7. Merle Haggard: “If We Make It Through December." He sings: "I wanted Christmas to be right for daddy's girl/ Now I don't mean to hate December/ It's meant to be the happy time of year/ And why my little girl don't understand/ Why daddy can't afford no Christmas here." If you think you don’t like “country” (as if this is mainstream Nashville Garth Brooks drivel), then grow up. There’s a reason why recovering punk-rockers have turned to classic American country (John Doe of X, Jon Langford of the Mekons,etc.).
8. The Smiths: “There Is A Light That Never Goes Out.” It’s tough to choose one Smiths pearl out of their considerable showcases of sad jewels — they have a monopoly on them in underground niche markets of the last twenty years. But this one is inevitably sad-tinged and yet bold, romantic, hopeful: “And if a double-decker bus, crashes into us, to die by your side, well the pleasure, the privilege is mine.” Morissey, a strange hybrid descendant of Wilde, Goethe, and Poe.
9. The Cure: “Pictures of You.” Sadness, regret, hope aren’t just evoked by music. The visual evidence is a haunted house, a torture chamber, or an oasis on the horizon.
10. Johnny Cash: “Hurt.” The Man in Black — ‘nuff said about qualifications. He wears it for the poor, broken-hearted, etc. and if you’re still reading this that includes you. In the last few years before he died, he did some of the most eerie, astonishing, monumental covers in the history of modern popular music. This is my favorite, a cover of Nine Inch Nail’s “Hurt.” Throw all sharp objects out the window before listening to this.
11. Serge Gainsbourg: “Les Feuilles Mortes” (The Autumn Leaves). This classic (originally in France, 1942, lyrics by the poet Jacques Prevert) has been covered many, many times. If you've never heard it, time to grow up musically. After all, you've grown up unwillingly thanks to heartache, misery, doubt, bad luck, and angst. This dirge is suitably in French, but if you have an "English-only" policy, try Edith Piaf's version (she's the greatest French chanteuse of all time but sings this in English and French) or jazzed-up ones like Chet Baker's or Miles Davis'.
12. Jerry Jeff Walker: “Mr. Bojangles.” This gem has been covered many many times, by the Byrds, Nitty Gritty Dirt Band, Harry Nilsson, Bob Dylan, Harry Belafonte, Arlo Guthrie, Nina Simone, John Denver, David Bromberg, Neil Diamond, Sammy Davis, Jr, Tom T. Hall, John Holt, Robbie Williams and David Campbell among others, and for good reason. Another beautifully sad tale of a hapless man who finds some spring in his step (indeed, he’s a dancing man by métier).
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