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(Left to right) Lesley Ann Warren, Julie Andrews and Brandy Norwood
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This fall, Camila Cabello — you might know her from her hit radio singles “Havana” and “Señorita” — brings her considerable pop-star charisma to a new modern musical take on Cinderella, in which Ella dreams of starting her own fashion empire (coming Sept. 3 to Amazon Prime). The empowering film co-stars Idina Menzel (50) as Cinderella's stepmother, Minnie Driver (51) and Pierce Brosnan (68) as the king and queen, and Billy Porter (51) as the scene-stealing Fab G, a fairy godparent. But it's the latest in a long line of cinematic adaptations that stretches back all the way to the silent-film era.
So who is the fairest Cinderella in all the land? We searched the pop culture kingdom, from silent films to Disney to, well, Disney, not just to discover all the Cinderellas but to rank them from number 16 to number 1. Grab a grandkid (or childhood pal) to stream these princess pics, and we'll see you at the ball!
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16. Happily N'Ever After (2006)
The Cinderella: Sarah Michelle Gellar
The Gist: A critical and box office bomb, this computer-animated film feels a bit like a warmed-over Shrek, combining the Cinderella story with elements from the Brothers Grimm and Hans Christian Andersen. Cinderella must escape from Fairy Tale Land after her power-hungry stepmother (Sigourney Weaver, 71) tips the scales of good and evil, sending the characters’ happy endings into chaos.
Why It's Magical: George Carlin voices a wizard in one of his final screen performances.
Watch it: Happily N'Ever After, on HBO Max
15. A Cinderella Story (2004)
The Cinderella: Hilary Duff
The Gist: You might know Duff from her recent role on the TV show Younger, but she starred in this modernized teen rom-com at the height of her power as a pop singer. The plot follows two teens who develop a relationship online as pen pals and agree to meet at the school Halloween dance — despite constant sabotage from Sam's evil stepmother Fiona (Jennifer Coolidge, 60).
Why It's Magical: Oscar winner Regina King, 50, plays the manager at the diner where our heroine works, and lends her a wedding dress for the dance. It turns out that you don't need to have fairy powers to be a godmother figure.
Watch it: A Cinderella Story, on HBO Max
14. Ella Enchanted (2004)
The Cinderella: Anne Hathaway
The Gist: Cursed with a “gift” by a well-meaning fairy (Vivica A. Fox, 57), Ella of Frell is compelled to obey every command that's directed at her — all while falling for Prince Char (Hugh Dancy). The fantasy rom-com features many of the trademark Cinderella plot points (a cruel stepmother, a ball), plus plenty of other magical elements, including elves, ogres, a talking snake (voiced by Steve Coogan, 55) and even a giantess named Brumhilda played by supermodel Heidi Klum.
Why It's Magical: Nearly a decade before winning her Oscar for singing in Les Misérables, Hathaway peppily covers “Somebody to Love” and “Don't Go Breaking My Heart” in this film.
Watch it: Ella Enchanted, on HBO Max
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13. Cinderella (1914)
The Cinderella: Mary Pickford
The Gist: The first movie version of the Cinderella story was directed by French film pioneer Georges Méliès in 1899. Fifteen years later, “America's Sweetheart” took on the role in a silent version, which the original Los Angeles Times review summed up as follows: “Miss Pickford portrays every phase of the fairy heroine's career, from pathetic cinder girl to bejeweled princess, with equal charm and winsomeness, and every scene is made more appealing by the beauty and grace of the beloved little film star."
Why It's Magical: Think Cinderella and the prince had good chemistry — even without uttering a word? That's because he was played by Pickford's then-husband, Owen Moore.
Watch it: Cinderella, on YouTube
12. Cindy (1978)
The Cinderella: Charlayne Woodard, 67
The Gist: Featuring a nearly all-Black cast, this TV musical in the vein of The Wiz (which debuted the same year) follows Cindy, a young Southern girl who moves to Harlem during World War II and falls for a dashing Marine on leave. Nell Carter, from the NBC sitcom Gimme a Break!, co-stars as one of Cindy's stepsisters.
Why It's Magical: Instead of a glass slipper, Cindy loses a sneaker — proving you don't need flashy duds to catch a man's attention if the feelings are right.
Watch it: Cindy, on YouTube
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