The 50 Best R-rated Rom-Coms of the Past 50 Years

Gillian Robespierre directed and co-wrote this film that subverts the rom-com genre in telling the story of a comedienne (Jenny Slate) whose fling with a graduate student results in an unplanned pregnancy, causing her to address the challenges of independent womanhood.

Billy Wilder produced, directed, and co-wrote this farce about the son (Jack Lemmon) of a millionaire who goes to the Italian island of Ischia to recover the body of his deceased dad and uncovers less-savory aspects of his dead father’s life. While in Italy he has a romantic relationship with a free-spirited Brit (Juliet Mills). This was one of seven Wilder and Lemmon collaborations.

Directed and written by Paul Thomas Anderson, “Licorice Pizza” takes place in California’s San Fernando Valley in 1973, and is about the first love of a teen (Cooper Hoffman – Philip Seymour Hoffman’s son) who sets his sights on a young woman living a purposeless life.

Another rom-com/drama written and directed by Paul Thomas Anderson, this film stars Adam Sandler as a sexually frustrated man whose call to a phone-sex line triggers an unfortunate set of events that could complicate his budding relationship with a mysterious woman (Emily Watson). The film is darker than other rom-coms Sandler has appeared in.

A galaxy of stars distinguishes this quintessential date movie about a high school reunion at which Willie (Tim Hutton), Tommy (Matt Dillon), and Paul (Michael Rapaport) are prepared to connect with “beautiful girls” Lauren Holly, Natalie Portman, Mira Sorvino, and Uma Thurman. The film featured three Oscar winners: Hutton, Portman, and Sorvino.