Watchworthy
223 voters

30+ Very Preppy Movies with the Preppiest Characters

Updated February 26, 2020 1.8k votes 223 voters 13.2k 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.

Photo:
...more
  • Dead Poets Society1
    83
    20

    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
  • Metropolitan2
    68
    12

    Metropolitan

    Taylor Nichols, Chris Eigeman

    Released1989

    Directed byWhit Stillman

    Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.
  • The Talented Mr. Ripley3
    77
    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
  • School Ties4
    47
    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

    More School Ties 

    #39 of 75 The Best Football Movies Ever#23 of 38 The Best High School Sports Movies

  • Scent of a Woman5
    40
    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
  • Making the Grade6
    38
    11

    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

    More Making the Grade 

    #150 of 259 The Greatest Teen Movies of the 1980s#8 of 59 The Best Movies About Prep School

  • American Psycho7
    49
    26

    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
  • The Great Gatsby8
    44
    21

    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
  • Trading Places9
    45
    22

    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
  • The Great Gatsby10
    55
    36

    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
  • Cruel Intentions11
    43
    26

    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
  • Rushmore12
    35
    16

    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

    More Rushmore 

    #483 of 1,137 The Absolute Funniest Movies Of All Time#441 of 456 The Most Quotable Movies of All Time

  • Good Will Hunting13
    41
    24

    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

    More Good Will Hunting 

    #33 of 355 The Best Rainy Day Movies#15 of 277 The Top Tearjerker Movies That Make Men Cry

  • Love Story14
    31
    14

    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
  • Mona Lisa Smile15
    28
    13

    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

    More Mona Lisa Smile 

    #209 of 836 The Greatest Chick Flicks Ever Made#10 of 84 Great Movies That Take Place in Autumn

  • Brideshead Revisited16
    19
    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
  • The Graduate17
    31
    18

    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

    More The Graduate 

    #726 of 1,189 Every Oscar Winning Film Ever#38 of 369 The Best Movies Based On Books

  • Match Point18
    25
    12

    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

    More Match Point 

    #215 of 242 The Best Psychological Thrillers of All Time#462 of 675 The Best Movies Roger Ebert Gave Four Stars

  • The Skulls19
    21
    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

    More The Skulls 

    #36 of 141 The Best College Movies Ever#88 of 280 The Best Whodunit Movies

  • Thoroughbreds20
    20
    6

    Thoroughbreds

    Olivia Cooke, Anya Taylor-Joy

    Released2018

    Directed byCory Finley

    Thoroughbreds is a 2018 American drama thriller film directed by Cory Finley. After years of... more on Wikipedia
  • National Lampoon's Animal House21
    29
    17

    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

    More National Lampoon's Animal House 

    Behind The Scenes Stories From 'Animal House' That Are Way More Insane Than The Movie#87 of 372 'Old' Movies Every Young Person Needs To Watch In Their Lifetime

  • Igby Goes Down22
    29
    17

    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

    More Igby Goes Down 

    #27 of 31 The Greatest Movies with Precocious Teen Stars#7 of 20 The Best Independent Films Starring Huge Hollywood Actors

  • Breakfast at Tiffany's23
    30
    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
  • Oxford Blues24
    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

    More Oxford Blues 

    #138 of 145 The Most Inspirational Sports Movies#16 of 26 The Best Brat Pack Movies

  • Caddyshack25
    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

    More Caddyshack 

    #3 of 314 The Funniest '80s Movies#159 of 553 The Greatest Epic Movies Ever Made