WARNING! Potential spoilers on this list.
We’ve been trained by Hollywood to expect that the guy will always get the girl at the end of the movie. The couple will be greater than their differences, overcome their enormous obstacles, and fight against all odds to stay together in order to live happily ever after. That’s how all great romantic movies end, right? Yes. Except when they don't.
This is not a list of films where relationships end because someone died like in Love Story. Instead, this list ranks the best movies and rom coms that dare challenge Hollywood conventions and shove past genre codes, even at the expense of audience delight. In these movies, the guy doesn't get the girl, there isn’t a happy ending, and we can’t imagine a future filled with children and Disney vacations.
Sometimes romantic comedies and other films about relationships are actually like real life. And in real life, most relationships simply don't work out. Not every couple is meant to overcome their differences (The Way We Were), not every couple can fight against uncontrollable odds and stay together (Casablanca), and not every couple is meant to last for the long haul (500 Days of Summer).
We might cry at the end of Casablanca every time we see Bogey watch Bergman get on that plane, but admit it, doesn’t the bittersweet ending help to make Casablanca one of the best films ever made? Life isn’t all about happy endings anyway. There has to be some truth, even in our entertainment. So vote up the best movies about in which guys don't get the girl and hope that your own attempts at true love are more successful.
An epic story of romance during the American Civil War, a Southern belle and an outsider fall madly in love. But Scarlett (Vivien Leigh) turns Rhett (Clark Gable) away, then begs him to come back to her. The guy doesn't get the girl in the end, because he frankly didn't give a damn about her crying pleas that she never stopped loving him.