A Meander Through the Christmas Music Wonderland

A collection of impressions on the sounds of the season

Welcome music lovers to another edition of ‘Listening Sessions’!

This time around, I’ve put down some thoughts on Christmas music, why I love it, some of my favourite seasonal recordings and a few other digressions. It was fun letting my mind meander a bit and to discuss a wide range of music. I hope you enjoy the essay and will share your thoughts as well.

Prior to taking a bit of a break for the holidays, I will have one more essay to send along this year. Coming on December 23 will be a look at the recordings Frank Sinatra made for the Yuletide season.

Until then, may good listening be with you all!

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While I have never felt particularly disposed to compose any type of comprehensive best-of list, I can still easily tell you what would be at the top of some of them. The best book? Invisible Man by Ralph Ellison. The best movie? The Graduate. The best sports team? The Boston Celtics. The best album? Miles Davis and Gil Evans’ version of Porgy and Bess. The best song? The Beatles’ ‘A Hard Day’s Night.’ The best Christmas song? Why, that would be Elvis Presley’s ‘Santa Claus is Back in Town.’

It’s not usually what you hear by Presley at this time of the year. That would be ‘Blue Christmas,’ of course, or perhaps his version of ‘Silver Bells,’ but it should be too. The tune was whipped up quickly by Jerry Leiber and Mike Stoller to add a blues number for the singer to complete his full-length seasonal release for Christmas 1957. The final result is the perfect balance of Presley belting out sassy lines like “got no sleigh with reindeer / no sack on my back / you won’t see comin’ / in a big, black Cadillac” with the refinement of the Jordanaires’ backing vocals. Notable as well is that it is a Presley rocker that is piano, not guitar, driven. Playing the keys was Dudley Brooks. He was also a songwriter and by far his most famous credit is co-writing with Irving Taylor and Hal Stanley, ‘(Everybody’s Waiting for) The Man with the Bag’ for Kay Starr who had a big hit with it in 1950.

It’s a song that is still widely heard this time of the year and often where you would not otherwise hear an artist of Starr’s vintage, whether it be the radio, the local crowded shopping mall or perhaps even your own stereo. Christmas music has that effect. Tastes become wider. Listening habits become both more diffuse and more representative of a monoculture that long ago left town. We may not agree on much of anything these days but almost everyone will hear Nat Cole’s 1961 recording of Mel Tormé and Robert Wells’ ‘The Christmas Song’ at some point in December and then probably again and again. Most likely won’t give Cole another thought until Christmas time cheerily rolls around again in 2025 but some may be intrigued enough to delve deeper into his catalogue.

Either way, that many are listening to Nat Cole right now and still know of him is important, I think. It means that part of our collective musical history is still alive. I suppose this is a more substantial concern for me than some others of my generation (Generation X), being reared as I was by that kind of music—my musical education was completely out of time—so that it has become a personal thing for me. I recall being thrilled by the straight-laced swing of Glenn Miller’s ‘American Patrol’ (there was a jazz buff inside me long before I realized it), the ease of Bing Crosby’s ‘Swinging on a Star’ and the chronology of Frank Sinatra’s recording of ‘It Was a Very Good Year.’

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I’m not suggesting here we should remain trapped in the past but a culture that recognizes its history is a healthy, more vibrant one. Of course, the singer most emblematic of the greater look backward in December is Crosby. Certainly for me, that it's now an obligation to listen to him during the season is one exercised with joy. Nothing in my listening compares to listening to his 1955 album, Merry Christmas, collecting his foundational recordings of the Christmas repertoire.

The music is, of course, ace, full of his casual warmth and profound ability to make you feel through song. It’s more than that, though. It’s about how it connects the present day with the past, linking today’s celebrations with those when one was younger with those of parents, grandparents, aunts and uncles and the like when they were younger. It marks the time as it changes against the constancy of the shattering impact of Crosby’s 1947 re-recording of ‘White Christmas’ (necessitated by the constant re-pressing of the 1942 original), the longing for home during the Second World War evoked by ‘I’ll Be Home for Christmas’ and the back and forth between him and the Andrews Sisters on what are really reference recordings of ‘Jingle Bells’ and ‘Santa Claus is Coming to Town.’

Christmas music is one of our most potent examples of the artform. The core songs and hymns are ones that many, if not most, know by heart. The act of singing them together, whether at home or in the city square or in a concert hall or in a church, turn them into folk music. It may engender a tenuous unity but it’s one I’ll take these days, for sure. Voices linked in song can stir the heart, reminding us of our better angels.

Take the chorus of ‘The Holly and the Ivy’ with “the rising of the sun and the running of the deer / the playing of the merry organ / sweet singing in the choir.” It can be sung contemplatively—Natalie Cole’s recording from 1994 is a good example—or exultantly—Roger Whittaker’s mid-eighties version does this nicely even if the synth-y backing is more than a little cheesy.

Indeed, one reason, among many, why I love Christmas music is how it can project the gloriousness of it all. Houses made festive with lights, a tree that has been trimmed, mistletoe and holly (as the Frank Sinatra song goes) and other decorations, and lights and bric-and-brac outside to make the night inviting. Its promise that at the end of another year, we may once again undertake the rituals of the season has always seemed to me a reward. It may sound hokey—and much Christmas music straddles that line precariously—but I hold firm to that belief.

How to feel otherwise when hearing the clarion call of the horns on the opening of Stan Kenton’s recording of ‘Once in Royal David’s City’ from 1961 that makes the hymn’s figurative journey upward about as literal as it can be on earth, especially as the opening brass figure undergoes several key changes during the performance.

Or how about a transcendent moment on a tune called ‘The Bells of Christmas’ from a record André Previn made with Julie Andrews in 1967. After an opening verse of Andrews, singing with such precise diction (the mere hearing of her voice, with its identification with Mary Poppins and The Sound of Music, is like being hurtled right back to being a child), backed with a male chorus, Previn dials things back for a short interlude. At one point, the orchestra hangs back and out of the sudden silence, comes bells, shimmering, almost as if they are shooting out against the darkness. It’s a moment of indescribable beauty. The best thing I can write about it is to hear it for yourself and judge if I’m right here.

The album on which it appears, A Christmas Treasure, is full of such moments. To give one more example, the album’s regal opening of a trumpet and kettle-drum fanfare resolving into a brief canon by the chorus on the “joy” of ‘Joy to the World.’ Compare it with the version Dave Brubeck recorded for his 1996 recording, A Dave Brubeck Christmas.

I’ve deeply appreciated Lewis Porter’s recent two-part essay (here and here) that convincingly counters many of the reasons why many do not give Brubeck his due: he didn’t swing, his solos were burdened by chords upon chords upon chords and that he was ultimately a classical musician who tried to play jazz. As for me, I find the pianist fascinating. Dave Brubeck demands and rewards deep listening.

A Dave Brubeck Christmas presents him in a way in which he was not normally associated. Oh sure, there are moments of deep stride on ‘Winter Wonderland’ and ‘Santa Claus is Coming to Town’ as well as moments of abstraction on ‘O Little Town of Bethlehem,’ but, for the most part here, Brubeck is quiet and introspective. His intent was to evoke the music that marked his family celebrations growing up. It’s an intent fulfilled magnificently, particularly through direct run-throughs of ‘What Child Is This,’ ‘The Christmas Song’ and ‘To Us Is Given,’ which Brubeck created out a two-millennia old chant.

I suspect Christmas has been the subject of more songs than just about anything save for love. And they continue to be written just as there is a tranche of new seasonal releases every Yuletide—even today, such recordings can be an endurable catalogue item. For those that focus on the secular side of the holiday, there is a formula sometimes employed of a series of observations tied together by some unifying statement. That’s pretty much what ‘The Christmas Song’ is about as well as ‘Christmas Time Is Here’ and ‘Silver Bells,’ to give two other examples. All these have become among the most well-known songs ever written because of how the details sung relate to deeply resonant themes.

In the cases of ‘The Christmas Song’ and ‘Silver Bells,’ it’s anticipation. For the former, it’s the “tiny tots with their eyes all aglow / will find it hard to sleep tonight” and for the latter, it's that “soon it will be Christmas Day.” ‘Christmas Time Is Here’ connects with the retreat—if we’re lucky—from the whirl and grind of everyday life, if only for a few days. There are a litany of other songs that don’t navigate the formula as successfully but the occasional contemporary song shows there’s still life in it.

Here are a few that come to mind. Jamie Cullen’s ‘Christmas Never Gets Old, from 2020, though steeped in the sound of the glory days of pop singing of the fifties and sixties, is a vibrant take on the theme of anticipation crossed with the joy of tradition (speaking for myself, some of them for the holidays now stretch to almost 40 years and counting). He stresses how the combination of the two can inspire rapture. Dig these lyrics: “all the presents are wrapped and the stockings are hung / all the children relieved, all the waiting is done / the houses aglow / now look up, mistletoe / let’s get on with the show.”

‘Holidays,’ a collaboration between Meghan Trainor and Earth, Wind & Fire is another relatively new seasonal song that stands out for me. It’s fun and the throwback to the classic sound of ‘September’ and ‘That’s the Way of the World’ is irresistible. ‘Under the Mistletoe,’ a duet by Kelly Clarkson and Brett Eldredge is equally infused with nostalgia, fueled by the inextinguishable inspiration of Phil Spector’s A Christmas Gift for You. These aren’t the kind of songs or artists—Earth, Wind & Fire excepted—that I would listen to at any other time of the year but as mentioned at the top of this essay, many, including me, are far more receptive to a greater breadth of music right now. How many are enjoying Vince Guaraldi’s soundtrack to A Charlie Brown Christmas right now who would never think of listening to jazz at any other time of the year or for any other occasion than Christmas?

Rod Stewart’s ‘Red-Suited Super Man,’ with Trombone Shorty, from 2012 is another song that offers a refreshing take on a seasonal trope as does Anthony Hamilton’s ‘It’s Christmas’ which finds a new way to explore the sentiment of the warhorse ‘(There’s No Place Like) Home for the Holidays.’

Loving music comes with a curiosity to seek out more of it. Christmas music is, of course, no exception. There’s a drive—at least for me—to dive more into the vintage classics. Some of this year’s new discoveries are John Gary’s stirring version of ‘Sweet Little Jesus Boy,’ the Lettermen’s sentimental ‘What Can I Get You for Christmas,’ Jim Reeves’ breezy ‘Merry Christmas Polka’ and Charley Pride’s ‘Christmas and Love’ which hits at the heart of the holidays for many (me included).

But what about those less inclined to Christmas music, those for whom the repetition of Brenda Lee’s ‘Rockin’ Around the Christmas Tree’ is more like an assault to the senses? There’s something out there for you too. I like to think of Jimmy Smith’s Christmas Cookin’, from 1964, as the kind of recording that might fit the bill. It opens with Billy Byers’ gray-flannel suit arrangement of ‘God Rest Ye Merry Gentlemen’ and then has three choruses of gradually escalating lines by Smith egged on by Kenny Burrell’s guitar and Grady Tate’s drums. They wring a pan full of grease and then some from one of the most musically interesting of the traditional carols. A cutesy ‘Jingle Bells,’ a Basie-like ‘The Christmas Song’ and a chugging ‘Silent Night’ underline the album’s pure pleasure.

My favourite piece of Christmas music I discovered this year came early in the season, the day of the news of Quincy Jones’ passing. Someone posted the music video of the ‘Hallelujah’ chorus from Handel’s Messiah: A Soulful Celebration. Shown conducting a chorus of at least 40 voices was Jones. The choir was comprised of a litany of the luminaries of Black music, including Patti Austin, Gladys Knight, Chaka Khan, Johnny Mathis, Joe Sample and Al Jarreau (and that’s just for starters!). The rearranging of Handel’s choral piece by Mervyn Warren, Michael O. Jackson and Mark Kibble may be the ultimate act of seasonal transfiguration, defying the odds by taking a transcendent work and making it even more so.

I couldn’t possibly get tired of hearing it just as I couldn’t get tired of hearing Christmas music each year. I hope I never do.