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Some musical spirit-crushers make the argument that Christmas is far from the happiest season of all. Photo: Shutterstock

From Wham! to Elvis, the eight saddest Christmas songs – you’ll be in tears over the holidays

  • Some favourite Christmas tunes are real downers, whether or not you realise it as you’re singing them aloud or not
  • Here are the best ones to have you reaching for the tissues

For a season that is supposed to be all holly and jolly, many of our most time-honoured Christmas songs are anything but.

“Christmas music” is less a genre and more an entire season these days, as the passing of Thanksgiving beckons the takeover of radio stations and businesses’ soundtracks by a familiar songbook of holiday classics. Turns out, some of those favourite songs are actually real downers, whether you realise it as you’re singing them aloud or not.

There are several tiers of sad Christmas songs, from the unintentionally gloomy carols that attempt to stoke some nostalgia and just end up weepy, to the true heartbreakers such as Christmas Shoes and Joni Mitchell’s River – the latter spirit-crushers that make the argument for the holidays as far from the happiest season of all.

While enough depressing Christmas music exists to soundtrack an entire day’s worth of feelings, read on for the best-known holiday songs that may or may not make you cry.

I’ll Be Home For Christmas – Bing Crosby

This holiday classic unfolds as normal, until Crosby – and the many other people who have covered the standard over the years – casually drops this line that turns the narrator’s Christmas dream into a nightmare: “I’ll be home for Christmas / If only in my dreams.”

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Blue Christmas – Elvis Presley

Presley’s suave vocals aren’t a distraction from how depressed he is, spending Christmas without his person. In fact, there’s not a lighthearted lyric in the bunch: “And when those blue snowflakes start falling / that is when those blue memories start calling / You’ll be doin’ all right, with your Christmas of white / But I’ll have a blue, blue blue blue Christmas.”

Have Yourself A Merry Little Christmas – Various

First popularised by Judy Garland in the 1944 musical Meet Me In St. Louis, Have Yourself A Merry Little Christmas is different than the other downers on this list.

It’s not the song’s lyrics that make it sob-worthy, but rather its positively mournful melody.

Last Christmas – Wham!

Another famously sad Christmas classic, Wham’s Last Christmas depicts a miserable December 26. “Last Christmas, I gave you my heart / But the very next day you gave it away,” George Michael sings, sounding thoroughly bummed-out throughout the whole song, though he does maintain hope that “someone special” will come along this holiday season.

Christmas Time Is Here – Vince Guaraldi Trio

The Charlie Brown Christmas favourite may be a cheery tale of a winter wonderland, but it ends on a down note, lamenting, “Oh, that we could always see / Such spirit through the year.” Thanks for the reminder that the rest of the year is inherently more depressing than Christmastime, Vince.

Christmas (Baby Please Come Home) – Various

Originally sung by Darlene Love, with a more contemporary version popularised by Mariah Carey, the song’s cheery soul melody and repeated “Christmas” chorus may distract you from how much of a bummer the rest of the lyrics are, about someone’s love who is spending the holidays elsewhere: “Pretty lights on the tree / I’m watching them shine / You should be here with me / Baby, please come home.”

River – Joni Mitchell

Unlike the rest of the songs on this list, you probably will not find River on any seasonal party playlists. This 1971 Joni Mitchell tear-jerker is the quintessential holiday song for people who hate holidays, using the Yuletide season as the backdrop for a breakup, with its narrator wanting nothing more than to escape the happiness of the Christmas revellers around her.

The Christmas Shoes – NewSong

Critics say the song, and its tale of a dying mother whose son just wants to gift her a new pair of shoes, is emotionally manipulative. Fans say it’s one of the most moving holiday songs ever written. Wherever you stand in this debate, it’s inarguable that The Christmas Shoes is probably the saddest song on its list.