Lots of truly sad songs here but the ones that get me most are the ones about people who leave someone they love because of character flaws that the break up protects the loved one from.
This George Strait song is about a guy so obsessed with his profession, rodeo cowboy, that he loses his wife and the news is delivered in a way he seems to expect deep down because he knows he has put her through some lonesome times because of his obsession.
[ame=http://www.youtube.com/watch?v=rIkrnanfvZk]I Can Still Make Cheyenne (George Strait) with Lyrics - YouTube[/ame]
This Garth Brooks song is very similar
[ame=http://www.youtube.com/watch?v=RCi4X0pa0ok]Beaches Of Cheyenne - YouTube[/ame]
This one by George Strait is a classic along those lines
[ame=http://www.youtube.com/watch?v=RfIdqkATm2U]George Strait - Amarillo by Morning Lyrics - YouTube[/ame]
Its a cliche, but too often people spend so much time pursuing a proffession that destroys the family that they have thought they were doing it for but it was really all about themselves. And they realize it all too late to avoid the consequences.
Tim McGraw catches the feeling in a different way giving a fond farewell to someone he has hurt.
This one by the Dixie Chicks is a classic