Black Sheep

    Julie Benz, Gary Busey

    Released1996

    Directed byPenelope Spheeris

    Black Sheep is a 1996 comedy film directed by Penelope Spheeris, written by Fred Wolf and... more on Wikipedia

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  • 7
    Step Brothers
    45
    7

    Step Brothers

    Will Ferrell, Seth Rogen

    Released2008

    Directed byAdam McKay

    Step Brothers is a 2008 American buddy slapstick comedy film starring Will Ferrell and John C.... more on Wikipedia

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  • 8
    Jack
    42
    17

    Jack

    Jennifer Lopez, Robin Williams

    Released1996

    Directed byFrancis Ford Coppola

    Jack is a 1996 American comedy-drama film starring Robin Williams, Diane Lane, Jennifer Lopez,... more on Wikipedia

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  • 9
    Big
    50
    31

    Big

    Tom Hanks, Jon Lovitz

    Released1988

    Directed byPenny Marshall

    Big is a 1988 American fantasy comedy film directed by Penny Marshall, and stars Tom Hanks as... more on WikipediaAmazon_watch buy button

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  • 10
    Due Date
    37
    18

    Due Date

    Charlie Sheen, Robert Downey Jr.

    Released2010

    Directed byTodd Phillips

    Due Date is a 2010 American comedy road film directed by Todd Phillips, co-written by Alan R.... more on Wikipedia

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  • 11
    Happy Gilmore
    36
    19

    Happy Gilmore

    Adam Sandler, Ben Stiller

    Released1996

    Directed byDennis Dugan

    Happy Gilmore is a 1996 sports comedy film directed by Dennis Dugan and produced by Robert... more on Wikipedia
  • 12
    Billy Madison
    34
    16

    Billy Madison

    Adam Sandler, Steve Buscemi

    Released1995

    Directed byTamra Davis

    Billy Madison is a 1995 American family comedy film directed by Tamra Davis. It stars Adam... more on Wikipedia
  • 13
    Our Idiot Brother
    34
    17

    Our Idiot Brother

    Zooey Deschanel, Elizabeth Banks

    Released2011

    Directed byJesse Peretz

    Our Idiot Brother is a 2011 American comedy-drama film directed by Jesse Peretz and starring... more on Wikipedia

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  • 14
    Willy Wonka & the Chocolate Factory
    25
    14

    Willy Wonka & the Chocolate Factory

    Gene Wilder, Jack Albertson

    Released1971

    Directed byMel Stuart

    Willy Wonka & the Chocolate Factory is a 1971 musical fantasy film directed by Mel Stuart, and... more on Wikipedia

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  • 15
    Grandma's Boy
    45
    47

    Grandma's Boy

    Jonah Hill, David Spade

    Released2006

    Directed byNicholaus Goossen

    Grandma's Boy is a 2006 American comedy stoner film produced by Adam Sandler's production... more on Wikipedia

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  • 16
    Walk Like a Man
    14
    11

    Walk Like a Man

    Christopher Lloyd, Cloris Leachman

    Released1987

    Directed byMelvin Frank

    Walk Like a Man is a 1987 comedy film about a young man who finally returns to his... more on Wikipedia
  • 17
    Failure to Launch
    10
    7

    Failure to Launch

    Zooey Deschanel, Sarah Jessica Parker

    Released2006

    Directed byTom Dey

    Failure to Launch is a 2006 American romantic comedy film. In the movie a 35-year-old man... more on Wikipedia
  • 18
    Peter Pan
    9
    6

    Peter Pan

    June Foray, Bobby Driscoll

    Released1953

    Directed byWilfred Jackson, Hamilton Luske, Clyde Geronimi, Jack Kinney

    Peter Pan is a 1953 American animated fantasy-adventure film produced by Walt Disney and based... more on Wikipedia

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  • 19
    The Big Lebowski
    20
    30

    The Big Lebowski

    Julianne Moore, Jeff Bridges

    Released1998

    Directed byEthan Coen, Joel Coen

    The Big Lebowski is a 1998 stoner comedy film written, produced, and directed by Joel and... more on Wikipedia

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  • 20
    Fun Dip
    3
    4

    Fun Dip

    Amazon_watch buy button
  • 21
    Eight Crazy Nights
    12
    19

    Eight Crazy Nights

    Adam Sandler, Tyra Banks

    Released2002

    Directed bySeth Kearsley

    Eight Crazy Nights is a 2002 American adult animated musical comedy film directed by Seth... more on Wikipedia

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  • 22
    Mumford
    16
    26

    Mumford

    Zooey Deschanel, Kelly Monaco

    Released1999

    Directed byLawrence Kasdan

    Mumford is a 1999 American comedy-drama film written and directed by Lawrence Kasdan. It is... more on WikipediaAmazon_watch buy button
  • 23
    The Hangover
    35
    61

    The Hangover

    Mike Tyson, Bradley Cooper

    Released2009

    Directed byTodd Phillips

    The Hangover is a 2009 American comedy film, co-produced and directed by Todd Phillips and... more on Wikipedia
  • 24
    Rain Man
    21
    47

    Rain Man

    Tom Cruise, Dustin Hoffman

    Released1988

    Directed byBarry Levinson

    Rain Man is a 1988 American drama film directed by Barry Levinson and written by Barry Morrow... more on Wikipedia

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  • 25
    Zoolander
    16
    64

    Zoolander

    Natalie Portman, Paris Hilton

    Released2001

    Directed byBen Stiller

    Zoolander is a 2001 American comedy film directed by Ben Stiller and, starring Stiller and... more on Wikipedia

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