Entertainment

30+ Very Preppy Movies with the Preppiest Characters 

Ranker Film
Updated February 26, 2020 1.2k votes 176 voters 9.4k views 43 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.

list ordered by
1
Dead Poets Society is listed (or ranked) 1 on the list 30+ Very Preppy Movies with the Preppiest Characters
Robin Williams, Ethan Hawke, Lara Flynn Boyle

Released: 1989

Directed by: Peter Weir

Dead Poets Society is a 1989 American drama film written by Tom Schulman, directed by Peter Weir and starring Robin Williams. Set at the conservative and aristocratic Welton Academy in the ...more

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2
The Talented Mr. Ripley ... is listed (or ranked) 2 on the list 30+ Very Preppy Movies with the Preppiest Characters
Gwyneth Paltrow, Cate Blanchett, Matt Damon

Released: 1999

Directed by: Anthony Minghella

The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and directed by Anthony Minghella. An adaptation of the 1955 Patricia Highsmith novel of the same name, ...more

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3
Metropolitan is listed (or ranked) 3 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added Taylor Nichols, Chris Eigeman, Isabel Gillies

Released: 1989

Directed by: Whit Stillman

Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.
4
The Great Gatsby is listed (or ranked) 4 on the list 30+ Very Preppy Movies with the Preppiest Characters
Leonardo DiCaprio, Isla Fisher, Carey Mulligan

Released: 2013

Directed by: Baz Luhrmann

The Great Gatsby is a 2013 Australian-American 3D drama film based on F. Scott Fitzgerald's 1925 novel of the same name. The film was co-written and directed by Baz Luhrmann, and stars Leonardo ...more

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5
The Great Gatsby is listed (or ranked) 5 on the list 30+ Very Preppy Movies with the Preppiest Characters
Robert Redford, Mia Farrow, Bruce Dern

Released: 1974

Directed by: Jack Clayton

The Great Gatsby is a 1974 American romantic drama film distributed by Newdon Productions and Paramount Pictures. It was directed by Jack Clayton and produced by David Merrick, from a screenplay ...more
6
Trading Places is listed (or ranked) 6 on the list 30+ Very Preppy Movies with the Preppiest Characters
Eddie Murphy, Jamie Lee Curtis, Dan Aykroyd

Released: 1983

Directed by: John Landis

Trading Places is a 1983 American comedy film directed by John Landis, starring Dan Aykroyd and Eddie Murphy. It tells the story of an upper-class commodities broker and a homeless street ...more

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#13 of 1,009 The All-Time Greatest Comedy Films #25 of 1,196 The Absolute Funniest Movies Of All Time

7
American Psycho is listed (or ranked) 7 on the list 30+ Very Preppy Movies with the Preppiest Characters
Christian Bale, Willem Dafoe, Jared Leto

Released: 2000

Directed by: Mary Harron

American Psycho is a 2000 American neo-noir satirical psychological horror film directed by Mary Harron, based on the 1991 novel by Bret Easton Ellis. Wealthy New York City investment banking ...more

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8
School Ties is listed (or ranked) 8 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ben Affleck, Matt Damon, Brendan Fraser

Released: 1992

Directed by: Robert Mandel

School Ties is a 1992 sports film directed by Robert Mandel starring Brendan Fraser, Matt Damon, Ben Affleck, Chris O'Donnell, Cole Hauser, Randall Batinkoff, Andrew Lowery and Anthony Rapp. ...more

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9
Making the Grade is listed (or ranked) 9 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added Judd Nelson, Andrew Dice Clay, Gordon Jump

Released: 1984

Directed by: Dorian Walker

Making the Grade is an American film which was released in 1984. It was directed by Dorian Walker and written by Charles Gale and Gene Quintano. It was filmed at Rhodes College in Memphis,
10
Good Will Hunting is listed (or ranked) 10 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ben Affleck, Robin Williams, Matt Damon

Released: 1997

Directed by: Gus Van Sant

Good Will Hunting is a 1997 American drama film directed by Gus Van Sant, and starring Matt Damon, Robin Williams, Ben Affleck, Minnie Driver and Stellan Skarsgård. Written by Affleck and ...more

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#140 of 1,699 The Most Rewatchable Movies #98 of 599 The Greatest Epic Movies Ever Madelisted on Every Oscar Winning Film Ever

11
Cruel Intentions is listed (or ranked) 11 on the list 30+ Very Preppy Movies with the Preppiest Characters
Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

Released: 1999

Directed by: Roger Kumble

Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of Les Liaisons dangereuses, written ...more

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12
Scent of a Woman is listed (or ranked) 12 on the list 30+ Very Preppy Movies with the Preppiest Characters
Al Pacino, Philip Seymour Hoffman, Gabrielle Anwar

Released: 1992

Directed by: Martin Brest

Scent of a Woman is a 1992 American drama directed and produced by Martin Brest that tells the story of a preparatory school student who takes a job as an assistant to an irascible, blind, ...more

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13
Love Story is listed (or ranked) 13 on the list 30+ Very Preppy Movies with the Preppiest Characters
Tommy Lee Jones, Ray Milland, Ryan O'Neal

Released: 1970

Directed by: Arthur Hiller

Love Story is a 1970 romantic drama film written by Erich Segal, who also authored the best-selling novel of the same name. It was directed by Arthur Hiller and starred Ryan O'Neal, Ali MacGraw, ...more

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14
Rushmore is listed (or ranked) 14 on the list 30+ Very Preppy Movies with the Preppiest Characters
Bill Murray, Alexis Bledel, Brian Cox

Released: 1998

Directed by: Wes Anderson

Rushmore is a 1998 comedy-drama film directed by Wes Anderson about an eccentric teenager named Max Fischer, his friendship with rich industrialist Herman Blume, and their mutual love for ...more

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15
Igby Goes Down is listed (or ranked) 15 on the list 30+ Very Preppy Movies with the Preppiest Characters
Claire Danes, Susan Sarandon, Amanda Peet

Released: 2002

Directed by: Burr Steers

Igby Goes Down is a 2002 comedy-drama film that follows the life of Igby Slocumb, a rebellious and sardonic New York City teenager who attempts to break free of his familial ties and wealthy, ...more

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16
Mona Lisa Smile is listed (or ranked) 16 on the list 30+ Very Preppy Movies with the Preppiest Characters
Julia Roberts, Kirsten Dunst, Maggie Gyllenhaal

Released: 2003

Directed by: Mike Newell

Mona Lisa Smile is a 2003 drama film produced by Revolution Studios and Columbia Pictures in association with Red Om Films Productions, directed by Mike Newell, written by Lawrence Konner and ...more

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17
Pretty in Pink is listed (or ranked) 17 on the list 30+ Very Preppy Movies with the Preppiest Characters
James Spader, Gina Gershon, Molly Ringwald

Released: 1986

Directed by: Howard Deutch

Pretty in Pink is a 1986 American romantic comedy-drama film about love and social cliques in 1980s American high schools. It is one of John Hughes' films starring Molly Ringwald, and is ...more

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18
Breakfast at Tiffany's ... is listed (or ranked) 18 on the list 30+ Very Preppy Movies with the Preppiest Characters
Audrey Hepburn, Mickey Rooney, Mel Blanc

Released: 1961

Directed by: Blake Edwards

Breakfast at Tiffany's is a 1961 American romantic comedy film starring Audrey Hepburn and George Peppard, and featuring Patricia Neal, Buddy Ebsen, Martin Balsam, and Mickey Rooney. The film ...more

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19
Class is listed (or ranked) 19 on the list 30+ Very Preppy Movies with the Preppiest Characters
JoelOquendo added Rob Lowe, John Cusack, Jacqueline Bissett

Released: 1983

Directed by: Lewis John Carlino

Class is a 1983 American romantic comedy-drama film, directed by Lewis John Carlino, starring Jacqueline Bisset, Rob Lowe and Cliff Robertson, and is also the film debut of Andrew McCarthy, John ...more

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20
The Graduate is listed (or ranked) 20 on the list 30+ Very Preppy Movies with the Preppiest Characters
Dustin Hoffman, Anne Bancroft, Richard Dreyfuss

Released: 1967

Directed by: Mike Nichols

The Graduate is a 1967 American comedy-drama film directed by Mike Nichols. It is based on the 1963 novel The Graduate by Charles Webb, who wrote it shortly after graduating from Williams ...more

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21
National Lampoon's Anima... is listed (or ranked) 21 on the list 30+ Very Preppy Movies with the Preppiest Characters
Kevin Bacon, John Belushi, Donald Sutherland

Released: 1978

Directed by: John Landis

National Lampoon's Animal House is a 1978 American comedy film directed by John Landis. The film was a direct spinoff from National Lampoon magazine. It is about a misfit group of fraternity ...more

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22
Caddyshack is listed (or ranked) 22 on the list 30+ Very Preppy Movies with the Preppiest Characters
RobLein added Bill Murray, Chevy Chase, Rodney Dangerfield

Released: 1980

Directed by: Harold Ramis

Caddyshack is a 1980 American sports comedy film directed by Harold Ramis and written by Brian Doyle-Murray, Ramis and Douglas Kenney. It stars Michael O'Keefe, Chevy Chase, Rodney Dangerfield, ...more

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23
The Ice Storm is listed (or ranked) 23 on the list 30+ Very Preppy Movies with the Preppiest Characters
Katie Holmes, Christina Ricci, Sigourney Weaver

Released: 1997

Directed by: Ang Lee

The Ice Storm is a 1997 American drama film directed by Ang Lee, based on the 1994 novel of the same name by Rick Moody. The film features an ensemble cast of Kevin Kline, Joan Allen, Tobey ...more
24
Oxford Blues is listed (or ranked) 24 on the list 30+ Very Preppy Movies with the Preppiest Characters
Rob Lowe, Ally Sheedy, Cary Elwes

Released: 1984

Directed by: Robert Boris

Oxford Blues is a 1984 film written and directed by Robert Boris and starring Rob Lowe, Ally Sheedy and Amanda Pays. It is a remake of the 1938 Metro-Goldwyn-Mayer film A Yank at Oxford.

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25
Match Point is listed (or ranked) 25 on the list 30+ Very Preppy Movies with the Preppiest Characters
Scarlett Johansson, Jonathan Rhys Meyers, Emily Mortimer

Released: 2005

Directed by: Woody Allen

Match Point is a 2005 drama film written and directed by Woody Allen which stars Jonathan Rhys Meyers, Scarlett Johansson, Emily Mortimer, Matthew Goode, Brian Cox, and Penelope Wilton. Rhys ...more

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