Rembrandt's self portrait sold for a nice chunk of change at auction recently. It's really a great shot of him and you absolutely get a sense of the type of person he must have been.
Here is a link to the full article I read recently and it got me digging through some of my old sketch books to track down the times I did my own self portraits. Not as classic as Rembrandt's of course but I do think these two I found do both capture elements of my personality.
The first one is when I was in 35 - the other I believe was when I turned 40.