Five Very Good Christmas Albums You Should Listen To

I love Christmas music.

I'm not one of those mad people who starts listening to it in early October, but as soon as we're home from our Thanksgiving trip, I synchronize the iPod and load up my collection of Christmas music—416 tracks and counting. And it is my firm belief that if Christmas lasts twelve days, you ought to be able to keep listening to Christmas music until January 6th... though my wife strongly disagrees with that.

I don't know that I could articulate exactly what I like about it... joyousness, hope, redemption, certainly, but also cold, and a sense that we're keeping that cold at bay.

Every year I try to pick up one or two Christmas albums that I don't already own and add them to my rotation. Here are five Christmas albums that I've been enjoying recently:

Bing Crosby, Christmas Classics (2006)

I am a big fan of Bing Crosby's Christmas music; I own 45 different tracks by him. Mostly in two albums, this one and The Best of Bing Crosby: The Christmas Collection, but also some tracks by him on an album my family owned growing up, It's Christmas Time, which had a mix of stuff by him, Frank Sinatra, and Nat King Cole, and is what introduced me to him. His version of "God Rest Ye Merry Gentlemen" is definitive.

A few years ago I suddenly wondered if he had ever done "The Little Drummer Boy" because it seemed like one he would have done really well. Some poking around led me to this album, which collects sixteen of his Christmas songs, only three of which overlapped with ones I already owned. Not just "The Little Drummer Boy," but some others of my favorite Christmas songs like "O Holy Night" and "What Child Is This?" The most fascinating song on the album, though, is a second version of "The Little Drummer Boy," done intercut with an original song "Peace on Earth" sung by David Bowie. This was created for a Bing Crosby tv Christmas special.

Over the Rhine, Blood Oranges in the Snow (2014)

The first two Christmas albums of Cincinnati band Over the Rhine, The Darkest Night of the Year. (1996) and Snow Angel (2006), have been favorites of mine since introduced to me by my father. The first is a mixture of staples and original compositions, the latter is all original (I think). Like a lot of stuff on this list, they have a slightly melancholy tone that really captures the Christmas spirit for me. This year, it occurred to me that it's been seventeen years since Snow Angel, had they put out a third Christmas album? Yes... almost a decade ago!

All the tracks on this one are good of course, but one day my five-year-old was there when "Let It Fall" was playing and he started going, "No, don't let it fall!", which made me really pay attention to the lyrics to that one for the first time: "Whatever we’ve lost, / I think we’re gonna let it go. / Let it fall, / Like snow. / 'Cause rain and leaves / And snow and tears and stars, / And that’s not all my friend, / They all fall with confidence and grace. / So let it fall, let it fall." It's a good reminder that there are things we needs to let go of and let fall, we can't keep it all wound up inside ourselves.

Chris Standring & Kathrin Shorr, Send Me Some Snow (2011)

I first heard a song from this album at Panera Bread, actually, frantically getting some grading done the Saturday after finals week in 2019. I was instantly drawn to its "cool vintage style" and Shazamed it to discover it was the work of Chris Standring (who plays the guitar) and Kathrin Shorr (who does the singing). I think they're married? I believe he's an bestselling performer of... jazz or something.

Anyway, this is an album of entirely original Christmas compositions that instantly feel timeless. They feel like something you could imagine coming out of the Big Crosby era of music... only he never sang any of these songs because they didn't exist yet. Shorr is a breathy, beautiful vocalist and really the person who makes the album soar. I like "Naughty or Nice" a lot, and the title track is excellent, but the one I've elected to share here is "Someone's Gotta Get Something for Christmas." Could that someone be me?

Sting, If on a Winter's Night... (2009)

When we regularly went home to Cincinnati every Christmas, my friend David would have us over for dinner. One year, this was playing and he revealed to me that it was by Sting of all people. (Admittedly, when it comes to Sting, I mostly think of him as the depraved Harkonnen nephew from Dune, but I'm reasonably certain most people don't think of him as the kind of guy who puts out Christmas albums.) There are few Christmas standards here; rather, it's an album of traditional English folk songs with lutes, guitars, trumpets, and so on. More than any other item on this list, it captures that idea I mentioned in my opening: it's a cold album, but what it celebrates is how we push back against it. 

There are a lot of good tracks, but my favorite is "Soul Cake," about people going "souling" (door to door begging for a cookie-like food called a soul cake): "If you haven't got a penny, / A ha'penny will do; / If you haven't got a ha'penny, / It's God bless you." Sting's version mixes in some of the melody of my favorite Christmas carol, "God Rest Ye Merry Gentlemen," too. (Wikipedia tells me this owes a debt to a version by Peter, Paul, and Mary.)

Seth MacFarlane & Liz Gillies, We Wish You the Merriest (2023)

My choices can't all be original hipster nonsense, can they? When I was in grad school, a colleague—even more into Christmas music than me—was blaring some Bing Crosby-, Frank Sinatra-esque Christmas music in the program office. Who was singing, I asked, and I was astonished to learn that it was Seth "Family Guy" MacFarlane. I went home and picked up his album Holiday for Swing! (2014). He's no Bing Crosby, of course, but it's a pretty strong pastiche.

This year, he has a new one out, a set of duets with the former Disney Channel star Liz Gillies. The title track is strong, but my favorite is probably "Christmas Time All Over the World," where the two sing Christmas greetings from a variety of different languages. (Apparently this is originally a Sammy Davis, Jr. song, but as far as I know, this is the first I've heard it.)

Hopefully you've found something new here! This was fun to write up; maybe I'll do it again next year but with (somewhat) less pretentious picks.

Mele Kalikimaka!