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Culture > Entertainment

A Definitive Ranking of All the ‘Cinderella Story’ Movies

This article is written by a student writer from the Her Campus at UCSD chapter.

Here’s a fact: I will forever be a die-hard fan of cheesy rom-coms, namely the ones of the early-2000s era. And of the best of all the cheesiest, sappiest, almost sickeningly-but-still-can’t-look-away cliche rom-coms, the Cinderella Story franchise – no, legacy – takes the cake. It is the pinnacle of Hollywood’s success, and no other movie series will be able to fill the enormous footprint that these Cinderella remakes have left behind. In my heart, at least. 

To solidify the movies’ well-deserved spot in the Movie Hall of Fame, I (me) worked with a certified Cinderella Story expert (also me) to compile the ultimate ranking of all the movies from worst to best. 

5. A Cinderella Story: Christmas Wish (2019)

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I’m not sure that this would come as a surprise to anyone (if anything, it would come as a surprise that this movie even exists), but yes, the newest remake is at the bottom of the list. As far as cheesy rom-coms go, it does what it’s meant to do. Attractive, billionaire male lead meets attractive but down-on-her-luck female lead. Sparks fly, complications arise, the power of main characters is used to defeat the complications, and the couple lives happily ever after. Like I said, it does what it’s meant to do … but that’s also why it sucks.

4. A Cinderella Story: If the Shoe Fits (2016)

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It’s the same deal, except this time it’s a combination of Hannah Montana and High School Musical … if Troy Bolton had an English accent. While the plot sounds crazy, it’s actually not terrible, although I’m not sure if I’m being biased because of how beautiful Sofia Carson looks in every scene. And if that’s not enough of an incentive to take the plunge and watch it for yourself, then I don’t know what is. The movie is an hour and a half of cheesiness in all its glory, and if I’m being completely honest, I like it more than I’m letting on.

3. A Cinderella Story (2004)


Now this is the one that everyone knows. Despite being only third on the list, it is arguably one of the best rom-coms of our time. The casting is perfect, the storyline is magnificent, and the costumes are incredible. The acting could be better, but if we’re being honest, casually terrible acting is one of the most redeeming qualities of any early-2000s movie. We also got some famous dialogue from this one, including the classic “You’re throwing away your dream, son!” “But it’s not my dream, Dad, it’s yours!” interaction, as well as the unforgettable “Because waiting for you [Austin Ames] is like waiting for rain in this drought. Useless and disappointing.” A way for Californians everywhere to empathize and a roast all in one? I’m surprised Austin Ames didn’t disintegrate into ashes from the heat of Sam’s burn. Let’s let Hillary Duff teach us all a lesson: if someone, even if they are Chad Michael Murray, is embarrassed of you, ditch them. Unless, of course, he kisses you in the rain in front of everybody and their mothers, and gets accepted to Princeton. Then, by all means.

2. A Cinderella Story: Once Upon a Song (2011)

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This is the single most underrated film in the world, and I will stand by that statement until the very end. The songs are absolutely the best thing about this movie and remain in my playlist even to this day. And while all the other stepmothers and stepsisters are classic villain archetypes, we’re able to see a more fleshed out stepsister in this movie, revealing how most “villains” are likely just products of their environment. This remake was in consideration to be number 1, if only for two critical things that ruined its chances. One, the blatant cultural appropriation, and two, the male lead has zero personality. Sure, he was cute and sang a pretty (very) catchy song, and if I’m being honest I did have a crush on his character, but he was also so bland. And unfortunately, in comparison to Drew Seeley’s dynamic character in the ultimate winner, he was just lacking too much.

1. Another Cinderella Story (2008)

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This is hands down the best Cinderella Story remake there ever was. The stepmother and stepsisters are a hoot, the entire plot is engaging, and you can find yourself really rooting for the main couple. Drew Seeley as this movie’s Prince Charming is impeccable (because he actually has a personality) and Selena Gomez, as always, plays her part beyond fantastically. Imagine everything you ever needed given to you in a single hour and a half, complete with a masked dance, a quirky fairy godmother in a tutu, and Jane Lynch singing about bacne. Utter perfection.

Ashley Xu

UCSD '23

I'm a junior at UCSD majoring in economics, and I'm interested in playing music and reading!