Populate a bittersweet Christmas playlist

December 21, 2023 7:54 AM

If the first two songs on the playlist were Tom Waits' Christmas Card from a Hooker in Minneapolis, and So Much Wine by Phoebe Bridgers (or The Handsome Family original), what would the other songs be? Thanks in advance!
posted by muhonnin to Media & Arts (43 answers total)

"Nothin' Left to Do (Let's Make This Christmas Blue)" -- The Both (Aimee Mann and Ted Leo)
posted by We put our faith in Blast Hardcheese at 7:59 AM on December 21, 2023 [1 favorite]

Christmas Song also by Phoebe Bridgers ("it's Christmas, so no one can fix it").

tis the damn season Taylor Swift.

Low's whole Christmas album, especially Little Drummer Boy.
posted by Klipspringer at 8:05 AM on December 21, 2023 [3 favorites]

Fairytale of New York obviously, especially this year
posted by runincircles at 8:19 AM on December 21, 2023 [17 favorites]

White Wine in the Sun, by Tim Minchin?
posted by bunderful at 8:25 AM on December 21, 2023 [3 favorites]

The Chieftains with Elvis Costello St. Stephen's Day Murders
posted by hydropsyche at 8:25 AM on December 21, 2023 [4 favorites]

Hard Candy Christmas
posted by btfreek at 8:28 AM on December 21, 2023 [1 favorite]

Ooh, I specialize in this!
River by Joni Mitchell.
If We Make it Through December -- Merle Haggard original or Phoebe Bridgers (who else) cover.
It's Christmas So We'll Stop by Frightened Rabbit
Low's version of Blue Christmas
Nothing Left To Do (Let's Make This Christmas Blue) by The Both
2000 Miles By The Pretenders
posted by fancypants at 8:30 AM on December 21, 2023 [4 favorites]

Songs from my "Christmas is Melancholy" playlist which might suit:
Jonathan Rice - We Won't Be Lonely This Christmas
Phosphorescent - Christmas Down Under
Hard Candy Christmas, Dolly Parton original but I like the Tracey Thorn cover
Amy Grant - Melancholy Christmas
David Mead - The Smile of Rachael Ray
Jenny Owen Youngs - Maybe Next Year
Randy Stonehill - Christmas at Denny's (note: really fucking sad)
Merle Haggard's If We Make It Through December Phoebe Bridgers has an excellent cover
Maple Glider - Mama It's Christmas
Anna Vaus - Halloween on Christmas Eve

Songs from my "Christmas is Ambiguous" playlist which might suit:
The Heathen and the Holy - When Christmas Comes Around
Jonathan Coulton - Christmas is Interesting
Freedom Fry - Next Christmas
Half Man Half Biscuit - It's Cliched to be Cynical at Christmas

Agree with pretty much any Low song as above, also I'd add some of the Vince Guaraldi Charlie Brown tracks, also any cover of Joni Mitchell River (my favourite is Tami Neilson).
posted by cpatterson at 8:34 AM on December 21, 2023

Rilo Kiley - Xmas Cake
posted by eponym at 8:39 AM on December 21, 2023

Robert Earl Keen - Merry Christmas From The Family
posted by sharks don't eat potatoes at 8:41 AM on December 21, 2023 [5 favorites]

Jethro Tull - Another Christmas Song (I'd throw in the rest of the album too really.)
posted by mersen at 8:46 AM on December 21, 2023 [2 favorites]

I Was Thinking I Could Clean Up for Christmas by Aimee Mann
posted by rikschell at 9:01 AM on December 21, 2023 [2 favorites]

Surprised this hasn't been covered already, even if it doesn't have the same feel as your examples: I'll be Home for Christmas (if Only In My Dreams)
posted by amtho at 9:04 AM on December 21, 2023 [2 favorites]

LCD Soundsystem - Christmas Will Break Your Heart
posted by JoeZydeco at 9:12 AM on December 21, 2023 [1 favorite]

Calexico—Seasonal Shift
posted by corey flood at 9:17 AM on December 21, 2023

Phil Ochs - No Christmas in Kentucky
posted by General Malaise at 9:19 AM on December 21, 2023

Alexander 23 w/ Laufey - Ain't Christmas
posted by JoeZydeco at 9:21 AM on December 21, 2023

Response by poster: Thanks so much for these! A few of them I am familiar with, but am looking forward to exploring all the rest. If I could clarify the feeling I'm looking for beyond "bittersweet", it would be "Life has absolutely kicked me in the ass, but there's still a little spark there. . ." Thanks again to you all, and enjoy the holiday.
posted by muhonnin at 9:38 AM on December 21, 2023

Perhaps:
Winter by Tori Amos

Christmas Bells are Ringing medley from Rent
posted by space snail at 9:40 AM on December 21, 2023

Great selections here. I would also add Just Like Christmas by Low, and anything from Chilly Gonzales’ Christmas album
posted by rd45 at 9:41 AM on December 21, 2023

This Time Last Year by Rina Sawayama.
posted by methroach at 9:53 AM on December 21, 2023

A Christmas Duel - Cyndi Lauper & The Hives
posted by theBigRedKittyPurrs at 10:44 AM on December 21, 2023

Pearl Jam Let Me Sleep (It's Christmas Time)
posted by a humble nudibranch at 11:04 AM on December 21, 2023

I'm on ny phone, and can't YouTubs, but Judy Garland used the original "Until then we'll have to muddle through somehow" words for Have Yourself A Merry Little Christmas, and any Meet Me In St Louis soundtrack will, as well.
posted by DebetEsse at 11:11 AM on December 21, 2023 [2 favorites]

Most of my go-tos have been posted already but I'll add Jenny Owen Youngs - Things We Don't Need Anymore

(also thanks to cpatterson, now I know that Jenny Owen Youngs has two sad Christmas songs)
posted by egregious theorem at 11:15 AM on December 21, 2023

Two from John Prine, Silent Night All Day Long and, even moreso, Christmas in Prison.
posted by kate4914 at 11:23 AM on December 21, 2023 [3 favorites]

Chris Ligon - Christmas Eve
posted by hydrophonic at 11:47 AM on December 21, 2023

Si Kahn's Detroit December is a very exhausted song:

But thirty years of building gears
make Christmas seem untrue to me

More sonorous rendition from John McCutcheon on piano Lyrics and sheet music
posted by Jesse the K at 12:05 PM on December 21, 2023

Thanks for asking this question, some great suggestions above and looking forward to listening to others, but you want Fiona Apple - Please come Home For Christmas for this.
posted by the primroses were over at 12:44 PM on December 21, 2023

Harvey Danger - Sometimes you have to Work on Christmas. I watch the music video almost every Christmas and there's a moment - you'll know it when you see it - that almost always makes me cry.
posted by Ursula Hitler at 1:10 PM on December 21, 2023

Hah, I literally just recommended Tori Amos' album Midwinter Graces for somber vibes in a different askme.
posted by The demon that lives in the air at 2:38 PM on December 21, 2023 [1 favorite]

A Winter’s Tale by David Essex
posted by Samarium at 4:39 PM on December 21, 2023

Listening to Otis Redding at Home During Christmas - Okervil River
Joy - Tracey Thorn
7 O Clock News/Silent Night - Simon and Garfunkel.
posted by rongorongo at 4:50 PM on December 21, 2023

"Christmas in Paradise" by Mary Gauthier (she also has a bummer Thanksgiving song).
posted by goatdog at 5:36 PM on December 21, 2023

I answered in the other music question as well...but here is a link to my sad depressing indie Christmas playlist on Spotify. Hope you find something you like. :)
posted by fourpotatoes at 5:40 PM on December 21, 2023

Sufjan Stevens - Sister Winter
posted by eponym at 5:42 PM on December 21, 2023 [1 favorite]

Much more bitter than sweet (hell actually it's straight up depressing but very cathartic), Red Water (Christmas Mourning) by Type O Negative.

Type O apparently insisted they would never play it live, likely due to the subject matter of the song.
posted by mephisjo at 5:59 PM on December 21, 2023

My perennial answer is this trash 2007 recording of The Mountain Goats covering Merry Christmas from the Family. Perhaps more upbeat than you're hoping for, but the lyrics match the question for sure. This Year, also by The Mountain Goats is exactly the vibe, if not as explicitly Christmas.

John, if you're reading this, it's been 16 years, I beg you to record fresh version!
posted by matrixclown at 9:20 PM on December 21, 2023

Absolutely Paul Kelly - How To Make Gravy
(only a day late for Gravy Day!)
posted by Adifferentbear at 10:28 PM on December 21, 2023

Cappella SF's arrangement of Have Yourself A Merry Little Christmas is melancholy and has the original lyrics referenced above ("until then we'll have to muddle through somehow"). It's far, far superior to the Frank Sinatra version.
posted by kdar at 11:16 PM on December 21, 2023

Portions of Sting's If On A Winter's Night... album may suit, particularly Christmas At Sea. He was just coming out of his Lute Phase when he did this, but that may help.
posted by EmpressCallipygos at 5:03 AM on December 22, 2023

Not Christmas, specifically, but: Counting Crows - A Long December pretty much wrecks me ~

The smell of hospitals in winter
and the feeling that it's all a lot of oysters
but no pearls

posted by Bron at 9:05 AM on December 23, 2023

My Favorite Christmas by Brandy Clark
posted by SuperSquirrel at 4:35 PM on December 24, 2023