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
Hilary Duff
Sam Montgomery
Chad Michael Murray
Austin Ames
Jennifer Coolidge
Fiona
Dan Byrd
Carter Farrell
Regina King
Rhonda
Julie Gonzalo
Shelby Cummings
Lin Shaye
Mrs. Wells
Madeline Zima
Brianna
Andrea Avery
Gabriella
Mary Pat Gleason
Eleanor
Paul Rodríguez
Bobby
Whip Hubley
Sam's Dad
Kevin Kilner
Austin's Dad
Erica Hubbard
Madison
Simon Helberg
Terry
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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