Kate Long's "McNamara's Tear" hits me so hard that I get emotional just thinking about the song.The first song I thought of when I read the thread title was "Hollis Brown."
"The Railroad/Butcher Boy" didn't start affecting me until I became a parent.
I can't always get through the verse in "Little Musgrave & Lady Barnard" that goes "He's taken out his long long sword to strike the mortal blow."