Personally, I don't care much for Crewdson and his work. I saw a few interviews with him (first one was this
http://www.cbsnews.com/video/watch/?id=4048567n) and simply never got it. He admits never having even touched a camera in his life. He hires big movie crews, has his own personal photographer to set-up the camera and take the shots when he says so (he doesn't even handle the cable release). Takes multiple shots on 8x10 that he has drum scanned and combined in Photoshop by his own assistant (he doesn't touch the computer).
And he has a BIG budget. For one of his shots he even bought a house to burn it down.
One thing he is really good at is asking the question of what makes a photographer?
If you make an image without ever touching any piece of equipment, is it still your photography? Are you even a photographer?
For all I care, he's a millionaire kid who has too much money and too many thumbs in his hands.