… we can still be depressed! A long-time friend of mine has talked for years about his belief that “Have Yourself A Merry Little Christmas” is one of the most depressing songs in existence. I would contend that it isn’t even the most depressing Christmas song. For example, we have the contemporary Christian (which genre typically makes me want to kill myself just by virtue of its existence) tearjerker “The Christmas Shoes“…
The Nerd Girl, meanwhile, has a dark horse favorite in the form of “Do You Hear What I Hear?”, but it only works if you know the Paul Harveyesque backstory.
… and as I said, my buddy advocates for “Have Yourself A Merry Little
Existential Struggle Christmas” (with Judy Garland for extra added pathos):
There’s also someone who claims that there’s a song about a little boy who is lost in the woods on Christmas Eve, is found by Santa, and dies of exposure (a sort of “Little Match Girl” with extra holly), but I’ve not been able to chase that one down, so I’m declaring it apocryphal.
But for me, I’d have to say the Das Boot of Christmas songs is Gordon Lightfoot’s 1974 release, “Circle of Steel.” For those who like a little despair with their egg nog, this one’s hard to top.
Your nominations/votes are welcome as well!