Cruel Intentions was the risque 1999 film adaptation of Pierre Choderlos de Laclos' 1782 novel 'Dangerous Liaisons'. Set in New York City, as opposed to the original 18th-century France, the film follows wealthy Kathryn Merteuil (Sarah Michelle Gellar) and step-brother Sebastian Valmont (Ryan Phillippe) as they wage a bet he can't make the innocent Annette Hargrove (Witherspoon) fall in love with him. The tale is dark, twisted and with a humorous edge that is still highly praised today. Its soundtrack, featuring Bitter Sweet Symphony by The Verve, should also not go without mention.
A film that really needs no introduction. The 2001 comedy was based on Amanda Brown's novel of the same name and follows Elle Woods (Witherspoon) as a sorority girl who attempts to win back her ex-boyfriend Warner Huntington III (Matthew Davis). Woods heads to Harvard, in the process falling for Emmett Richmond (Luke Wilson), all the while bending and snapping her way to becoming a successful lawyer.
Sweet Home Alabama
Witherspoon returned to her Southern roots for Sweet Home Alabama. The actress starred as Melanie Smooter, a New York City socialite who, after getting engaged to eligible bachelor Andrew Hennings (Patrick Dempsey), is forced to return home to obtain a divorce from husband Jake Perry (Josh Lucas) after seven years of separation. On top of getting its titular name from Lynyrd Skynyrd iconic rock song Sweet Home Alabama, the film is a tale of destiny, past mistakes and the discovery of self.
Walk The Line
Walk The Line is an American biographical musical drama based on two autobiographies authored by singer-songwriter Johnny Cash; 1975's Man in Black: His Own Story in His Own Words and 1997's Cash: The Autobiography. It follows Cash's (Joaquin Phoenix) early life, his romance with June Carter (Witherspoon), and his ascent in the country music scene. Witherspoon went on to win an Academy Award, BAFTA Award and Golden Globe Award for her portrayal as Carter.
Just Like Heaven
If you're in need of a good cry, Just Like Heaven is always a guaranteed tear-jerker. The film, directed by Mark Waters, is based on the french novel If Only It Were True by Marc Levy. It follows the life of lonely landscape architect David Abbott (Mark Ruffalo) who falls for the spirit of the beautiful and brazen Elizabeth Masterson (Witherspoon) who used to live in his new apartment.