Sad Christmas Songs
1. Marvin Gaye, “I Want to Come Home for Christmas”
Marvin Gaye croons from the P.O.V. of a P.O.W. in this heart-wrenching ballad.
2. Bing Crosby, “I’ll Be Home for Christmas”
While most can relate to the sentiment of wanting to go home for the holidays, many don’t realize that this song was written with the narrator as a World War II soldier overseas.
3. Band Aid, “Do They Know It’s Christmas”
The song is about the devastating hunger crisis in Africa, but what also makes it sad is the white savior trope being employed so brazenly, even if for a good cause.
4. Darlene Love, “Christmas (Baby Please Come Home)”
The heartbreak in this Darlene Love Christmas classic is almost hidden by its pure pop sensibility.
5. Charles Brown, “Please Come Home for Christmas”
The crushing heartache and longing is palpable in this soulful staple.
6. Kacey Musgraves, “Christmas Makes Me Cry”
Loneliness and pondering your parents’ mortality makes for a sad Christmas indeed in this melacholy tune from Kacey Musgraves.
7. The Everly Brothers, “Christmas Eve Can Kill You”
A hitchhiker warns of the dangers of freezing to death while looking for a ride on Christmas Eve.
8. Judy Garland, “Have Yourself a Merry Little Christmas”
You can hear the sorrow in Judy Garland’s original 1944 rendition of “Have Yourself a Merry Little Christmas” from Meet Me In St. Louis, and it hits home extra hard in 2020.
9. The Carpenters, “Merry Christmas, Darling”
The Carpenters may have written the soundtrack to Christmas in 2020 in their ode to wishing they could spend Christmas with someone they love but knowing they’ll be physically apart.
10. Nat King Cole, “The Little Boy That Santa Claus Forgot”
You’ll never forget the heartache you felt listening to this Nat King Cole Christmas song.
11. Hermann Lammers, “Faith in Santa”
Don’t be fooled by the pleasant instrumentals in “Faith in Santa.” If you can make it through this song without breaking down sobbing, you’re either a sociopath or the Tin Man.
12. Skip Ewing, “Christmas Carol”
An orphan named Carol makes Santa Claus cry in this tune, but it has a happy ending.
13. Aimee Mann, “I Was Thinking I Could Clean Up for Christmas”
The throes of addiction are too real in this song from Aimee Mann.
14. Dwight Yoakam, “Santa Can’t Stay”
There are few scenarios more disillusioning for Christmas than kids seeing their drunk father dressed as Santa Claus fighting with their mom and her new boyfriend.
15. The Kinks, “Father Christmas”
You know the economy is bad when kids jump Santa for money.
16. Merle Haggard, “If We Make It Through December”
A factory worker loses his job near the holidays in this sorrowful but hopeful song.
17. Bob Carlisle, “Christmas Shoes”
Poverty? Check. Illness? Check. Sad child? Check. Death? Check. “Christmas Shoes” may well be a melodic argument for Medicare for All.
18. Johnny Cash, “Ringing the Bells for Jim”
Johnny Cash pulls hard at the heartstrings in “Ringing the Bells for Jim,” and you may apologize for crying upon listening, too.
19. Dolly Parton, “Hard Candy Christmas”
It’s been a tough year. Dolly Parton gives us a soundtrack for dealing with loss or heartbreak in December.
20. John Prine, “Christmas in Prison”
Few artists can tell a story quite like the late John Prine, who evokes empathy even for those who’ve done terrible things.
21. Prince, “Another Lonely Christmas”
It’s Prince, so of course “Another Lonely Christmas” is a bit sexy…but then it takes big a turn.
22. Dan Fogelberg, “Same Old Lang Syne”
“Same Old Lang Syne” nails the bittersweet (but mostly bitter) feelings that come with running into an ex-lover over the holidays and being reminded of the one who got away.
23. Taylor Swift, “Christmases When You Were Mine”
Taylor Swift does heartbreak like no one else, and she perfectly captures how badly it stings to remember details of your ex over the holidays in this song, which can be compared thematically to her fan-favorite Red tune “All Too Well.”
24. Simon and Garfunkel, “7 O’Clock News/Silent Night”
Dystopian true headlines dominate Simon and Garfunkel’s special rendition of “Silent Night,” none more harrowing than a message from Richard Nixon.
25. Stevie Wonder, “Someday at Christmas”
Stevie Wonder sings a message of hope for peace in “Someday at Christmas.” What makes it sad is that we haven’t come close to achieving it yet.
