open/close all folders
Sam Montgomery
Portrayed by: Hilary Duff(Aged 16)
Hannah Robinson(Aged 10)
A tomboyish girl raised by her Wicked Stepmother and lives with her two nasty step-sisters while working at a local diner.
- All of the Other Reindeer: The whole school seems to dislike Sam. During the pep-rally scene, everyone joins in chanting "Diner Girl" (Shelby's cruel nickname for her) at Sam. There is a later scene with people laughing and pointing at Sam in the hallway, while she's crying... It's implied that they don't like her because she works in an 'uncool' job. It's not actually that uncommon for kids who are better off to mock and belittle kids who have to work for a living.
- Bad Bedroom, Bad Life: Sam is forced to move into the family's attic after her father dies, showing the immediate downgrade she goes through.
- Break the Cutie: From losing her father, having an awful stepfamily and being hated by literally everyone at school, no wonder she’s so miserable.
- Clark Kenting: All she wore was a mask covering her eyes at the dance. Despite having a lengthy conversation with Austin at the dance, he can't tell she's Cinderella when they have a conversation at the diner after the dance.
- Deadpan Snarker: She has her moments, particularly towards Shelby when she’s forced to wait on her:Shelby: What can I get here that has no carbs, no sugar, and is fat free?Sam: Water.
- Didn't Think This Through: A downplayed example. When Sam announces to Fiona that she's moving out, Fiona asks her where she plans on living, and the look on Sam's face implies that she hadn't thought of that yet. However, Rhonda immediately volunteers to take Sam in.
- Diligent Hero, Slothful Villain: Between herself and her stepfamily and Shelby. She’s forced to wait on her stepfamily on every whim while they refuses to do ANY household chores nor help at the diner. Shelby is a popular, yet unemployed Alpha Bitch who revels at bullying Sam just because she’s forced to be employed at the diner.
- The Dog Bites Back: Once Sam finds her dad’s will, she finds out she’s the sole heir to his properties and wealth. The first thing she does is sell her abusive stepfamily’s cars to help pay for her new life at Princeton, leading to the cops to chase Fiona around the yard due to her witness statement of her late husband’s will and depriving Sam of all of her father’s belongings. She also forces her stepsisters to dig into garbage to find her acceptance letter. Rather than go to prison, Fiona and her daughters agree to work off their debt at the diner to pay back all the money they stole from her inheritance.
- Earn Your Happy Ending: At the end of it all, after moving in with Rhonda and confronting Austin over his cowardice at the pep rally, she finally gets together with him. Later, while packing up the rest of her things she finds her father's will which leaves everything (the house, the diner, etc.) to her. After consulting with the local D.A. about it, she has Fiona arrested for financial and inheritance fraud (because she knew the will existed and even signed it as a witness, but pretended that it didn't to get everything for herself and her daughters), and learns that she was in fact accepted to Princeton (after Fiona duped her into believing that she had been rejected) after her stepsisters retrieve the acceptance letter from the trash where their mother had "filed" it. Sam then seizes and sells her stepfamily's luxuries and possessions to pay for college (since all of them are legally hers due to her stepfamily buying them with money that was legally hers without her knowledge or permission), makes Rhonda co-owner of the diner, and with the help of the D.A. puts her stepfamily to work there to make back all the money they stole from her over the years. And finally, she ends up getting her cell phone back and going off to Princeton with Austin.
- Everyone's Baby Sister: She's this to her co-workers, and Carter.
- Hair of Gold, Heart of Gold: She's a blondie (due to being played by Hilary Duff and Hannah Robinson, who are blonde, albeit
naturally brunette) and has a sweet personality. - Nice Girl: In spite of her background, she's generally a sweet, likable person.
- Only Known by Their Nickname: Not to the audience, but Austin only knows her as "Princeton Girl" and "Cinderella," and the popular kids call her "Diner Girl".
- Service Sector Stereotypes: Poor, poor "Diner Girl." Somewhat justified in that her stepmother is taking advantage of the situation.
- Soul-Sucking Retail Job: She is severely underpaid and overworked as a waitress, something Shelby and her Girl Posse make fun of her for. Of course, she eventually quits alongside Rhonda.
- Tomboyish Name: She's exclusively called by a traditionally masculine name and has a number of masculine interests.
- Tomboy with a Girly Streak: Being raised by a single father, Sam grows up knowing more about sports than fashion, though this is more of an Informed Ability at best. She has no aversion to wearing a gown for the ball, is initially upset to learn her mystery boy is a jock, and is more interested in academics than sports. She also loves fairy tales.
- The Unfavorite: Most prominently, she's shown to be purposely excluded in Fiona's wedding photo.
- What the Hell, Hero?: She calls out Austin for not coming to her defense when she gets publicly humiliated at the pep-rally.
Austin Ames
Portrayed by: Chad Michael Murray
The local jock who becomes Sam's love interest.
- Alliterative Name: Austin Ames.
- Jerk Jock: Played with. He tries to be the Nice Guy and the movie expects us to sympathize with him. He is also tired of being part of the popular crowd and having to meet their expectations and his father's, wanting to recreate himself as a writer. On the other hand, he cheats on his girlfriend, practically stalks Sam, rejects her for being a waitress, makes no effort to stick up for her to Shelby, and appear to not care about Sam’s well being in the first place. He does not even appear to help Sam reclaim her inheritance back at the end, though it's possible he might've been hashing out things with his father at the same time. It's kind of a
Broken Aesop that his only redeeming characteristics are that he is rich and pretty. To his credit, it is implied that he never actually rejected Sam, he was just unsure what to do in the situation, and was possibly hurt by her not coming forward about her true identity when she had the chance (though this is still no excuse for not standing up for her). Sam certainly believes this, as why else would she tell him that she was not going to wait for him anymore. For what it's worth, he never goes back to Shelby and he doesn’t even call her out for all the horrid things she did to Sam, though in this case, he probably figured it wouldn't have made a difference since Shelby was clearly too stuck in her snobbish ways to change. - Lack of Empathy: When he finds out that Sam is unpopular and a waitress, he doesn't defend her, possibly out of hurt by her failure to confess who she was herself when she had the chance.
- Sympathetic Adulterer: He is essentially cheating on Shelby with Sam from the beginning. This is portrayed as a good thing as Shelby is "evil" and it's also noted that he had become disillusioned with their relationship due to wanting to start being true to himself instead of what everyone expected and/or wanted him to be.
Carter Ferrell
Portrayed by: Dan Byrd
Sam's best friend and an aspiring actor.
- Beware the Nice Ones: The nerdy, unimposing Carter turns out to be a surprisingly effective fighter due to extensive stage combat experience, easily knocking a football player out when he has to.
- Big Brother Instinct: He's protective of Sam, and supports her throughout the movie.
- Broken Pedestal: To Shelby, during the prep rally and after the prep rally, he realize what a terrible person she is.
- Dogged Nice Guy: To Shelby, even though she doesn't like him.
- Earn Your Happy Ending: He gets a spot on a commercial that makes him popular and gets him a lot of attention from women, even Shelby who he is no longer interested in.
- Grew a Spine: He becomes more confident and assertive, even dismissing Shelby after learning what a terrible person she is.
- Lonely Together: He and Sam don't seem to have any friends besides each other.
- Nice Guy: He's a very friendly and good-natured guy.
- The Not-Love Interest: He harbors no feelings for Sam, and supports her romance with Austin.
- Only Friend: Carter is Sam's only friend.
- Platonic Life-Partners: He's Sam's best friend and their relationship never goes beyond that.
- Pretty Fly for a White Guy: When white boy Carter tries to dress like a hip-hopper.
Fiona Montgomery
Portrayed by: Jennifer Coolidge
Sam's greedy and self-absorbed step-mother.
- Ambition Is Evil: She's rather opportunistic when money is concerned, as she constantly pushes her biological daughters to marry a good-looking rich guy.
- Bad Boss: She treats all the employees at the diner horribly and they all despise her in turn.
- Bitch in Sheep's Clothing: Not to the viewer, but it is implied she gets away with exploiting her stepdaughter because she is merely helping her to raise money for Princeton. Little does Sam know that Fiona has no intention of getting rid of her unpaid employee.
- Conspicuous Consumption: How the hell she is able to flaunt so much is never explained when she would logically have as much as Sam's father, but with even more dependents. Of course, she is at least saving money by extorting Sam, and is probably mooching off her husband's insurance (though this is never mentioned).
- Dirty Coward: When things go against Fiona, her arrogant demeanor completely disappears. She tries to hide behind Brianna and Gabriella when Rhonda finally stands up to her, and tries pitifully to run away from the police when her late husband's will is found.
- Evil Is Bigger: She's the main villain and played by Jennifer Coolidge who stands at 5'10, making her noticeably taller than Sam, played by 5'1 Hilary Duff, and Rhonda, played by 5'3 Regina King, who barely come up to Fiona's shoulders.
- Fostering for Profit: Unusually, her victim, Sam, is her stepdaughter rather than a foster-child, but the trope still applies, as she extorts the money Sam makes at the diner for herself. To make matters worse, she also stole Sam's inheritance. Sam could have saved herself years of abuse and humiliation if she just looked in her old storybook. Fortunately, she and her daughters are forced to work off every last cent they took from Sam, including the money Sam earned for them as a waitress.
- Fun-Hating Villain: At least as far as Sam's fun is concerned, as she has no problem ruining her stepdaughter's social life to make her work.
- Global Ignorance: Boasts that she gets her salmon from "Norweigia". Those versed in world geography will notice that there is no such place.
- Gold Digger: It's implied she married Sam's father for his money and once he died, she wastes no time in spending the money he left for Sam.
- Hate Sink: Each trope here defines how detestable Fiona is.
- Insufferable Imbecile: Fiona isn't just a loathsome human being. She's also very stupid and possesses a massively overblown ego, thinking herself far more savvy than she actually is.
- It's All About Me: Fiona very clearly doesn't care about anyone but herself, not even her own daughters.
- Jerkass: Fiona is selfish, unpleasant, greedy, emotionally abusive, vain, rude and generally just a horrible person, through and through.
- Large Ham: Oh yeah. Jennifer Coolidge is clearly having a wonderful time and not a scene goes by where she doesn't gleefully devour the scenery.
- Laughably Evil: Occasionally. It's difficult to overstate just how wretched a person Fiona is but Jennifer Coolidge's wonderful performance makes her a delight to watch all the same.
- Makeup Is Evil: Exaggerated in that she is also obsessed with plastic surgery and her makeup is exagerated compared to the comparatively natural looking Sam and Rhonda.
- Obnoxious Entitled Housewife: She is a rude and greedy woman who makes a show of her Conspicuous Consumption, mistreats her workers at the diner, feels entitled to having a green lawn to reflect her wealth even in a drought, and thinks to argue with the LAPD even after she is caught having stolen Sam's inheritance.
- Pet the Dog: Zigzagged. She’s hidden Sam’s acceptance letter to Princeton, and once she finds Sam crying her eyes out over the pep-rally incident, then gives her a fake rejection letter from Princeton, Fiona “acts” just as sad but gives Sam a whole plate of chocolate chip cookies.
- Politically Incorrect Villain: As if she weren't horrid enough already, she makes subtly racist remarks to Rhonda, calling her "the Betty Crocker of the hood".
- Small Name, Big Ego: Somehow owning a diner makes her comparable to Jennifer Lopez.
- Trademark Favorite Food: She has a fixation on salmon that borders on an obsession.
- Wicked Stepmother: Even on her wedding day to Sam's father, she does little things to belittle Sam and takes it up to eleven well into Sam's teen years.
- Wicked Wastefulness: One subtle aspect of Fiona's greed and cruelty is that she needlessly wastes water on keeping her lawn green in the middle of the California drought. Sam points this out to her, but she refuses to back down.
Brianna & Gabriella
Portrayed by: Madeline Zima and Andrea Avery Ray
Sam's two snobby step-sisters.
- Beauty Equals Goodness: They might just be awkward in appearance, but are truly ugly on the inside.
- Color-Coded for Your Convenience: They usually wear pink and green, though not consistently, as a reference to the Disney version of the story.
- Crocodile Tears: Both of them use this and Shelby and her posse to get them to help the two humiliate Sam.
- The Ditz: Brianna, who even forces Sam to do her homework for her. Gabriella is a bit craftier.
- Fat and Skinny: Gabriella's fat to Brianna's skinny (In fact, Andrea Avery was instructed to become Hollywood Pudgy in order to invoke the trope).
- Gasshole: Brianna. As if farting (while in the pool) in her sister's general direction wasn't enough, during the "race" back to the diner, she says (out loud, and in a cat costume, no less) that she needs the "litter box".
- The Glorious War of Sisterly Rivalry: They spend a good portion of their screen time sniping at one another.
- Meaningful Name: Their names are a play on Anastasia and Drizella.
- Spoiled Brat: Both; their spending come back to bite them in the asses when they are forced to pay off their debts for the money they stole from Sam.
- Straw Loser: They may be Rich Bitch and Spoiled Brat twin stepsisters, but they just don't achieve anything.
- Those Two Guys: They practically don't do anything until three-quarters into the movie.
- Wounded Gazelle Gambit: They lie to Shelby that Sam set up the whole "Cinderella" game in an attempt to hurt her, and add on that they only waited to tell her because she threatened them. Also see "Crocodile Tears".
Shelby Cummings
Portrayed by: Julie Gonzalo
The local bully who enjoys making Sam miserable.
- Absurdly Powerful Student Council: How the hell does she go unpunished for the pep-rally scene? Seriously, the faculty are visually mortified at what she did to Sam, but they seem to have forgotten they have the power to punish her.
- Alpha Bitch: She not only mocks and belittles Sam for presumably years, she seems to have turned the whole school against "Diner Girl."
- Beauty Is Bad: She's very pretty and a deeply unpleasant person.
- Betty and Veronica: The Veronica to Sam's Betty, though it turns out that Sam is likely richer than her, as well as to Astrid.
- Book Dumb: She thinks that The Three Musketeers is just a candy bar and cheats off of Carter on tests.
- Cruel Cheerleader: Shelby has the cheerleaders perform a skit during the pep rally based on the email exchange between Sam and Austin and then names Sam as the "Cinderella" in the email exchange.
- Domestic Abuse: She flat out refuses to let Austin break up with her, accusing him of being temporarily insane afterward. In the same scene, she demands that they discuss any private issues they have in front of her friends (i.e, in a situation where peer pressure is against him).
- Diligent Hero, Slothful Villain: Between her and Sam. If anything indicates, she’s an unemployed yet popular Alpha Bitch, while Sam is forced by her stepmom to work at her family’s diner.
- Evil Is Petty: Let's make fun of the girl who has to work for a living! Borders on Fridge Horror and hypocritical when you realize she does not have a problem with Austin being a gas-station attendant (who like Sam, works for his family's business, they are just taking advantage of the situation like Sam); when you think about it, she essentially tortures Sam for being an abuse victim.
- For the Evulz: She abuses Sam merely for her own sadistic amusement.
- Hate Sink: She's needlessly cruel to Sam and the pep-rally scene will surely get her underneath your skin.
- Hypocrite: She hates Sam and leads the bullying against her just because she’s employed at her family’s business. Yet her boyfriend is also employed at his family’s business and doesn’t so much as taunt him over it.
- Immune to Slapstick: In contrast to her Co-Dragons Brianna and Gabriella (who got a physical Humiliation Conga), the only comeuppance she got was ending up without a boyfriend. Averted in the novelization.
- Jerkass: She's pretty mean-spirited to Sam and domineering to both Austin and Carter.
- Karma Houdini: Because Fiona and the stepsisters are the real villains of the movie, she doesn't receive any punishment for being so cruel to Sam, even when relentlessly bullying her in public in front of multiple teachers during the pep rally scene and Sam doesn’t even confront her, nor does she get called out for being a bitch by anyone else (Austin gives her the silent treatment). She does get knocked down a peg or two emotionally when Austin clearly chooses Sam at the final game, but since everyone's attention is on them rather than her, it's hardly a real comeuppance. Though the finale does imply she's no longer as popular as she's now trying to boost her reputation by getting with Carter who no longer wants anything to do with her.
- Karma Houdini Warranty: In the novelization, Shelby does get her comeuppance by having some of the football players accidentally knocking her down into the mud after the end of the football game.
- Kick the Dog: If her rejecting Carter was not enough for you, the pep-rally scene kills what little sympathy you might have for her.
- Lack of Empathy: She makes fun of Sam for her Soul-Sucking Retail Job as a waitress and remorselessly drives Sam to tears by having the entire school chant "diner girl" at her.
- Laser-Guided Karma: At least in regards to her relationships. Austin dumps her for the girl she spent the movie bullying and Carter rejects her advances because he knows she's just using him for his newfound popularity after he stars in a commercial. So she loses any chance for a popular boyfriend.
- Popular Is Dumb: She's the mean popular girl who has to cheat off a "geek" to pass tests, only thinks that The Three Musketeers are chocolate, and doesn't even know what a foreign word for "goodbye" means. To top it off, she and her posse were stupid enough to even believe the lies that the stepsisters told her about Sam wanting to steal away Austin.
- Rich Bitch: Probably, though the movie never actually mentions that she has money except in a deleted scene, but this is presumably why she looks down on Sam, who was to work for her keep. It is also possible, however, that she is merely a Gold Digger, as she is clearly aware of Austin's money and status.
- Sadist: She clearly takes joy in making Sam miserable.
- Took a Level in Jerkass: While she is a bully from her first appearance, the movie sets her up for a Heel–Face Turn when she shows interest in Carter. She later snobbily rejects him in public when she realizes he is an outcast boy, and when she realizes Sam is "Cinderella," she publicly humiliates her at the pep-rally scene.
- Ungrateful Bitch: To Carter. He is probably the first guy to ever treat her like a lady, but later wants nothing to do with an outcast like him. After Austin finally leaves her for Sam, Shelby makes another pass at Carter (just because he's moderately famous now), who in turn rejects her for Astrid.
- Villain with Good Publicity: The pep-rally scene. It may have not lasted. The people cheering for Carter at the end might also be cheering that he rejected her.
- Villainesses Want Heroes: Technically subverted in that Austin started out as her boyfriend, though this is partially played straight in that she bullied Sam before she became her rival to Austin.
- Woman Scorned: Though she victimizes Sam more than her ex, Austin, she exposes Sam as "Cinderella" during a cruel pep-rally skit.
Madison & Caitlyn
Portrayed by: Erica Hubbard and Kady Cole
Shelby's posse of bullies who harass Sam.
- All There In The Credits: Caitlyn's name is never spoken onscreen in the movie itself.
- Beauty Is Bad: Like Shelby, they are as pretty on the outside as they are ugly on the inside.
- Even Evil Has Standards: They never try to trick Austin into thinking they are "Cinderella," though this is probably more out of a fear of Shelby than anything.
- Green-Eyed Monster: Lampshaded by Shelby when Madison tells her to quit ranting about the guy (Carter) who saved her during the costume party.Shelby: "Madison, I think there's a green monster on your back called 'Mr. Jealousy'!"
- Karma Houdini: They gleefully help Shelby torture and humiliate poor Sam, as if she did not have enough problems, and Carter throughout the movie. The closest they get to a comeuppance is when Carter rejects the three of them when Shelby makes an unsuccessful pass at them. It is possible that they were also trying to flirt with him, or that the whole thing was a last-ditch attempt to save face and it's implied they've lost their social standing, same as Shelby has.
Rhonda
Portrayed by: Regina King
Sam's co-worker and manager and mother figure of the diner.
- Dark and Troubled Past: She got into fights in school and left some guy at the altar. Fortunately, she kept the dress...
- The Dog Bites Back: After years of putting up with Fiona's mistreatment of her for Sam's sake, she ends up Fiona's supervisor and works her very hard.
- Girl Friday: To both Sam and her father, she is the one whom they trust to take care of things in the diner and their lives her devotion and hard work earns her a position as a co-owner of the diner in the end.
- Hyper-Competent Sidekick: She's pretty much the only reason the diner operates efficiently and she knows it.
- Karmic Jackpot: Sam, after discovering her father's will, makes Rhonda the diner's co-owner, and she keeps a sharp eye on her former Bad Boss Fiona.
- Nice Girl: She's a very kind person who is one of the few people in Sam's life to care about her and show her any kindness.
- Parental Substitute: To Sam. Fittingly, she adopts Sam by the end.
- Sassy Black Woman: She is usually a friendly, caring person, but she will get sassy if you deserve it. Partially subverted in that she puts up with Fiona for Sam's abuse.
- Screw the Rules, I Have Connections!: She is able to get away with going against Fiona's abuse because she practically runs the place, and especially brings in the clientele. She manages to get the entire diner to walk out on Fiona in Sam's defense towards the end.
- Service Sector Stereotypes: Played with. Being a waitress is actually portrayed as a decent job for Rhonda when she worked for Sam's father, and only became demeaning when Fiona took over. Played straight in that her happy ending is being promoted to "co-owner."
- Servile Snarker: She makes almost no effort to hide her contempt for Fiona when talking back to her.
- Team Mom: To the whole diner staff, especially Sam. When Rhonda quits, everyone else follows as well.
- You Are Not Alone: After losing everything towards the climax, Rhonda assures Sam this is the case.
Hal(Harold) Montgomery
Portrayed by: Whip Hubley
Sam's deceased sports-loving father.
- Benevolent Boss: He is a well-loved guy, loved by his employees who stay loyal to his memory and work at his diner despite his wife's mistreatment of them and is shown to be a decent boss who wants to serve food that people can enjoy.
- Deceased Parents Are the Best: Though he was stupid enough to marry Fiona, he at least had the sense to leave everything to Sam.
- Didn't Think This Through: He didn't leave his will with anyone who could legally and automatically enforce it should he die unexpectedly, but instead hid it inside one of his daughter's books. If she had found it right after his death, would she even have known what to do with it? As it is, she doesn't find it for eight years, and is emotionally abused and financially exploited by her step-family for all that time.
- Good Parents: He was a kind and loving father to Sam who still misses him dearly.
- Uncle Pennybags: Probably; the movie never mentions how financially well-off he was, but considering how much Fiona flaunts his wealth after his death, he probably was not doing so bad. He was also a loving father and a kind boss.
