The Beach Boys/Tear Jerker

At least one-third of all this '60s pop band's songs may qualify, due to their sheer beauty -- even if the subject matter isn't necessarily sad.

"I'm a leaf on a windy day Pretty soon, I'll be blown away How long will the wind blow? How long will the wind blow? Until I die..."
 * "Til I Die"


 * "Caroline, No". Brian Wilson wrote it about an unrequited love of his.
 * The They Might Be Giants cover is also quite heartwrenching, John Flansburgh can sure pull of any sad love song.
 * Also: "Surfer Girl", "God Only Knows", "Don't Worry Baby", and especially "In My Room".
 * Despite the rather cheerful music, "When I Grow Up To Be A Man" is this to those unsure of where they will be when they reach adulthood.