Since you've made a study of so many different adaptations of Cinderella, I wonder: Do you have any thoughts on what different versions of the two main characters (Cinderella and the Prince) would think of each other? Are there versions who you think would get on particularly well? Particularly badly?
That’s an interesting thought…
Mary Pickford's 1914 Cinderella and Yanina Zhejmo's 1947 Russian Cinderella would probably be fast friends, because they're both such innocent, adorkable little cutie-pies. Soyuzmultfilm's 1979 animated Cinderella could join them too, although I almost consider her the same character as Zhejmo's Cinderella, because that animated short is an unofficial remake of the 1947 film.
I could also see Angelina from Rossini's opera La Cenerentola, Lucette from Massenet's opera Cendrillon, and Lesley Ann Warren's Cinderella from the 1965 version of Rodgers & Hammerstein's musical as friends, because they're all such sweet, delicate, melancholy waifs. Of the three, Angelina grows the most in commanding presence and dignity by the end, so she could help the other two to find their inner strength, while Lucette, who's the saddest of them all, might be inspired by how the other two find comfort in their singing and imagination.
Brandy Norwood's 1997 Rodgers & Hammerstein Cinderella and the heroine of the anime Cinderella Monogatari I could see as friends too, because of their similar "girl next door" characterizations with quiet inner strength and initially low self-esteem that grows by the end. Other "girl next door" Cinderellas like Belinda Montgomery from the Muppets' Hey, Cinderella!, Jennifer Beals from Faerie Tale Theatre, and Emilia Schüle from Märchenperlen could join them too.
Disney's two Cinderellas (animated and Lily James) would probably get along well with each other, as well as with Julie Andrews' 1957 Rodgers & Hammerstein Cinderella and Gemma Craven's Slipper and the Rose Cinderella, because they're all slightly more mature Cinderellas, who blend sweetness and dreaminess with a core of strength and ladylike dignity even in rags. Disney's animated Cinderella might feel a little out of place among the other three at first, because they're all refined young British ladies while she's more of a down-home American girl, but they would make her feel at home.
Meanwhile, the tomboy Cinderellas, like Libuše Šafránková in Three Wishes for Cinderella, Aylin Tezel in Sechs auf einen Streich, Lesley Caron's Ella in The Glass Slipper, Christianne Tisdale's Angelina in A Tale of Cinderella, and of course Drew Barrymore's Danielle in Ever After would probably all have scrappy and mischievous fun together.
Barrymore's Danielle would also connect with Anne Hathaway's Ella from Ella Enchanted and with Ella from the 2013 Broadway version of Rodgers & Hammerstein's musical, because they're all strong-willed, political-minded idealists, whose hard lives have made them champions of other downtrodden people.
Camilla Cabello's Ella from the 2021 Kay Cannon musical and Cinderella from Alma Deutscher's 2016 opera would bond over the fact that they're both artists (a dressmaker and a composer, respectively) whose dream is to share their craft with the world. Deutscher's Cinderella might even ask Cabello's Ella to design costumes for her latest opera.
I suspect most of them would be a little put off by Andrew Lloyd Webber and Emerald Fennell's "Bad Cinderella," because of her rude and belligerent Not Like Other Girls attitude. But Leslie Caron's Ella, who is similarly prickly although much less smug about it, would reach out to her... although I'm not sure if they would ultimately become friends or end up fighting.
As for the different Princes...
I think all four versions Rodgers & Hammerstein's Prince Christopher would relate to each other and get along well, although Jon Cypher and Stuart Damon's version might need some time to warm up to Paolo Montalbán's version and "Topher" from the 2013 Broadway version, because they're both slightly less mature. Both of Disney's Princes (animated and Richard Madden's Kit) would get along with them too, and maybe the rest of them could encourage Disney's animated Prince to talk more. Don Ramiro from the opera La Cenerentola would probably be their friend too, though he's a little more hot-blooded than the rest of them, while Michael Wilding's Prince Charles from The Glass Slipper could be like a wise older brother to them all. All of these Princes share similar gentlemanly dignity, tenderness, and strength of character in their own ways.
Topher from the Broadway version would also relate to Hugh Dancy's Char from Ella Enchanted, because they're both orphans who were sheltered from the world and treated like puppets by their villainous regents, until their respective Ellas opened their eyes and helped them step into their power.
Meanwhile, Montalbán's Christopher would also bond with the many other Princes who share his "rebellious bird in a cage" aspect. (To quote @ariel-seagull-wings' phrase.) These include Richard Chamberlain's Prince Edward from the Slipper and the Rose, Prince Niccolo from A Tale of Cinderella, Prince Theodore from Alma Deutscher's opera, Prince Sebastian from the Lloyd Webber musical, Nicholas Galitzine's Prince Robert from the Kay Cannon musical, Prince Charles from Cinderella Monogatari, the Prince from Three Wishes for Cinderella, and of course Prince Henry from Ever After. The two Princes from German Christmastime TV, Max Felder's Prince Leonhard from Märchenperlen and Florian Bartholomai's Prince Viktor from Sechs auf einein Streich, can join them too, because they're also fun-loving slackers who don't always like their royal duties.
That said, while all these boys complain about their lack of freedom, some of them are more mature and dutiful than others. I think most of them might find Charles from the anime to be a little too mischievous, while even Charles might find the Three Wishes Prince too rude, and they all might find Henry to be too spoiled and classist at first. (Yet Henry himself might also find the Three Wishes Prince too rude – he at least has standards from the start about treating a lady with chivalry.)
Meanwhile, the other Prince Henry, played by Matthew Broderick in Faerie Tale Theatre, and Robin Ward's Prince Arthur from the Muppets' Hey, Cinderella!, would get along well because they're both such sweet, adorkable goofballs.
Prince Charming from Massenet's opera, Aleksey Kornovsky's Prince from the 1947 Russian version, and most of the Princes from the early silent films would probably be fast friends, because they're all such innocent, hopelessly romantic "Romeo" types. But I think most of the other, "manlier" Princes might be slightly turned off by their melodramatic pining for love – they could empathize with the yearning, but would find the moping, crying, and fainting to be a little too much. Though some of the more mischievous Princes would probably find it amusing and could become Mercutio-like friends to these Romeo Princes – especially to Kornovsky's Prince, because he has a mischievous streak too.
All these adaptations have excellent potential for crossovers.