I was asked to do a one-man workshop at a festival and it was up to me what the topic would be. I chose Politically Incorrect Songs as the name of the presentation. My idea was to take songs from my repertoire that, because of the passing of time and changing values, had become politically incorrect to at least some people---offended some other people---maybe polarized an audience as well.
All of the songs were, I thought) too good not to sing. They just had to be introduced in the right way---like Abe Lincoln did when he'd tell a story to set up a serious point he wanted to make with a lighter way of approaching the serious topic.

Here's the list I picked from just my personal song list back around 1996:

The Ballad Of Sherman Wu(from Pete Seeger)
Blow Boys Blow (whaling song)
Greenland Whalers (as above)
The Diamond (as above)
Cock Fighting Song (animal rights)
Buffalo Skinners
The Union Maid
East Of West Berlin
Tramp On The Street
East Texas Red
Blackjack County Chain (murder-revenge-violence)
The Killer (or Dobe Bill)(as above)
Louis Collins (violence)
Electric Chair Blues (from Bessie Smith)Oh The Wind And Rain (violence toward women and dismemberment--offensive to fiddle makers)
The South Coast (winning your wife in a card game)
The Ladies Auxilliary (from Woody--before women were in unions)
Old Lady That Swallowed A Fly (cruelty to animals)
The Bitter Withy (spanking children)
The Cherry Tree Carol (cruelty to trees and deceiving husbands about paternity)
Zack The Mormon Engineer (wife in every town)
Pie In The Sky When You Die (blasphemy)
Sioux Indians (self-explamatory)
We've Got Franklin D. Roosevelt Back Again (as above)
God Don't Like Ugly - Baby Your Home Is In Hell (ugly people get upset whenever I'd sing this one)

I never quit singing these. It's just how you set 'em up. And we had a fine time at the workshop extending this list.

Art Thieme