I have always adored her work - mostly because she makes me laugh - I guess because you can just tell she loves what she does, she enjoys it, and it comes out. Also, I love her work because it's meaning is very subjective, and more broadly, is an excellent illustration of why Context Matters.
For example, last night on PBS I just happened to pass by the TV and Art21 was doing a short (too short) bio on her and her work. She seems to have had a fairly normal suburban childhood, from the way she described it, and as she talked about her work, she discussed this one - take a look at it and before going any further and reading the text below it, consider what you think is happening or what the context of the photo is:
Actually, I believe the photo is supposed to be oriented landscape:
http://img2.oneartworld.com/images/uploaded/large/354-Cindy+Sherman.jpgSo Ms. Sherman discussed her work, and what it means for those who have seen it, and she said about this particular photo that her thought process for this photo was, here's a woman who is really, really tired, a little hungover, just got back home at 4:30 a.m., hit the bed, and the sun is coming up, and that's what the context was for the photo in her mind. Meanwhile, after it was released, people started telling her that it strikes them that the woman has just been raped. !
IMO, that's the power of her work - it's not beautiful in a traditional way or in a classical way; but it gets you THINKING, reflecting on context and I just really, really love that. So much contemporary photography is good, don't get me wrong, but very in your face, tells you exactly what you are supposed to think, doesn't challenge your stereotypes and presumptions about gender (a world in which women are made up, stockings, leather, heels, men are cowboys, wolves, lechers). Sherman's work is just the opposite, IMO. I guess that's why it makes me laugh, because it's challenging, who knows.
When I was just a kid, I actually wanted to be a photographer just like her - that didn't pan out, but she will always be an artistic goddess to me! :)