Kirsty MacColl, "Here Comes That Man Again" (2000)

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I know most of us are still not prepared to talk freely about cybersex among ourselves, but 13 years ago the late Kirsty MacColl gave it a perfectly charming, lighthearted whirl. It's fully marinated in the Cuban sounds and rhythms that mark the album it comes from, Tropical Brainstorm (see also). It's dated, to be sure, lurching out of what suddenly now appear to be more innocent times, the late '90s. You don't hear modem tones so much anymore, for one thing, and "get your rocks off" goes back even further to the era of "humping." But this shticky number sketches the screaming weirdness with almost clinical precision, sighing contentedly at one point, "Who'd have thought I'd have so much fun ... I never knew I had it in me." She always treads lightly, but seems to have the basics right: "oops, another file on the email, oh oh-oh ohh," so on so forth. The compulsion, the payoffs, the many surprises, not all good. It's extremely silly, nearly as silly as it is intoxicating, thus a topic perfectly suited to her style of songwriting. Through the swirl of rhythms and arrangement, broad sound gags bubble up and charge the energy, such as a wacky muted trumpet that serves as ba-da-boom for one of the punch lines. There's a Monica Lewinsky joke too, in the thick of the big finish, which lets loose with a tattoo of "sha la la la la, get your rocks off baby." This may or may not be my favorite song by Kirsty MacColl but everything I like about her is in it: it's equally funny and poignant and fearless, and musically it's Tin Pan Alley sophisticated with an eye on the rest of the world and winning popcraft all the way.

Tropical Brainstorm (2000)

The late Kirsty MacColl, who died in a boating accident the same year her fifth and final (and best, as far as I can tell) album was released, may be best remembered now either for singing on the Pogues' "Fairytale of New York" or for being married to producer Steve Lillywhite. The only thing you might learn about her from either of those items is her pluck, of which there was plenty. Other things you should understand: she knows her way around a pop song, and she can be very funny when she has a mind, as she does here, and often. It's mostly tossed-off gesture and gags, which is no surprise because she also had some luck as a comic actor on British TV and knew how to do it. And she really did know how to do it, slyly embedding a good deal of it in the throwaways, plumbing layers of meaning and quickly moving on. For example, I don't think there's anyone alive or dead who could ever match her reading of the line, "I've got a powerful horse outside," which only becomes more funny the more times I hear it—and notice it—sitting there in the song "In These Shoes?" Sometimes, as on that self-same song, she does flirt dangerously close to shtick, but that comes with the territory of someone trying so hard, and with so much good creative energy, to provoke both laughs and tears. She shuttles back and forth between both ends of the spectrum even as she sticks close to what she's best at, working an everywoman's various takes on fashion, men, sex, fun, and sadness. She's fearless and never stops trying things. She draws heavily for many songs from Cuban, Brazilian, and other Latin musical sources, which indeed is the album's most distinguishing feature for many (e.g., Christgau), and certainly keeps the set crackling with energy. She entertains elements of sadomasochism and boo-hoos about tiny failed relationships in ways I had only heard before in conversation, not song. And she "goes there" in "Here Comes That Man Again," goofing on cybersex and the niceties, though the modem sound effects now serve to put it all in the vicinity of quaint. "Celestine" is the song that sold me on her once and for all, a meditation on alter egos that is effortlessly natural, closely observed, and resonant. This is a pretty big album too, nearly an hour long with 16 tracks—many rooms in the mansion. Worth spending time in nearly all of them.

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

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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.