My fave artist - looking at the lyrics is really useful because his lyricism and imagery are amazing, but his songs are just generally beautiful and cross a range of genres. Most of these songs make me cry.
Josh Ritter - Girl in the War
http://www.youtube.com/watch?v=kqLssKusGzM
(love song on the futility of war/discourse between Paul and Peter/literally, someone you love in the war [in danger])
Josh Ritter - Temptation of Adam
http://www.youtube.com/watch?v=kvCeCVmJAUA
(love song through the metaphor of the cold war)
Josh Ritter - Right Moves
http://www.youtube.com/watch?v=Skxi14RSJN0
(return of an old love. MUCH peppier and more upbeat than the last few. Makes me smile, not cry.)
Josh Ritter - The Curse
http://www.youtube.com/watch?v=KXBI2_zH9Js
(love story between a mummy and the archaeologist that discovers him. Video is esp interesting.)