Lyric discussion by MsMolly 

To me it definitely sounds like it's speaking from the point of view of a black man in the South who's about to be murdered by a lynch mob for associating with a white woman. His father blames him, saying if he had followed the "should've, could've, would've" restrictions of the white men and stayed away from the woman, he wouldn't have had to die. The son, however, asserts his humanity, saying that even though he will be killed, he will swing "free until they cut me down".

This is a beautiful song and recalled to my mind the lyrics from Arrested Development's song Tennessee, where the singer goes to the South and climbs "the trees my forefathers hung from".

This is what I got from it, a bit of a satirical song against racism in the south and executed blacks on false accusations. This might be something he saw as a kid?

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