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The only Bailey I've met is a girl, and there was a country act called Bailie and the Boys back in the late 80's, early 90's. Bailie was the female singer's last name, but somehow the execs at their company started calling the group Bailie and the Boys, and it stuck. I can't imagine it on a boy.
As a last name, there's the comic strip Beetle Bailey. He's a lazy soldier, and I don't think I'd want a son to be associated with that image. Not that it's a horrible one, but I wouldn't want people to think he's lazy like the character. http://en.wikipedia.org/wiki/Beetle_Bailey
https://www.youtube.com/watch?v=6L_nbNf5ueA