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The Most Depressing Christmas Songs of All Time

Written by Sharon Knolle

Christmas songs are usually cheerful little numbers, about Santa Claus coming to town or chestnuts roasting on an open fire. Even more contemporary numbers are usually upbeat, such as “All I Want for Christmas is You.” But there are several holiday songs whose lyrics are downright gloomy.

Since Christmas is one of the most stressful times of year, it’s only fair that some more ambivalent feelings about the season surface.

Except for the one about the little boy that Santa Claus forgot.

That one’s just cruel.

“Fairytale of New York”
Written by Jeremy Finer, Shane MacGowan
Originally recorded by The Pogues and Kirsty MacColl (1987)



How many Christmas songs have explicit language warnings? This one has two lovers calling each other “a bum, a punk” and “an old slut on junk” as well as “you scumbag, you maggot, you cheap lousy faggot.” The Pogues classic starts out in the drunk tank of Christmas Eve where an old man says he’s sure it’ll be his last. What saves this from being utterly depressing is the wistful hopefulness at the end and the absolutely beauty of the melody and Kirsty MacColl’s voice. (Sadly, MacColl died in 2000, after being hit by a boat in Mexico. RIP.)

So while this isn’t your standard Christmas song by a long shot, it’s still a favorite that gets played possibly as much (or more) than Bruce Springsteen’s “Santa Claus is Comin’ to Town” or “Happy Xmas (War is Over).”

Lyrics: 

It was Christmas Eve, babe
In the drunk tank
An old man said to me, won’t see another one
And then he sang a song
The Rare Old Mountain Dew
I turned my face away
And dreamed about you

Got on a lucky one
Came in eighteen to one
I’ve got a feeling
This year’s for me and you
So happy Christmas
I love you baby
I can see a better time
When all our dreams come true

They’ve got cars big as bars
They’ve got rivers of gold
But the wind goes right through you
It’s no place for the old
When you first took my hand
On a cold Christmas Eve
You promised me
Broadway was waiting for me

You were handsome
You were pretty
Queen of New York City
When the band finished playing
They howled out for more
Sinatra was swinging,
All the drunks they were singing
We kissed on a corner
Then danced through the night

The boys of the NYPD choir
Were singing “Galway Bay”
And the bells were ringing out
For Christmas day

You’re a bum
You’re a punk
You’re an old slut on junk
Lying there almost dead on a drip in that bed
You scumbag, you maggot
You cheap lousy faggot
Happy Christmas your arse
I pray God it’s our last

The boys of the NYPD choir
Still singing “Galway Bay”
And the bells were ringing out
For Christmas day

I could have been someone
Well so could anyone
You took my dreams from me
When I first found you
I kept them with me babe
I put them with my own
Can’t make it all alone
I’ve built my dreams around you

The boys of the NYPD choir
Still singing “Galway Bay”
And the bells are ringing out
For Christmas day

“Santa Can’t Stay”
Written and recorded by Dwight Yoakam (1997)



When Mom and Dad split up, that means that Santa (aka Daddy) can’t stay and little Bobby just doesn’t understand in this song that should be a tearjerker, but whose jaunty melody makes it surprisingly upbeat.

Lyrics:

Cold tears fall from his eyes

As he turns into the night and walks away

Lucille runs outside


Just to see if there might be a sleigh

Little Bobby stares down

At the plate where cookies still lay

And tries to understand 

Why momma said Santa can’t stay



[Chorus]

Momma said Santa can’t stay

Said she told him that twice yesterday

Then a car just like Dad’s 

Pulled out and drove away

After mom said Santa couldn’t stay



They both heard him coming

Saw Mom run down the hall and holler wait

Doug you’re drunk don’t come inside
I’m not joking I’ve had all this I can take

He threw a present really hard

That almost hit Mom’s new boyfriend Ray

And yelled ho-ho lucky for you she’s here

And said that Santa can’t stay

“Happy Xmas (War is Over)”
Written by John Lennon and Yoko Ono (1971)
Also recorded by Damien Rice, Maroon 5, Andy Williams, Neil Diamond, Diana Ross, Darlene Love, The Fray, Sarah McLachlan, Carly Simon



This song is always going to make most of us sad because it reminds us that John Lennon died far too young. And war is never really over, is it? The sentiment, for “a very happy new year, let’s hope it’s a good one, without any fear,” is one that is sure to be dashed each year, and everyone who’s recorded this sings it with that sad knowledge. The Damien Rice cover is especially melancholy.

Lyrics: 

So this is Christmas and what have you done,

Another year over, a new one just begun.
And so this is Christmas, I hope you have fun,

The near and the dear ones, the old and the young.
A very merry Christmas and a happy New Year

Let’s hope it’s a good one without any fears.
And so this is Christmas for weak and for strong,

The rich and the poor ones, the road is so long.
And so happy Christmas for black and for white

For the yellow and red ones let’s stop all the fights.
A very merry Christmas and a happy New Year

Let’s hope it’s a good one without any fear.
And so this is Christmas and what have we done
A
nother year over, a new one just begun.
And so happy Christmas we hope you have fun

The near and the dear ones, the old and the young.
A very merry Christmas and a happy New Year

Let’s hope it’s a good one without any fear.
War is over if you want it, war is over now.

“I’ll Be Home For Christmas”
Written by Kim Gannon (lyrics) and Walter Kent (music)
Originally recorded by Bing Crosby (1943)



This nostalgic war-time classic must have really hit hard with soldiers who couldn’t make it home for Christmas that year. And listening to it now, you can’t help but think of all those doughboys who never made it home at all.

The song begins with the soldier singing “you can plan on me,” and detailing all the things he’s looking forward to enjoying at home. But the realization that that’s not likely to happen makes the final line, “I’ll be home for Christmas, if only in my dreams,” one of the saddest last lines in any holiday song.

Lyrics:

I’ll be home for Christmas

You can plan on me

Please have snow and mistletoe

And presents on the tree
Christmas Eve will find me

Where the love light gleams

I’ll be home for Christmas

If only in my dreams
I’ll be home for Christmas

You can plan on me

Please have snow and mistletoe

And presents on the tree
Christmas Eve’ll find me

Where the love light gleams

I’ll be home for Christmas

If only in my dreams

“Christmas (Baby Please Come Home)”
Written by Ellie Greenwich, Jeff Barry and Phil Spector
Originally recorded by Darlene Love (1963)
Also recorded by U2 (1987), Mariah Carey (1994), Death Cab for Cutie (2004)



Nothing like heartbreak around the holidays to put you in the Christmas mood!

This classic, in which the singer repeatedly begs her (or his) baby to “please come home” is decidedly downbeat. If you’ve had a break-up right before the holidays, listen to this at your own peril!

Complete lyrics HERE.

“Pretty Paper”
Written by Willie Nelson
Originally recorded by Roy Orbison (1963).
Also recorded by Nelson, Glen Campbell (1968), Mickey Gilley (1976), Randy Travis (1986), Asleep at the Wheel (1997), Kenny Chesney (2003), Chris Isaak (2004), Reverend Horton Heat (2005), and Emmy Rossum (2013).

The message of this song – which is about an amputee who begs holiday shoppers to stop and buy his “Pretty Paper” – is to stop in the midst of your whirlwind holiday shopping and consider the less fortunate. It’s not a message most people want to hear at the holidays.

According to Wikipedia, Nelson was inspired to write it after seeing an amputee in Fort Wort, Texas.

Instead of using a wheelchair, the man crawled on rollers, selling paper and pencils in front of a department store during the holiday season. To attract the attention, the man would yell, “Pretty paper! Pretty paper!”

Lyrics:

Pretty paper, pretty ribbons of blue

Wrap your presents to your darling from you

Pretty pencils to write “I love you”

Pretty paper, pretty ribbons of blue
Crowded street, busy feet hustle by him

Downtown shoppers, Christmas is nigh

There he sits all alone on the sidewalk

Hoping that you won’t pass him by
Should you stop?, better not, much too busy

You’re in a hurry, my how time does fly

In the distance the ringing of laughter

And in the midst of the laughter he cries
Pretty paper, pretty ribbons of blue

Wrap your presents to your darling from you

Pretty pencils to write “I love you”

Pretty paper, pretty ribbons of blue

“Have Yourself a Merry Little Christmas”
Written by Ralph Blane (lyrics) and Hugh Martin (music)
Originally recorded by Judy Garland (1943)



This Christmas classic, first featured in Meet Me In Saint Louis, was originally even sadder! As Hugh Martin told NPR in 2006: (https://www.npr.org/2010/11/19/131412133/the-story-behind-have-yourself-a-merry-little-christmas)

“The original version was so lugubrious that Judy Garland refused to sing it. She said, ‘If I sing that, little Margaret will cry and they’ll think I’m a monster.’ So I was young then and kind of arrogant, and I said, ‘Well, I’m sorry you don’t like it, Judy, but that’s the way it is, and I don’t really want to write a new lyric.’ But Tom Drake, who played the boy next door, took me aside and said, ‘Hugh, you’ve got to finish it. It’s really a great song potentially, and I think you’ll be sorry if you don’t do it.’ So I went home and I wrote the version that’s in the movie.”

Of course, the version most people know today doesn’t feature the depressing “We’ll have to muddle through somehow” line. When Frank Sinatra went to record it in 1957, he supposedly told Martin, “The name of my album is A Jolly Christmas. Do you think you could jolly up that line for me?” Martin changed the line “Hang a shining star upon the highest bough.”

Even with that change, it’s still one of the most melancholy of holiday songs.

“Gift X-Change”
Written and performed by Calexico (2000)



Damn, this is a sad one, made even more so by the melancholy, sparse instrumentation. “The spirit is broken…. your heart is snowed-in…”

I suppose it ends on a hopeful note, but if you’ve had too much spiked eggnog, this might not be the best choice if you’re feeling blue.

Lyrics:

You say you’re leaving, going back home

Where’s your family? Where do you come from?

Something’s missing in your life? You’ve felt it all along.

Retrace your steps, balance and check where it all went wrong

The spirit is broken, the path is overrun

You can’t move forward and now nothing gets done

I hope you find some inner peace along the way

Whatever it takes, I pray you’ll make it home on Christmas Day

In case you don’t find what you need when you finally arrive

And your heart is snowed-in, there’s no warmth or light

Take this candle with you and this book of matches as well

As you’re climbing the walls there’s no answer at all

Except the gift you give yourself

I trust that you’ll find some inner peace through times that are rough

What would it take to hear you say the gift you give is love

“The Little Boy that Santa Claus Forgot”
Written by Michael Carr, Tommie Connor & Jimmy Leach
Originally recorded by Vera Lynn (1937)
Also recorded by Nat King Cole



Definitely the strangest and saddest Christmas song ever: A little fatherless boy has no Christmas at all because “Santa” never arrives. It was written in the Depression and it sure sounds like it.

The Vera Lynn version was used in the opening scene in “Pink Floyd – The Wall” and A portion of the song was sung by Jim Belushi in the 1996 film “Jingle All the Way.”

Lyrics:

He’s the little boy that Santa Claus forgot

And goodness knows, he didn’t want a lot
He sent a note to Santa

For some soldiers and a drum

It broke his little heart

When he found Santa hadn’t come
In the street, he envies all those lucky boys

Then wanders home to last year’s broken toys

I’m so sorry for that laddie, he hasn’t got a daddy

The little boy that Santa Claus forgot
You know, Christmas comes

But once a year for every girl and boy

The laughter and the joy they find in each brand new toy
I’ll tell you of a little boy that lives across the way

This little fella’s Christmas is just another day

He’s the little boy that Santa Claus forgot

And goodness knows, he didn’t want a lot
In the street, he envies all those lucky boys

Then wanders home to last year’s broken toys

I’m so sorry for that laddie, he hasn’t got a daddy

The little boy that Santa Claus forgot
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