I start rehearsing kids on holiday music in October. Truth be told, none of it really gets me in the holiday spirit until I bust out the stuff that I really like. This is at least a sampling of such. Some of it is what critics might call good. Some of it is ostensibly not. But I enjoy it all. There's a lot of slowed down, sparsely arranged indie rock versions of hymns, some of which use unusual instrumentation, on the list, too, so if that's what you're into, you might like this.

(Also, the holiday season is the time during which I most enjoy streaming services. I have paid Apple way too much money for holiday music over the past 7 years.) 

1. The Pogues with Kirsty MacColl - "Fairytale of New York"  A classic, and one I can't play around my students ever. I start playing this song a lot once break starts, which by association makes me love it even more.
2. The Smashing Pumpkins - "Christmastime"  This song is proof that Billy Corgan, a songwriter prone to doing only and exactly what he wants, is really capable of anything. It's also very confusing to hear the Pumpkins in CVS this time of year, and that makes me smile.
3. Squirrel Nut Zippers - "Gift of the Magi"  Honestly one of my favorite bands in high school, I didn't find their Christmas album until about 15 years after it was released. I was glad that I did, and this song give you plenty of Katharine Whalen singing.
4. Andrew Bird - "So Much Wine, Merry Christmas"  I love Andrew Bird, although I haven't kept up with his latest output. This song pretty well lyrically captures some of the less joyful feelings associated with the season.
5. Low - "Just Like Christmas"  From one of the best Christmas albums (EPs, whatever?) ever released, this mellow tune isn't even harmed by the presence of jingle bells. For me, it doesn't feel like Christmas until I hear this song. 
6. The Kinks - "Father Christmas"  A time capsule of class warfare in England in the late 70s. Also, The Kinks are my favorite British Invasion band.
7. She & Him - "The Christmas Waltz"  This is a nice version of this tune, but it's not even my favorite rendition by a sitcom star. That would be Jane Krakowski singing it on 30 Rock, s4ep8.
8. Sufjan Stevens - "Away in a Manger"  I don't know about you, but to me it really seems that Sufjan could make an entire career out of only Christmas tunes.
9. Luther Vandross - "Have Yourself a Merry Little Christmas"  It's not even my favorite arrangement of this song, but Luther's voice transcends all things. 
10. Darlene Love - "Christmas (Baby Please Come Home)"  If we can get Mariah back on the charts, can we get some love for Darlene, too? 
11. The Ronettes - "Frosty the Snowman"  I know we're dipping into a little bit of a Spector Christmas, but as much as we enjoy the Wall of Sound, despite the fact that Phil Spector was a horrorshow of a person, Ronnie & Darlene & the many other women who worked with him would still be pretty amazing even without said wall.
12. The Carpenters - "Merry Christmas Darling"  I have a deep & abiding love for The Carpenters, unironic & pure. This song is perfect for Karen's voice, too.
13. Bruce Springsteen & the E Street Band - "Merry Christmas, Baby"  It took me a long time to come around to Springsteen, but it was worth the wait. The other day I saw a bunch of photos of him kissing his dear friend & bandmate Clarence Clemons onstage, and now that's all I think of when I hear this song. And that's pretty cool.
14. Run DMC - "Christmas in Hollis"  An early example of holidays going hip-hop. I love playing this in my car with the windows down as much as possible. 
15. Tim Reynolds & Dave Matthews - "Christmas Song"  An unconventional take on the life of Christ, this quiet song with lots of changing meter is also a favorite of mine.
16. Tom Petty & the Heartbreakers - "Christmas All Over Again"  I miss Tom Petty a lot. Again, this song is a little bit of proof that he was capable of almost anything.
17. Nancy & Ann Wilson - "Blue Christmas"  Dude, does Ann sing the heck out of this song or what?
18. The Civil Wars - "I Heart the Bells on Christmas Day"  A fun little arrangement of this song.
19. Eleanor Friedberger - "Santa Bring My Baby Back (To Me)"  She always sounds a little, shaky? And her song structures, especially going back into the Fiery Furnaces days are a bit odd, but I love Eleanor so so much.
20. The Head & the Heart - "What Are You Doing New Year's Eve?"  This is a nicely uncertain & anxious rendition of this tune, appropriate for describing how awkward asking that kind of question can be.
21. Belle & Sebastian - "O Come, O Come Emmanuel"  Prototypical indie rock weirdness in covering (and playing hard & fast with the meter of) a hymn, but it works here I guess.
22. Bobby Darin - "O Come All Ye Faithful"  This is my mother's favorite hymn, and it makes sense to hear it in a faithful, well sung manner. 
23. Wham! - "Last Christmas"  You got Wham'd! I'm not sorry.
24. The Magnetic Fields - "Everything Is One Big Christmas Tree"  One of my favorite uses of temple blocks & a German choir in a pop song. 
25. On Dead Waves - "In the Bleak Midwinter"  This is one of my favorite songs, going back to my high school days of music ministry and playing 2-4 masses every Christmas. I remember walking to and from school with this song unmoveable from my head. I appreciate the totally fuzzed out electronic version of it and find it oddly fitting.
26. The Pretenders - "2000 Miles"  Chrissie Hynde is one of my absolute favorite singers and songwriters. And this song is just another tally in the Reasons I Love Chrissie column.
27. The Waitresses - "Christmas Wrapping"  I can't properly explain it, but this song features one of my favorite brass licks in all of popdom. The contrast between Patty Donahue's disaffected singing and the bopping brass makes it that much better.
28. Sharon Jones & the Dap-Kings - "Silver Bells"  We lost Sharon far too soon, but she left us with more than we probably deserved before she was gone. This song is a lovely showcase for her tremendous voice and funks up a sometimes tiresome classic.
29. David Bowie & Bing Crosby - "Little Drummer Boy"  Probably my favorite Christmas song ever. Even before Bowie's passing, my husband had memorized the introductory banter about Sir Percival and his piano. Bowie leaves us wondering, as he sings plaintively, "Peace on Earth / can it be?" Somehow that last line gives me hope for the future. Pretty thing, indeed.
30. Tom Waits - "Christmas Card from a Hooker in Minneapolis"  I've listened to this song too many times today. I'm particularly fond of the piano opening of the original, but I'm honestly a little partial to the Neko Case cover. 

I find refuge in many of these songs, especially when the demands of the holiday season start to wear on me. I hope that you also have music that marks this time of year and also brings you peace.