Forget Sex and the City or Girls: This unsung classic brilliantly understands the dynamics of female friendships. Even within the close-knit friend group, there are cliques. Teeny and Samantha, who both have family trouble, form one unit; Roberta and Chrissy another. You can see the beginnings of what will eventually divide them: The first two want nothing more than to get out of Shelby, and live bigger, bolder lives. To the latter, loyalty matters above all. It’s because of a pact Chrissy suggests that they all end up coming together nearly two decades later to help her through the last days of her pregnancy. She alone has conformed to the expectations society had for women at the time they were all growing up. And to young girls watching the film in the late ‘90s, Now and Then conveyed that they had options.