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The 10 Best Christmas Songs, According to an Ex-Record Producer

RealClearLife music columnist Tim Sommer compiles a list of the popular and obscure, uplifting and melancholy.

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Let us consider the baby Jesus on the first Christmas.

His life, which shall make the epoch shudder with love and war, is only hours old.

His simple cradle, constructed out of olivewood that expands gently with the daytime heat and contracts, with no threat of shattering, in the chilly desert night, is mostly still. The carpenter and his wife are asleep, laying an arm’s length away from the child. Every now and then, the cradle, built and balanced with a technique taught to the carpenter by a friendly Roman soldier whose name has been swallowed by history, stirs most gently as the Savior inside shifts in his dreamless sleep. Once, when a nearby ass, shivering, suddenly moves its palm-trunk of a neck, the little angel’s eyes flutter behind their nearly transparent lids, but they do not open.

There are hours to go before the first sprays of morning, pink and milky opal, will scratch the Eastern Sky and cause the first shimmers of wakefulness within His cradle.

But on that cool early morning where Asia, Europe, Africa, the sprits of the past and the passions of the future met, there was yet no sign of the music that would eventually be created to celebrate the day.

So, sixty-one generations after the birth of Jesus, let us consider Tim’s Ten Favorite Christmas Songs.

10. “Christmas Time is Here” (Vince Guaraldi, 1965). It’s that damn Peanuts song…because Christmas numbers absolutely ought to be as sad as that winter afternoon when you were nine and your father forgot to pick you up from Hebrew School, and you sat on the curb, weeping, for two-and-a -half hours. Honestly, it sounds like the Cowboy Junkies playing at Morrissey’s funeral.

“A Charlie Brown Christmas” (Photo by ABC Photo Archives/ABC via Getty Images)

9. “Christmas Wrapping” (The Waitresses, 1982). The definitive early ’80s Christmas song, and any of us who were young in the early 1980s will let you know, again and again, that we are stuck in the early 1980s! Greek diners on every block! Midnight dinners at Wo Hop and Veselka! The Odd Couple on WPIX at 11 pm! That one crazy friend who dared to live on Avenue B and paid $60 a month rent! Lost in the ubiquity of “Christmas Wrapping” are two prime factors: A beautiful text—it reads like Don DeLillo writing an episode of Sex and the City—featuring deeply cynical lyrics about incomplete and unsatisfying romantic encounters in the Big City—though there’s a truly realistic happy ending. And let’s not forget that one MONSTER of a chorus.

8. “Merry Christmas Everybody” (Slade, 1973). With their rolling rhythms and greaser-rock boogie blur, Slade understood the heart of rock’n’roll as well as any band of their time; they updated the Memphis/New Orleans four-to-the-floor and the Beatles-in-Hamburg-meth stomp for the glitter age, and made some of the best rock qua rock of all time. Now, I’m not big on “rock” Christmas songs. They tend to sound either like they were made by Cabbage Patch Dolls who have put too much Equal in their tea or like Cheap Trick imitating Cheap Trick (i.e., “This is a Christmas song, but we are gonna play it ROCK, because we are a ROCK band, and we ROCK!”). However, “Merry Christmas Everybody” is nearly perfect: Slade-steady, Slade-snotty, and super-melodic. And it too features an Everest of a chorus.

7. “Christmas in New Orleans” (Benny Carter & Louis Armstrong, 1955). New Orleans loves its holidays the way a North Korean despot loves his cognac. This smutty, smashed, cracked, low, louche, lit up and lit Miss Havisham of a Town comes especially alive at Christmas, where the usual sway and shout of drunken revelers is sprayed with a twinkle and a joy, a sort of slutty generosity. And this song says it pretty damn well.

Photo of Louis Armstrong with his trumpet (Photo by William Gottlieb/Redferns)

6. “‘Zat You, Santa Claus?” (Benny Carter & Louis Armstrong, 1955). Now, this one is a little more sinister; someone has thrown some absinthe into the punch, and we are dodging obstacles and enemies, real and imagined. On one hand, this number hints at the essentially horrifying nature of Santa: All year long he judges your behavior, and then one night every winter he enters your house through the one portal that he knows doesn’t have an alarm on it. On the other hand, it sounds like what happens if you mix the Makers Mark and Benadryl, causing you to see things that are not there in the carpet you are face down in. I once spent the entirety of Christmas Day—midnight to midnight—in a casino in Budapest. I did this just because, well, I wanted to see how it would feel. It felt like a cross between cheap champagne, Marlboro fog, and this song.

5. “Drunk This Christmas” (Paul Sanchez, 2000). Paul Sanchez is one of the greatest singers/storytellers in America, and his name deserves to be up there alongside John Prine, Springsteen, and Tom Waits. Did you ever walk (or drive by) a dive bar on Christmas eve—a true dive bar, not the kind of dive bar where the Pixies are on the jukebox—and you see, through the greasy window, a narrow aisle of olive green walls and cracked neon, and some vague, penny-colored light seeping in from a men’s room sign? Y’know, it’s the kind of place that lost half its light when they took away the cigarette machine. Against this sub-Weegeeian tableau, you see the silhouettes of middle-aged men in lumber jackets and sweat-gray Cleveland Indian baseball caps, and terribly thin women wearing Wolves Howling At the Moon sweatshirts, unironically. And you wonder, what is Christmas like in a place like that? Well, it’s like this song. Not sad, just different.

4. “Forgotten Dreams” (Leroy Anderson, 1954). Not a Christmas song per se, but it certainly has a holiday feel to it. See, it’s Sunday night in a lonely, large city. The streets are slippery with salt, shit, and scales of ice, and you are staring down another Cup Noodles dinner. It is that awkward time between Christmas, spent with an uncle and aunt who are mostly strangers, and New Year’s, for which you have no plans. Only the cold prevents you from sending some really ugly texts. Yet you turn the corner and the red and green lights of a storefront, the sky split with gold and blue city spires, and the perfect taxi passing through the perfect lazy slice of steam fill you with warmth and hope.

(Note: Leroy Anderson wrote one really famous actual Christmas song, “Sleigh Ride” (it’s the one that goes “La-la-la-wing-ding-diddy-ding, ding-ding-diddy-ding doo, sleigh ride together with youuuuuu”). I prefer “Forgotten Dreams,” though, because it describes the actual sadness inherent in Christmas. And why is Christmas inherently sad? Because it ends, friends, because it ends.)

3. “Christmas Night In Harlem” (Jack Teargarden & Johnny Mercer with Paul Whiteman, 1934; Louis Armstrong & Benny Carter, 1955). I first heard this song on December 16, 1978, when Elliot Gould (!) sang it (!!) as his opening monologue when he hosted Saturday Night Live (Gould hosted SNL five times between 1976 and 1980; he was once a very big star, reminiscent of what would happen if Bobby Canavale and Ron Jeremy had a baby and gave it to Paul Rudd to raise). I immediately fell for the song’s wonderful mixture of Radio Days sepia cool and Chrysler Building silver. When I listen to it, I think of those nights when the Great White Walker in the Sky has dumped a foot or two of snow over the boroughs, and for an hour or two the only noise is joy, as normally rushed and cynical New Yorkers leap about like children in a city briefly cloaked in nature’s downy blanket.

I make mention of the Armstrong version, because he is one of the three or four most important and spectacular pop stars of the last century, but honestly, I prefer The Paul Whiteman/Teargarden/Mercer rendering. It has some of that hoppy-boppy old cartoon music feel that positively shrieks of Gershwin, Louise Brooks and OhhhhTheHumanity. Though I must say that the Whiteman recordings are not for people easily offended by the word “colored” (please note, however, that Whiteman, controversially, was a pioneer in integrating his recording sessions).

Judy Garland (NBC archives)

2. “Have Yourself A Merry Little Christmas” (Judy Garland, 1944). From the star-spray of twinkle and dark at the beginning of the song (which sounds like the Milky Way weeping), every moment in this recording is nearly perfect. True, it makes the Debbie Downer of a Peanuts number discussed earlier sound like “Walking On Sunshine,” but, honestly, that’s the whole point. “Have Yourself A Merry Little Christmas” was a beautiful but dark shawl draped on us during the Second World War. It highlighted that the horror of the bone-spray of war and the boot heel of fascism was the literal opposite of the Christmas spirit (and it’s interesting to note that many subsequent recordings of the song, including Sinatra’s well-know 1957 version, softened up the darkness of the original lyrics). We have all experienced the scar of loneliness during Christmas, the aching desire to be anywhere else but away from the ones we love: this is the anthem of that feeling.

1. “Stop the Cavalry” (Jona Lewie, 1980). Lewie, the world’s only electro-Cajun Brit musician, produced a lot of magical, minimal, absolutely distinctive pop songs (including “Hallelujah Europa” and “You’ll Always Find Me In The Kitchen at Parties,” two tracks that are the definition of enchanting). Like “Have Yourself a Merry Little Christmas,” “Stop the Cavalry” is not just about missing someone or missing home; it’s about a world at war missing peace, about how the insanity of mechanized death is the opposite of the message of the Lamb of God. A strange mixture of synth pop and Salvation Army band topped with a lovely, deeply affecting everyman vocal, this is a song of loss and hope, winter graceful and winter grim. It is my all-time favorite Christmas song.

Take a listen to some of the songs on this Spotify playlist: