Entertainment

30+ Very Preppy Movies with the Preppiest Characters  

Ranker Film
1.1k votes 158 voters 8.1k views 41 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 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.

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
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
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
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
3
The Great Gatsby is listed (or ranked) 3 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
4
Metropolitan is listed (or ranked) 4 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added Taylor Nichols, Chris Eigeman, Isabel Gillies
Metropolitan is a 1990 comedy, drama film written and directed by Whit Stillman.
5
School Ties is listed (or ranked) 5 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
6
Love Story is listed (or ranked) 6 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
7
The Great Gatsby is listed (or ranked) 7 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
8
Cruel Intentions is listed (or ranked) 8 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
9
Good Will Hunting is listed (or ranked) 9 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
10
Making the Grade is listed (or ranked) 10 on the list 30+ Very Preppy Movies with the Preppiest Characters
Ian Steaman added 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,
11
Scent of a Woman is listed (or ranked) 11 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
12
American Psycho is listed (or ranked) 12 on the list 30+ Very Preppy Movies with the Preppiest Characters
Christian Bale, Willem Dafoe, Jared Leto
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
13
Trading Places is listed (or ranked) 13 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
14
Igby Goes Down is listed (or ranked) 14 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
15
Mona Lisa Smile is listed (or ranked) 15 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
16
Thoroughbreds is listed (or ranked) 16 on the list 30+ Very Preppy Movies with the Preppiest Characters
carlybobarly added Olivia Cooke, Anya Taylor-Joy, Anton Yelchin
Thoroughbreds is a 2018 American drama thriller film directed by Cory Finley. After years of growing apart, upper-class teenagers Lily (Anya Taylor-Joy) and Amanda (Olivia Cooke) rekindle their ...more
17
Rushmore is listed (or ranked) 17 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
18
The Graduate is listed (or ranked) 18 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
19
National Lampoon's Animal Hous... is listed (or ranked) 19 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
20
Caddyshack is listed (or ranked) 20 on the list 30+ Very Preppy Movies with the Preppiest Characters
RobLein added 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
21
Brideshead Revisited is listed (or ranked) 21 on the list 30+ Very Preppy Movies with the Preppiest Characters
carlybobarly added Emma Thompson, Hayley Atwell, Felicity Jones
Brideshead Revisited is a 2008 British drama film directed by Julian Jarrold. The screenplay by Jeremy Brock and Andrew Davies is based on the 1945 novel of the same name by Evelyn Waugh, which ...more
22
The Skulls is listed (or ranked) 22 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
23
Breakfast at Tiffany's is listed (or ranked) 23 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
24
Pretty in Pink is listed (or ranked) 24 on the list 30+ Very Preppy Movies with the Preppiest Characters
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
25
Oxford Blues is listed (or ranked) 25 on the list 30+ Very Preppy Movies with the Preppiest Characters
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.