I think what makes these two films special right off the bat are the protagonists, played by Brandy and Drew Berrymore respectively. Brandy's Cinderella is a wistful dreamer who is deeply depressed with how her life has played out thus far. It's a really interesting take on the character since most Cinderellas are played as extroverted and positive despite their circumstances with only a brief moment of grief. Not only is Brandy's Cinderella very much an introvert, she has two songs that discuss her mental struggles ("The Sweetest Sounds" and "In My Own Little Corner"). She wants more for herself, but feels that she can't leave because of a promise she made to her father to not separate the family. She feels stuck with no way out and that is some bleak stuff for a children's musical. But it's also the most realistic depiction of a person in her situation, which makes it all the more inspiring when she finally leaves.
On top of that, Brandy playing Cinderella was the first time the character had been portrayed by a Black woman. That was and still is a huge deal for representation, something that this version has an abundence of. The movie doesn't address the fact that there are two interracial families and it's better off for it.
Drew Berrymore's Cinderella, whose real name is Danielle, is also stuck not because of a promise made to her father (who literally died in her arms on screen) but to ensure that her step mother doesn't run his farm into the ground. Her Cinderella reminds me a lot of Belle from BatB: she finds comfort in her books and is incredibly headstrong, something that most Cinderellas can't do because they have to obey their families. She's intelligent and uses her wits to solve problems (dressing as a courtier to pay off a servant's debts, using her mother's name to not be discovered, saving Prince Henry from the bandits by turning their own words around, etc). She cares deeply about the well being of her fellow peasants and vocally advocates for class reform to the future king of France. She's a badass.
[The Step Mother]The Step Mother
I don't even know where to begin, Bernadette Peters and Angelica Huston are phenominal Step Mothers. I'd argue that this is one character that is almost impossible to get wrong and most adaptations get right (paging Jennifer Coolidge), but these two eat up every scene they're in and it's delicious to watch. Peters has such a whimsical and theatrical air about her that fits perfectly with this adaptation. Her song "Falling in Love with Love" is a bop and a mood, while also giving viewers a look into how her relationship with Cinderella's father and his death forever skewed her outlook on romance (I fell in love with love / With love everlasting / But love fell out with me). She's a Stage Mom to the umpteenth degree and watching her coach her daughters in etiquette and How to Get a Man will never not be entertaining. "Remember girls, don't let the Prince know how clever you are. Men can't stand smart women."
Angelica Huston, on the other hand, is as cold as ice. I mean, what can I said that hasn't been said? She's calculating and manipulative from the first moment we lay eyes on her. She knows when the play the Baroness and when the play the Chess Master. Not only does she pit Danielle against her family, but she pits her own daughters against one another. She has no problem with throwing her servants in jail to cover her debts and to blame the few servants she has left for items that she herself is stealing. She is evil and she loves it, while also giving us glimpses into her humanity when she discusses her own mother and the immense pressure she felt as a girl to be perfect. At first we think that maybe, just maybe, she once had a soft spot for Danielle. But she brings Cinderella and the audience back to a harsh reality: "How can one love a pebble in their shoe?" Brilliant.
[The Fairy Godmother]The Fairy Godmother
Since Ever After doesn't have magic, the Fairy Godmother is played by Leonardo Da Vinci. He's fine. He has cool moments and he's an enjoyable character but there's not much else to say. He does, however, have one of the most beautiful lines in a fairy tale: "Then I shall give you wings."
Okay, let's move onto the person we really want to talk about: Whitney Houston. This absolute legend. This queen. I wanted her to be my Fairy Godmother so badly when I was a kid. As most people know, Whitney Houston was the network's first choice to play Cinderella. After discussions between Houston and the producers, they had her play the Fairy Godmother instead (Houston was happy to play the part since it was less demanding on her schedule). She then decided to be an IRL fairy godmother by hand selected Brandy to play the titular role and called her herself to give her the news.
Houston's FG is funny, charming, caring, and nurturing in a way that most FGs are not. Sure, they're all nice and give Cinderella one night of freedom, but none of them challenge Cinderella's reasoning to stay with her step family the way Houston's does ("This can't be what you daddy wanted"). Her song "Impossible" is the best of the soundtrack due to her vocals and chemistry with Brandy. It offers the viewers the advice that we can all do impossible things, Fairy Godmother or not. She's perfection.
[The Prince]The Prince
Cinderella's ticket out. On paper the princes are pretty similar: both have overbearing parents, they like to escape palace life whenever they can, they want to marry for love, and they're both snarky. What makes them different are the actors and they're approach to playing this character.
Prince Christopher [Rupert Windermere Vladimir Carl Alexander François Reginald Lancelot Herman Gregory James] is played by the insanely handsome Paolo Montalbán and yes I did have a huge crush on him as a child. His Prince, while considered a bad boy by his parents, is very sincere and kind. He values beautiful things in the world and longs for true love. He's a tease when he's talking to a woman, but not in an offensive way. He cares deeply for his parents and for his country. Does he have a little privilege from being a prince? Sure, but for the most part it's just making Lionel's life a little hard and it's funny to watch. He absolutely adores Cinderella and you can see it every time he looks at her.
Prince Henry, on the other hand, is a little more rough around the edges. Played by Dougray Scott, he's definitely a dick and needs to check his privilege like yesterday. He's first interested in Danielle because, unlike most women at court, she openly challenges his station and belief system. What makes him fall in love with her is her passion, something he claims he's never had even though he's supposed to rule France one day (which he doesn't want to do). He's stubborn, but not opposed to having someone change his mind. Prince Henry and Danielle's relationship is dynamic because they constantly debate, but it's not played for laughs the way sitcom couples fight. He genuinely enjoys his conversations with her and can't get enough.
While this discussion isn't to rank one aspect of a movie over the other (except the Fairy Godmother, it's an objective fact that Whitney's is superior), I have to say that Rodger & Hammerstein's supporting cast is more well rounded than Ever After's. Whoopi Goldberg and Victor Garber make an odd couple that somehow works. She's overbearing while he rolls with the punches, but they both dearly love their son and each other. They way they dismiss Lionel, played by Jason Alexander, is hilarious and he seems to take it all in stride. The sisters are ditzy and have great chemistry when they bicker. Overall, every cast member is charming and is clearly having fun in their roles.
Speaking of sisters, they're the best of the SC in Ever After. Marguerite (Megan Dodds) and Jacqueline (Melanie Lynskey), as mentioned before, have been pitted against one another since they were children. Marguerite is the favorite child, while Jacqueline is mocked and teased for her weight (which, like, isn't even a thing? She just has a rounder face). I always enjoy Cinderella adaptations where the sisters are given more character development and the dynamic between these two has always helped enhance the film. You're rooting for Marguerite to fall on her face and for Jacqueline to leran to stick up for herself.
While there are other members of the SC in Ever After (the king and queen, Danielle's fellow servants, that Hook guy named Le Pieu, Gustave, etc) they don't hold the same punch as the rest of the cast. And for the most part that works in this type of film where they're not ever trying to outshine the main cast.
[Conclusion & Poll]
In conclusion, ladies and gentlemen, these two films offer us not only great adaptations of a fairy tale but two movies that stand on their own as entertaining and engaging. They were made with heart and each challenge the viewer to think critically about serious topics (interracial families/representation in media vs socioeconomic divides and philosophy) in a way that's accessible to adults and children alike. The costumes and production sets fit perfectly for the themes that each movie went for, and depending on your mood you can enjoy delightful musical numbers or devious court intrigue. While Cinderella has always been a story about a person who gets their deserved due, these two movies offer so much more than that.
That said, let's put it to a vote!
Which version of Cinderella do you like best?