There's a book called Freakonomics, which I highly recommend, that has a whole section on names (and naming data). A couple of highlights:

A woman named her daughter Temptress, didn't know what the word meant. This came up at the daughter's hearing on prostitution charges.

A man named his son Winner, thinking this was a sure way to guarantee success for the child. Later, he named a subsequent son Loser. The book says something along the lines that Winner's most impressive acheivement was the length of the list of crimes he'd been charged with . . . Meanwhile Loser went on to become a well respected sergeant (or detective) with an overall contented life. His friends and coworkers had a hard time calling him Loser, I think it said he went by Lou or some such thing.

There is also a nice list of unbelievable names taken from public records, including things like Doctor, Lawyer, etc.