Have Yourself a Depressing Little Christmas

The Dark Stories Behind Your Favourite Christmas Songs

Nicholas Scott
Alternative Perspectives
5 min readDec 19, 2021

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Pixabay License

As new headlines of a fear and uncertainty abound on a near-hourly basis, we are once again faced with a holiday season of division, worry, and isolation. Omicron, Delta, business closures, and lockdown measures are just a few of the things that may be occupying our brains just days away from holiday festivities. However those who partake end up celebrating — and to what degree, there is no denying that it won’t be the holiday season we had hoped for.

Approaching the beginning of a third year of our shared and global pandemic made me think of the context with which one of my favourite Christmas songs was written. Last year, the lyrics of “Have Yourself a Merry Little Christmas” could not have felt more poignant:

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

It is worth noting that Judy Garland’s version of the song (with heavily revised lyrics than what was originally pitched for her film, Meet Me In St. Louis), became extraordinarily popular among US troops serving in World War II and it’s easy to see why:

Next year all our troubles will be out of sight.

As Bing, Frank, Dean, Judy, and the Andrews Sisters serenade me through another dreary winter, I am inspired to delve into the stories behind many of the songs we hold dear this time of year. Not just because of their relevance to what may be happening right now, but because of their importance to the generations who listened to them when they were first released.

Have Yourself a Merry Little Christmas

The initial criticism with “Have Yourself a Merry Little Christmas” was that it was far too dark. This lasted all the way until Frank Sinatra covered it, insisting on yet another lyric change from the adjustments Judy Garland made: “From now on, we’ll have to muddle through somehow” to “Hang a shining star upon the highest bough.”

Going back to its initial draft, this song is about misery and a loss of hope, with Judy Garland insisting on it being rewritten with more optimistic lyrics.

Written for the MGM film, “Meet Me in St. Louis”, by Hugh Martin, the holiday classic was featured in a scene in which the family of the protagonist are sharing in the misery over celebrating their last Christmas in the home they had grown up in. At the same time, in the real world, soldiers were out on battle fields while their families spent Christmas Eve yearning for their safe return. It is no surprise that lyrics like: “Have yourself a merry little Christmas, it may be your last” needed a rewrite.

I’ll Be Home for Christmas

Similarly, hearing Bing Crosby croon, “I’ll be home for Christmas, if only in my dreams…” can bring a sense of melancholy to those who may be facing isolation yet again this year — whether due to COVID or otherwise.

Like the song before it, “I’ll be Home for Christmas” was written by Walter Kent and James Gannon during the midst of World War II. Though, unlike “Have Yourself a Merry Little Christmas”, it wasn’t done for the movies. Instead, it was intentionally written with families separated by the war in mind.

It remains ever relevant and powerful today.

Rudolph the Red-Nosed Reindeer

There was a viral story going around a few years back that suggested 34-year-old copywriter Bob May wrote the original story of “Rudolph” to comfort his daughter while her mother was dying. And while its true; her mother was dying. That’s not the reason he wrote the story. He was commissioned from his boss to write something that would be easily marketable as a promotion gimmick. While he may have tested it out on his daughter, the story was a pay-check that ended up coming through for him. After his brother-in-law turned the book into a celebrated song, Rudolph really did go on to become the most famous reindeer of all.

That said, the story was written at a time when Bob felt hopeless in both his home-life and his career. He was heavily in debt. His wife was dying of cancer. And he was nowhere near writing the next great American novel as he had one day dreamed.

It goes to show that sometimes, when we feel at our lowest, the greatest of opportunities can present themselves — if we are willing and able to listen.

Do You Hear What I Hear?

So the story goes that, while this cold-war written classic by Noël Regney and Gloria Shayne Baker conjures majestic imagery of the Nativity story, it also paints a stark and haunting picture of the Cuban Missile Crisis going on at the time.

A star, a star, dancing in the night with a tail as big as a kite

While this is clearly referring to the Star of Bethlehem, as featured in the Nativity, it also could easily be compared to the characteristics of a wartime missile sailing through the air.

In this context, the song’s plea for people everywhere to pray for peace becomes an urgent call to all of mankind to end the threat of violence for once and for all.

Winter Wonderland

This one is surprising in that nothing in the lyrics such anything dark or sinister under the surface. And you would be right to come to that conclusion. However, the situation through which Dick Smith wrote the song makes listeners look at the song in a whole new light.

Smith was bed-ridden with tuberculosis and it was while receiving treatment for it in a Sanitarium that he looked out the window to see children frolicking in the snow outside. He then scribbled down the poem that would go on to becoming “Winter Wonderland”.

With this lens, we see the imagery depicted in the song through the eyes of a man unable to truly enjoy what he is describing. Smith succumbed to the disease when he was 34-years-old.

Photo by Steven Wright on Unsplash

There’s a reason these songs stand the test of time and maintain their air-play year after year. As dark as some of them may be, as juxtaposed as their writing was to the situation of the author, they tell deep and relatable stories of what it means to be human; something we are learning more and more of as the years of our pandemic pass.

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Nicholas Scott
Alternative Perspectives

Entertainer, TEDx “What Performing in Nursing Homes Taught Me About Slowing Down”, Writer (Elephant Journal, Mindful Word), https://www.imnicholasarnold.com/