Why all the best Christmas songs are just a little bit sad

It was Christmas Eve, babe,

In the drunk tank,

An old man said to me,

‘Won’t see another one.’

– The Pogues, ‘Fairytale of New York

I have no shame or hesitation calling this one of the most devastating lines in music. No matter how many times I’ve heard it, it hits with all the weight of human mortality packed into it. And the heart-stopping tragedy in this lyric lies not just in a man knowing his death is near. Instead, it’s the context of Christmas, of this recurring milestone, marking out the years of our lives, that turns the man’s sobering statement into a crushing blow. It’s not merely the last year he will live, it’s the last time he will wish someone a merry Christmas.

The Pogues choose to open their 1987 Christmas single not with celebration or joy, or even nostalgia, but with a stark reminder of the simple fact that our Christmases are finite. Without this, none of the rest of the song, from Kirsty MacColl’s glittering reminiscence of the couple’s first Christmas in New York, through the flying insults, to Shane MacGowan’s bittersweet reflection, ‘I built my dreams around you’, would have the same emotional weight.

Christmas is never just about now, about the present. It’s the memories of past Christmases, the hopes and fears of future ones and the knowledge we only have so many Christmases with the people we love that gives the 25th December any meaning at all.

This is why the greatest Christmas songs are never simply about how wonderful the season is, but rather how great it once was, or how better times are yet to come. As Laura Snapes of the Guardian observed, it was ‘straddling that late-December divide between nostalgia and optimism’ that won Slade’s ‘Merry Xmas Everybody’ the chart battle over Wizzard’s bombast of festive cheer, ‘I Wish It Could Be Christmas Everyday’.

The inherent sadness inside the joy of Christmas is something the Pogues and Kirsty MacColl immortalised in their evergreen folk-rock ballad. It’s also something I believe Judy Garland implicitly understood when she put voice to one of the greatest Christmas songs ever composed, ‘Have Yourself a Merry Little Christmas’.

Written by Hugh Martin and Ralph Blane, the song first featured in the 1944 film Meet Me in St. Louis, wherein Garland’s character Esther sings the song to comfort her younger sister Tootie after their parents announce the family will all be moving to from St. Louis, Missouri to New York City in the New Year.

Watching the film for the first time a couple years ago, I was surprised to hear the song performed in this context. To me, Garland’s voice, longing for a time when ‘all our troubles will be out of sight’, had always seemed loaded with age and experience, and with a far deeper pain than that of a teenager reluctantly leaving her hometown. And, though of course we can’t know what inspired this particular performance, knowing about Garland’s lifelong struggles with addiction, mental and physical illness, and abuse at the hands of Hollywood executives only makes the song more poignant.

Though only in her early twenties when she starred in St. Louis, there’s a maturity to Garland’s voice that suggests one who has endured trials beyond her years. Raw, reflective and determined, her performance lends a vulnerability to the fragile optimism of the lyrics.

Some day soon we all will be together, if the fates allow.

Until then, we’ll have to muddle through somehow.

The song very deliberately asks us to have a merry little Christmas, the humility and measured expectation in its title acknowledging the challenges and hardship Christmas can bring to the fore for many people. It’s a far cry from Wizzard’s festive overload or the simplicity of ‘Winter Wonderland’ or ‘Jingle Bell Rock’.

This is not a call for Christmas songs to be as depressing as possible, or to be indifferent to the spirit of the season altogether. But it’s songs that capture that inexplicable mix of joy and nostalgia, nostalgia sometimes for something that’s not even over yet, that will always be closest to my heart at this time of year. From Bing Crosby reminiscing about the white Christmases of his youth, to Chrissie Hynde of the Pretenders observing the familiar December traditions while numbed by loneliness on ‘2000 Miles‘, musicians have connected Christmas with sorrow for as long as there have been Christmas songs.

That’s not to mention the plethora of wartime classics, still enjoyed today, which tell of soldiers unable to spend Christmas with their families, including ‘I’ll Be Home for Christmas’ and ‘I’m Sending a Letter to Santa Claus’. And such songs surely would have resonated with many people spending Christmas away from home during the Covid-19 pandemic.

Even some of our oldest Christmas carols are incredibly sombre, not gushing with unadulterated elation but rather conveying solace and hope to an anxious or burdened listener. ‘God rest ye merry, gentlemen, let nothing you dismay,’ church choirs sing each year. ‘The hopes and fears of all the years,’ another carol tells us, ‘are met in [Bethlehem] tonight’.

In today’s Christmas charts, a lot of the sorrow stems from themes of heartbreak or unrequited love. It’s curiously ironic that we get ourselves into the Christmas mood listening to Darlene Love cry out ‘they’re singing “Deck the Halls”, but it’s not like Christmas at all’, perhaps even more puzzling a paradox than our choice to soundtrack our seasonal gift shopping with Mariah Carey claiming not to care ‘about the presents underneath the Christmas tree.’

Interestingly, after Love recorded ‘Christmas (Baby Please Come Home)’ for Phil Spector’s 1963 Christmas compilation album, he had her record another, non-festive version of the track, believing it had the potential to be a perennial hit. Though neither version was a great success at the time, the original has been a staple of the winter months since the mid-80s, while its non-seasonal counterpart ‘Johnny (Please Come Home)’ is now all but forgotten.

It seems that, while Love’s passionate, exhilarating performance, is just as jaw-dropping on both versions, there’s something about her heart-wrenching plea for her baby to return home that makes it the perfect fit for Christmas.

Furthermore, the emotional power of the song is only heightened by its context within Love’s career. Spector credited some of her recordings to other artists without her consent, rejected her in favour of different singers at the last minute, and denied her the royalties she was due (for which she successfully sued him in 1993). She retired from singing in the 70s to raise a family, and later began working as a maid in Beverly Hills.  

In the spectacular 2013 documentary, 20 Feet from Stardom, Love recalls catching her more or less forgotten ‘Christmas (Baby Please Come Home)’ on the radio in one of the mansions she cleaned for a living in the early 80s. Hearing her own record all those year later shocked her with the realisation that this wasn’t the life she wanted, and that she had to return to singing. In 1986, she was given the chance to perform the song on David Letterman’s Christmas show, which would go on to become an annual tradition that revitalised the track into the beloved hit we know today.

Much like Garland, Love was singing words given to her by someone else in an industry that disrespected and exploited her. Yet each woman poured her heart into her respective song, delivering a performance that could only come from her, and none of the many, many cover versions of each track can even hold a candle to. 

It’s this sense of defiance, this resilience in the face of hardship that gives these songs their power. Like ‘Fairytale of New York’, they are less about now than they are about the past and the future. They are nostalgic and reflective, heartfelt and determined. They are sad songs, but they are also hopeful songs. They are Christmas songs.

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