This is a real old one (1976)...but has always been one of my favorites
She's a Broken Lady by The Gatlin Brother's....
http://www.youtube.com/watch?v=XqdHpx-9b2s
I have lots of favorite male country singers, but if I had to choose my favorite song by a male country singer, it would definitely be Josh Turner "Your Man". His voice just makes me melt.
I'm going to go with "Hurt" from the man in black Johnny Cash, I think it is the best country song to be done in the last 10+ years, and Trent Reznor loved Johnny's version of his song.
__________________ Though I walk through the shadow of the valley of death,
I will fear no evil, cause I'm the biggest son of a b***ch in the Valley