films 30+ Very Preppy Movies with the Preppiest Characters  

Ranker Film
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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 the preppiest characters feature all of the relationship drama, desperation, and struggle we all experience in life – but their characters are typically much better dressed. This is a list of great preppy movies, featuring everything from The Great Gatsby to Clueless to PCU.

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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Dead Poets Society is listed (or ranked) 1 on the list 30+ Very Preppy Movies with the Preppiest Characters
Dead Poets Society Robin Williams, Ethan Hawke, Lara Flynn Boyle 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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Pretty in Pink is listed (or ranked) 2 on the list 30+ Very Preppy Movies with the Preppiest Characters
Pretty in Pink James Spader, Gina Gershon, Molly Ringwald 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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The Graduate is listed (or ranked) 3 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Graduate Dustin Hoffman, Anne Bancroft, Richard Dreyfuss 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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Good Will Hunting is listed (or ranked) 4 on the list 30+ Very Preppy Movies with the Preppiest Characters
Good Will Hunting Ben Affleck, Robin Williams, Matt Damon 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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Love Story is listed (or ranked) 5 on the list 30+ Very Preppy Movies with the Preppiest Characters
Love Story Tommy Lee Jones, Ray Milland, Ryan O'Neal 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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American Psycho is listed (or ranked) 6 on the list 30+ Very Preppy Movies with the Preppiest Characters
American Psycho Reese Witherspoon, Christian Bale, Willem Dafoe American Psycho is a 2000 American psychological thriller comedy film co-written and directed by Mary Harron, based on Bret Easton Ellis's 1991 novel of the same name. It stars Christian Bale, ...more

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Clueless is listed (or ranked) 7 on the list 30+ Very Preppy Movies with the Preppiest Characters
Clueless Alicia Silverstone, Brittany Murphy, Paul Rudd Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It stars Alicia Silverstone, Stacey Dash, Paul Rudd, and Brittany Murphy. The film is set in Beverly Hills ...more

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The Great Gatsby is listed (or ranked) 8 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Great Gatsby Leonardo DiCaprio, Isla Fisher, Carey Mulligan 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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Cruel Intentions is listed (or ranked) 9 on the list 30+ Very Preppy Movies with the Preppiest Characters
Cruel Intentions Reese Witherspoon, Sarah Michelle Gellar, Tara Reid 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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Breakfast at Tiffany's is listed (or ranked) 10 on the list 30+ Very Preppy Movies with the Preppiest Characters
Breakfast at Tiffany's Audrey Hepburn, Mickey Rooney, Mel Blanc 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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Trading Places is listed (or ranked) 11 on the list 30+ Very Preppy Movies with the Preppiest Characters
Trading Places Eddie Murphy, Jamie Lee Curtis, Dan Aykroyd 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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The Great Gatsby is listed (or ranked) 12 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Great Gatsby Robert Redford, Mia Farrow, Bruce Dern 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

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Rushmore is listed (or ranked) 13 on the list 30+ Very Preppy Movies with the Preppiest Characters
Rushmore Bill Murray, Alexis Bledel, Brian Cox 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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Scent of a Woman is listed (or ranked) 14 on the list 30+ Very Preppy Movies with the Preppiest Characters
Scent of a Woman Al Pacino, Philip Seymour Hoffman, Gabrielle Anwar 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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Caddyshack is listed (or ranked) 15 on the list 30+ Very Preppy Movies with the Preppiest Characters
RobLein added Caddyshack Bill Murray, Chevy Chase, Rodney Dangerfield 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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Igby Goes Down is listed (or ranked) 16 on the list 30+ Very Preppy Movies with the Preppiest Characters
Igby Goes Down Claire Danes, Susan Sarandon, Amanda Peet 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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The Talented Mr. Ripley is listed (or ranked) 17 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Talented Mr. Ripley Gwyneth Paltrow, Cate Blanchett, Matt Damon 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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The Way We Were is listed (or ranked) 18 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Way We Were Barbra Streisand, Robert Redford, James Woods The Way We Were is a 1973 American romantic drama film, starring Barbra Streisand and Robert Redford, and directed by Sydney Pollack. The screenplay by Arthur Laurents was based on his college ...more

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Making the Grade is listed (or ranked) 19 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added Making the Grade Judd Nelson, Andrew Dice Clay, Gordon Jump 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,

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The Social Network is listed (or ranked) 20 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Social Network Justin Timberlake, Rashida Jones, Rooney Mara The Social Network is a 2010 American drama film directed by David Fincher and written by Aaron Sorkin. Adapted from Ben Mezrich's 2009 book The Accidental Billionaires: The Founding of ...more

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School Ties is listed (or ranked) 21 on the list 30+ Very Preppy Movies with the Preppiest Characters
School Ties Ben Affleck, Matt Damon, Brendan Fraser 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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Oxford Blues is listed (or ranked) 22 on the list 30+ Very Preppy Movies with the Preppiest Characters
Oxford Blues Rob Lowe, Ally Sheedy, Cary Elwes 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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National Lampoon's Animal Hous... is listed (or ranked) 23 on the list 30+ Very Preppy Movies with the Preppiest Characters
National Lampoon's Animal House Kevin Bacon, John Belushi, Donald Sutherland 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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Metropolitan is listed (or ranked) 24 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added Metropolitan Taylor Nichols, Chris Eigeman, Isabel Gillies Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.

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Guess Who's Coming to Dinner is listed (or ranked) 25 on the list 30+ Very Preppy Movies with the Preppiest Characters
Guess Who's Coming to Dinner Katharine Hepburn, Sidney Poitier, Spencer Tracy Guess Who's Coming to Dinner is a 1967 American comedy-drama film produced and directed by Stanley Kramer and written by William Rose. It stars Spencer Tracy, Sidney Poitier and Katharine ...more

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The Ice Storm is listed (or ranked) 26 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Ice Storm Katie Holmes, Christina Ricci, Sigourney Weaver 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

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Funny Games is listed (or ranked) 27 on the list 30+ Very Preppy Movies with the Preppiest Characters
Funny Games Naomi Watts, Tim Roth, Michael Pitt Funny Games is a 2007 psychological thriller film written and directed by Michael Haneke, a remake of Haneke's 1997 Austrian film Funny Games. Naomi Watts, Tim Roth, Michael Pitt, and Brady ...more

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Sabrina is listed (or ranked) 28 on the list 30+ Very Preppy Movies with the Preppiest Characters
RobLein added Sabrina Audrey Hepburn, Humphrey Bogart, William Holden Sabrina is a 1954 American romantic comedy film directed by Billy Wilder, adapted for the screen by Wilder, Samuel A. Taylor, and Ernest Lehman from Taylor's play Sabrina Fair. It stars Humphrey ...more

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The Philadelphia Story is listed (or ranked) 29 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Philadelphia Story Katharine Hepburn, Cary Grant, James Stewart The Philadelphia Story is a 1940 American romantic comedy film directed by George Cukor, starring Cary Grant, Katharine Hepburn, and James Stewart and featuring Ruth Hussey. Based on the ...more

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Mona Lisa Smile is listed (or ranked) 30 on the list 30+ Very Preppy Movies with the Preppiest Characters
Mona Lisa Smile Julia Roberts, Kirsten Dunst, Maggie Gyllenhaal 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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PCU is listed (or ranked) 31 on the list 30+ Very Preppy Movies with the Preppiest Characters
PCU David Spade, Jeremy Piven, Jon Favreau filmography PCU is a 1994 American comedy film written by Adam Leff and Zak Penn and directed by Hart Bochner about college life at the fictional Port Chester University, and represents "an exaggerated ...more

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Proof is listed (or ranked) 32 on the list 30+ Very Preppy Movies with the Preppiest Characters
Proof Gwyneth Paltrow, Jake Gyllenhaal, Anthony Hopkins Proof is a 2005 American drama film directed by John Madden and starring Gwyneth Paltrow, Anthony Hopkins, Jake Gyllenhaal, and Hope Davis. It was written by Rebecca Miller, based on David ...more

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Match Point is listed (or ranked) 33 on the list 30+ Very Preppy Movies with the Preppiest Characters
Match Point Scarlett Johansson, Jonathan Rhys Meyers, Emily Mortimer 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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The Dangerous Lives of Altar B... is listed (or ranked) 34 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Dangerous Lives of Altar Boys Jodie Foster, Jena Malone, Vincent D'Onofrio The Dangerous Lives of Altar Boys is a 2002 independent comedy-drama film directed by Peter Care. The film stars Emile Hirsch, Kieran Culkin, Jena Malone, Jodie Foster, and Vincent D'Onofrio. ...more

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Ordinary People is listed (or ranked) 35 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ordinary People Mary Tyler Moore, Donald Sutherland, Adam Baldwin Ordinary People is a 1980 American drama film that marked the directorial debut of actor Robert Redford. It stars Donald Sutherland, Mary Tyler Moore, Judd Hirsch and Timothy Hutton. The story ...more

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The Skulls is listed (or ranked) 36 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Skulls Malin Åkerman, Paul Walker, Joshua Jackson The Skulls is a 2000 American psychological thriller film starring Joshua Jackson, Paul Walker and Leslie Bibb, directed by Rob Cohen. Its plot is based upon some of the conspiracy theories ...more

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With Honors is listed (or ranked) 37 on the list 30+ Very Preppy Movies with the Preppiest Characters
With Honors Brendan Fraser, Joe Pesci, Patrick Dempsey With Honors is a 1994 comedy-drama film starring Joe Pesci and Brendan Fraser. The film was directed by Alek Keshishian, who has more famously directed music videos for Madonna and Bobby Brown.

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The Falling is listed (or ranked) 38 on the list 30+ Very Preppy Movies with the Preppiest Characters
The Falling Scott Gabelein, Rory Colin Fretland, Michael Ayden Amidst his broken life, Police Officer Grayson Reed is about to be thrown into the middle of a feud between the five Angels of Heaven and the leader of Hell. As faith ends in the world around ...more

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Back to School is listed (or ranked) 39 on the list 30+ Very Preppy Movies with the Preppiest Characters
Back to School Robert Downey Jr., Rodney Dangerfield, Sam Kinison Back to School is a 1986 comedy film starring Rodney Dangerfield, Keith Gordon, Sally Kellerman, Burt Young, Terry Farrell, William Zabka, Ned Beatty, Sam Kinison, and Robert Downey, Jr. It was ...more