Cast
- Hilary Duff as Samantha "Sam" Montgomery, a tomboy who used to be employed at her father's diner and now is the owner of the diner and Austin's new girlfriend.
- Chad Michael Murray as Austin Ames. He hides who he is because of his father and Shelby, but with help from Sam, he finds the courage to stand up for what he wants and becomes Sam's boyfriend.
- Jennifer Coolidge as Fiona Montgomery. When Hal was killed in the earthquake, she got all his belongings which went to Sam after she found the will.
- Regina King as Rhonda, Sam's co-worker and friend
- Madeline Zima as Brianna Montgomery. She is the younger twin and much more dimwitted than Gabriella.
- Andrea Avery as Gabriella Montgomery. She is the older twin by a minute and 26 seconds. She is dimwitted but smarter than Brianna.
- Dan Byrd as Carter Farrell, an aspiring actor and Sam's best friend.
- Julie Gonzalo as Shelby Cummings, Austin's former girlfriend and cheerleader
- Aimee-Lynn Chadwick as Astrid, the school's DJ who becomes Carter's girlfriend
- Brad Bufanda as David, Austin's friend
- J.D. Pardo as Ryan Henson, Austin's friend
- Simon Helberg as Terrence, a boy at Sam's school. He is possibly the only character who refers to Sam as "Samantha".
- Erica Hubbard as Madison
- Kady Cole as Caitlyn
- Mary Pat Gleason as Eleanor
- Paul Rodriguez as Bobby, the head chef at Hal's/Fiona's
- Lin Shaye as Mrs. Wells
- Whip Hubley as Harold "Hal" Montgomery, Sam's father.
- Kevin Kilner as Andy Ames, Austin's father.
- James Eckhouse as Mr. Farrell, Carter's father
- Hannah Robinson as Young Sam
- Rory Thost as Young Carter
- Carly Westerman as Young Brianna
- Lilly Babb as Young Gabriella
Read more about this topic: A Cinderella Story
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