6. Chasing Amy (1997)
Although Chasing Amy gets a lot of criticism for being a film that feels very dated, it still functions as an original contribution to cinema. What makes Chasing Amy so effective is the way it captures the fragility of the male ego. Kevin Smith, no stranger to creating immature male characters, made a film that features the same immature characters we would expect and gives them a life lesson to remember. Chasing Amy may be perceived as problematic by today’s standards, but it deserves a nod for attempting to put a serious story in a comedy.
7. Love Story (1970)
There are similar movies like Love Story that feature familiar tropes. For example, we’ve seen a man fall in love with a woman who has been diagnosed with an illness before (most recently in The Big Sick). However, Love Story remains a film worth watching for its earnestness. It’s definitely a sappy romantic film, but it was nominated for seven Oscars for a reason. Even though it may not be as challenging as some of the other films on this list, Love Story is a classic.
8. Brief Encounter (1945)
Before David Lean would become well known for making sweeping Hollywood epics like Lawrence of Arabia, he made one of the most ahead-of-its-time relationship films ever. For a black and white film, Brief Encounter feels surprisingly unique in its portrayal of a couple that love each other but cannot be together. Another great pre-epic David Lean film to tackle the complexity of relationships: The Passionate Friends.
9. Stromboli (1950)
Roberto Rossellini’s work with Ingrid Bergman is important when discussing relationship films due to the groundbreaking way in which the theme is explored. In Stromboli, Ingrid Bergman’s character falls in love only to realize it won’t make her happy. She suffers from the strange dynamic of being in love, yet still feeling unfulfilled. It’s a challenging predicament to be in: what do you do when love isn’t the answer it seems to be? Another Rossellini film worth mentioning on this list: Journey to Italy.
10. War of the Roses (1989)
This is the most unusual film on this list. It’s a film with a mature premise that gets incredibly silly, and that really works to its benefit. The strength of this movie is that it really goes for its goofy humour. A movie that has divorce and comedy could easily go wrong, but War of the Roses is a lot of fun. It’s outlandish to the point of being almost in cartoon territory, and that’s somehow extremely fitting.
Author Bio: Dilair Singh is a film lover from Toronto. He particularly enjoys screenwriting, and hopes to sell a screenplay someday. You can find him on Twitter: @dilairsingh.