"First Christmas," Stan Rogers
This is not only the saddest Christmas song of all time, it is quite possibly the saddest song of all time period. The legendary Canadian folksinger presents three different scenarios of people spending their first Christmas away from their family: a young man working through the holidays, a teenage runaway and an old man in a nursing home.
Most heart-wrenching moment: Just thinking about the third verse is making me a little verklempt, but the dam really busts when Rogers gets to this line: "When the old girl passed away he fell apart more every day, each had always kept the other pretty well." That's quickly followed by a description of the "huge and cold and lifeless" tree in the common room with a "lit-up, flashing Santa Claus on top." Oh, man, that's some sad stuff.
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