You Better Not Cry: The Sad Songs Of Christmas : World Cafe Happy holidays? More like Sappy Bawlidays. If Christmas sends you down the chimney of despair, these 10 of the season's saddest ditties will meet you there.
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You Better Not Cry: The Sad Songs Of Christmas

If the holidays make you feel like this, these 10 songs can sympathize. H. Armstrong Roberts/ClassicStock/Getty Images hide caption

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H. Armstrong Roberts/ClassicStock/Getty Images

If the holidays make you feel like this, these 10 songs can sympathize.

H. Armstrong Roberts/ClassicStock/Getty Images

Happy holidays? More like Sappy Bawlidays. If Christmas time sends you barreling down the chimney of despair, here are 10 of the season's saddest ditties to meet you at the fireplace and tearfully eat all of Santa's cookies with you.

Hear The Songs

  • Elmo & Patsy, "Grandma Got Run Over By A Reindeer"

    File this next to fruitcake under "things I will never understand about the holidays." How do Elmo & Patsy have the audacity to give such a cheery holiday treatment to such a heartbreaking tale of senility? In short, the worst grandchild of all time tells the tale about that time Grandma forgot her medication, got loaded and wandered out into the snow. Nobody looked for her until the next morning. When they found her trampled by reindeer, they took her death as proof that Santa exists. For the love of grandmas everywhere, do not clap along to this deplorable tragedy about a bad family.

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  • Nat King Cole, "The Little Boy That Santa Claus Forgot"

    As Nat King Cole croons about a boy who asks Santa in earnest for soldiers and a drum, his warm and welcoming voice makes you forget the title of the song he is singing. For more than a moment, your heart swells as you feel a happy ending coming. Santa will remember this sweet "laddie... who doesn't have a daddy." Of course he will — it's the holidays, right? Spoiler alert: He does not. Santa straight-up forgot.

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  • Dolly Parton, "Hard Candy Christmas"

    Nothing says family-friendly fun like a song stripped from the soundtrack of a movie-musical called The Best Little Whorehouse in Texas. The song was written by Carol Hall, and in the film it's sung by Dolly Parton and her fellow ladies of the (silent) night after their brothel shuts down. If you happen to hear this song at a moment when you, like Dolly's character, are "barely getting through," consider asking Santa for some waterproof mascara.

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  • Tom Waits, "Christmas Card From A Hooker In Minneapolis"

    If you thought the Christmas card from your third cousins in Minneapolis was depressing, what with their matching Santa sweater vests and Von Trapp Family-style arrangement of children in order of descending height, here's some healthy perspective. Tom Waits sings (reads? groans?) the Christmas card that an unnamed hooker from Minneapolis sent to Charley. She's pregnant, she's got no money and no man, she's a recovering addict and she's in prison. But, as always on Christmas, there's a silver lining. She'll "be eligible for parole come Valentine's Day."

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  • NewSong, "The Christmas Shoes"

    You can bet any song that sparks its own made-for-TV-movie starring Rob Lowe will have at least a couple spoonfuls of sap. But when it comes to holiday heartbreak, NewSong has really outdone itself with a song about a poor boy trying to buy his mom shoes because he wants her "to look beautiful if Mama meets Jesus tonight." And by "meets Jesus tonight," he does not mean "meets Jesus tonight for cookies." You know where this is going. Now if you'll excuse me, I have some shoes in my eye.

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  • Johnny Cash, "Ringing the Bells For Jim"

    Believe it or not, everyone's favorite Folsom Prison ray of sunshine went depressing for the holidays. I'll give you one guess as to why he's ringing the bells for his brother Jim. Here's a clue: Cash rhymes it with "cryin.' "

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  • Simon & Garfunkel, "7 O'Clock News/Silent Night"

    This is pretty much what it would sound like if Simon & Garfunkel were jamming "Silent Night" post-Christmas feast in your living room with a guitar, if your intense uncle insisted on keeping the TV blaring CNN in the background. In this particular version, released in 1966, Lenny Bruce overdoses, Nixon predicts five more years of the Vietnam War and Chicago police threaten to call in the National Guard over an open housing march planned by Dr. Martin Luther King. 50 years later, nobody wants to hear the 2016 contemporary-headlines remix.

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  • Marvin Gaye, "I Want To Come Home For Christmas"

    I will admit to a somewhat salty tone in the rest of this post about sad Christmas songs — but the only salt I will sprinkle on this one by Marvin Gaye is the salt of my salty, salty tears. This song about a prisoner of war lying in a cell and thinking about his family at home is legitimately the saddest holiday song ever written.

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  • Dwight Yoakam, "Santa Can't Stay"

    At first listen, this is a happy rockabilly honky-tonk holiday jam about Santa — unless you pay attention to the lyrics, in which case you'll learn that Santa can't stay because Santa is Dad. And Dad is drunk. And little Bobby chases Dad's car down the driveway after Mom kicks him out of the house. And Dwight Yoakam ruined Christmas.

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  • The Everly Brothers, "Christmas Eve Can Kill You"

    In this jaunty classic, a freezing man with nowhere to go cries out into the night as he walks alone, "Christmas Eve can kill you when you're trying to hitch a ride anywhere." He imagines that the cars ignoring him as they zoom past are all fathers going home to play Santa for their children in warm houses with lots of presents. And just in case you were wondering, as you cry into your cocoa, "What is the saddest part of this song?," the Everly Brothers tell you right there in the lyrics: "The saddest part of all is knowing if I switched with him, I'd leave him stumbling ragged by the road. I'd ride that highway to arms of my sweet family and forget about the stranger in the cold." Glad we cleared that one up and learned our holiday lesson, Everly family.

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  • If you've got any tissues left, here's an extended playlist for ultimate holiday wallowing: