[As if I need to say it: Warning: long post]
Ok, I'm back. I watched The Princess Bride for the first time possibly since it came out, and listened to the [Redacted]/WAYDM commentary to get a sense of what people really like about it. I suppose I should begin by apologizing to anyone who sunk their life savings into popcorn futures, as I didn't hate it as violently as I did originally. (Seeing it in the comfort of my own solitude rather than with a bunch of people who all thought it was the greatest thing ever probably helped.) However, it didn't really work for me, and there are certainly chunks of it I do find really annoying. A lot of it I think is just I like oysters and you like snails (and then there's Olivier, who likes both). However, I do have this sense that, in the abstract, there is a problem with what it's trying to do, so in the interests of trying to provide value for money, I'll try to articulate it at the end.
So particularly Brian in the commentary refers to the line that that the film is walking between being serious and being a parody. And he, and presumably others who really like it, feels that it's successful in doing that. For me, though, the main reason why it doesn't work is that I didn't feel like either the serious part or the parody part worked.
So, looking at it first as an attempt to tell a sincere adventure story, for me it's generally too knowing and too (deliberately) cliched/sabotaged storywise to be successful. For example, I don't really buy the argument that just because it's a fairy tale we're off the hook and get to just go "yeah, true love. Ok."; that's part of the "boring bit" that we're going to leave out, and therefore the film doesn't need to make any effort whatsoever. So as a result most of the scenes between Wesley and Buttercup for me play out as a notch above Attack of the Clones (and maybe not even that). I don't find their relationship remotely plausible and so I don't have anything invested in it and couldn't care less about them as characters. A surely related aspect of this is that I also think that Robin Wright Penn is terrible and has no chemistry whatsoever with Cary Elwes. (You may say "well that's kind of the point because it's a parody", and I'll come to that in a second, but I think these are fair things to expect from the point of view of taking the story seriously.)
To kind of illustrate what I think the film should have been doing, and what for me does work, I'd point to Mandy Patinkin's character. His is a 100% cliched revenge narrative, but the film makes an effort by giving him that little speech to Wesley. It's nicely written, it's well-executed, it takes two seconds, and that's all we need to get on board with his role in the narrative. But there's nothing equivalent for, say, Buttercup.
On the villain side of things, nothing really works for me. Chris Sarandon is awful -- very (post-)modern and knowing in his performance, in addition to seeming bored and half-assed. He's certainly not remotely menacing. Wallace Shawn takes me out of the story simply by being Wallace Shawn. The best one by far is Christopher Guest, and I think that's because he's the one who's really allowed by the script and/or director to play it straight.
So the 'straight' part didn't work for me, but then the 'parody' part didn't either. Part of my problem I think is that, as a parody, I'm not sure I get what the point is supposed to be. If it's just that we're gonna stand around and point at fairy tales and laugh at them for being cliched, that seems pretty feeble. I think I realized that when I was about 10.
And then a lot of the other comedy bits kind of just fell flat for me, though this is obviously very much a personal taste thing. The film clearly thinks that it's being clever, and often takes up a lot of time doing it, and that just annoyed me. So the running gags grate from moment one. Things like the whole convoluted bit about which glass is poisoned wears out its welcome very quickly, the Billy Crystal cameo is tedious, etc.
Actually, having said that, it could be that the Billy Crystal cameo is a kind of clever double-bluff. We're heading to the part of the cliche where we go to the old crone with magical powers, except, surprise!, the magical crone is an old Jewish guy. How droll. So we're laughing at fairy tales for being a hoary old load of bollocks, but nothing could really be more of a cliche than Billy Crystal's character. Mel Brooks was doing that schtick with Rob Reiner's dad in the 50's (see the 2000 Year Old Man), and I'm sure it goes back earlier than that. If it was some kind of meta-double-bluff though, deliberately psuedo-subverting a cliche with something that was, in its way, just as much of a cliche, then that might actually be kind of witty. But I'm not sure that that's what's going on, or that that's why most people think that Billy Crystal's character is hilarious.
I do think the film really does want to have it both ways. It wants to be both a genuine fairy tale adventure and also a parody of the genre. The question though is whether that's actually a coherent thing to try to do, and I'm not sure that it is. So something like The Adventures of Robin Hood is a genuine adventure story. It may rely on cliched elements or not be well-executed in some respect or other, but it is sincere with respect to those elements and to its core narrative.
Something like Airplane! on the other hand is a parody. We're precisely not supposed to be invested in the suspense/distress of the stricken airliner, for example. The film relates to those aspects of the narrative in a way that's not sincere or genuine. And it's precisely the way in which this lack of sincerity is manifested that makes the film funny (for those people who find the film funny). In other words, you can be watching Airplane! and thinking "that's not funny", but if you're watching Airplane! and thinking "gosh, I hope that little girl's heart transplant goes OK", then you've misunderstood what's going on.
So anyway, if I were trying to take it beyond "yeah, just nothing about it really worked for me", in which case there's nothing really further to say, and into "there is actually something 'objectively' wrong with the film", that's what I'd go with. To the extent that the film is supposed to be a parody, the purpose of the film doesn't derive from the audience's engagement with the narrative (so there's no issue about, for example, whether Wesley and Buttercup's relationship makes sense or is believable). But that's then incompatible with the film being 'serious' or 'sincere', because the point of the film then is the audience's connection with those things (even if that doesn't happen in a particular film because of incompetence or poor execution or what have you). So it can't be then that the film is really walking a line between these two things, since they're mutually exclusive, and to the extent that it's trying, it's incoherent/at cross purposes with itself.
So I'm really not familiar with it at all. 