The Best Christmas Album of All Time! (Volume 3)

It’s been five years since I first posted a playlist that I humbly referred to as the Best Christmas Album of All Time. The following year I, with nary a whiff of irony, posted a new playlist that also purports to be the Best Christmas Album of All Time, albeit a second volume. Doing a third entry seemed positively indulgent, so I didn’t…for a while. But Christmas music—for some reason that I’m sure years of therapy would help me uncover—is a thing that makes me happy, and if ever there was a year in need of a little happiness this is it.

So the Best Christmas Album of All Time has grown one volume larger and, as a result, one album better. Feel free to listen along on whatever Google has foisted off on us as this year’s music platform as you read (or just listen and don’t read)(or hey, don’t read OR listen, I’m not your supervisor).

Enjoy! (or not, again, not your supervisor)

  1. The Christmas Song by Bob Dylan — I said it before, and I’ll say it again: any Christmas album that doesn’t include this song isn’t worthy of the name. I really appreciate Dylan’s spare version of the song, plus, you could still understand him at this point.
  2. Winterglow by Grant-Lee Phillips — You might recognize that name (and I think this song as well) if you’re a Gilmore Girls aficionado. Most folksy holiday songs skew very maudlin. This almost entirely avoids that. It’s gorgeous.
  3. It Came Upon a Midnight Clear by Russ Taff — This is one of two Christmas tunes that I absolutely hate that made it on here with a version that I not only don’t hate, but actively seek out each year. That voice and the backing guitar are pretty much perfect.
  4. Christmas at the Zoo by The Flaming Lips — There’s “non-Traditional holiday fare”, then there’s “The Flaming Lips sing about letting animals out at the zoo for Christmas”. If you love the Lips, you already know about this. If you don’t love them, hopefully this fixes that.
  5. Santa Claus is Comin’ to Town by Lou Rawls — There are two versions of this song that I consider to be THE canonical version. I was torn between this one and the Jackson 5 version. I think I made the right choice in picking this one.
  6. Deck the Halls by Red Hot Chili Peppers — It’s just a short, fun interlude, but it makes me smile every year. Apparently I can’t share a link directly to it. Weird.
  7. Like It’s Christmas by The Jonas Brothers — This is a fun, poppy, catchy tune that has never really gotten the love that it deserves. Honestly, their whole Christmas album is worth a listen this time of year.
  8. Oh Little Town of Bethlehem by Bright Eyes — A few years back I found out that Bright Eyes had a Christmas album and it has been in my rotation ever since. While I love the whole thing, it wasn’t hard for me to pick which song from it should be listed here. (This one. Keep up.)
  9. Someday at Christmas by Pearl Jam — Pearl Jam manages with this one to do what they did with Last Kiss: create a song that feels simultaneously like a throwback and very modern.
  10. Santa Claus and His Old Lady by Cheech & Chong — “You don’t know who Santa Claus is, man”…”naw man, I’m not from here, I’m from Pittsburgh.” This is 50 years old and it still doesn’t fail to make me laugh. It was the B-side to Dave and I used to listen to it nearly continuously.
  11. Wonderful Christmastime by The Shins — You know that fairly insipid song about Christmas that the Beatles guy did? This is the good version that doesn’t make me want to drive something into both ears until the sounds go away.
  12. Jingle Bells by Gwen Stefani — The album this comes from is hit-or-miss, but I love the upbeat energy (and obviously Gwen’s vocals) on this one.
  13. Nothing for Christmas by New Found Glory — What is it about punk bands doing stripped down, earnest songs that makes me love them so? I don’t know, but, this is all kinds of that.
  14. O Come All Ye Faithful by Weezer — I don’t care if you think that Weezer hasn’t made a good album since the green album (you’re wrong, but, I don’t care), or if you think they just keep improving (because you understand good music), their Christmas EP is immune from such squabbles. It’s perfect.
  15. Christmas Time Again by Ashanti — Here’s the cycle every year when a song off Ashanti’s Christmas album comes up: “Did we ever get another Ashanti album? No? Damnit! *sigh* Well, let’s fire up Chapter II again.”
  16. Carol of the Bells by Lindsey Stirling — This is the other Christmas song that I abhor. It turns out, there’s one version of it that I don’t absolutely despise, and this is it. This is lovely and interesting and should be the only version ever played ever again.
  17. Auld Lang Syne by Colbie Caillat — In elementary school I was a part of our school’s swing choir and for our Christmas Concert, we did a really frustratingly complicated version of this song. This is a really good version of the song. The story had nothing to do with it. I was sharing an anecdote…it’s a blog, what did you expect? Just listen to the bloody song!

I hope the end of your 2020 is a break from the endless hellscape of doom and stupidity that has characterized the first 80% of the year, and may your 2021 be a happy, healthy, and hopeful one.