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The Five Saddest Christmas Songs

Seriously Random List XXXIV / Mrs. Pajiba-hyphenate

Music | December 8, 2008 | Comments (85)


We all need an antidote to the over-the-top forced jollity of holiday songs, most of which are better known for their ability to become lodged in your brain than for their quality. For every song as beautiful and sweet as “Silent Night” or “Christmas Must Be Tonight” there are seemingly 20 versions of “Jingle Bells” blasting from every available speaker this time of year. It’s enough to make you want to join Grandma underneath those reindeer hooves. And as much as I love a rousing “Good King Wencenslaus,” I realize that a) I am in the minority on that one, and b) sometimes the intensity of holiday cheer in these songs collides headlong with the reality of challenging family members, exhausting social obligations, and impossible-to-execute recipes. I find it helpful to remember that northern Europeans celebrate holidays at this time of the year because it is incredibly cold and dark. So while you may be contending with a sense of postmodern ennui as you brace yourself for another round of festivities, keep in mind that many of our forebears spent this time of year in mortal terror that the sun was never going to return.

So in that spirit, here are my favorite songs to remind you that the holidays aren’t uniformly pleasant for anyone, and that if you’re feeling ambivalent this season, you’re not alone.

Honorable Mention: “Fairytale of New York” — The Pogues and Kirsty MacColl

5. “Christmas Time Is Here” (Theme from “A Charlie Brown Christmas”): A lot of people find the holidays difficult precisely because there is such pressure to be happy, and for everything to go perfectly. That stress, combined with the sense that everyone else is having more fun than you, can make the holiday season feel interminable. This song describes the joys of the season, but to me the children’s voices sound somewhat world-weary, and the downbeat tempo seems almost unnaturally slowed-down. A great song to keep it all in perspective and to remind you of the profundity of Charlie’s forlorn little tree.



4. “Not Dark Yet” — Bob Dylan: My least literal of the bunch — yes, I realize this isn’t a Christmas song. At all. But it makes me feel like I’m trudging along some sidewalk at twilight, facing the wind, watching the twinkling of colored lights on the snow.

3. “Have Yourself a Merry Little Christmas” — Traditional: This is kind of a sleeper — it’s not one people think of as sad, but listen to the words and delivery and trust me: If you’ve left the house on some pretext involving replenishing the nutmeg just to get away from the flaming turkey/drunken houseguest/horror that your family has become, when this song comes on at the Quik-Mart, you may find yourself in tears before you know quite what’s going on.

2. “A Long December” — Counting Crows: This song totally captures that strange mix of hope and regret that can accompany the end of another year. I remember driving around in the snow with a good friend singing it at the top of our lungs when it first came out. Makes me want to go smoke a cigarette outside in the cold.


1. “River” — Joni Mitchell: Incredibly gorgeous, evocative and painful, this is so good that it’s become a kind of alternative standard, finding its way onto holiday albums by artists from James Taylor to Aimee Mann. I still love Joni’s original, but my first year in college I listened to it so much that its actually tough for me to hear now. If you’re up for some thoughtful wallowing, pour yourself a drink and listen to Robert Downey, Jr.’s uniquely devastating version.


Mrs. Pajiba-hyphenate is a lady lawyer in Portland, Maine.


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Comments

Hiding behind your high-powered lawyer woman, ah Rowles?

Posted by: BarbadoSlim at December 8, 2008 5:06 PM

"What Do The Lonely Do (At Christmas)" -- The Emotions. They slit their wrists after listening to this song.

Posted by: Tracer Bullet at December 8, 2008 5:07 PM

What better person to write sad Christmas songs than the King of Melancholy himself, Sufjan Stevens?

Two of my faves: "That was the Worst Christmas Ever" and "Did I Make You Cry Last Christmas? Well You Deserved It."

I found the first one... take out the tissues... http://www.youtube.com/watch?v=TpmiPbDkvBQ

Posted by: Swedish Mike at December 8, 2008 5:10 PM

Strangely enough the first Christmas I had to face w/out my father alive (he died Sept 2002)....the oddest songs would really get to me.

"Winter's Night" by Sarah McLaughlin (whom I can't stand usually), and any Elvis holiday songs (which my father played incessantly around the clock in Dec) just devastated me.

And as much as I don't like the Crows anymore, Long December is still pretty sad but Joni still takes the cake.

Posted by: Be Adequite! at December 8, 2008 5:18 PM

"I'll Be Home For Christmas" as sung by Bing Crosby reigns supreme for me because I always envision some poor bastard shivering in a foxhole in France during World War II and him knowing that he won't be home for Christmas, if at all. I guess it could apply to any time period and to servicemen anywhere, but it is most appropriate to that time (WWII). Probably because it was very popular then.

Posted by: Forrest at December 8, 2008 5:29 PM

Well, I don't willingly listen to Counting Crows, but you have my favorite first name, so I'll let it slide.

I know what you mean about "Not Dark Yet", I made a mix once that I wanted to sound like driving with the window down in 20 degrees on a clear night. I think it pulled it off fairly well.

The Peanuts song is depressing. I much prefer the "Merry Christmas" album by Bing Crosby. "Christmas in Killarney" and "Mele Kalikimaka" will forever make me crave a bowl of orange sherbet that's starting to melt.

I suppose The Pretenders' "2000 Miles" is pretty good company for these.

Oh and however cold it is, don't smoke with gloves or mittens, it's just so clumsy and unsatisfying and you've gotta give up long before the filter.

Posted by: Jay at December 8, 2008 5:47 PM

"Christmas in Prison" by John Prine can make me cry in the middle of July. That's one for the ages.

Posted by: Catherine at December 8, 2008 5:48 PM

Ee - "One Less Year" (a local band here in San Francisco).

Not a Christmas song per se, but always seems so poignant to me around this time. Download and give the song a listen if you'd like.

"One less year to decide I'm okay.
One less year to deny I'm just fine."

Posted by: JapJay at December 8, 2008 5:49 PM

"I'll Be Home for Christmas" is pretty gosh darned sad.

Also, "And So This is Christmas" - John Lennon. Natch.

Posted by: greer at December 8, 2008 5:50 PM

Oh man, no matter how many times I see Meet Me In St. Louis, that scene with Judy Garland and leeeettle Margaret O'Brien gets me every time. NICE CHOICES.

Posted by: coveredinbees at December 8, 2008 5:51 PM

Or how about "Christmas Card From A Hooker In Minneapolis" by Tom Waits?

Posted by: Redrider at December 8, 2008 6:04 PM

Coming out of lurkdom to express surprise that "Have yourself a merry little Christmas" is not considered sad by some. To me, it always has the ring of a drunk about to blow his/her brains out in despair. No matter who sings it. Speed it up, and it just becomes more bitter and sarcastic. I've never understood its appeal.

Posted by: cecilia at December 8, 2008 6:04 PM

I encourage one and all to buy Kiki and Herb's Christmas CD: Do You Hear What We Hear. Not sad. Uproarious, insane, laugh out loud funny. Their version of "Frosty the Snowman" blended (mashed up?) with "Smells Like Teen Spirit" might be the best holiday song ever. Well, that and "The Little Match Girl".

http://www.kikiandherb.com/site1/images/cdcover.jpg

As for sad...Low's version of "Little Drummer Boy".

Posted by: Adam at December 8, 2008 6:04 PM

I approve completely! Joni and Judy are always on my xmas mixes. I mean, what is sadder than Joni's line "I wish I had a river I could skate away on"??? Gets me every time.
Also, Meet Me in St. Louis is the best.

Posted by: VeinsRHiways at December 8, 2008 6:11 PM

I think I need to get away from this page.

Posted by: Jay at December 8, 2008 6:15 PM

Greer beat me to the Lennon.

Y'know, "Blue Christmas" ain't exactly cheerful.

Also: You ever read the words to "The First Noel"? Song always makes me cry, the lyrics are so awesomely insipid.

Flip side, there's something so awe-inspiringly beautiful about a soprano singing "O Holy Night" that I can't get through it without tearing up (I know, I know, it's not a SAD song, but still ...).

Posted by: bucdaddy at December 8, 2008 6:17 PM

Hello Mrs. P-H, what a note (see what I did there?) to start contributing on. There are some (not naming names or pointing fingers) who weren't even sure you actually existed!

I don't know if it's the saddest song, but I've gotta second the "Song for a Winter's Night" by Sarah McLachlan, pointing out that the original Gordon Lightfoot version also brings the melancholy. I don't know why people focus so positively on the blowing-sunshine-up-their-asses inanely annoying and repetitive chipper tunes that everyone and their dog sings day after day after day after day - I love me a good, sober, borderline depressing tune once in a while. So, thanks for triggering these ideas, I'm now better equipped to be a wet blanket!

Posted by: lordhelmet at December 8, 2008 6:18 PM

Or how about "Christmas Card From A Hooker In Minneapolis" by Tom Waits?
Posted by: Redrider at December 8, 2008 6:04 PM

^^^
Came here to post this
http://www.youtube.com/watch?v=12qBoy2rhVw

Posted by: Peter at December 8, 2008 6:19 PM

Great, now I'm crying in my Ben & Jerry's. Thanks a lot, RDJ.

Posted by: LB at December 8, 2008 6:50 PM

"Please Come Home for Christmas" by Charles Brown, although you gotta love The Eagles' version.

Posted by: Eep at December 8, 2008 6:54 PM

Now I know that some of you will believe this to be too commerical for these purposes but to read the original byline for this song hopefully you will agree.

The Song: Christmas Eve (Sarajevo 12/24) Originally on Savatage's Dead Winter Dead. Better known through Trans-Siberian Orchestra: Christmas Eve and Other Stories.

The song is set in the Bosnian capital of Sarajevo, home of the 1990s version of ethnic cleansing.

"An old man has been playing his cello in a square of the war torn area, as if to prove the soul of his country, of humanity was not dead.

http://trans-siberian.com/multimedia/index.shtml
for the link to the song.

Posted by: richmac at December 8, 2008 7:03 PM

Something about the Christmas season inevitably grabs me every year, breaking the shell around me and finding that little nugget of belief I keep hidden deep inside. And every year, it's this one song that facilitates that process for me.

"Welcome To Our World" by Chris Rice

http://www.youtube.com/watch?v=1Z1mRFpeJPk

If, by the time you get to this line, you aren't choked up at least a little, then you shouldn't be allowed to celebrate Christmas. You should just call it Festivus and go about your business.:)

Fragile fingers sent to heal us/
Tender brow prepared for thorns/
Tiny heart whose blood will save us/
Unto us is born.. Unto us is born...

Posted by: The Pink Hulk at December 8, 2008 7:10 PM

You know what, Robert Downey Jr? Fuck you. Everyone already wants you to smear your man musk all over them because of your gorgeousity and stone cold acting chops and now you're going to add beautiful singing to the list? Fuck you in the ear, sir. Are you going to decide to be a genius programmer too? Solve world hunger while on the john? Become telepathic through sheer force of willpower and sweaty abs? Solve global warming with a single smoldering gaze? You're like the hippie gen-x version of Chuck Norris.

I, for one, give up.

Posted by: stipe42 at December 8, 2008 7:14 PM

This is my list exactly, although I subsitite the Diana Krall version of "Christmas Time is Here." And although it doesn't have the exact melancholy as those mentioned above, I love Dave Matthew's "The Christmas Song." I listen to it all year long and would think it'd be a big hit on Christian radio. The last lines "Father up above, why in all this hatred do you fill me up with love?" gets me every time. I listened to it a lot during the election.

Okay, now you all can laugh at me, you miserable bastards!

Posted by: Austin at December 8, 2008 7:26 PM

OK, a few more, because these songs also really break my heart:

If you can find "December" by Kenny Loggins, and you're completely masochistic, it is one of the most heartbreakingly beautiful songs I know:

Only in December, can the broken heart feel so alive,
In the Autumn ashes, become the fires of December,
Can I be inside,
And out of the cold,
Still I know December always leads me home,
I still believe in magic,
And I still believe in miracles.
I still believe in Christmas.
I still believe in love.

And while you're listening to Kenny Loggins, give his version of "Celebrate Me Home" a listen. It might also break your heart a little.

http://www.youtube.com/watch?v=TmaKSpTIJzI

Next up, Tori Amos's version of "Have Yourself a Merry Little Christmas": aaaaalmost as good as Judy. Listen here:

http://www.youtube.com/watch?v=nwX62HL2vKo

Next, Bette Midler's "Somewhere In My Memory" from Home Alone. Gets me every time:

http://www.youtube.com/watch?v=j_B7hAYV4mc

Finally, Linda Eder's "Bells of St. Paul," for those who have lost love:

http://www.youtube.com/watch?v=0tp3YrWuIDI


Enjoy cutting yourself to all of these songs!

Posted by: The Pink Hulk at December 8, 2008 7:26 PM

What about "the christmas shoes". The wife thinks it's sad. I think it's depressing because of its thinly veiled manipulation

Posted by: bitter pill at December 8, 2008 7:33 PM

Oh and however cold it is, don't smoke with gloves or mittens, it's just so clumsy and unsatisfying and you've gotta give up long before the filter.

Jay, my dear, it is a finely acquired art form. You have to wear small gloves, certainly not fleece as they will burn and be very careful.

Lennon - "So this is Christmas".

Ms. P-H, I also happen to love "Good King Wencenslaus", but I am a sucker for a well-sung standard. My ultimate favorite is still "Ring Christmas Bells" as sung by a real choir.

Posted by: Melody at December 8, 2008 7:37 PM

Auld Lang Syne by Dan Fogelberg, mostly because they couldn't find an open bar on Christmas eve. That's so saaaaaaaaad! I, too, adore Meet Me In St Louis and watch it every Christmas. Still waiting for that jackass to remember to have his tux ready so he can take her to the dance.

Posted by: slower lower at December 8, 2008 7:48 PM

Definitely second "Song For a Winter's Night" Sarah McLachlin version. Woah.

AND I'm so pissed I can't buy the Robert Downey Jr version of River on iTunes. And god knows I'm too computer stupid to get it any other way on my iPod.

Posted by: Blackbird at December 8, 2008 8:02 PM

If everyone else is going to put up videos, so am I.

http://www.youtube.com/watch?v=mdFZDKGO-A8

Posted by: Austin at December 8, 2008 8:04 PM

http://www.youtube.com/watch?v=iOic7t1kZog

I totally forgot this one. It almost always makes me cry.

If you will excuse me, I must go listen to some death metal now.

Posted by: Melody at December 8, 2008 8:18 PM

I third (or fourth, or fifth, or whatever) the "Song for a Winter's Night" vote. I have spent many-a-snowy night looking out the window and feeling sorry for myself with the company of that particular tune. That said, I daresay that it's a Gordon Lightfoot original, and that SM covered it. The original is definitely worth a listen as well.

And thank you for reminding me about "River", I had forgotten about it...also, I had no idea 'til now that RDJ was a singer, let alone a GOOD singer. Great version of that track.

Posted by: paperback_writer at December 8, 2008 9:17 PM

While it's not as wrist-slittingly depressing as some of these, I'm a big fan of the Ramones "Merry Christmas (I Don't Wanna Fight Tonight)" when I want to cut through the treacle. Also seconding the Pretenders' "2000 Miles." Greg Lake (of Emerson, Lake and Palmer) did "I Believe in Father Christmas" which is pretty damn bleak, too. And as others have said, John Lennon's "So this is Christmas / War is Over" is beautiful and perfectly suits my year-end retrospective mood.

Posted by: Edith at December 8, 2008 9:18 PM

How does "Fairy Tale of New York" only get honorable Mention? It's like the greatest song in the bunch!

"I coulda been some one!
Well, so could anyone!"

Posted by: Withnail at December 8, 2008 9:19 PM

"Merry Christmas Darling" -- Karen Carpenter

Posted by: Lilly at December 8, 2008 9:43 PM

"How to Make Gravy" by Paul Kelly (Australia's best songwriter, by a country mile). It's a message from a man in prison to his brother, talking about the upcoming Christmas roast. It's full of remembrance and regret, and it breaks my heart every time I hear it.

Here's a live version from Womadelaide 2006:

http://www.youtube.com/watch?v=urRc_ntHjMM

Posted by: kushiro at December 8, 2008 9:47 PM

"Frosty the Snowman". It's all about immanent and closely impending death. Merry Christmas!

Posted by: Reding at December 8, 2008 10:08 PM

Can't find a video anywhere, which is a bummer, but Christmas in America by Melissa Etheridge. Beautiful.

http://music.yahoo.com/Melissa-Etheridge/Christmas-In-America/lyrics/24393289

Posted by: Gabs at December 8, 2008 10:18 PM

Reding, I totally agrees on Frosty. His rapidly approaching demise always made me sad as a kid. I could never really watch the cartoon about him either.

It's a terrible, manipulative, corny song - actually the musical equivalent of a Thomas Kincaide painting- but "The Christmas Shoes" makes me cry EVERY DAMN TIME. Thank goodness Patton Oswalt taught me how to laugh at it.

http://www.youtube.com/watch?v=_ysMpr8mNRM

Posted by: Empress of All the Russias at December 8, 2008 10:26 PM

I'm going to join in the love for "Good King Wenceslas". Also, I love "Greensleeves" and tend to associate it with Christmas, I can only assume because my parents had a Jim Nabors Christmas album (yes, that Jim Nabors) when I was a child, and on it was his rendition of "What Child is This", which has the same tune and it was a lovely version. Also, his "We Three Kings". Not sad, but lovely.

Wow. That sounded far less dorky in my head. I'm just not cool, am I? Hee!

Posted by: Anna von Beaverplatz at December 8, 2008 10:59 PM

I... wont... let this.... Whahahaha!

(Weeps for 5 hours)

Thanks, Mrs. Pajiba, I needed that. In the Bleak Mid Winter is also really sad.... Whahahaha!

Posted by: George at December 8, 2008 11:05 PM

I'll own up to my never-ending love for the Crows. Mrs. P-H, let's go cruise a backroad, smoke some Marlboro Menthol Ultra Lights and wonder where our younger selves got off to.

Posted by: superEdna at December 8, 2008 11:17 PM

Can't quarrel with the inclusion of "Have Yourself a Merry Little Christmas." Not sure if it's that the woman singing it is now dead (and died relatively young) or that it came out in 1944, during WW2 or if it's just the way she sang it. Beautiful song.

Posted by: Slash at December 9, 2008 12:30 AM

Xmas Cake, Rilo Kiley.
The year I was unemployed at Christmas and faced a long day of family togetherness, I woke up and put this on. It is the perfect antidote to all the forced cheerfulness. Oh, holidays... how I dread thee.

Posted by: majandratoo at December 9, 2008 12:35 AM

I dunno, although Charlie Brown is basically the original emo kid, I grew up listening to Vince Guaraldi's Charlie Brown Christmas album and I think it sounds rather happy. Especially the song "Christmas is Coming," you totally feel the anticipation. Call me biased, but Snoopy and the Gang are what makes my Christmases.


For some reason, O Holy Night gets me every time, and I'm an atheist. Go figure.

Posted by: Corinna at December 9, 2008 1:19 AM

For xmas melancholy, "So Much Wine" by the Handsome Family - "I had nothing to say on Christmas day when you threw all your clothes in the snow.

When you burnt your hair, knocked over chairs, I just tried to stay out of your way.

But when you fell asleep with blood on your teeth, I got in my car and drove away."

Posted by: moggy at December 9, 2008 1:29 AM

Thank fucking Christ hanging on a mistle-toed cross that you didn't include the "Christmas Shoes". These are actually decently sad songs... unlike the Christmas Shoes which is so manipulating it makes me want to Urethrally Sound myself with a DVD box.

Posted by: Ryan at December 9, 2008 1:38 AM

For some reason, the Pogues' song never hits me as being horribl sad. I mean, sure, they're two broken, ruined people, but there's still enough passion in them to fight, and to sing for one last Christmas, and that kinda strikes me as hopeful.

My favourite sad Christmas song, on the other hand, is just downright depressing - Lisa Hannigan's version of Silent Night. All I could find was a Doctor Who fan video of it: http://www.youtube.com/watch?v=YuOOXL8nLik so I'd recommend just turning up the sound and ignoring the images. (Not that I don't have a Who-shaped soft spot, but it's not a particularly good video...)

Posted by: Shay at December 9, 2008 3:35 AM

I agree about Have Yourself a Merry Little Christmas. The Conor Oberst version is even more of a heartbreaker.

Posted by: Jenny N at December 9, 2008 4:05 AM

One year my wife (now ex-wife) insisted I listen to this one country&western song, that represented itself as a Christmas song.

It was awful. It was about a little girl who was abused by her father and only wanted some love for Christmas. After listening to half of it I switched the radio off and asked her to please never, NEVER play it again where I could hear it.

Posted by: The Wanderer at December 9, 2008 4:56 AM

River wasn't on Aimee Mann's Christmas album. If it had been my nether regions may have exploded from the sheer awesomeness. My favourite artist covering one of my favourite songs? Lordy.

It IS probably the most depressing Christmas album ever anyway, which is awesome. I mean, it's called One More Drifter in the Snow. Come on.

Posted by: Arran at December 9, 2008 5:10 AM

Honorable Mention???

Fairytale of New York has, is and always will be the greatest Christmas song of all time!!

I for one know that in my drunken stagger home through Irish country roads on x-mas eve I will be belting it out at the top of my lungs.

What other x-mas tune makes you want to get drunk and sing along?

Posted by: Paul Mc at December 9, 2008 7:03 AM

Seriously - Fairytale as only an honourable mention? No song is simultaneously more uplifting and tear-in-my-beer for the holiday season.

I'd also like to add as an actual honourable mention - Over the Rhine's "Darkest Night of the Year". That whole album was made for lonely winter nights.

Posted by: amanda at December 9, 2008 7:09 AM

One could say that last comment about any Over the Rhine really, amanda.

I'm just stoked someone else likes them. One of the great under-heard bands.

Posted by: Arran at December 9, 2008 8:46 AM

Sarah McLachlan's 'Wintersong' is the most depressing Christmas song I have ever heard.

http://www.youtube.com/watch?v=lZwI5wXU1z4

Posted by: twig at December 9, 2008 8:47 AM

"I'll Be Home For Christmas" as sung by Bing Crosby always brings a tear to my eye. I live in TX and my family lives in NJ and I always miss them terribly this time of year!

Posted by: Alice at December 9, 2008 9:47 AM

"Christmas time is here, By Golly!
Disapproval would be folly.
Deck the halls with hunks of holly
Fill the cup and don't say when.

Kill the turkeys, ducks and chickens
Hang the socks, drag out the Dickens.
Even tho the process sickens
Brother, here we go again."
Tom Lehrer
This says it for me...

Posted by: Arkansan at December 9, 2008 10:02 AM

Have Yourself a Merry Little Christmas is a sad song. It's full of hope for better things that may never happen.

But I remember reading that the original lyrics were far worse and they were rewritten for Meet Me in St. Louis.

Posted by: April at December 9, 2008 10:05 AM

I find the tone of ANY Charlie Brown movie to be overwhelmingly sad. Ugh. What a bleak world they live in.

Posted by: AM at December 9, 2008 10:29 AM

Okay, I must be old. How can you have a depressing-ass Christmas song list without Stevie Wonder's "Bedtime for Toys"? "Bless the child who has no tin soldier, no brass drummer boy to put him to bed"? The little soliloquy in the middle about how "Sometimes, just sometimes" Santa doesn't have time to visit all the children because the world is so big and how we should sing a song for them? I was a shell of my former self hearing that song at the age of five.

"O Holy Night" kills me, as does "Ave Maria" (not really a Christmas song, I suppose, but I do hear it a lot this time of year). Also, Crosby/Bowie "Little Drummer Boy" makes me shed a tear b/c it's so wistful "Peace on earth....can it be?"

Posted by: samantha t at December 9, 2008 10:36 AM

I loooove depressing Christmas songs.

I never understand people who love Christmas as adults. I dread it! Songs like these are like a comforting hug.

Also, I looooove Judy Garland. What a talented, sad, beautiful mess.

Posted by: Park at December 9, 2008 11:07 AM

Hey, juicyspambot, least you could do is label your post "Extraordinarily off topic."

Posted by: bucdaddy at December 9, 2008 11:10 AM

I think I might win the "most ridiculous inclusion" award by nominating "The Chipmunks Song" to the list. I know most people HATE it, and there isn't a damn sad thing about it, but it always used to make me cry as a little kid. The tune is so mournful! And those lil chipmunks are just BEGGING for Christmas to get here, as though it might never come!

Posted by: jimbob at December 9, 2008 11:20 AM

well, my sister ruined elvis' "blue christmas" for me. we put my dog miles to sleep (RIP old buddy....) right before xmas in 2003, and she made that song her ringtone. it made us cry everytime it came on! to this day, i can't hear that song without crying about my awesome old chow-mix dog with the blue tongue.

sniffle....

Posted by: glittergirl at December 9, 2008 11:43 AM

I, for one, am very sad that I just heard what turns out to have been Destiny's Child's "Rudolph The Red-Nosed Reindeer" while at the grocery store on a break.

VERY sad.

Posted by: Jay at December 9, 2008 11:47 AM

Ditto, Edith, on "I Believe in Father Christmas."

Also, Everclear's "Hating You for Christmas."

Posted by: frumpiefox at December 9, 2008 12:01 PM

Amarga Navidad. Sing it Jose Alfredo! Great song for those who like to drink tequila at x-mas. The Enrique Bunbury version is good too, but nothing compares to the Wally Gonzales tex-mex version on his album Chistmas Bandito, available for cheap at many flea markets in South Texas. No, I don't work for Wally. I just think everyone should experience the unintentional hilarity of his x-mas CD.

Posted by: Michin at December 9, 2008 12:19 PM

Hardly anybody knows this one, but Fisher's "Christmas Face" is one of the most heartbreaking Christmas songs out there.

Posted by: lilybeth at December 9, 2008 12:43 PM

The top three Christmas songs are:

3. The Didjits "Under the Christmas Fish"
2.El Vez's version of "Feliz Navidad"
1. Robert Earl Keen's "Merry Christmas from the Family"

Posted by: Jez at December 9, 2008 1:36 PM

The Pogues win this one, for me.

But I love the Crosby/Bowie "Little Drummer Boy", too. Something about the way their voices go together so well. And the 'Meet Me in St Louis' version of 'Have Yourself a Merry Little Christmas' makes me mist up. Oh, and 'Oh Holy Night', sung by almost anybody with a great voice.

I also like Jeff Buckley's 'Corpus Christi Carol'. It's just so heartbreakingly beautiful!

Posted by: Tarn at December 9, 2008 2:02 PM

That litte crayon-drawing girl's rendition of "Blue Christmas" written to Santa in The Year Without a Santa Claus, when Santa had a cold? I cry. Every. Time.

Posted by: Sweetie Dahling at December 9, 2008 2:06 PM

"The Year Without a Santa Claus"! That brings me back. So sad.

Posted by: samantha t at December 9, 2008 2:22 PM

There's an old Prince B-side called "Another Lonely Christmas". Girlfriend dies on Christmas, song is written on a later anniversary as he remembers back. Sad as hell, great song (albeit lyrically not very sophisticated).

Posted by: eddie at December 9, 2008 2:25 PM

How did we get this far in the comments without someone mentioning John McDermott's Christmas in the Trenches. It has to be the most depressing yet up lifting Christmas songs ever. "who's family have I fixed my sight tonight" just kills you.
http://www.youtube.com/watch?v=s9coPzDx6tA

Posted by: sevngang at December 9, 2008 4:56 PM

Yeah, Aimee Mann deserves a little more discussion for this list. Check out her Christmas album. (I just saw her third annual holiday concert this past weekend.) I don't know if her song "Christmastime" (composed by Jon Brion and Michael Penn and appearing on the Hard Eight soundtrack) qualifies for this list, but it sure hits me in the gut.

In answer to the above, Aimee Mann did do a cover of "River" for a different holiday album - not Drifter In The Snow - but it only appeared on the iTunes version apparently.

Beyond that, the Charlie Brown song rules.

Posted by: DarthCorleone at December 9, 2008 6:54 PM

Okay, I followed the Youtube links.

Apparently Sarah McLachlan wants us all dead. It's the only reasonable explanation. What in the hot buttered fuck we ever did to her I just can't imagine. But now I'm not depressed. I'm just pissed.

Posted by: greer at December 9, 2008 7:25 PM

"Christmas in the Trenches" always gets to me. I'd probably consider it manipulative if it wasn't based on a real event that itself is a tearjerker. What do people think of the movie about that event (Joyeux Noel)? I'm considering watching it soon and giving myself a nice holiday cry if it's worth my time.

Posted by: Kat at December 9, 2008 11:07 PM

Sufjan Stevens' "Sister Winter" gets my vote.

Posted by: JK at December 9, 2008 11:20 PM

Apparently, there aren't any Country fans posting here. Two great (and sad) Christmas country songs:

Hard Candy Christmas - Dolly Parton (though, it being Dolly, she has to make it upbeat in the end, but it's about a person alone at Christmas.)

http://www.youtube.com/watch?v=pttkAyWvAhU&feature=related

If We We Make It Through December - Merle Haggard

http://www.youtube.com/watch?v=gbaxCG6mjMc

Posted by: Judith at December 9, 2008 11:50 PM

for everyone who is interested in finding the lennon christmas song, its actually called "happy christmas (war is over)", not "so this is christmas"....just thought id be "that guy" for a moment...

Posted by: jordan at December 10, 2008 12:54 AM

Good King Wenceslas looked out on the Feast of Stephen,
Where the snow lay round about, deep and crisp and even.
Brightly shone the moon that night, though the frost was cruel,
When a poor man came in sight gathering winter fuel.

"Hither, page, and stand by me. If thou know'st it, telling.
Yonder peasant, who is he? Where and what his dwelling?"
"Sire, he lives a good league hence underneath the mountain.
Right against the forest fence by Saint Agnes' Fountain."

"Bring me flesh and bring me wine. Bring me pine logs hither.
Thou and I will see him dine when we bear them thither."
Page and monarch, forth they went, forth they went together,
Through the rude wind's wild lament and the bitter weather.

"Sire, the night is darker now, and the winds blow stronger.
Fails my heart, I know not how. I can go no longer."
"Mark my footsteps, my good page. Tread thou in them boldly.
Thou shalt find the winter's rage freeze'th thy blood less coldly."

In his master's steps he trod where the snow lay dinted.
Heat was in the very sod which the saint had printed.
Therefore, Christian men, be sure, wealth or rank possessing,
Ye who now will bless the poor shall yourselves find blessing.


FUCK YES. When I am King, I will decree that all Christmas music must be good and worthy.

Posted by: Lucas at December 10, 2008 10:57 AM

Posted by: QueBarbara at December 12, 2008 10:47 PM

Aimee Mann's cover of Joni Mitchell's River appears on the UK version of her Christmas Album as well on one of Starbucks' Christmas compilations. It is extremely difficult to find online anywhere.

Posted by: maverick2464 at December 13, 2008 3:46 AM

"Have Yourself a Merry Little Christmas" is an incredibly poignant song when you think about when it came out -- but it's not "Traditional," it was introduced in "Meet Me In St. Louis," by Garland. It was written by Hugh Martin and Ralph Blane.

Posted by: Brenda at December 13, 2008 10:26 PM

looking for the title of a christams tune played on the rock radio stations late 1990s'...cello muic background remember mary being in the lyrics thought it was tied to bosnia/serajevo but none of the songs researched on net have matched my memory...re x-mas serajevo mary did you know any suggestions?

Posted by: pat at December 26, 2008 12:46 AM