37. Pogues, "Fairytale of New York" (1987)

(listen)

Apparently I have been living in a cave because until just now via Wikipedia I had not realized the efforts people have made to turn this into a holiday classic—as admirable as they are ludicrous as they are perfect. Ludicrous because the song is so determinedly squalid, so dank and fetid, a drunk man in jail on Christmas Eve who pines uselessly for better days; perfect because with all that it works so well. My hat is off to those who hear this so clearly now. It gives me cause for hope after all. The album it comes from, If I Should Fall From Grace With God, is an utter revelation itself, but this was the point where it tipped over for me into something so strange and bewildering and good I don't have adequate words for it. I have been known to play it again and again. Shane MacGowan's gruff, whiskey-soaked, forever off-pitch growl matched with Kirsty MacColl's forever upbeat pop fashionista femme warble, the lush grand piano that launches it, the strings that carry it home, all the Irish strains, the nostalgia and regret and other symptoms of despair, the presence of law enforcement, and overall the sense of a nagging sadness, omnipresent, only temporarily, fleetingly redeemed, are overwhelming when heard under the right circumstances, e.g., alone, whether by oneself literally or in a madding crowd or at the family hearth. Maybe it's the Christmas theme that makes it hit so hard. Maybe I'm vulnerable to any flavor of pop music syrup that comes along. But the tension here is visceral, operating at multiple levels: a strange duet, foul-mouthed and sweet, with intimations of both jail and joy, bittersweet, wise, and knowing.