Revisiting "A Cinderella Story": An Early 2000s Millennial Fairy Tale
Courtesy of Warner Bros. Pictures
When I was in high school, I always dreamed of a prince sweeping me off my feet. At the time, the fantasy was far-fetched; the stuff of dreams. After all, I was a brown girl at a mostly white high school, where people were incapable of being themselves because of social status, parental pressure, and the deep-seated insecurity that motivates suburban youth from the precarious ages of 14 to 18. I liked reading books, I didn’t enjoy playing sports, and my voice was marred by the lilt of an accent I’d picked up from learning Urdu and English at the same time as a child of immigrants from Pakistan.
Boyfriends, girlfriends, and relationships were for the white girls at my school, clad in Abercrombie and Hollister, and smacking their lips with tacky gloss. Or it was for the gorgeous mixed girls, who were hyper-sexualized by the boys and a target of jealousy by the rest— their exoticism both desired and reviled.
As for me, I was not worthy of a relationship with anybody, much less the most good-looking bachelors at school. I was opinionated, dark-skinned, nerdy, and didn’t possess the beauty and docility that qualified teenage girls for a fairy tale romance.
That didn’t mean I didn’t dream of it. When I re-watched A Cinderella Story, just a few days shy of my twenty-fourth birthday, after organizing in Black Lives Matter and the other movements that redefined our generation and happily married to a feminist prince of my own choosing, I realized that my life in high school had not been so different from the plight of Samantha Montgomery, the titular Cinderella of the film, portrayed by Disney Channel teen icon, Hilary Duff.
A rom-com film released in the nexus of my preteen years, A Cinderella Story was the proverbial DVD rented from Blockbuster and then forgotten in the back of the closet. Starring Duff opposite of Chad Michael Murray, the high school heartthrob who paved the way for soft boy representation on TV (before we had words for it), the flick scored a measly 12% rating on Rotten Tomatoes and wasn’t taken seriously beyond the teenybopper generation, which has since grown up and moved on to more tasteful cinema.
Yet, for us, A Cinderella Story is an underrated classic of the early 2000s, not just because of Duff and Murray’s onscreen chemistry or the nostalgia kick you get downloading it during quarantine, but because of the movie’s perennial message of finding true love and expressing yourself regardless of what society thinks.
Sam grows up as an orphan in the San Fernando Valley after losing her father in an earthquake. Raised on dreams of going to Princeton, she slaves away at her father’s old diner for her botox aficionado stepmother, Fiona, in the hope that Fiona will allocate the family money to her college fund. Best friends with Carter, a self-proclaimed method actor, and quasi-nerd, she encounters her first romance in a Princeton chat room with a mysterious writer named Nomad.
The film is riddled with technology that makes it obvious it’s the early 2000s, when we used Walkmans and Nokia cellphones, and flirted in chat rooms or over email, because before Tinder, there was IM, MSN Messenger, and MySpace. Unpopular at school and nicknamed “diner girl” by the it-crowd, Sam’s messages with Nomad become a way of escaping the world she actually lives in.
It’s soon revealed her digital Prince Charming is hidden in plain sight. Austin Ames, the school quarterback and the glassy, inscrutable boyfriend of popular cheerleader Shelby Cummings, is secretly a tortured writer struggling against his father’s expectations to play football in college and inherit the local business. For Austin, the chat room with Sam is the only place where he can be himself.
“Do you ever feel that if you show someone who you really are, they won’t accept you?” Austin asks Sam at the diner, not knowing who she really is.
“Yeah, I do. Like being yourself isn’t good enough. Like you’re wearing a mask,” Sam replies.
Sam and Austin may come from polar opposite ends of society, but they’re wearing the same mask. Austin invites PrincetonGirl818 to the homecoming dance:
“I’ll be waiting for you at 11 o’clock in the middle of the dance floor.”
But Sam can’t go because she has to work the late shift. That’s when Rhonda, a waitress and an old friend of Sam’s dad, intervenes.
Rhonda is portrayed by Regina King, who won an Academy Award in 2019 for her role in Barry Jenkins’ If Beale Street Could Talk. With TV shows like Gossip Girl, The O. C., and One Tree Hill featuring nearly white ensemble casts, the early 2000s was hardly known for representation, but King’s masterful acting and a tender script prioritizing Rhonda and Sam’s friendship above all saves Rhonda from potentially stereotypical depiction. Glimmers of vulnerability appear when Rhonda tells Sam she has a boxed wedding dress waiting for her next “attempt” down the aisle, and when she shuts down everyone’s micro-aggressions, including Carter’s cringe-worthy attempt to speak AAVE— truly ahead of its time.
Sam attends the dance and serenades Austin Ames, who asks her if she’s disappointed it’s him. Just as they are about to kiss in a candlelit gazebo, her alarm rings. "Where are you going?” Austin calls. “I’m late. . . for reality.” In true 2000s fashion, when Cinderella clambers up the steps and out the door, it’s not a slipper she leaves behind, it’s her cellphone.
The film veers towards tragedy when Sam is exposed as Cinderella by her stepsisters, and her anonymous romance with Austin is performed as a skit in front of the entire school. At this point, the injustice Sam faces as a penniless, jobless young woman can’t be denied. But Austin's decision to ignore and not speak to her again is all too mundane, and a reminder that real life is not a fairy tale after all.
What makes A Cinderella Story so great isn’t just the happy ending, but how Sam ultimately chooses her self-respect over Prince Charming, a feminist subversion of the original fairy tale, which used a rich prince’s marriage proposal to validate the existence and upward mobility of the poor, struggling heroine.
On the night of the big football game, Sam marches into the boys’ locker room and tells Austin she’s accepted who she is and feels sorry for him because he’s living a lie. Anyone who has survived high school with middle-class white people knows what it means for an outcast girl to march into the testosterone-fueled underbelly of the suburban American education system. The way in which Hilary Duff—who gives a stunning monologue—silences Chad Michael Murray, the blue-eyed wonder child of early 2000s high school fantasies, into shame is a feat we all wish we’d accomplished with the people who bullied, wronged, and disappointed us in high school.
The film is filled with iconic moments from Hilary Duff’s tousled blonde waves and shimmering white ball gown, Rhonda’s witty ripostes, and the scene when Briana and Gabriella, Sam’s stepsisters, accidentally tumble into a carwash. But nothing beats the football game at the end of the movie. Jimmy Eat World’s “Hear You Me”, composed in memory of two Weezer fans who tragically died in a car accident, plays during the scene, and the juxtaposition of a tear-jerking song about people who died over an actual football game is not just irreverent as hell to the hyper-masculine, sports-driven American psyche, but pure cinematic genius.
When Sam gets up to leave during the game, the star quarterback—whose mascot is incidentally a frog—notices. In an iconic scene that’s imprinted on the memories of all Disney Channel millennials for time to come, and which Murray himself poked fun at last year for E! News, Austin runs off the field right before his team can score the final touchdown. Aghast, his dad stops him, and Chad Michael Murray delivers probably the most unforgettable lines of his career.
“Austin, you’re throwing away your dream,” his dad says.
“No, Dad. I’m throwing away YOURS.”
For the brown girl who never had the chance for a high school romance, the symbolism of a quarterback running off the field to kiss the underdog heroine and transform into the prince he’s always been is nothing short of epic. It's also a slap in the face to bullies, who believe humiliating a person into submission equates to love or confidence.
In the present tense, Chad Michael Murray recently played a sexy cult leader manipulating high school students on Riverdale, and Hilary Duff sub posted her neighbor smoking up their building in New York City. The culture has shifted and reality isn’t a fairy tale, but this high school rom-com still endures, if not for the nostalgia then because of the timeless message it gives teenagers and young people.