"So I'm curious Peter, what about Crewdson hits you so wrong that you singled him out as the example of "not good" in a thread about good photography?"
It is hard to say why I do not much appreciate his work. (And by the way I am just using him as an example that sprang to mind - I am sure that there are others too but he is so well known I can cite him and be confident that others will know what and who I am speaking about). I think Crewdson worked in film and it certainly shows in his work which has a kind of cinematically staged look about it. I think that this is part of the problem for me - knowing that in fact it is wholly staged, not real in the sense that it was taken from life. This makes it artificial and therefore lacking somehow. Shots like this remind me of the old joke - success is all about sincerity - once you can fake this you have it made. In this case it is not sincerity its about being able to get away with something artificial so long as it does not look and feel artificial (although I am sure he might say he wants it to look and feel artificial as that is his intention, its part of his "thing"- but sadly that is not enough for me).
He carefully sets his images up and takes them - in fact his role is more of a Director than a photographer and I believe these days he does not even take the image - that is done for him once he has directed the staging. In principle I do not object to that if it can be -pulled off but to me it has the kind of quality that far far too many Hollywood films have - big, expensive, highly produced and directed, technically brilliant but contrived and lacking soul or interest. I can admire his technical skill but there is nothing in any of his images that grab my eyeballs or more importantly, my heart for that matter.
To me a good image is often like poetry - you will be more likely to enjoy it if you can relate to it from your own life or have to invest yourself in interpreting it from your own life. And it must evoke a pleasurable emotion - nostaligia perhaps. Crewdson's work just does not speak to me on an emotional level in that way. I get that it works for others and that he is a big name. So who am I to say this? I am not even saying it to be critical of him, more as an expression of my own befuddlement I suppose over the same question that you have asked me - I have the same question about why I don't like him and others do, except its from the opposite perspective from you.
BTW on the subject of the role of nostalgia in making good images - watch this WONDERFUL WONDERFUL WONDERFUL clip from the series Mad Men in which Don Draper has to sell a pitch to the people of Eastman Kodak. It makes me blubby every time I see it. (The photos he shows incidentally, are of his own family and the wife with whom he has recently broken up so the pain "from an old wound " he speaks of is his own -blub,blub,blub. And while none of his images seem particularly good to me, to him they are obviously very, very wonderful images. That's how personal this issue of "good" images can be - and its why it can be so elusive to answer).
https://www.youtube.com/watch?v=suRDUFpsHus