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30+ Very Preppy Movies with the Preppiest Characters

Updated February 26, 2020 1.7k votes 209 voters 12.4k views43 items

We can't all live like the rich, but we can get a glimpse into the world of the preppy elite through great films. Very preppy movies with characters who went to prep school or living the prep life feature all of the relationship drama, desperation, and struggle we all experience in life – but their characters are typically much cleaner cut, in oxfords, khakis, sweaters, and somehow always ready to step onto a sailboat, even during tragedy. This is a list of great preppy movies, featuring everything from The Great Gatsby to Love Story to Ordinary People.

What films will you find on this list of the preppiest movies? Any adaptation of The Great Gatsby has to make the cut. Whether you prefer Robert Redford or Leonardo DiCaprio in the title role, this classic preppy tale is undeniably a classic. The Ice Storm is another good movie with a preppy aesthetic and impeccable acting. The Graduate follows a recent college graduate as he enjoys the luxuries of preppy life – and a scandalous love affair – while wiling the days away as only the wealthy can. Other films featured on this top preppy movies list include Rushmore, Good Will Hunting, and The Social Network.

Which movie do you like the best? Give your favorites a thumbs up and please add any good films featuring preppy characters that are missing.

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  • 1
    Dead Poets Society is listed (or ranked) 1 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    Dead Poets Society

    Robin Williams, Ethan Hawke

    Released1989

    Directed byPeter Weir

    Dead Poets Society is a 1989 American drama film written by Tom Schulman, directed by Peter... more on Wikipedia
  • 2
    The Talented Mr. Ripley is listed (or ranked) 2 on the list 30+ Very Preppy Movies with the Preppiest Characters
    69
    21

    The Talented Mr. Ripley

    Gwyneth Paltrow, Cate Blanchett

    Released1999

    Directed byAnthony Minghella

    The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and... more on Wikipedia
  • 3
    Metropolitan is listed (or ranked) 3 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    12

    Metropolitan

    Taylor Nichols, Chris Eigeman

    Released1989

    Directed byWhit Stillman

    Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.
  • 4
    School Ties is listed (or ranked) 4 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    16

    School Ties

    Ben Affleck, Matt Damon

    Released1992

    Directed byRobert Mandel

    School Ties is a 1992 sports film directed by Robert Mandel starring Brendan Fraser, Matt... more on Wikipedia

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  • 5
    Making the Grade is listed (or ranked) 5 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    10

    Making the Grade

    Judd Nelson, Andrew Dice Clay

    Released1984

    Directed byDorian Walker

    Making the Grade is an American film which was released in 1984. It was directed by Dorian... more on Wikipedia

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  • 6
    The Great Gatsby is listed (or ranked) 6 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    The Great Gatsby

    Robert Redford, Mia Farrow

    Released1974

    Directed byJack Clayton

    The Great Gatsby is a 1974 American romantic drama film distributed by Newdon Productions and... more on Wikipedia
  • 7
    American Psycho is listed (or ranked) 7 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    24

    American Psycho

    Christian Bale, Willem Dafoe

    Released2000

    Directed byMary Harron

    American Psycho is a 2000 American neo-noir satirical psychological horror film directed by... more on Wikipedia
  • 8
    Trading Places is listed (or ranked) 8 on the list 30+ Very Preppy Movies with the Preppiest Characters
    41
    21

    Trading Places

    Eddie Murphy, Jamie Lee Curtis

    Released1983

    Directed byJohn Landis

    Trading Places is a 1983 American comedy film directed by John Landis, starring Dan Aykroyd... more on Wikipedia
  • 9
    Scent of a Woman is listed (or ranked) 9 on the list 30+ Very Preppy Movies with the Preppiest Characters
    32
    13

    Scent of a Woman

    Al Pacino, Philip Seymour Hoffman

    Released1992

    Directed byMartin Brest

    Scent of a Woman is a 1992 American drama directed and produced by Martin Brest that tells the... more on Wikipedia
  • 10
    The Great Gatsby is listed (or ranked) 10 on the list 30+ Very Preppy Movies with the Preppiest Characters
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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
  • 11
    Love Story is listed (or ranked) 11 on the list 30+ Very Preppy Movies with the Preppiest Characters
    30
    11

    Love Story

    Tommy Lee Jones, Ray Milland

    Released1970

    Directed byArthur Hiller

    Love Story is a 1970 romantic drama film written by Erich Segal, who also authored the... more on Wikipedia
  • 12
    Cruel Intentions is listed (or ranked) 12 on the list 30+ Very Preppy Movies with the Preppiest Characters
    41
    23

    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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  • 13
    Rushmore is listed (or ranked) 13 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    15

    Rushmore

    Bill Murray, Alexis Bledel

    Released1998

    Directed byWes Anderson

    Rushmore is a 1998 comedy-drama film directed by Wes Anderson about an eccentric teenager... more on Wikipedia

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  • 14
    National Lampoon's Animal  is listed (or ranked) 14 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    14

    National Lampoon's Animal House

    Kevin Bacon, John Belushi

    Released1978

    Directed byJohn Landis

    National Lampoon's Animal House is a 1978 American comedy film directed by John Landis. The... more on Wikipedia

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  • 15
    Good Will Hunting is listed (or ranked) 15 on the list 30+ Very Preppy Movies with the Preppiest Characters
    36
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    Good Will Hunting

    Ben Affleck, Robin Williams

    Released1997

    Directed byGus Van Sant

    Good Will Hunting is a 1997 American drama film directed by Gus Van Sant, and starring Matt... more on Wikipedia
  • 16
    Igby Goes Down is listed (or ranked) 16 on the list 30+ Very Preppy Movies with the Preppiest Characters
    28
    13

    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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  • 17
    Thoroughbreds is listed (or ranked) 17 on the list 30+ Very Preppy Movies with the Preppiest Characters
    20
    5

    Thoroughbreds

    Olivia Cooke, Anya Taylor-Joy

    Directed byCory Finley

    Thoroughbreds is a 2018 American drama thriller film directed by Cory Finley. After years of... more on Wikipedia
  • 18
    The Graduate is listed (or ranked) 18 on the list 30+ Very Preppy Movies with the Preppiest Characters
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    The Graduate

    Dustin Hoffman, Anne Bancroft

    Released1967

    Directed byMike Nichols

    The Graduate is a 1967 American comedy-drama film directed by Mike Nichols. It is based on the... more on Wikipedia

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  • 19
    Mona Lisa Smile is listed (or ranked) 19 on the list 30+ Very Preppy Movies with the Preppiest Characters
    26
    11

    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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  • 20
    Oxford Blues is listed (or ranked) 20 on the list 30+ Very Preppy Movies with the Preppiest Characters
    23
    11

    Oxford Blues

    Rob Lowe, Ally Sheedy

    Released1984

    Directed byRobert Boris

    Oxford Blues is a 1984 film written and directed by Robert Boris and starring Rob Lowe, Ally... more on Wikipedia

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  • 21
    The Skulls is listed (or ranked) 21 on the list 30+ Very Preppy Movies with the Preppiest Characters
    20
    7

    The Skulls

    Malin Åkerman, Paul Walker

    Released2000

    Directed byRob Cohen

    The Skulls is a 2000 American psychological thriller film starring Joshua Jackson, Paul Walker... more on Wikipedia

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  • 22
    Match Point is listed (or ranked) 22 on the list 30+ Very Preppy Movies with the Preppiest Characters
    23
    11

    Match Point

    Scarlett Johansson, Jonathan Rhys Meyers

    Released2005

    Directed byWoody Allen

    Match Point is a 2005 drama film written and directed by Woody Allen which stars Jonathan Rhys... more on Wikipedia

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  • 23
    Caddyshack is listed (or ranked) 23 on the list 30+ Very Preppy Movies with the Preppiest Characters
    22
    11

    Caddyshack

    Bill Murray, Chevy Chase

    Released1980

    Directed byHarold Ramis

    Caddyshack is a 1980 American sports comedy film directed by Harold Ramis and written by Brian... more on Wikipedia
  • 24
    Breakfast at Tiffany's is listed (or ranked) 24 on the list 30+ Very Preppy Movies with the Preppiest Characters
    28
    18

    Breakfast at Tiffany's

    Audrey Hepburn, Mickey Rooney

    Released1961

    Directed byBlake Edwards

    Breakfast at Tiffany's is a 1961 American romantic comedy film starring Audrey Hepburn and... more on Wikipedia
  • 25
    Brideshead Revisited is listed (or ranked) 25 on the list 30+ Very Preppy Movies with the Preppiest Characters
    16
    4

    Brideshead Revisited

    Emma Thompson, Hayley Atwell

    Released2008

    Directed byJulian Jarrold

    Brideshead Revisited is a 2008 British drama film directed by Julian Jarrold. The screenplay... more on Wikipedia
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