Sobbin’ Around the Christmas Tree: The 100 Greatest Sad Holiday Songs

Most performers sing the version with the happy, rewritten lyrics that Frank Sinatra asked songwriter Hugh Martin to come up with in the ‘50s to “jolly it up a little.” But the superior version is the more ominous and morose “have to muddle through somehow” original, as sung in the ‘40s by Judy Garland. The tune originated in “Meet Me in St. Louis,” in which Garland sings it to cheer up her sister, Margaret O’Brien, as they prepare to move away from the home they hold dear after the holidays. The consoling goes so well that the little girl breaks down in sobs and proceeds to immediately murder a snowman.

Mitchell’s Christmas-set ballad was just another “Blue” album track for decades, then suddenly became the number that everybody covers on their holiday albums as their token downbeat number. Notably, while most other sad seasonal songs are about getting dumped for the holidays, Mitchell is guilt-racked because she made a dude cry. Joni is one sad Christmas boss.

Haggard is trying to keep the family’s spirits up, probably in vain, in this classic slab of Christmas neo-realism. The kids’ gifts may not be so great this year, because Daddy “got laid off down at the factory” — but he suggests it’ll be better next year if they move to California. Or maybe not? Substitute “got laid off by a major media company” and you’ve got an anthem for Hollywood in 2024.

The weather outside is frightful, and the belief in humanity runs just as cold, in the brothers’ soaring but remarkably despondent ballad. A forlorn hitchhiker wards off frostbite on a snowy roadside as cars speed by … even as he admits that if he had a family waiting, he’d pass himself up too.

When the Waitresses go out to the A&P on Christmas Eve in “Christmas Wrapping,” a meet-cute ensues. But when Fogelberg goes out for last-minute groceries, he runs into an ex, and they crack open a six-pack in his car as she details her loveless marriage. Then the snow turns to rain, because of course it does.

Accompanied by the E Street Band on this unofficial sequel to “Christmas (Baby Please Come Home),” she sings out for all the souls who don’t have a baby to even long for. But it’s always OK not to have anyone to cuddle up with at Christmas when you’ve got Darlene Love’s voice to keep you warm.

Aimee Mann has a few terrific melancholy Christmas tunes. The catchiest might be this collaboration with Ted Leo under the umbrella of their superduo the Both. The duet partners each resign themselves to a lonesome night of radio carols and doing without an ex for Xmas — but, in a coda with the slightest twinge of hope, they add, “The door is open.”

Not the caroling standard you’re probably thinking of — happily, this is a pretty unhappy, entirely different tune than that. The “Santa” in this fairly obscure but brilliantly nuanced ’90s ballad is the narrator’s ex-husband, who wants to come over for Christmas and see the kids, which brings up all the divorce feels. The usually sassy Reba probably never sounded more ambivalent, before or since, but knows seeing him come through the door with an armload of presents will “turn my whole world upside down.”

The sisters’ 2006 holiday collection was called “Acoustic Hearts of Winter,” but there was nothing acoustic about this rocking tune that unexpectedly closed their otherwise cheerful album on a note of furious depression. “This is the time to smile, I can’t fake it,” they complain, with no reason given for their melancholia (but is any really required?). If Taylor Swift had been going through an indie-rock phase when she recorded her Christmas record, it would’ve sounded like this, a classic still waiting to be discovered.

When James Murphy released this one-off track in 2015, he described it as “another one of those songs which had about 75 lines of lyrics, though we’ve knocked down to eight to keep the suicide rate in check.” He’s exaggerating a little — there are more than a couple dozen downer lines to get through here, highlights from which include “Christmas will crush your soul… Christmas will shove you down… Christmas will drown your love.” And: “Christmas can wreck your head / Like some listless awkward sex / So you refuse to leave your bed / And get depressed when no one checks / Yeah, Christmas will break your heart / Like the armies of the unrelenting dark / Once the peace talks fall apart.” Has he made himself clear? Yet the song is not completely life-unaffirming: He also sings, “Still, I’m coming home to you,” even though he sounds unsure whether he’ll be welcomed or shunned when he comes around.

Seasonal affective disorder had an early advocate in Stafford, whose classy, brassy reading of this 1953 Tin Pan Alley classic by Sammy Cahn and David Jack Holt really gets to the heart of what a lot of unpaired souls feel during the holidays:

When somebody wants you
Somebody needs you
Christmas is a joy of joy
But friends when you’re lonely
You’ll find that it’s only
A thing for little girls and little boys
May all your days be merry
Your seasons full of cheer
But ’til it’s January
I’ll just go and disappear

It was also famously done by Dean Martin, and maybe infamously done by Bob Dylan, but when we want to hear some of these ’50s-based holiday songs, it’s all about bringing Jo to the world.

Bundle up for severely wistful conditions. There are so many varieties of Christmastime loneliness. But in this haunting ’90s track, Griffith really got at a unique brand of it — the kind you feel when you’re far away from your hometown, remembering a warm time you had there during a holiday season long ago with someone who’s been gone from your life for many, many years. Being in the midst of merry strangers, there’s no one around to confide these feelings of bittersweet nostalgia and longing to. Except, of course, for the inner songwriter who’s keeping a record of all of it in your head.

Sometimes, you’re just not ready to miss someone yet.

Well, doesn’t it everybody?

Plenty of ballads on this list, but sometimes you need a harder edge to put to your Christmas sorrow. The guitars get kind of cranky here as Dave Lowery goes on a nostalgic reverie recalling popping pills and getting drunk with an ex named Emily, “from a good family / They fucked up your head and sent you to me.” Some of the details of this long-gone relationship are rather specific, but the core couple of lines are something almost everybody can relate to in cataloguing Christmases past: “I still think about you.
Do you think about me?”

A wonderful song for those who are still in a relationship during the holidays… but aren’t sure if they’re really in that relationship. Afraid that you’re getting ghosted for Christmas? This is the catchy anthem of crazy-making uncertainty that was written just for you.

Hey, we all get aspirational this time of year.

In the YouTube caption for this Sobule song, she writes, “I recorded this years ago on an 8-track cassette machine with an old drum machine from the early ’70s. I put it on a little holiday CD that I sold at my shows. So, I was surprised when I saw that I made Entertainment Weekly’s ‘100 Greatest Down-and-Out-on-Christmas Songs.’ I was number 10, right above William S. Burroughs’ ”A Junkie’s Christmas.’ Bum out and enjoy the song. It’s actually quite pretty.” Dear reader, I confess, I was the one who bought that rare EP at a show and put her rather obscure little tune on that Entertainment Weekly list back in the 2000s. I’m glad it prompted her to put this track online on YouTube, though it’s apparently available nowhere else. It states the title sentiment so bluntly — and sweetly! — it deserves to become a perennial.

This is probably the most ebullient-sounding track on this list, but underneath the rocking exterior is a woeful tale of a divorced dad who crashes his family’s Christmas celebration, with drunkenness and disaster to spare. Listen to the more sober flip side of this scenario — Reba’s aforementioned “Santa Claus Is Coming Back to Town” — and then spin this to see just how disastrously the whole situation could turn out.

You weren’t thinking we’d forget all the classics, do you? If Hozier’s not going to, we most definitely are not. There’s something so invigorating about “Fairytale of New York” that it’s nearly impossible to really think of it as sad, which, of course, it is, truly and deeply. If Sid and Nancy had gotten it together to write and perform a Christmas duet… well, it would not have been one-one-hundredth this brilliant, but it might have had the same sinking-ships-going-down-together vibe. Hide your tender ears at the appropriate moment — this is the original version with the offensive “maggot” lyrics. So much about this suite-like masterpiece is hilariously specific, yet the couplet that gets to us sometimes is the one that speaks most to thinking about thwarted dreams at the end of the year: “I could have been someone…” “Well, so could anyone!”

Love has to get two spots on this list, of course. If she’s not the Queen of Christmas — and she deserves the title as much as anyone, copyright-seeker or otherwise — she is very much the queen of lonesome holiday wailing. And there is no better modern Christmas song, period. Does it feel despondent? In lyric alone, close enough to make the sad list… even if the only appropriate response to ever hearing this track is a spontaneous eruption of joy.

We don’t want to harsh anyone’s Christmas mellow — or marshmallow — by annotating all 100 songs at once. But here are 80 more great ones for you to discover on your own time:

Marvin Gaye, “I Want to Come Home for Christmas”
Dwight Yoakam, “Santa Can’t Stay”
Prince, ”Another Lonely Christmas”
John Prine, ”Christmas in Prison”
The Moonglows, ”Just a Lonely Christmas”
Frank Sinatra, ”Whatever Happened to Christmas”
Phoebe Bridgers, “Christmas Song”
Wes Lachot, “Christmas Is the Only Time I Think of You”
Mike Viola, “Give Me Another Chance for Christmas”
John Denver, ”Please Daddy, Don’t Get Drunk This Christmas”
Material Issue, ”Merry Christmas Will Do”
Sufjan Stevens, “Did I Make You Cry on Christmas Day? (Well You Deserved It)”
Low, ”If You Were Born Today (Song for Baby Jesus)”
Staple Singers, ”Who Took the Merry Out of Christmas?”
Nat King Cole, ”The Little Boy That Santa Claus Forgot”
Ralph Stanley, ”Please Daddy, Don’t Make Us Cry on Christmas Day”
Over the Rhine, ”All I Get for Christmas Is Blue”
The Kinks, “Father Christmas”
Roberta Flack, ”25th of Last December”
Willie Nelson, ”Pretty Paper”
Buck Owens, ”Blue Christmas Lights”
Woody Guthrie, ”1913 Massacre”
Vince Gill, ”It Won’t Be the Same This Year”
Aimee Mann, ”Calling on Mary”
Loretta Lynn, ”Gift of the Blues”
Jim Croce, ”It Doesn’t Have to Be That Way”
Jimmy Witherspoon, ”Oh, How I Hate to See Christmas Come Around”
Chris Isaak, ”Christmas on TV”
Commander Cody, ”Daddy’s Drinking Up Our Christmas”
Emerson Lake and Palmer, ”I Believe in Father Christmas”
Sarah McLachlan, ”Wintersong”
Del McCoury, ”Call Collect on Christmas”
Ernest Tubb, ”I’ll Be Walking the Floor This Christmas”
The Emotions, ”What Do the Lonely Do at Christmas”
The Mighty Mighty Bosstones, ”Xmas Time (It Sure Don’t Feel Like It)”
The Long Blondes, ”Christmas is Canceled”
Pearl Jam, ”Let Me Sleep (It’s Christmas)”
George Jones, ”Lonely Christmas Call”
Loretta Lynn, ”Christmas Without Daddy”
Lyle Lovett, ”Christmas Morning”
Bobby Bare, ”Christmas at the Jersey Lily Lounge”
Ernest Tubb, ”I’m Trimming My Christmas Tree With Teardrops”
Jo Stafford, ”Toyland”
Kitty Wells, ”Christmas Ain’t Like Christmas Anymore”
Burt Bacharach, “The Bell That Couldn’t Jingle”
Aimee Mann & Michael Penn, ”Christmastime”
Buck Owens, ”It’s Christmas Time for Everyone but Me”
Irma Thomas, ”Christmas Without the Creole”
Wes Lachot, ”Christmas Is the Only Time (I Think of You)”
Johnny Paycheck, ”Mommy for Awhile on Christmas Day”
Band Aid, ”Do They Know It’s Christmas”
Toby Keith, ”Santa, I’m Right Here”
Randy Stonehill, ”Christmas at Denny’s”
Jerry Lee Lewis, ”I Can’t Have a Merry Christmas, Mary, Without You”
Sun 60, ”Mary Xmess”
Billy Bob Thornton, ”My Dreams of Christmas”
Saffire and the Uppity Blues Women, ”One Parent Christmas”
Tom Waits, ”Christmas Card From a Hooker in Minneapolis”
They Might Be Giants, ”Santa’s Beard”
Taylor Swift, ”Christmases When You Were Mine”
Marvin Gaye, ”I Want to Come Home for Christmas”
Mary Gauthier, ”Christmas in Paradise”
Mary J. Blige, ”No Happy Holidays”
Trick Daddy, ”Ain’t No Santa”
Randy Newman, ”Christmas in Capetown”
The Be Good Tanyas, ”Rudy”
Everything but the Girl, ”25 December”
Julia Fordham, ”December 24”
The Orioles, ”(It’s Gonna Be a) Lonely Christmas”
Elvis Costello, ”St. Stephen’s Day Murders”
Jackson Browne, ”The Rebel Jesus”
The Whites, ”Christmas Without Mama”
Franki Valli and the Four Seasons, ”Christmas Tears”
Loretta Lynn, ”I Won’t Decorate Your Christmas Tree”
Bob Wills, ”Empty Chair at the Christmas Table”
Billy Idol, ”Yellin’ at the Xmas Tree”
Kelly Willis & Bruce Robison, ”Shut In at Christmas”
Timbuk 3, ”All I Want For Christmas (Is World Peace)”
Ernest Tubb, ”Christmas Is Just Another Lonely Day”
William S. Burroughs, ”A Junky’s Christmas”
Johnny and Jon, ”Christmas in Vietnam”
Simon and Garfunkel, ”7 O’Clock News/Silent Night”
John Prine, ”All the Best”