It's taken awhile for me to come to this conclusion, but I now feel a little guilty about making any lists since I still haven't seen Lilo & Stitch. But, here goes (YET another revamped list from the one I made only two months ago - all originals, of course):

20. The Black Cauldron

19. The Sword in the Stone

18. Snow White and the Seven Dwarfs

17. 101 Dalmatians

16. The Three Caballeros

15. Cinderella

14. Aladdin

13. Pocahontas

12. Robin Hood

11. The Jungle Book

10. The Great Mouse Detective

9. Pinocchio

8. The Rescuers

7. Fantasia

6. Fun and Fancy Free

5. The Little Mermaid

4. Alice in Wonderland

3. The Many Adventures of Winnie the Pooh

2. Sleeping Beauty

1. Dumbo
Now, about the list:
The Black Cauldron has slipped immensely in my opinion after getting the DVD. I need to watch it all the way through, but from what I've picked up on the last partial rewatch (I watched the, pre-credits, latter 60 minutes of it- I just skipped the opening introduction to Taran and Henwen), it's not a convincing adventure in terms of the stakes and Taran being in danger. The dragons and the arrival at the castle is all useless. The characters need a lot more work. Especially Flewdur, whose honesty-harp is a downright annoying cliche. There's not enough of The Horned King. There's not enough mystique or atmosphere. But, the magic sword and Taran's recurring "I am such a great warrior" thing I think do pay off. The witches are okay. The Creeper is fun and likable. Eilonwy doesn't get a lot but she immediately takes Taran to a place where he becomes a better character (maybe it's just that she gets the plot moving, the focus taken off of him). I liked her. And the little pixies are also okay. I had to war with myself a little over what would get #20- Cauldron or
Ichabod & Mr. Toad. And for that movie, I think the Ichabod section is spectacular but the Toad section is still painfully flawed.
Sword in the Stone might be technically weak in many ways with most people, but I have to just admit I love the damn movie too much. I really do. Archimedes, Merlin, Mim, and Kay are all a blast for me. And I like the score a lot if not the songs (Mim's song is great and "Higitus Figitus" is quite good). It's not too religious. It has good atmosphere. There is some darn good comedy. And it's mostly fun.
Snow White of course makes the list because of the stellar animation, the amazing score (better than the individual songs, easily), and the pretty good villainness. Other than that, this movie is overrated. Snow White is a brainless and condescending character (no, I'm not letting that one drop), the Dwarfs are dorky and aloofishly old-fashioned characters with no real anything I like, and... I don't care for the vast majority of the songs. And it's too long. This was clearly a test run to teach Walt how to cut scenes for time and superfluousness. Because there's enough pointless and uninteresting stuff here to fill the holes in every single story they ever made which didn't make complete sense. "Womanly wiles"? Does that even lead to anything? Examples like this abound.
Dalmatians has a lot less magic than Snow White, but I give it points for sophisticated characterization for the humans. I literally liked all the human characters. Even the small supporting ones you see on TV were a hoot. But dang it, the dogs are a bore. Except for that, and the fact that there's only 1 good song, it's a weird middle-of-the-road movie in terms of reputation. I think it's simultaneously overrated and underrated. The great flaw in
Caballeros is obvious, so let's not go there. I love the fact that it's a package feature. Were people really bothered that there was no single driving story that didn't make them feel like tacky tourists? Maybe Disney was tacky anyway (I've heard some fascinating critique on
Bambi's backgrounds - its' only saving grace - being melty for the purpose of cheap manipulation). The music and the animation (in my opinion) are glorious, frequently. The characters are fun. It's a heady movie, tonally (where its' biggest copy reference / influence, Dumbo, was actually pretty sober about its' animation during "Pink Elephants" which is why to me it's so dynamic). And some of the humor borders on that Fun and Fancy Free line of violent devilishness that I love to death.
Cinderella's great flaws, other than the cheapness of Cinderella's ambition and the movie's general tonally fancy regal haze (not quite on the level of Bambi's breeder-cuteness in terms of suffocating thematic obnoxiousness), are the King and the mice. The King is the worst thing here (and I've ranted enough about him elsewhere here recently). The mice are... well, every word out of their mouths is pretty much "formula." "We're action now, to keep the boys awake, now we're vocal admirers of Cinderella's kindness... For the girls' benefit?" But this movie deserves credit above Snow White for me because the mice are just better than the Dwarfs. Jacques was on the verge of being a genuinely cool character (whose leader status comes without attitude or pretention, he's what Peter Pan as a character should have been). Gus Gus isn't as annoying as he should be (he's at least miles more tolerable than the boy kids in Robin Hood or the boy kittens in The Aristocats and... well, he's more annoying than Mowgli but it was close). But anyway, I think the songs are better than Snow White's if the score isn't. The villain does more damage, on a personal level. The Prince at least gets more dialogue (moot point, I know). And Cinderella has a great brassy attitude, which at least perks up certain scenes / shows us that she isn't taking any of the cat's nonsense. Which created a good understated conflict with a quality (and shocking) resolution (the cat got iced).
Goliath recently said everything for
Aladdin and
Pocahontas in the past few months, so I'll just say I agree. As for strengths and flaws, I would say Aladdin's strengths are its' AMAZING animation and the characters. Great voicework, perfect casting. And the quality of the backgrounds and the effect of those delirious and harsh colors makes the movie something else in Disney's filmography. No, honestly- the whole movie made me have to breathe in deep to catch a breath. At least to my memory, Aladdin could stand a re-watch. Pocahontas may not have been the truly compelling account of how indians are viewed as savages by white man's ignorance leading to them not giving any white man a fair chance, etc. But for Disney, it came REMARKABLY close to being the studio's most emotionally serious piece of work. That's all I can say for other people who couldn't get into the movie. Somewhere in that "Savages" sequence, I found myself RIVETED by a Disney film. It definitely had more dramatic weight than the mob scene from Beauty and the Beast, which is why I'm glad they tried the idea again. The moment - one of Disney's best, period - felt like it was less about this one movie's story of incidental racism and more like it was just a moment where one person was willing to risk their life to send a message that killing someone over wars of race / class / creed (etc) is wrong. That 2 wrongs don't make a right. That communicating was the right way to stop the war. It may not be realistic to life but it was right where it counted.
Robin Hood is in the same boat as Peter Pan. All things considered, the only great difference is in animation quality. So, in comparison, Robin Hood has better characters. Unless you're comparing the Lost Boys to the rabbit children, who are inferior versions of Thumper's family from Bambi. And, though I would say Hook roped in a few more laughs than Prince John, together I found Prince John and Hiss a more entertaining villain duo with darker moments together than Hook and Smee. Plus, Robin Hood added a third and far more threatening villain with the Sheriff of Nottingham. So, there was more emotional weight when you see the damage John, Hiss, and the Sheriff were responsible for as a team. Which brings me to the scene where Friar Tuck fights back. Which makes him more likable than any single protagonist anywhere in Peter Pan. And he's not even considered one of the heroes in the film. Robin Hood is far more likable than Peter Pan, who's a jerk. When he's not actually saving anyone. There was even a part of me who wanted to see Hook win that fight on the ship. Even though I like the final scene of the ship flying off in Peter Pan more than the little wedding coda in Robin Hood. (The DVD's alternate ending scene idea would have helped make that coda more substantial, even though I LOVED the reprise of "Love" they played and the final shot of the coach/carriage driving off for whatever reason and more than Cinderella's same shot.)
Does anyone really have to shout
The Jungle Book's praises anymore? It's just a really well fleshed-out adventure, musical, and story of friendship especially in terms of tone. It's probably the final post-Sleeping Beauty Disney animated film that really plays with that ominous, rising feeling of danger which gives Shere Kahn a terrifying mythos until we see him park it and decide to start too casually talking to Kaa. But of course this leaves room for Kaa and King Louie to present interesting threats to Mowgli. Which they do. And the important thing is that Disney really started toning down a lot of the darkness of some original stories. Which hurt Peter Pan. But here, they found a thoughtful way of making the villains more complex. By turning them into charming opportunists who try to "seduce" Mowgli with songs and disguised promises. But unlike Pinocchio's Honest John and Gideon, these villains do all the legwork and Pied Piper luring in the victim themselves. This is just really important because we know the music is great and the casting is stellar. The great classic Disney formula just isn't quite complete without an appropriate amount of darkness and devious intrigue.
The Great Mouse Detective is just brilliant and unexpectedly not afraid to take risks. Even though it's emotionally bare and lacks almost all that trademark heady magic essencey stuff I love, I was REALLY impressed with the details of Basil's deductions. And how much motivation there was to Ratigan. As I mentioned in another thread, there's no doubt in my mind that Ratigan's crimes are largely motivated by the fact that he's the only rat in the movie. His entire chorus of supporters are either not rodents at all or they're mice and it's assumed if any of them call him a "rat," it's because even Ratigan knows rats are considered second-class citizens in their social heirachy. Then look at how his big plot is against the royal monarch where he doesn't want to simply dethrone the "official" (Queen in this case, which I'll get to in a second) who was in control during the time he spent as an outcast judged for being a rat- he wants to outright replace the monarch himself. So he'll never have to answer to the upper class ever again. Then... there's that little matter of Basil being "outsmarted" by Ratigan. The sexual tension in that scene is very strange. The Nostalgia Chick suggested they were former lovers but I think it also has the potential of being one of those "size contests" to put it mildly. I thought that was also a little bold for Disney. They really let all that baggage between the characters hang out in the open.
Pinocchio is entirely self-explanatory. But the reason I rate it lower than
The Rescuers is because I felt the magic was almost as strong in the latter. But I found the protagonists stronger in the latter too. There's no question the former has stronger villains. I think it's just as interesting that in Pinocchio, the real main character seems to be Jiminy Cricket and though he's clever enough, he just doesn't seem to be as likable as his big trademark song would suggest he was supposed to be. Also, I've tried, but there is absolutely nothing for me that has even begun to explain the scenes where Pinocchio is caught up in the villains' ruses and Jiminy doesn't realize what's happening until JUST the moment when it's too late. He sleeps in? He walks off and doesn't realize Pinocchio's not talking back? He's racing Pinocchio and... vanishes into thin air? Oh, and all the butt references in the opening of the movie were off-puttingly corny. I'm sure there's more to it but as a complete film, Rescuers holds up better in my estimation. With the exception of maybe the addition of the helpful swamp family / animals. Not sure what they were doing there but they weren't really characters.
Fantasia, of course, is incredible. Though I did just get done mentioning yesterday about how the cherub scene is downright intolerable. I also thought the dinosaur sequence felt too long-in-the-tooth (no pun intended). In this case, I would say the music might have been the flaw. But I loved the very beginning section with the bubbling volcanos and the earth / cosmic stars, etc. And there's one more thing that really irritates me about this movie. In anyone else's eyes, it's tiny. But it's those ostriches. When that one ostrich is being generous and decides to share the food with everyone. Everyone gets their own special food but THEN they all go and steal the grapes from the ostrich handing out the food. Don't you just want to get a shotgun when you see that? They fixed this kinda thing in Cinderella but here, they leave it unchecked and... it's always bothered me.
And the very last movie I want to talk about, of course, is
Fun and Fancy Free - the SINGLE most underrated Disney movie of all-time. Ever since I saw this movie in its' complete form for the very first time back in spring of 2005, this movie has been one of my top favorite Disney films EVER. The Bongo segment isn't perfect. Lulu Bell isn't a very memorable character unless you loved almost the entire segment. Which I did. The songs are still wonderful. Even if the lyrics to "Say It with a Slap" are silly to the point of being mockable, it's still a highly infectious and hummable song. And Lumpjaw is a villain right out of a Goofy or Donald cartoon but, I forgive that kind of thing since this is a package feature. The Mickey and the Beanstalk half of the movie however, in my opinion, is absolutely perfect. Top to bottom, front to back, start to finish, etc. From the HILARIOUS pre-Mystery Science Theater 3000 commentary from Charlie and Mortimer to Willie the Giant's fun / likable yet scary villain (he still gives me the major creeps) to the animation to the music to Donald Duck (who's also hilarious) to the ending. Even Jiminy's part here is great. The scene where Mickey comes back with the beans and the moonlight scene where the stalk grows is masterful. As is the first scene with Mickey, Goofy, and Donald starving. Again, reminded me of one of the animated shorts. But I loved those things too. And I thought Edgar Bergin's commentary over that scene was funny. "Have they given up hope? Yes. 3 friends and 1 bean. Were it 3 beans and 1 friend, but, no." Etc. Watch it again, sometime. Seriously. Give it a real chance. I think you'll see I'm right.