'Thelma & Louise'
Thelma & Louise is a hard film to categorize. It's a chick flick, but it's also a crime-spree-based road trip movie featuring plenty of sex and violence. Like several other titles on this list, the meaning of personal freedom is questioned and plays a large role in the subtext of the film, but from a decidedly feminine perspective. Sure, it's a fun, entertaining movie, but it's also a fantastic character study offered up by two Oscar-winning actresses (Geena Davis and Susan Sarandon in their respective titular roles).