Only happened once, but I guess it counts - Neutral Milk Hotel - Two Headed Boy. That being said - Louis Armstrong Black and Blue gets me close every time.
Continuing tony1954's theme of music to wallow in:
Cowboy Junkies: Cause Cheap is How I feel
Janis Ian e.g. Between the Lines
Jewel: Foolish Games
Warren Zevon: Knockin on Heaven's Door (Zevon was dying of cancer)
Jennifer Warnes: Famous Blue Raincoat
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