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It's also a really charming film that inspires young women to break the mold and march to the beat of their own drums. Anne Hathaway's breakthrough role as an ordinary San Francisco teen who suddenly finds out she's heir to the throne of a fictional European country called Genovia speaks to the secret teenage need to feel like you're special in a way that no one else recognizes. While it's funny, it's also not as purely fun as some of the other movies on this list. Veronica Sawyer Winona Ryder , is a member of a clique of beautiful and wealthy girls who all share the name Heather. And yet, there's something so deliciously enjoyable about the teen rom-coms of the '80s, '90s, and early aughts, with their stock characters, formulaic plots, and happy endings.

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