Ah... Back when a four quadrant film aimed at families and young people could still have some teeth in terms of themes and imagery and weren't afraid to be off the beaten path or strange or off putting... On the other hand... These are also films that weren't runaway block busters either so there is that. Also...
NO NEVER ENDING STORY ON THE LIST? Shame. SHAME!!
For the films that are on the list though...
Willow is the most straight forward of the bunch. It's clearly Lucas and Howard doing their gloss on a pure sword and sorcery fantasy film but keeping it in the wheelhouse of Lucas' Star Wars Trilogy. It has some darkness and it's a story of a hero's journey but it's not trying to be a warts and all fantasy like say, EXCALIBUR or CONAN THE BARBARIAN. It mostly works for me, but... Even back in the day there's just something missing, or something that keeps it from soaring. It might come down to the script's treatment of the villains, who are not particularly memorable even though they look great and the performers are fine. But in all honesty, can you name a truly memorable scene with the villains in them from the movie that's NOT an action scene of some kind? We all remember the great sorceress show down and how balls out crazy it was... But the evil queen character... Do we remember anything else? The evil general/enforcer character Martigan faces at the end... Anything memorable about him? Our heroes are a fine rag tag band of misfits with some definition but the bad guys are just... Bad. Not terrible as characters go but merely serviceable. And thus there's not a lot of meat on the bones in terms of the conflict. Fun enough but I would say Willow for me is mostly a nostalgia piece remembered because it was a big budget fantasy film from Lucas more than anything the film gives me. It's inoffensive and the leads are really likable but it doesn't stick with you.
Labyrinth is... I've always had issues with this film. It feels like it wants to get by just on it's weirdness, which people often forget how effing weird Henson could be with the Muppets. Which is something I admire in say, short skits but a full blown movie with not much to recommend it other than it being odd in visuals and story and of course Bowie hamming it up, mind you it's TASTY ham but kinda wasted in film that's more interested in being strange than necessarily engaging. And as much as we all love her now the issue comes down to both the writing of Connelly's character and how she plays it. I just never bought into the issues the character had or how she played them. And maybe it's me but I just find the world in the film and the creatures just so... fake. It's like... Bowie looks like this epic fantasy character interacting with, well... puppets. Obvious puppets. The kind of opaque nature of the story and it's undertones of female sexual awakening while also trying to be a standard story of rescuing someone from a strange land doesn't gel well enough. I get it's place in the fandom of Bowie since he's the best part of the film but as a movie it's always left me cold.
Legend is also a pretty imperfect film... Bud damn if Sir Ridley didn't make an amazing looking imperfect film. I always note that despite our looking at Tom Cruise as this mega star, now and then, this movie is closer to a fantasy story with some depth and interesting themes one might find in literature as compared to a regular Hollywood film. Cruise is presented as a boy of the forest much more than a traditional warrior type. This isn't the story of Conan or Dar the Beastmaster besting all comers in single combat. He's much more say, Frodo than he is like say a Aragorn. He's an innocent coming to terms with sexual desire and manhood, and the complications that those things have on the simplicity of youth. What I liked a lot about the film despite it's narrative and character un-eveness is that it doesn't take place in a domesticated, Disney influenced type fairy tale world. This is much more akin to the original nature of the folk stories and fairy tales as they truly were. Those stories were about wonder and awe and uplift but they could also be filled with scary creatures, dark themes and didn't shy away from violence or the less savory aspects of people and society. Unlike Willow though I have less a ready answer as to the flaws of the film, but it doesn't quite totally work. A visual feast, something about the central characters on the hero's end doesn't quite add up to anything all that compelling perhaps? Certainly the villain of the piece is not at all an issue. Tim Curry is chewing scenery like he's carbo loading for a marathon. He can truly be JUST evil, just the very flower of the seductive but frightening malign force without any need for layering in the story. Here, that just works on the back of his insane performance. I guess it does come down to Cruise and his companions and the female lead in Mia Sara. Sara is truly a sight to behold, but... There's not much to her, and I'm not sure what the movie is trying to tell us about her, or about the relationships between young men and young women in general. Once more a rather opaqueness to the overall proceedings is part of the issue. It's all gorgeous, it transports you into a beautiful fever dream that only a master like Scott could produce but what it's all supposed to add up to is something I'm still trying to figure out, outside of again, giving Fairy Tales their teeth back.
Now The Dark Crystal as a film just shouldn't work at all. It really shouldn't. There are no "human" characters, it's pacing is bat guano crazy fast and it leaves all kinds of questions for the audience to ponder about this world and it's nature on the table. But... I think it does work the best out of all the films listed here. It probably doesn't have quite the scope and texture of Legend but I think it might surpass it in terms of you as an audience member going along on this journey into a place so different to our own mundane world. I certainly think it accomplishes this feat far better than Labyrinth. Yes, the lead characters are a bit bland, I can't argue that they are particularly well rounded, but they are effective and likable and you get enough info about them. Besides, as stated, it's the journey they are on in this strange universe of the film that's the whole point of the movie. And it's a wildly interesting and intriguing world. I think it does a better job of being a movie from a diminutive character's POV than say Willow. A simple story that finds no real false notes, this is a movie that can make it's way purely on the visuals almost. So many ideas in the film are presented with it's on screen action with not too much in the way of exposition. Now, as much as I like it I do think I get where someone could come away from it thinking it was nice to look at but not much else. That said, I would argue for any flaws it has it still is the most complete film on this list. It's not for everyone but that's hardly the worst thing one could say about a movie and is in no way the last word on it's quality.