Hilary Duff as Sam Montgomery
Fun fact: Hilary told People that kissing Chad was better than her first kiss but "way more awkward" because of the amount of people watching. They actually practiced kissing in one of their trailers before they shot their first kiss three days into filming. Ooh la la.
Chad Michael Murray as Austin Ames
Fun fact: Rupert Grint, aka Ron Weasley, was initially offered the role of Austin Ames but had to turn it down due to filming conflicts with Harry Potter and the Prisoner of Azkaban.
Jennifer Coolidge as Fiona
Regina King as Rhonda
Fun fact: A Cinderella Story was the third movie Regina appeared in with Jennifer Coolidge. They appeared together in Down to Earth in 2001 and Legally Blonde 2: Red, White & Blonde in 2003.
Dan Byrd as Carter Farrell
Fun fact: In an interview with About Entertainment, Dan confirmed exactly what kind of a person Hilary Duff is. He said, "She's just incredibly down-to-earth and just a genuinely nice person. There's really no dirt I can give you on her because there's nothing there." No surprise! We ❤️ Hilary.
Julie Gonzalo as Shelby Cummings
Fun fact: Julie and Chad Michael Murray also starred together in the 2003 version of Freaky Friday!
Andrea Avery as Gabriella
Fun fact: The same year that A Cinderella Story was released, Andrea appeared in the movie First Daughter with Katie Holmes.
Madeline Zima as Brianna
Fun fact: Before Madeline played a nasty wicked stepsister, she played Grace Sheffield for six years on The Nanny!