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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8320Dead Poets Society
Robin Williams, Ethan HawkeReleased: 1989
Directed by: Peter Weir
Dead Poets Society is a 1989 American drama film written by Tom Schulman, directed by Peter... more on Wikipedia2
6812Metropolitan
Taylor Nichols, Chris EigemanReleased: 1989
Directed by: Whit Stillman
Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.3
7721The Talented Mr. Ripley
Gwyneth Paltrow, Cate BlanchettReleased: 1999
Directed by: Anthony Minghella
The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and... more on Wikipedia4
4716School Ties
Ben Affleck, Matt DamonReleased: 1992
Directed by: Robert Mandel
School Ties is a 1992 sports film directed by Robert Mandel starring Brendan Fraser, Matt... more on Wikipedia5
4013Scent of a Woman
Al Pacino, Philip Seymour HoffmanReleased: 1992
Directed by: Martin Brest
Scent of a Woman is a 1992 American drama directed and produced by Martin Brest that tells the... more on Wikipedia6
3811Making the Grade
Judd Nelson, Andrew Dice ClayReleased: 1984
Directed by: Dorian Walker
Making the Grade is an American film which was released in 1984. It was directed by Dorian... more on Wikipedia7
4926American Psycho
Christian Bale, Willem DafoeReleased: 2000
Directed by: Mary Harron
American Psycho is a 2000 American neo-noir satirical psychological horror film directed by... more on Wikipedia8
4421The Great Gatsby
Robert Redford, Mia FarrowReleased: 1974
Directed by: Jack Clayton
The Great Gatsby is a 1974 American romantic drama film distributed by Newdon Productions and... more on Wikipedia9
4522Trading Places
Eddie Murphy, Jamie Lee CurtisReleased: 1983
Directed by: John Landis
Trading Places is a 1983 American comedy film directed by John Landis, starring Dan Aykroyd... more on Wikipedia10
5536The Great Gatsby
Leonardo DiCaprio, Tobey MaguireReleased: 2013
Directed by: Baz Luhrmann
The Great Gatsby is a 2013 romantic drama film directed by Baz Luhrmann, based on the 1925... more on Wikipedia11
4326Cruel Intentions
Reese Witherspoon, Sarah Michelle GellarReleased: 1999
Directed by: Roger Kumble
Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,... more on Wikipedia12
3516Rushmore
Bill Murray, Alexis BledelReleased: 1998
Directed by: Wes Anderson
Rushmore is a 1998 comedy-drama film directed by Wes Anderson about an eccentric teenager... more on Wikipedia13
4124Good Will Hunting
Ben Affleck, Robin WilliamsReleased: 1997
Directed by: Gus Van Sant
Good Will Hunting is a 1997 American drama film directed by Gus Van Sant, and starring Matt... more on Wikipedia14
3114Love Story
Tommy Lee Jones, Ray MillandReleased: 1970
Directed by: Arthur Hiller
Love Story is a 1970 romantic drama film written by Erich Segal, who also authored the... more on Wikipedia15
2813Mona Lisa Smile
Julia Roberts, Kirsten DunstReleased: 2003
Directed by: Mike Newell
Mona Lisa Smile is a 2003 drama film produced by Revolution Studios and Columbia Pictures in... more on Wikipedia16
194Brideshead Revisited
Emma Thompson, Hayley AtwellReleased: 2008
Directed by: Julian Jarrold
Brideshead Revisited is a 2008 British drama film directed by Julian Jarrold. The screenplay... more on Wikipedia17
3118The Graduate
Dustin Hoffman, Anne BancroftReleased: 1967
Directed by: Mike Nichols
The Graduate is a 1967 American comedy-drama film directed by Mike Nichols. It is based on the... more on Wikipedia18
2512Match Point
Scarlett Johansson, Jonathan Rhys MeyersReleased: 2005
Directed by: Woody Allen
Match Point is a 2005 drama film written and directed by Woody Allen which stars Jonathan Rhys... more on Wikipedia19
217The Skulls
Malin Åkerman, Paul WalkerReleased: 2000
Directed by: Rob Cohen
The Skulls is a 2000 American psychological thriller film starring Joshua Jackson, Paul Walker... more on Wikipedia20
206Thoroughbreds
Olivia Cooke, Anya Taylor-JoyReleased: 2018
Directed by: Cory Finley
Thoroughbreds is a 2018 American drama thriller film directed by Cory Finley. After years of... more on Wikipedia21
2917National Lampoon's Animal House
Kevin Bacon, John BelushiReleased: 1978
Directed by: John Landis
National Lampoon's Animal House is a 1978 American comedy film directed by John Landis. The... more on Wikipedia22
2917Igby Goes Down
Claire Danes, Susan SarandonReleased: 2002
Directed by: Burr Steers
Igby Goes Down is a 2002 comedy-drama film that follows the life of Igby Slocumb, a rebellious... more on Wikipedia23
3018Breakfast at Tiffany's
Audrey Hepburn, Mickey RooneyReleased: 1961
Directed by: Blake Edwards
Breakfast at Tiffany's is a 1961 American romantic comedy film starring Audrey Hepburn and... more on Wikipedia24
2311Oxford Blues
Rob Lowe, Ally SheedyReleased: 1984
Directed by: Robert Boris
Oxford Blues is a 1984 film written and directed by Robert Boris and starring Rob Lowe, Ally... more on Wikipedia25
2211Caddyshack
Bill Murray, Chevy ChaseReleased: 1980
Directed by: Harold Ramis
Caddyshack is a 1980 American sports comedy film directed by Harold Ramis and written by Brian... more on Wikipedia
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