"The Warmth of the Sun" comes immediately to mind, penned by a melancholy Brian Wilson on the night of JFK's assassination, as I recall. Who wasn't sad on that night? I know I sure was (age 7 at the time). The chord progression on that song just slay me...they're all over the place. Minor. Major. Back to minor. Goes right to my heart.
"Back to the Island" by Leon Russell always touches me deeply, for personal reasons. Had to say goodbye to a beloved girlfriend and played that song for her as we parted ways, many years ago. The background singers almost seem to be crying, too.
"So Sad the Song (That Says Goodbye)" by Gladys Knight & The Pips. "Song for a Winter's Night" by Gordon Lightfoot. If you've never heard it, try "A Love So Beautiful" by Roy Orbison, from his final album, "Mystery Girl". It'll make the hairs on your neck stand up, when you consider it as one of his last works.
I hear such a sadness in Jo Stafford's voice, always, but it peaks for me in her amazing rendition of the WWII era's "I'll Be Seeing You". Jo and The Pied Pipers get the billing, but Jo's unique voice and the poignant lyrics just blend perfectly here.
Sorry to go on so long here! But this list would not be complete without Skeeter Davis' "The End of the World". My sense is Skeeter had kind of a tough life, married young to Ralph Emery and facing serious illness and a death WAY too young. The darned song was sad enough when it was released, but knowing her personal history makes it all the more touching now when I hear it.
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