20 Years Later: This Rom Com Is Still The Most Underrated Thing Hilary Duff Has Ever Done

It's been 20 years since A Cinderella Story came out, and it's still a banger. Here's why.

If you were to track the amount of times I’ve watched every romantic comedy, there are certain films that top the frequency list. Bangers and classics like The Holiday, You’ve Got Mail, and The DUFF are up there, but none of that would be a surprise. Alas, perhaps the tippy top of my list is a totally underrated Hilary Duff rom com–and today marks 20 years since it came out. We’re of course talking about the text message-filled Cinderella retelling, A Cinderella Story starring Duff and Chad Michael Murray. Here’s why it’s a classic and why it’s criminal if you still haven’t seen it after all these years.

Who doesn’t want to fall in love online?

A Cinderella Story is like a cross between a classic Cinderella retelling and the anonymous online love of You’ve Got Mail. Rather than just meeting the love of her life at a ball (although that does happen, too, thanks to the high school costume dance), it instead starts on the Internet. Sam has connected with someone online and all she knows about him is that he goes to her school and he loves poetry. They fall for each other online without pictures, but with words. It’s like you’ve removed all the gross swiping of 2024 and replaced it with adorableness.

THIS is 2000s fashion.

2000s fashion is back according to my TikTok FYP. But while today’s “youngsters” are wearing their low-rise boot cut jeans and low-slung fashion belts, they aren’t exactly accurately repping the era. If you want fashion, just look to Hilary Duff in A Cinderella Story. You can’t get much more authentically y2k than her layered tees.

The plot is so obvious, and that’s okay.

You’d expect a well-worn plot from a classic fairytale retelling–especially when it matches the vibe of a movie smack dab in the middle of the golden era of romantic comedies. Sam and Austin have been texting anonymously online and quietly falling for each other. When they agree to meet at the school dance, she dons a mask at the last minute for fear that he’ll be disappointed. Now he’s dead set on returning the bejeweled flip phone she accidentally left behind.

Indeed, you get the loner girl falling for the star football player. You get the guy who doesn’t recognize her even though he sees her literally every day. You get the “I’m not like other girls, I eat cheeseburgers” conversation. And yet…for some reason, even though A Cinderella Story is cliché, that’s okay. These are beloved tropes for a reason.

Jennifer Coolidge is the evil stepmother we didn’t know we needed.

She’s silly, she’s bright, she’s colorful, and she’s an icon. Jennifer Coolidge is a master when it comes to the evil stepmother. Does she want loads of salmon for her weird all-salmon diet? Definitely. And does she want Sam to work at her dad’s former diner forever, always under her pink-nailed thumb? Of course.

It has that certain something that has never been recaptured (although they definitely tried).

Is the acting great? Is it at all believable? Not really, but that’s not why we’re here. We’re celebrating A Cinderella Story’s 20th anniversary not because it was an Oscar-worthy teen rom com masterpiece, but because it hit all the right beats at exactly the right time. Even though the tech is dated and the evil stepsisters are anachronistally cringe, everything coalesced for this to become a classic that works decades later. Of course, they couldn’t capture the lightning in a bottle for the four–FOUR!–easily forgotten sequels, but we should all be thankful that Hilary Duff still graced our screens with this cute little flick.

You can watch A Cinderella Story on Amazon Video.