Over at Althouse, a post about the 50 most heartbreaking songs of all time - #1 is "I'm So Lonesome I Could Cry" - got me thinking about some of my favorite songs that are meant to tear your heart out. I mostly listen to older music - by which I mean 1950s, 60s, and 70s - especially the Rat Pack and classic country music. I think those eras had some of the best emotional, heartbreak music.
The list that Althouse links to is good; these are four of my favorite (only the first made the list):
Frank Sinatra: "One for My Baby (And One More for the Road)"
Ray Charles: "I Can't Stop Loving You"
Conway Twitty: "The Clown"
Merle Haggard: "A Place to Fall Apart"
I'm not usually the one to post music links here, but I'm interested to know what everyone else thinks of the best "pain" songs.