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Ten Depressing Christmas Songs to Make You Cry

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Is it just me, or is the holiday season kind of … sad? Don’t get me wrong—I love the shiny lights, the presents, and the surplus of nog, but I still can’t help but feel a bit melancholy when Christmas rolls around. Luckily, I’m not the only one. I’ve compiled my list of the ten most depressing Christmas, along with my grades for overall quality and ability to make you feel dead inside.

Song: “Have Yourself A Merry Little Christmas”
Performer: Judy Garland
Notes: Forget the jaunty covers—this is all about being away from your loved ones on Christmas. Yeah, it talks about brighter times, but the way Judy sings it, you’re not so convinced those will ever appear. The first line of the original version? “Have yourself a merry little Christmas, it may be your last.”
Sample lyric: “Someday soon we all will be together, if the fates allow / Until then, we’ll have to muddle through somehow.”
Sadness grade: B+. Totally depressing, but there’s some hope there.
Overall grade: A. One of the greatest Christmas songs ever. I could listen to it on a loop—and have.

Song: “That Was the Worst Christmas Ever”
Performer: Sufjan Stevens
Notes: Now we’re talking. Sufjan Stevens doesn’t beat around the bush here, and his light, mellow tones are perfect for expressing the kind of sadness that gets under your skin and doesn’t go away.
Sample lyric: “Our father yells, throwing our gifts in the wood stove, wood stove / My sister runs away, taking her books to the schoolyard, schoolyard.”
Sadness grade: A-. Slight deduction for the mildly uplifting music.
Overall grade: A-. Not the best on Stevens’ five-volume Christmas album, but still damn good.

Song: “Christmas Really Sucks”
Performer: Jay Brannan
Notes: Like Sufjan Stevens, Jay Brannan gets straight to the point. His voice is equally well-suited to the utterly depressing lyrics. This song manages to incorporate plenty of Christmas imagery, but it’s an effective break-up song with or without the holiday dread.
Sample lyric: “It’s cold, but light outside / Another sleepless night / And Santa never made it.”
Sadness grade: A. Just try to listen to this without curling up into the fetal position.
Overall grade: A-. One of Brannan’s best.

Song: “Christmas Shoes”
Performer: Newsong
Notes: Yes, I’m including this treacly piece of crap here. I hate, hate, hate the song, from its misguided message to its manipulative lyrics. At the same time, you can’t deny its objective sadness. I mean, I can’t think of any other Christmas songs about a boy’s dying mother.
Sample lyric: “Sir, I want to buy these shoes for my mama, please / It’s Christmas Eve and these shoes are just her size / Could you hurry, sir, Daddy says there’s not much time.”
Sadness grade: B-. Lyrics-wise, it’s depressing, but the over-the-top story takes away from its effect.
Overall grade: D-. I’d basically rather listen to any other Christmas song.

Song: “Blue Christmas”
Performer: Elvis Presley
Notes: Another song about being alone on Christmas, so alone that Christmas will be BLUE. (Not literally, I imagine.)  It’s such a classic that it almost doesn’t feel sad, despite the content.
Sample lyric: “And when those blue snowflakes start falling / That’s when those blue memories start calling.”
Sadness grade: B. Again, a break-up song but more of an Elvis song than anything else.
Overall grade: B+. Still a very good one. Small deduction for the minimal lyrics and repetition.

Song: “Do You Hear What I Hear?”
Performer: Bing Crosby
Notes: The only reason this not really depressing song is included here is that it was written as a plea for peace during the Cuban Missile Crisis. We all know how that turned out and the lyrics itself aren’t all that sad, so it’s a bit misplaced out of context.
Sample lyric: “Said the king to the people everywhere / Listen to what I say / Pray for peace, people everywhere.”
Sadness grade: C. The Cuban Missile Crisis came and went. We survived.
Overall grade: C+. Too religious for my tastes, and really not all that catchy. Next!

Song: “Christmas Bells”
Performer: The Cast of “Rent”
Notes: There’s a whole lot going on in this song, which doesn’t really work outside the musical. Still, it has a nice and cynical message about consumerism and being poor and hungry. Festive!
Sample lyric: “You’ll be merry, I’ll be merry / Though ‘merry’ ain’t in my vocabulary.”
Sadness grade: B. The first minute or so is a solid A, but there’s way too much more of the song for it to score much higher than a B on sadness.
Overall grade: B. Far from the best song in “Rent.” On the other hand, it has some really nice moments.

Song: “Christmas at Ground Zero”
Perfomer: “Weird Al” Yankovic
Notes: Relax, this was written pre-9/11, and the Ground Zero in the song’s title refers to the earth following a nuclear holocaust. It’s a fun song, because it’s Weird Al. Still, death and destruction do make me kind of sniffly.
Sample lyric: “It’s Christmas at Ground Zero, there’s panic in the crowd / We can dodge debris while we trim the tree / Underneath the mushroom cloud.”
Sadness grade: D-. “Weird Al” wasn’t really trying to be sad, so it’s OK that it fails on that level.
Overall grade: B+. Very funny song. I wish it got played more often, but the legitimately depressing associations of the title make that almost impossible.

Song: “I’ll Be Home for Christmas”
Performer: Frank Sinatra
Notes: Aw, isn’t that nice? Well, until you realize that the guy singing the song probably won’t actually be home for Christmas. This always fills me with intense nostalgia, as I was apparently alive several decades ago.
Sample lyric: “I’ll be home for Christmas / If only in my dreams.”
Sadness grade: A-. It sounds so positive until the end, but those last lines are rough.
Overall grade: A. Another of the best Christmas songs ever sung.

Song: “Did I Make You Cry on Christmas? (Well, You Deserved It!)”
Performer: Sufjan Stevens
Notes: Sufjan Stevens made it on this list twice! What an overachiever. This song has the distinction of having my favorite title for a Christmas song, possibly for any song ever. More about a terrible relationship than Christmas, though.
Sample lyric: “Did I make you cry on Christmas day? / Did I let you down like every other day?”
Sadness grade: A. Some great reflection on what sounds like the worst pairing possible.
Overall grade: B+. Solid song. I just wish there were more Christmas to it!

Well, that’s my list. If there are any bawl-worthy Christmas songs I missed, feel free to let me know in the comments. Now if you’ll excuse me, I’m going to hide under my blanket until it’s January. Happy holidays!

Photo by Flikr user crimfants, courtesy Wikimedia Commons.