An oldie but a goodie, Casablanca will never be irrelevant in the chick flick world. The best part is that with Humphrey Bogart starring, the men won't complain too much if you insist on watching it one rainy evening. Set during World War II, this 1942 film was ahead of its time, considering the war didn't end until 1945.
The plot is centered around Rick Blaine (Humphrey Bogart), an American who runs a bar in Casablanca, Morocco, during World War II. Though it's illegal, his bar is a hot spot for refugees hoping to escape to America. When his ex-lover, Ilsa (Ingrid Bergman) and her husband show up, he has to make some difficult decisions. The film went on to win an Academy Award for Best Picture, as well as Best Director and Best Adapted Screenplay.