Go for it. I don't think they'll mind if they get two letters from you, it'll just show your a dedicated fan and really wanted to be sure you would reach them.
Good luck!

x Pirates-Fan x

i tihnk that all celebrities get surpirsed the first couple of times they get some fanmail
but after the first 100 it probably numbs them
and i think that in both leters you should explain that you sent it to two locations
then they would have no reason to be "upset"

Do you think that not so known celebs that don't get so much fanmail are surprised when they do? Also, I'm thinking of sending to a different location to one of those people. If both addresses work and he gets both letters, will he be annoyed?