Benny & Joon
1 / 14VIEW ALL
Johnny Depp memorably portrayed the eccentric Sam in the 1993 dramedy Benny & Joon. Sam, who models himself after silent screen star Buster Keaton, woos the mentally ill Joon (Mary Stuart Masterson) in this tender love story.
2 / 14VIEW ALL
The Holiday (starring Cameron Diaz, Jude Law, Kate Winslet, and Jack Black) features four neurotic characters struggling with relationships. When Iris and Amanda trade homes in different countries over Christmas, they develop new outlooks on love.
Splendor in the Grass
3 / 14VIEW ALL
In the classic 1961 melodrama Splendor in the Grass, teenage Deanie (Natalie Wood) has a mental breakdown and is institutionalized when she loses her boyfriend, Bud (Warren Beatty). But Deanie later gets another chance at love with a fellow psychiatric patient.
Silver Linings Playbook
4 / 14VIEW ALL
Arguably the best collaboration between Bradley Cooper and Jennifer Lawrence is this romantic dramedy about former psychiatric patient Pat, who enters a dance competition with recent widow Tiffany in exchange for her help in winning back his ex-wife.
The Perks of Being a Wallflower
5 / 14VIEW ALL
This coming-of-age movie is based on Stephen Chbosky's bestselling novel and follows Charlie (Logan Lerman), a troubled insecure high school freshman who begins to explore life and love with the help of two exciting seniors.
13 Going on 30
6 / 14VIEW ALL
Some great dysfunctional characters come out of fantasy, like the deeply flawed Jenna (Jennifer Garner) in the time-travel comedy 13 Going on 30, who must get her priorities straight before she can be with her soul mate Matt (Mark Ruffalo).
7 / 14VIEW ALL
An important aspect of Sylvester Stallone's iconic Oscar-winning sports drama Rocky is the sensitive love story between Rocky and the socially challenged Adrian (Talia Shire), which adds much to the inspiring theme of the film.
8 / 14VIEW ALL
in the 2001 romantic comedy Shallow Hal, Jack Black portrays a superficial, immature womanizer who falls in love with the very overweight Rosemary (Gwyneth Paltrow) after being hypnotized by Tony Robbins to see just inner beauty.
Only the Lonely
9 / 14VIEW ALL
In the 1991 romantic dramedy Only the Lonely, aspiring makeup artist Theresa (Ally Sheedy) tries to overcome her extreme shyness to build a relationship with Chicago cop Danny (John Candy), who is struggling to break free of his domineering mother.
10 / 14VIEW ALL
This comedy about four middle-aged suburban guys who form a biker gang and go on a road trip features a funny but heartwarming romance between socially inept computer geek Dudley (William H. Macy) and sexy restaurant owner Maggie (Marisa Tomei).
Swept from the Sea
11 / 14VIEW ALL
This romantic drama (starring Rachel Weisz and Vincent Perez) centers on two misfits in a small 19th-century English town: the eccentric, antisocial Amy and the Russian shipwreck survivor Yanko, who resist their community's efforts to tear them apart.
12 / 14VIEW ALL
The 1995 drama Mad Love, starring Drew Barrymore and Chris O'Donnell as two love-struck runaways (Matt and Casey), looks like a Romeo and Juliet story on the surface but turns more complex when Casey's mental illness is revealed.
13 / 14VIEW ALL
This critically acclaimed film tells the offbeat story of a romance between an English woman (Emily Watson) and a lonely, psychologically troubled novelty supplier (Adam Sandler), who is being extorted by a phone-sex hotline.
As Good As It Gets
14 / 14VIEW ALL
Critically acclaimed box office hit As Good As It Gets (starring Jack Nicholson, Helen Hunt and Greg Kinnear) tells the story of three unlikely companions and centers on an intriguing potential romance between the cynical, neurotic author Melvin and the good-hearted waitress Carol.