I stumbled onto this old thread and after almost 10 years - and find I have a bit more to add. So here goes:

I rarely sing to general audiences, songs that have sensitive racial content - except I sometimes sing "Yellow Rose of Texas." BUT when I sing it, I use the very commonly accepted set of lyrics that have long since replaced the word "darkie" with "fellow."

The oldest known written set of lyrics for this song, from around 1830 - say "She's the sweetest rose of color this darkie ever knew" but in America, we have long been singing, "She's the sweetest rose of color this fellow ever knew." And leave the rest of song original (there are exceptions - some Civil War versions have appeared and some local versions).

"The Yellow Rose" song is about the singer's fondness for a lovely girl of color, as he tells us - presumably a mulatto of "high yellow color" - and those words are gentle enough. They never were intended to be anything more then a loving description - so they seem to pass modern correctness tests.

The song is hugely popular in the US. Everyone, it seems has heard it and enjoys it. Still I think people haven't always paid close attention to its lyrics, so when I sing it, I watch for a few gears turning behind the audience member's eyes - when they realize he is singing about a Yellow Rose, or pretty girl of color.

As for other songs - other songs that might now have sensitivity, though they had a very different understanding of race issues when they were written - I don't usually have a place to sing them. And I wouldn't without comment, or should I say "explanation."

Here's a good example of such a song:

In the song Honest Pat Murphy - aka SONG OF THE SPLINTERED SHILLELAGAH (a version of this song is in the DT).

There is a verse that is commonly left out now-a-days, and one I sing only when I have a Civil War history focused audience and I have the chance to comment on it.

The song lists the Irish immigrant's reasons for joining, willingly in the American struggle to preserve the Union. The singer says they think it's a bit queer for brother to fight brother, and they prefer to rush into battle against the English - but they are happy to lay down their lives to preserve the Union. However, in this one verse that I commonly do not sing, they say they have no interest in joining the struggle to end slavery. This was a common feeling among the newly immigrant Irish in America (perhaps even a majority feeling in that crowd). These guys, or at least this singer was not Abolishionist! Here's the verse:

Jeff Davis ya thief if I had ya but here
Your beautiful plans I'd be ruinin'
I'd give a taste of me bedad
For tryin' to burst up the Union
And there's a crowd in the North too
And they're just as bad
Abolishionist Spouters, so scaley
For troublin' the negroes I think they deserve
A whack from me sprig of shillelagah

The verse is well worth singing, in the context of historical discussion. It is clever and beautifully captures a common (not ubiquitous) Irish immigrant sentiment from that place and time - but it's meaning would be lost or misunderstood to a general audience, without discussion. (And by the way, there many Union loyalists who felt like the Irish singer of this song - Civil War to save the Union, NOT to end slavery.)

The song itself, is rich with historical and cultural value - most of which can be lost on a general audience - but it is a strong song, a "stand alone" song and it works really well for a general audience without explanation. I believe the listeners who think about it will get it, or get some of it - and I believe the song may very well plant seeds of question that listeners seek answers to later on - or it will motivate them to listen more carefully next time around.