- Crazy Awesome: Prince Charming jumping out a window after his father forbids him to "take another step down these stairs". Charming in general seems like a completely different character than his previous depiction, and the fans love him for it.
- Crosses the Line Twice: When Anastasia first presents the magic wand to her mother and sister.Lady Tremaine: ...A stick?
Drizella: (gleefully) Ooh! Let's beat her with it!
- Even Better Sequel: This movie addresses many of the first movie's problems, like Prince Charming being a Flat Character, Cinderella being a Damsel in Distress, the "Whoever Fits in the Glass Shoe Will Marry Me" plot point, and a few others. Therefore, some fans regard him as even better than the original. Given the second was a poorly disguised Failed Pilot Episode while this was made with the intent of being a feature length film with higher production values, needless to say it definitely excels far past that.
- Evil Is Cool: Lady Tremaine - with a magic wand. She was already scary when she didn't have it, but once she did...
- Fashion-Victim Villain: Played (for laughs?) with when Drizella messes with the Fairy Godmother's wand by changing her clothing. She gives herself giant jewelry, big hair and a giant dress, all in clashing colors.
- Harsher in Hindsight: If you thought Lady Tremaine was bad here, wait until you learn what she tried to do to Cinderella in Kingdom Hearts: Birth by Sleep. Also in that canon, Anastasia never pulls a HeelFace Turn, and crosses the Moral Event Horizon at the same time as her mother and sister.
- Hilarious in Hindsight: In Spider-Man: The Animated Series , Black Cat was often shipped with Spider-Man. Their respective voice actors, Jennifer Hale and Christopher Daniel Barnes, would go on to voice Cinderella and the Prince themselves starting with Cinderella 2, and it's this movie where they Took a Level in Badass.
- Even more hilarious when two years after this movie was released, Disney bought Marvel Comics. (Though they had owned Spider-Man: TAS prior to that, after they bought out the assets of Saban Entertainment and what was then Fox Family in 2001).
- On a related note, two years after this film's release, producer Eddie Guzelian found himself in a similar situation to this project— having to convert a cute, kid-aimed property to fit a darker, more action-oriented story. The project? Power Rangers RPM.
- Memetic Mutation: The scene in which Charming jumps off a balcony to escape his dad◊ has become quite the favorite among gif makers.
- Moral Event Horizon: She may or may not have already crossed the MEH by that point (see the YMMV page for the original classic for her earliest possible MEH), but Lady Tremaine definitely cements it in this film when she poofs Cinderella in a twisted pumpkin carriage with Lucifer as its human driver, and attempts to get Lucifer to kill Cinderella. Especially heinous because up until that point she was satisfied with just making Cinderella's life a living hell. She also has Anastasia posing as Cinderella to fool the prince. If anyone doesn't know, this is rape by deception (or at least it would be if this weren't a Disney movie)... and worse, she tries to use one of her own flesh and blood daughters for such shit, and right when Anastasia is becoming more and more sympathetic!
- Narm Charm: Lady Tremaine chanting, "Bibbidi, bobbidi, boo!" to kick off the time-reversing spell. And then the spell not firing, causing her to cast an odd look at the wand and give it a few irritated flicks. You can practically hear her thinking "What's wrong with this thing?".
- Rescued from the Scrappy Heap: A lot of the characters of the first movie that were, to various extents, disliked for being too bland or too unsympathetic are given Character Development here, making the fans warm up to them.
- Anastasia's Character Development that began in Cinderella 2 continues here, and she performs a HeelFace Turn at the end.
- Prince Charming is often criticized for being one of the blandest Disney Princes, as he's basically a Satellite Love Interest in the first movie. In this sequel, he receives character development and more screen time, and performs several Crazy Awesome stunts.
- Not to mention the King, to some degree. The sequel makes him more fleshed out, not limiting him to his Hair-Trigger Temper, turning him into a positive role model for Anastasia. Especially when he tells Anastasia about his own wife, and how they loved each other even though she was an... unconventional queen.
- Cinderella was never completely a scrappy but she was an unpopular Disney Princess, alongside Aurora and Snow White. While iconic, all three of them have been hit hard by "Seinfeld" Is Unfunny and are largely seen as "boring" and "bland" compared to future princesses. This movie however gave Cinderella more character depth than the original film. That, combined with her athletic moments, helped many people like Cinderella more.
- Signature Scene: Two. One is the Prince jumping out the window, mainly for being one of the biggest laughs in the film. The other is the demonic carriage ride, partially because that entire sequence is a testament to how good Disney sequels can be if the filmmakers really try, and because it's genuinely unnerving, and even scary for younger kids.
- Special Effect Failure: Since the animators lacked the money for a Transformation Sequence as detailed as that from the first movie, any scene in which the Fairy Godmother changes someone's outfit basically consists of one character model fading into another.
- Spoiled by the Format: Prince Charming rescues Cinderella from being sent far away and they're on their way to their wedding... only there's twenty minutes left in the movie.note
- Surprisingly Improved Sequel: Fans generally agree that the third film is a big improvement over the second due to having a single cohesive plot (instead of 3 unconnected vignettes) that goes in a different direction, and that it on the whole is one of the better Direct-to-DVD Disney sequels.
- Tastes Like Diabetes: The first three minutes of the movie, in which Cinderella recounts her rags-to-riches life to the viewers before she, Prince Charming, the mice and the Fairy Godmother sing about how "Perfectly Perfect" things have been since the wedding. Although considering how the movie plays with the issues of the original film, this could almost be intentional.
YMMV / Cinderella III: A Twist in Time