These songs are perfect if you are in need of a good cry this winter breakCckaiser on Flickr (CC by 2.0)

If the excruciating cheeriness of Christmas songs is getting too much for you, why not opt from something a little darker? From drug addiction to the Vietnam War, the topics of these songs are a far cry from your traditional “chestnuts roasting on an open fire” but perfect if you’re in need of a good cry this winter break.

LCD Soundsystem – ‘Christmas Will Break Your Heart’

There’s nothing subtle about this song: it clearly says that “Christmas will break your heart”. More surprisingly, the song served as LCD Soundsystem’s comeback single in 2015 after they claimed to be breaking up in 2011. Apparently, the track was a deliberate attempt by singer James Murphy to create a “perfect depressing Christmas song”. Comparing the season’s cheery effects to “listless awkward sex” and “the armies of unrelenting dark”, the track has you covered for pretty much every awful situation the festive season could throw at you.

“The Vietnam War and Christmas are self-evidently complimentary topics”

Joni Mitchell – ‘River’

Beginning with a sombre spin on ‘Jingle Bells’, Mitchell quickly turns our familiarity with this melody into a melancholy reflection on a recent breakup. Her voice, as ever, is the highlight of the track. When she explains that she wishes she “had a river to skate away on”, the soaring heights of her voice make you believe her. The song eventually appeared on the Glee soundtrack, which is enough to send shivers down my spine.

Bob Dylan – ‘The Christmas Blues’

Throughout his long career, Dylan has always endeavoured to be unpredictable. Hence, this spontaneity has itself become predictable. Nevertheless, his 2009 Christmas album was undoubtedly unexpected. Most of the record, which I highly recommend, is full of the old man’s festive cheer. However, on ‘The Christmas Blues’, we get to hear him grumble about how he will “go and disappear” when December arrives. Some Dylan fans may wish this album would disappear. Yet, who could do without Dylan’s festive – and depressive – drawl?

Lou Reed – ‘Xmas in February’

The Vietnam War and Christmas are self-evidently complimentary topics for a holiday sing-along. Reed narrates, in his usual, dry monotone, the tale of a Vietnam veteran at Christmas time. Instead of the typical white snow and green trees, we’re treated to descriptions of Agent Orange “spread against the sky like marmalade”. Later, when the veteran does eventually make it home, he finds that most of his friends are dead and his wife and kids have left him. MERRY CHRISTMAS!

Kurt Cobain and William S. Burroughs – ‘The “Priest” They Called Him’

If Christmas is the season of giving, this song is the ultimate – and strangest – gift. Burroughs tells the tale of a junkie searching for a fix at Christmas in his iconically squeaky and borderline incomprehensible voice. Eventually, our dear drug dealer realises that the best high can be obtained by giving his drugs to others. He then achieves “the immaculate fix” and promptly dies. For plot, I’d rate it 10/10. However, behind this verbal chaos, Cobain plays a screeching version of ‘Silent Night’ that is barely music but compliments the story perfectly. The song is truly the meeting of two great – and very disturbed – minds.

“The award for strangest Christmas song must surely go to Scott Walker”

Scott Walker – ‘The Day the “Conducator” Died (An Xmas Song)’

The award for strangest Christmas song must surely go to Scott Walker. A 1960s heartthrob known for his exquisite baritone, Walker swapped swelling string-sections for experimentation in his later years. I have never heard bells rattled with such threat and venom. The song’s “lyrics” take the form of a questionnaire being answered by “the Conducator”, who is the Romanian dictator Nicolae Ceaușescu, murdered on Christmas Day 1989 during a revolution against his repressive regime. Simple, right? This description only scratches the surface of the song which feels more like a Joycean monologue than anything jolly or even musical.


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Tom Waits – ‘Christmas Card From a Hooker in Minneapolis’

This little ballad takes the form of a letter from a prostitute to her friend Charlie. We learn that the sender has been improving their life and kicking their addictions… before discovering that they are lying and are actually waiting for parole on Valentine’s Day. It’s very romantic. Combined with Waits’ signature rasp, the song’s twist always gives me an emotional gut punch.

Sufjan Stevens – ‘That Was the Worst Christmas Ever!’

Sufjan Stevens had a tradition of releasing a Christmas EP every year. Most of the songs were sympathetic readings of festive classics… but that’s not what this playlist is for. With a title so bold – and tongue-in-cheek – it was impossible to ignore this Sufjan original. It’s a beautiful little reflection on a lost Christmas, with the devastating final line, “Silent night, nothing feels right”.

Phoebe Bridgers feat. Fiona Apple and Matt Berninger – ‘7 O’Clock News / Silent Night’

If you’ve made it this far without crying, I congratulate you… but that won’t last long. Bridgers, with the help of Fiona Apple and Matt Berninger of The National, covers Simon & Garfunkel’s memorable take on a Christmas classic. ‘Silent Night’ is hardly the most cheerful festive tune anyway. However, this version’s haunting harmonies only deepen a sense of existential dread. After hearing the bleak news reports read by Berninger, you will start to wonder if there is any hope left in the world. Still, the song is beautiful and we may, at least, take comfort in the carol’s endurance.