We seem to have broadened this conversation quite a bit, but I would like to take us back to what Dick originally posted and examine in more carefully.

He spoke of singer/songwriters who were not from America singing in (their own approximation to) an american accent. So we are talking about someone who writes a song for themselves to sing, but in a accent which is not their own. So the question is not just why sing in an accent that is not your own, but also why write a song for yourself to sing in that false accent? I agree that taking a song in a different dialect even to your own can be challenging, but why deliberately make if more difficult for yourself to sing successfully by writing it in this way? Way up near the top of this thread people have mentioned the influence of pop culture, where the same problem has existed for years IMO. The only other explanation I can think of is that they write the song hoping some big star will take up on it, rather than for them to sing themselves.

I don't like it either Dick. It makes me cringe when I hear it at singaround sessions or open mikes around here. It often destroys the feeling of sincerity one can get from some singer/songwriters.