The 30 Saddest Christmas Songs – InsideHook

This time of year, there tends to be a lot of ink spilled over The True Meaning of Christmas. Of course, your definition depends largely on your religious beliefs and whether you find Linus reciting a Bible verse in A Charlie Brown Christmas to be more compelling than Love, Actually‘s assertion that Christmas is for coming clean about the crush you’ve been harboring. But no matter how secular you like to keep your celebrations, we all seem to have a general understanding that Christmas is about making the most out of an otherwise cold, bleak time of the year.

December is dark and depressing, so we hang festive lights and decorations and get all dressed up in sparkly metallics or rich jewel tones to brighten things up a bit. We convince ourselves that the snow we nearly throw our backs out shoveling is cozy and beautiful. We make toasts and eat big, hearty meals and go out of our way to show our loved ones just how much they mean to us with perfect, thoughtful tokens of our affection. We save all that warmth for the part of the year when we most desperately need our days to be merry and bright; we polish the lump of coal life handed us until it shines like a diamond.

But there are two sides to every coin. There’s an inherent sadness to the holiday that comes from the expectations we’ve attached to it. For every person traveling home to be with their family, there’s another spending the day alone. For all the beautifully wrapped gifts sitting under the tree waiting to be opened, there’s a less fortunate person wondering how they’re going to explain to their kids that Santa won’t be coming or just looking for a way to get out of the cold. It can be a day of tight, forced smiles at awkward family gatherings. And for some reason, it all hits harder than on any of the other 364 days of the year; there’s nothing sadder than being sad on Christmas, the day we’ve collectively willed to be the most joyful of all.

Perhaps that’s why there’s an entire sub-genre of Christmas songs devoted to this phenomenon. Some, like the Darlene Love classic “Christmas (Baby Please Come Home)” hide their melancholy lyrics behind a deceptively upbeat wall of sound, while others go straight for the jugular with tales of lost love, poverty, dying or dead relatives, or realizations like McCarthy Trenching’s deeply upsetting, to-the-point “Sadness comes crashing like a brick through a window, and it’s Christmas, and no one can fix it” — but they all scratch a certain emotional itch this time of year, no matter what your circumstances are. With that in mind, we’ve put together a playlist of some of the saddest Yuletide jams we know. (We’re not just talking about sadness alone, here, however. All the tracks on this list are included with the understanding that in addition to being very sad, they are actually well-written, enjoyable songs. That means you won’t see any emotionally manipulative, overwrought crap like “The Christmas Shoes” here.)

This Christmas, of course, is bound to be much sadder than usual for all of us as we’re forced to spend it away from the ones we love due to the ongoing pandemic. What better excuse, then, to find a little catharsis and embrace these devastating odes to the holiday’s darker side? As the great Judy Garland once sang, “We’ll have to muddle through somehow,” so it might as well be by allowing yourself to get a little misty-eyed while you queue up these tunes and count down the days to 2021.

Bing Crosby, “I’ll Be Home for Christmas” (1943)

Premise: A soldier stationed abroad during WWII writes a letter to his family imagining what it’d be like if he was able to come home for Christmas.

Most devastating line: “I’ll be home for Christmas, if only in my dreams”

Judy Garland, “Have Yourself A Merry Little Christmas” (1944)

Premise: This Christmas is bad, and our loved ones are far away, but keep your chin up and try to have a merry Christmas anyway.

Most devastating line: “Someday soon we all will be together/If the fates allow/Until then, we’ll have to muddle through somehow”

Elvis Presley, “Blue Christmas” (1957)

Premise: Simple: the narrator’s sad to be celebrating Christmas without the one he loves.

Most devastating lyric: “Decorations of red on a green Christmas tree/Won’t be the same, dear, if you’re not here with me”

Wham!, “Last Christmas” (1984)

Premise: Last year, the narrator got dumped the day after Christmas, and to add insult to injury he has to see his ex again this year.

Most devastating lyric: “A crowded room, friends with tired eyes/I’m hiding from you and your soul of ice/My God, I thought you were someone to rely on”

Charles Brown, “Please Come Home for Christmas” (1960)

Premise: The narrator’s spending Christmas alone without the object of his affection.

Most devastating line: “Bells will be ringing/The sad, sad news/Oh what a Christmas/To have the blues/My baby’s gone/I have no friends/To wish me greetings/Once again”

Darlene Love, “Christmas (Baby Please Come Home)” (1963)

Premise: It doesn’t feel like Christmas when you can’t spend it with the one you love.

Most devastating lyric: “They’re singing ‘Deck the Halls,’ but it’s not like Christmas at all/Cause I remember when you were here/And all the fun we had last year”

Joni Mitchell, “River” (1971)

Premise: A breakup song (believed to be about Mitchell’s relationship with Graham Nash) set against the backdrop of Christmas.

Most devastating lyric: “It’s coming on Christmas/They’re cutting down trees/They’re putting up reindeer/And singing songs of joy and peace/Oh, I wish I had a river I could skate away on”

Merle Haggard, “If We Make It Through December” (1974)

Premise: The narrator gets laid off from his factory job right before Christmas.

Most devastating lyric: “Got laid off down at the factory, and their timing’s not the greatest in the world/Heaven knows I been workin’ hard/I wanted Christmas to be right for daddy’s girl/Now I don’t mean to hate December/It’s meant to be the happy time of year/And my little girl don’t understand why Daddy can’t afford no Christmas here”

John Prine, “Christmas in Prison” (1973)

Premise: A prisoner yearns for the one he loves on Christmas.

Most devastating lyric: “The search light in the big yard swings round with the gun/And spotlights the snowflakes like the dust in the sun/It’s Christmas in prison/There’ll be music tonight/I’ll probably get homesick/I love you/Goodnight”

Vince Guaraldi, “Christmas Time Is Here” (1965)

Premise: Maybe it’s the minor key, but this one sounds sadder than it actually is: it’s celebrating the fact that the holiday season is upon us, but it does end with the melancholy wish that the rest of the year could be like December.

Most devastating lyric: “Oh, that we could always see such spirit through the year”

Kacey Musgraves, “Christmas Makes Me Cry” (2016)

Premise: This one runs through a laundry list of reasons why Christmas is sad, from being single and lonely to being unable to travel home and even noticing your parents are getting visibly grayer and bumming yourself out by thinking about their mortality.

Most devastating lyric: “It’s the ones we miss, no one to kiss under the mistletoe/Another year gone by, just one more that I, I couldn’t make it home/And I know that they say, ‘Have a happy holiday’/And every year, I swear I sincerely try/Oh, but Christmas, it always makes me cry”

Stevie Wonder, “Someday at Christmas” (1966)

Premise: Someday at Christmas, there’ll be peace on earth and equality, but we sadly haven’t reached that point yet.

Most devastating lyric: “Someday all our dreams will come to be/Someday in a world where men are free/Maybe not in time for you and me/But someday at Christmastime”

Marvin Gaye, “I Want to Come Home for Christmas” (1972)

Premise: A prisoner of war yearns to be freed and return home in time for Christmas.

Most devastating lyric: “I can’t promise my eyes this sight unless they stop the fight/Cause I’m a prisoner of war lying here in my cell/Hoping my family is well/Wish they wouldn’t worry so much about me/Just try to get us home in time for the Christmas tree”

LCD Soundsystem, “Christmas Will Break Your Heart” (2015)

Premise: Christmas will break your heart.

Most devastating lyric: “Christmas will shove you down, so just lay back in the snow/That quiet wind won’t wake what inside you has grown cold/And Christmas will drown your love like a storm down from above/On your fading memories of a normal life”

Willie Nelson, “Pretty Paper” (1963)

Premise: An impoverished street vendor sells wrapping paper and pencils on the sidewalk during the holiday season.

Most devastating lyric: “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”

Nat King Cole, “The Little Boy That Santa Claus Forgot” (1960)

Premise: A poor, fatherless boy is sad on Christmas because Santa Claus “forgot” him.

Most devastating lyric: “In the street he envied all those lucky boys/Then wandered 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”

The Everly Brothers, “Christmas Eve Can Kill You” (1972)

Premise: A homeless hitchhiker tries to catch a ride and avoid freezing to death on a frigid Christmas Eve.

Most devastating lyric: “The cold and empty evening hangs around me like a ghost/I listen to my footsteps in the snow/The sound of one man walking through the snow can break your heart/And stopping doesn’t help, so on I’ll go”

Aimee Mann, “I Was Thinking I Could Clean Up for Christmas” (2005)

Premise: An addict plots his suicide, planning on getting clean for Christmas to give his loved one a final happy memory of him and then killing himself after the holiday.

Most devastating lyric: “I was thinking I could clean up for Christmas/Then, baby, I’m done/’Cause I can’t live loaded and I can’t live sober/And I’ve been this way since the end of October/And I know enough to know/That, baby, when it’s over, it’s over”

The Supremes, “Just A Lonely Christmas” (1965)

Premise: Another Christmas spent pining over someone who isn’t there.

Most devastating line: “I’ll sit and watch as the snowflakes fall on my window pane, wishing that my baby would hurry home again”

The O’Jays, “Christmas Just Ain’t Christmas Without the One You Love” (1973)

Premise: The title says it all!

Most devastating lyric: “Underneath the mistletoe I saw a face all aglow/Last year, this time/Now I stand all alone and my house is not a home/Without that girl of mine”

The Emotions, “What Do the Lonely Do at Christmas?” (1973)

Premise: Being alone on Christmas sucks.

Most devastating lyric: “A silent night, I know it’s gonna be/Joy to the world, but it’s gonna be sad for me”

Simon & Garfunkel, “7 O’Clock News/Silent Night” (1966)

Premise: Simon & Garfunkel sing “Silent Night” while Charlie O’Donnell reads the news of the day, illustrating some of the horrors of the tumultuous era like racism, the death of Lenny Bruce, the Vietnam War and the Richard Speck murders.

Most devastating lyric: “Former Vice-President Richard Nixon says that unless there is a substantial increase in the present war effort in Vietnam, the U.S. should look forward to five more years of war.”

McCarthy Trenching, “Christmas Song” (2008)

Premise: Even when you’re in a room full of people going through all the motions on Christmas, it can be a real bummer.

Most devastating lyric: “You don’t have to be alone to be lonesome, it’s so easy to forget/And sadness comes crashing like a brick through the window/And it’s Christmas, and no one can fix it”

The Carpenters, “Merry Christmas, Darling” (1970)

Premise: A woman alone on Christmas imagines what the holiday would be like with the one she loves.

Most devastating line: “Merry Christmas darling, we’re apart that’s true/But I can dream, and in my dreams I’m Christmas-ing with you”

The Killers ft. Dawes, “Christmas in L.A.” (2013)

Premise: Our disillusioned narrator spends a green Christmas in Los Angeles alone.

Most devastating lyric: “My parents sent a Christmas card and tennis shoes/’We understand you staying, and we’re proud of you’/There’s a well-rehearsed disinterest in the atmosphere/I don’t know if that’s what this town gave me, or if it led me here”

John Eddie, “Another Lonely Christmas” (1997)

Premise: Another song about how rough it is to spend Christmas alone.

Most devastating lyric: “Looks like another lonely Christmas/I’m hanging lights on a shabby little tree/The Christmas cards say ‘to you and your loved ones’/But they’re addressed just to me”

Dolly Parton, “Hard Candy Christmas” (1982)

Premise: The women in the brothel in The Best Little Whorehouse in Texas try to figure out their next moves after their business gets shut down and they have to leave the house

Most devastating lyric: “Lord, it’s like a hardy candy Christmas/I’m barely getting through tomorrow”

Tom Waits, “Christmas Card from a Hooker in Minneapolis” (1978)

Premise: A prostitute sends a letter to an ex, revealing she’s happily married and pregnant and has gotten sober, before eventually giving up the ruse and revealing in the last verse that it was all a lie; she’s in jail and needs money.

Most devastating lyric: “Hey Charlie, for chrissakes, if you want to know the truth of it/I don’t have a husband, he don’t play the trombone/I need to borrow money to pay this lawyer, and Charlie, hey/I’ll be eligible for parole come Valentine’s day”

Johnny Cash, “Ringing the Bells for Jim” (1963)

Premise: A little girl sneaks into a church tower at midnight to ring the bells for her dying brother.

Most devastating lyric: “Please Father, pray for him this Christmas/ He’s sick and he’s in so much pain/The doctors all say he’ll be gone any day, so I must ring the bells again”

Dwight Yoakam, “Santa Can’t Stay” (1997)

Premise: Two kids get an unexpected, awkward visit from their alcoholic dad on Christmas.

Most devastating lyric: “They both heard him coming/Saw Mom run down the hall and holler away/’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”

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