Britney Spears Was the Inspiration for Hilary Duff’s ‘A Cinderella Story’ Character, Screenwriter Reveals

While it’s hard to imagine anyone but Hilary Duff starring in A Cinderella Story 20 years after its release, another pop princess was initially eyed for the movie’s lead role.

“I distinctly remember I was on a train, and I had the cover of Rolling Stone magazine that Britney Spears did — the first one she ever did that was sort of controversial because she was so young and it was very sexualized,” the film’s screenwriter, Leigh Dunlap , told TV Insider in an interview published on Tuesday, July 16. “I wrote it with her in mind at the time.”

Because the film wasn’t made until a few years after Spears’ 1999 cover — which featured her lying on a bed in a black bra and polka dot pajama shorts — Dunlap and the movie’s crew had to look elsewhere for their leading lady.

“By the time we got years down the road, she had moved on to becoming a massive star, and it didn’t matter anymore,” Dunlap said of Spears, 42.

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Duff, 36, ultimately won the role of modern-day Cinderella Samantha “Sam” Montgomery, marking her first breakout role following the conclusion of her Disney Channel series Lizzie McGuire . “We got the right girl in the end,” Dunlap declared.

A Cinderella Story follows Sam as she dreams of getting into Princeton University to escape life with her self-absorbed stepmother and stepsisters, played by Jennifer Coolidge , Madeline Zima and Andrea Avery Ray , respectively. At a school Halloween dance, she discovers that her online pen pal is none other than the captain of the football team, Austin Ames ( Chad Michael Murray ). Rather than lose a shoe, Sam loses her cell phone while fleeing the dance to make it back to her late father’s diner before curfew.

While Sam plans to reveal her identity to Austin at the right moment, she is exposed at a school pep rally by her stepsisters and Austin’s evil ex, Shelby ( Julie Gonzalo ). The reveal leads to one of the movie’s most memorable moments in which Sam calls out Austin in the boys’ locker room, uttering the iconic line, “Waiting for you is like waiting for rain in this drought, useless and disappointing.”

According to Dunlap, the scene was one of the hardest to nail. “We went through so many rewrites of that because we went into production so quickly,” she explained. “They brought in other writers to write on stuff too. That scene went through many, many forms because it was the big scene of the whole movie. It was something we all worked on a lot.”

A personal favorite line of Dunlap’s is the phrase Sam’s father ( Whip Hubley ) shared with her — “Never let the fear of striking out keep you from playing the game” — which ultimately motivates Sam to stand up to her stepmother.

As the film celebrated its 20th anniversary, Dunlap says it “excited” her that A Cinderella Story still holds a special place in fans’ hearts. “When you write something and somebody actually says it means something to them, it’s the greatest feeling in the world. It just means so much. It touches me,” she gushed. “I can’t believe it’s been 20 years, and new people are discovering it. Old people are rediscovering it. It’s so cool that somebody is literally sitting on a plane on Delta watching the movie. That is the coolest.”

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A Cinderella Story also starred Regina King , Dan Byrd , Simon Helberg , Brad Bufanda , Mary Pat Gleason and Lin Shaye , among others. Murray, 42, wished the film a “Happy 20 year anniversary” via his instagram Story on Tuesday by reposting pics from Austin and Sam’s dance scene to Edwin McCain ’s “I’ll Be.”

The original spawned several spinoff films: 2008’s Another Cinderella Story starring Selena Gomez , 2011’s A Cinderella Story: Once Upon a Song starring Lucy Hale , 2016’s A Cinderella Story: If the Shoe Fits starring Sofia Carson , 2019’s A Cinderella Story: Christmas Wish starring Laura Marano and 2021’s A Cinderella Story: Starstruck starring Bailee Madison .