CBS via Getty Images; Courtesy Everett Collection; Walt Disney Television/Courtesy Everett Collection
En español | 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!
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
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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
11. Cinderfella (1960)
The Cinderella: Jerry Lewis
The Gist: In this gender-swapped farce, Lewis stars as the klutzy but good-natured Fella, who lives with his snobby step-family and later meets Princess Charming (Anna Maria Alberghetti, 85) at a ball where the Count Basie Orchestra is playing. The King of Comedy brings a ton of heart to the role, especially in the surprisingly poignant musical numbers.
Why It's Magical: Vaudevillian clown Ed Wynn — the voice of the Mad Hatter in Alice in Wonderland — plays the Fairy Godfather, who first appears to Fella on a candy-striped raft as our hero is cleaning his stepmother's swimming pool.
10. Into the Woods (2014)
The Cinderella: Anna Kendrick
The Gist: Cinderella takes a supporting role in this beloved Stephen Sondheim (91) revisionist fairy tale musical, in which all the characters seem to get their wishes fulfilled halfway through the film — and then quickly learn that happy endings aren't permanent. Spoiler alert: The Prince (Chris Pine) is a bit of a philandering jerk.
Why It's Magical: Christine Baranski, 69, plays Cinderella's stepmother, and she knows a thing or two about performing Sondheim — she won a Helen Hayes Award for playing Mrs. Lovett in the Kennedy Center's production of Sweeney Todd.
Watch it: Into the Woods, on Disney+
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9. Rodgers & Hammerstein's Cinderella (1957)
The Cinderella: Julie Andrews, 85
The Gist: Richard Rodgers and Oscar Hammerstein II wrote their only made-for-television musical specifically for the 22-year-old Andrews, who was starring on Broadway in My Fair Lady at the time. An astonishing 107 million Americans tuned in to the CBS broadcast, which represented about 60 percent of all television-owning households in the country, and it ranks as one of the most-watched events in TV history.
Why It's Magical: Unsurprisingly, Andrews’ crystal-clear soprano sounds gorgeous on songs like “Do I Love You Because You're Beautiful?” and “In My Own Little Corner.”
Watch it: The only surviving copy of the performance is a black-and-white kinescope recording that had been shown on the West Coast (the East Coast saw the musical live and in color) and is available for purchase on DVD from Amazon or streaming on YouTube. The film isn't higher on this list, because it's just so darned hard to find!
8. Cinderella (2015)
The Cinderella: Lily James
The Gist: James — who starred in Downton Abbey and Mamma Mia! Here We Go Again — steps into the glass slippers for this live-action Disney romance by director Kenneth Branagh, 60. She is joined by an all-star cast that includes Cate Blanchett, 52, as Cinderella's stepmother and Helena Bonham Carter, 55, as the Fairy Godmother.
Why It's Magical: Swarovski provided more than 1.7 million crystals for the film's extravagant gowns, which earned costume designer Sandy Powell, 61, her 12th out of an eventual 15 (and counting) Oscar nominations — she's already won three times, for Shakespeare in Love, The Aviator and The Young Victoria.
7. The Glass Slipper (1955)
The Cinderella: Leslie Caron, 90
The Gist: Decked out in her trademark pixie cut, Caron (of Gigi and An American in Paris fame) stars as a tomboyish outsider in this MGM musical, opposite Michael Wilding — the then-husband of Elizabeth Taylor, who reportedly got him cast after he complained that he wasn't getting any roles! The French-American actress and dancer makes for a feisty and rebellious Cinderella who stands in contrast to the meeker portrayals that came before it.
Why It's Magical: Not your typical musical, the film features only one song (performed by the prince and dubbed by a different actor) but three lush and beautiful ballet numbers.
6. The Slipper and the Rose (1976)
The Cinderella: Gemma Craven, 71
The Gist: Known for writing the music for such family classics as Mary Poppins and Chitty Chitty Bang Bang, the Sherman Brothers penned the tunes and worked on the screenplay for this British musical, which costarred Richard Chamberlain, 87, as the prince. Critics praised the script's wit and originality, though at 143 minutes, the plot has space for some unexpected twists — including a threat of war with neighboring kingdoms and a song in which the prince sings to his dead relatives in the royal crypt.
Why It's Magical: The Sherman Brothers earned an Oscar nomination for the song “The Slipper and the Rose Waltz (He/She Danced With Me).”
5. Faerie Tale Theatre (1985)
The Cinderella: Jennifer Beals, 57
The Gist: Hot off her career-making turn in Flashdance, Beals played Cinderella in an episode of the star-studded fairy-tale anthology series from Shelley Duvall, 72, with a cast that also includes Jean Stapleton as the Fairy Godmother and Eve Arden as the stepmother. Beals makes for a subtly empowered future princess, and she has great chemistry with her prince, played by Matthew Broderick, 59.
Why It's Magical: The script is filled with such delightfully deadpan wit as when Cinderella asks the prince if he knows anything about kissing. “Yes,” he replies, “I'm almost certain it has something to do with the lips.”
Watch it: The episode is not currently available to stream or purchase online, but you can find clips on YouTube.
4. Rodgers & Hammerstein's Cinderella (1965)
The Cinderella: Lesley Ann Warren, 74
The Gist: If you've seen a version of the Rodgers and Hammerstein television musical, chances are it might have been this 1965 remake, starring the 18-year-old Warren and future General Hospital actor Stuart Damon (who sadly died this June) as the prince. This version included a new song, “Loneliness of Evening,” which was composed for and ultimately cut from South Pacific.
Why It's Magical: The supporting cast is a dream come true, including Ginger Rogers as the queen, Celeste Holm as the Fairy Godmother and Pat Carroll, 94 (the voice of Ursula in The Little Mermaid), as one of Cinderella's stepsisters.
3. Rodgers & Hammerstein's Cinderella (1997)
The Cinderella: Brandy
The Gist: Sixty million viewers tuned in to this ABC-TV movie — the third iteration of the classic musical — which earned kudos for its color-blind casting and updated script. Grammy-winning pop star Brandy plays Cinderella, alongside a stacked cast that included Whoopi Goldberg (65), Bernadette Peters (73), Jason Alexander (61) and Victor Garber (72).
Why It's Magical: Whitney Houston, who co-produced and stars as the Fairy Godmother, delivers the definitive rendition of the joyful song “Impossible.”
2. Ever After: A Cinderella Story (1998)
The Cinderella: Drew Barrymore
The Gist: This romantic drama does away with the fairy-tale elements and recasts the Cinderella story as historical fiction, set in Renaissance-era France and filmed at the stunning Château de Hautefort. Barrymore brings a decidedly un-16th century feminist spark to her role as Danielle de Barbarac, and Leonardo da Vinci even makes an appearance to paint Danielle's portrait — resulting in the real c. 1508 da Vinci painting Head of a Woman.
Why It's Magical: Anjelica Huston, 70, is deliciously wicked as Danielle's stepmother.
GLASS SLIPPER: Cinderella (1950)
The Cinderella: Ilene Woods (voice)
The Gist: This Disney animated classic is probably the first image that pops into your head when you hear the princess’ name, and that's for good reason: It's an iconic movie, ranking ninth on AFI's top animated films list, with a sweeping soundtrack that includes songs like “A Dream Is a Wish Your Heart Makes” and “Bibbidi-Bobbidi-Boo.” Cinderella was almost single-handedly responsible for turning around Disney's fortunes after a string of commercial flops, and it earned three Oscar nominations in the process.
Why It's Magical: The Fairy Godmother's transformation of Cinderella and her dress was one of Walt Disney's personal favorite animated scenes of all time.
Watch it: Cinderella, on Disney+
Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines’ Hemispheres magazine and his work has appeared in The New York Times, Condé Nast Traveler, Travel & Leisure, Sunset and New York magazine.