

Routinely exploited by her wicked stepmother, the downtrodden Samantha Montgomery is excited about the prospect of meeting her Internet beau at the school's Halloween dance.
Acting
Jennifer Coolidge's unhinged stepmother is camp perfection.
Costume
That rhinestone mask lives rent-free in millennial brains.
Writing
'Waiting for you is like waiting for rain in this drought' — devastating.

Director
Mark Rosman
Trivia, insights & behind the scenes
This launched the 'modern fairy tale' boom of the 2000s alongside 'Ella Enchanted' and 'What a Girl Wants,' directly influencing Netflix's later rom-com factory.
The Princeton acceptance letter prop misspelled 'acceptance' as 'acceptence' — editors noticed too late, kept it, and now it's immortalized in screencaps.
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