Certainly we shouldn't look for modern mores in songs which are centuries old. Everyone is a child of their time.

I agree. One problem is that some people do this, i.e. try to apply modern 'rules' to old songs, and try to stop people singing them for fear of offending people. Yes, there are some songs that would be offensive because of the language used, but others where it's not so easy to draw the line between what is offensive. As was said in another thread recently, there would be very few old songs we could sing if we take this modern 'puritanism' to extremes, as some folk are wont to do.

As long as the singer is aware of the song's context in history, and sensitive to modern views, and takes the trouble to explain to the audience, I don't see a problem myself (with the exception of certain songs which may be directly insulting to people).

In the case of the Whistling Gypsy / Gypsy Rover, I never really thought of it as being offensive. I thought of the 'gypsy' as a romantic, roving blade type of character, which seems complimentary to me rather than derogatory, but I suppose it depends on your view.

I think the song mocks the rich father for looking down on the gypsy, and trying to stop his daughter running off with him, rather than being derogatory to the 'gypsy' himself, or the gypsy people. The message I get from it is that the daughter fell in love with a man she believed to be a gypsy, and it was only later she found out he was a rich man in disguise (or something like that).

Similar to "Hi for the Beggarman", where a beggar turns out to be rich. Again the story is about a girl who falls for a poor man (the beggar) and pokes fun at her parents for trying to stop the match. The message is "love is more important than money".

(Apologies if these points were made above, I only had time to skim through the posts).