When we think of Christmas music, we tend to think of sleigh bells and chimes and happy horns and declarations of peace and joy and love and presents — but there are some damn sad Christmas songs that pop up on even the most jolly playlists this season. Below I have ranked 15 of the saddest ones, on a scale of one to five crying Therese Belivets. Happy holidays!
“Where Are You Christmas,” Faith Hill
This song is very upsetting! It’s about a woman who used to love Christmas and Christmas loved her back and now she can’t find Christmas and Christmas can’t find her either! They’re lost to each other! Because her world has changed, rearranged, and she’s grown up now, so — according to the music video, at least — she’s wandering around in the woods in the snow calling out for Christmas and creepy-peeping into people’s frozen windowpanes in case Christmas is maybe inside by the fire and can’t hear her mournful plea over the sound of the winter storm. It’s exactly what happened to Susan Pevensie who got kicked out of Narnia for discovering lipstick. Worst of all, one of the windows Faith Hill looks into, Jim Carrey’s Grinch is in there. A true horror. Three crying Therese Belivets.
“Christmas (Baby Please Come Home),” Darlene Love
You’re probably more familiar with Mariah Carey’s version of this song than the original recording by Darlene Love, but they’re equally depressing. The bells are jangling and everything seems really upbeat, all snow and church bells and pretty lights on the tree, and Darlene (and Mariah) are just smiling and waving to all the people. About every fourth line, though, she slips in a, “Baby, please come home” — but no one can even hear her because they keep going “CHRISTMAS!” “CHRISTMAS!” “CHRISTMAS!” the whole time. She’s not letting on that anything’s wrong and they wouldn’t hear her even if she did. Two and a half crying Therese Belivets.
“Christmas Time Is Here,” Vince Guaraldi Trio
You know this song as the jazz music that plays while Charlie Brown travels around town and finds out all his friends and also Snoopy are into Christmas just for the gifts, and not for Jesus. It’s not really sad, but it’s definitely somber. Cue it up on Christmas Eve with a glass of wine if you want to wait for Santa in a super chill, melancholy stupor. One crying — sniffling, really — Therese Belivet.
“Merry Christmas, Darling,” The Carpenters
Poor Karen Carpenter! She’s got all the makings of a holly jolly Christmas, even a crackling fire. But her darling isn’t there to share it with her. She’s going through the motions with the cards and the stockings. One second she’s saying it’s no big deal because everyday is a holiday when they’re together and the next second she’s stopped lying to herself, talking about oh if she had just one wish on Christmas Eve it’d be that they were together. Her darling won’t even be there by New Year’s Eve! Three crying Therese Belivets.
“Same Old Lang Syne,” Dan Fogelberg
Woof, this one’s depressing. It starts like a meet-cute in a grocery store and ends with two exes sitting in a car drinking a six pack of beer in the liquor store parking lot on Christmas Eve and she’s married to a man she doesn’t even like and he’s got a nice career but the traveling is killing him, and then he gets out and watches her drive off (drunk?) while the snow turns to rain turns to slush. Four crying Therese Belivets.
“You’re a Mean One, Mr. Grinch,” Thurl Ravenscroft
I saw this on at least ten different lists of sad Christmas songs, as if Thurl Ravenscroft — the original voice of Frosted Flakes’ Tony the Tiger, by the way — was bullying The Grinch and that’s why he turned to a life of crime. No! This song doesn’t even start playing until The Grinch is well on his way to stealing Christmas. Anyway, there’s nothing sad about the sick burns Ravenscroft lays down. You’re a three-decker sauerkraut and toadstool sandwich, with arsenic sauce? Classic. Zero crying Therese Belivets.
“Have Yourself a Merry Little Christmas,” Judy Garland
Ironically, Judy Garland sings this to raise the spirits of her little sister in Meet Me in St. Louis. If you think it’s sad now (and obviously it is!) get a load of the lyrics before Garland begged Hugh Martin to change them. “Let your heart be light / Next year all our troubles will be out of sight,” for example, was originally, “It may be your last / Next year we may all be living in the past.” What a thing to say to cheer up a five year old! Also, honestly, the title just feels sarcastic. Oh? Oh yeah? Well have yourself a merry little Christmas, pal! Three crying Therese Belivets.
“Both Sides Now,” Joni Mitchell
Don’t try to tell me this isn’t a Christmas song. As soon as Emma Thompson put on the album in Love Actually and sobbed silently and alone in her bedroom — while her children opened their gifts by the Christmas tree — because she just found out her marriage was dead on Christmas Eve, it became a Christmas song. The most heartbreaking Christmas song in human history! Five entire crying Therese Belivets.
“Please Come Home for Christmas,” Charles Brown
The Eagles version of this song gets more play these days, but it was Charles Brown’s forlorn Christmas entreaty first. This sad guy’s baby has left him and he’s been moaning about it so much he doesn’t even have any friends left. He begs her to come home for Christmas, which he knows she’s not gonna do, so he tacks on a little prayer at the end of his appeal, like, okay, maybe by New Year’s night? You can tell he knows she’s gone, though, and that he needs a different hobby besides pining so maybe his buddies will start hanging out with him again. Two and a half crying Therese Belivets.
“I’ll Be Home For Christmas,” Bing Crosby
What makes this song so sad is that Bing Crosby (and his ghost, Michael Bublé) make the whole thing sound like a promise. He’s gonna be home for Christmas, you can count on it, here’s a list of things he’d like you to have ready for his arrival (snow, mistletoe, presents) — but just kidding! He might only be home in his dreams! Way to get a person’s hopes up and then pull the Christmas Tree skirt out from under them, Bing. Three crying Therese Belivets.
“Blue Christmas,” Elvis
It sounds like a bummer, but I think writers Billy Hayes and Jay W. Johnson were hallucinating when they wrote this, due to the fact that they take the blue Christmas metaphor and make it literal. He’s gonna be blue without his lady but whoa man like everything’s blue, yeah? Look at these blue snowflakes falling. Look at these blue memories calling. I had a medical situation that required me to spend an entire would-be stressful-as-heck Christmas on Vicodin. All in all? Not a bad holiday. One crying Therese Belivet.
“7 O’Clock News / Silent Night,” Simon & Garfunkel
Just imagine someone singing a beautiful hymn to you on Christmas Eve in one ear while another person reads Twitter to you in real time in your other ear. The real nightmare before Christmas. Five crying Therese Belivets.
“Another Lonely Christmas,” Prince
You think this is going to be another song where the singer’s lover left them, and it does start out like that. She’s gone. He’s lonely. They had such good times and the holidays are extra hard without her and her sister’s ice skating on the pond and isn’t that so festive. Why oh why did she have to go? Because she died! On the on the twenty-fifth day of December! “Your mother said it was strep, but the doctor said you were dead” is an actual lyric from this song. I would give it five crying Therese Belivets but to be honest it feels like an episode of This Is Us that’s manipulating me into crying so I’m only giving it four.
“Last Christmas,” Wham
It is sad that George Micahel gave his heart to someone on Christmas and the very next day she gave it away, but that seems like a lesson he could have learned from. Instead he’s following her around the city and still being in love with her and scowling at her from the corner of his friends’ Christmas parties and hell bent on rushing out and giving his heart to an entirely different person on Christmas day again! You Need Help: Stop Cuffing For One Second, Dude. One and a half crying Therese Belivets.
“The Christmas Shoes,” New Song
I guess everyone on earth thinks this song about a girl rushing out to Woolworth’s or whatever to buy her mom some “Christmas shoes” with a sack of pennies so she can dance with Jesus when she goes to heaven later that night is super sad, but let me tell you something. When I was growing up in rural Georgia we didn’t have haunted houses at Halloween; we had Judgement Houses, which is where you would go into a house and each room was a different horror scenario like premarital sex or drinking alcohol or swearing, and then the characters in that room would die tragically on the very night of their sin. Finally you’d get to a room that was about a hundred and five degrees and completely dark and there was wailing and teeth-gnashing and someone with a Satan voice modulator microphone would call out to the drunk, unchaste, cursing teens and drag them into the pits of hell. Then the final room was a cool, well-lit place where a nice old lady told you how you could accept Jesus into your heart that very night, in the event of your untimely death, and not have to spend eternity in torment. “Christmas Shoes” is Judgment House, but in December. Five furious Therese Belivets.
