It'll never work, Matt. Well, actually he looks pretty good. This probably the best example I've seen of the fedora's recent resurgence.
When I was looking for a good picture of Lauer in his, I came across this Live Journal post, and marvelled how someone could get 247 comments just for asking if the fedora thing is good or bad (incidentally, I don't think any of the fedoras in her collage are all that great, except maybe Terrence Howard's, but his crown is too thin for his head, making him look like a turnip).
Meanwhile, the blog of Diablo Cody, beautiful young former stripper whose screenplay for Juno is up for an Oscar, regularly receives no comments. How did this world get this way?
Apparently she married an internet boyfriend. I guess there's a message there about quality versus quantity.