By pmichaels

December 15, 2014 2:52 PM PT

Holiday Playlist: Philip Michaels

Note: This story has not been updated for several years.

[Philip Michaels worked at Macworld for more than a decade, and now is available for your freelance writing and editing needs.]

Really, I blame a lot of this on iTunes.

It’s hard to remember this, more than a decade after Steve Jobs cajoled and arm-twisted the music industry into selling electronic versions of songs for 99 cents, but in the Before Times, when one wanted music, one bought The Whole Damn Album. (If one did not want to feel like donning a ski mask and a switchblade as one downloaded songs illegally, of course.) So when you strolled the aisles of a store during the holiday season and came face to face with an entire array of Christmas CDs, you had to ask yourself this question: Do I really want to buy this entire Dean Martin CD of Christmas songs when only one, maybe two of the tracks will be any damn good? And thus was snuffed out another impulse buy.

iTunes knows no such mercy. You want to hear Dean-o crooning out “Silver Bells?” Be our guest, friend… and why don’t you download “It’s a Marshmallow World at Christmas” while you’re at it? You want John Denver twanging out Christmas songs? (With or without Muppets?) Kenny Chesney? Kenny G? Kenny from South Park? They are all there, adding their particular takes on holiday standards, and they can be yours with just the click of a button.

All of this is a long-winded way of saying that the iTunes Store coupled with the impulse control of a magpie has caused my library of holiday tunes to swell like an overstuffed stocking in recent years. And that’s not necessarily because the songs I bought and paid for are all outstanding — far from it. Many are quite terrible, as I expounded on at length in an episode of a podcast that inexplicably keeps having me on and in an article for a website that stopped employing me. I guess when it’s 99 cents to $1.29, the prospect of downloading John Travolta and Olivia Newton-John dueting on a creepy-even-for-this-song version of “Baby, It’s Cold Outside” for a good chuckle doesn’t seem so off-putting. Until you listen to the song, of course, and realize that you own it forever.

But we’re not here today to talk about regret. Jason asked me if I could write an article about good Christmas songs — songs that I actually like and would play around others without reservation during the holidays. This is probably because Jason is a relentlessly positive person, which is an absolutely off-putting trait if I’m being honest, though I suspect it’s also because he bet somebody that I couldn’t come up with a couple hundred words worth of niceness.

Well, I’ll take that bet.

So here are 15 songs for the Festive Season that I actually honest-to-goodness enjoy listening to. Which is not to say that you will necessarily enjoy them. Nothing is more subjective than musical taste, as I’m reminded every time I glance at the pop charts and see a bunch of songs that all might as well be titled “Not Recorded With You In Mind.” Like the stuff you like, I always say, and so the songs listed below tend to be in the style that I prefer, which is to say things veer heavily toward blues and jazz and themes that are a few blocks east of reverent.

When possible I’ve tried to avoid recommending obvious stuff — or at least opting for more obscure versions of popular favorites. You do not need me to tell you the Charlie Brown Christmas soundtrack from The Vince Guaraldi Trio needs to be on your holiday playlist, and if you do, this article is about to end badly for you.

Finally, eagle-eyed readers will detect a certain… ambivalence toward the holiday in my musical choices. Before you demand that I appear before the Fox News War on Christmas Tribunal to stand trial for unorthodoxy, let me just assure you that I like Christmas just fine even if some of the more commercial aspects of the holiday bum me out. If these songs reflect that attitude, well, as a Victorian Era businessman was known to remark around this time of year, keep Christmas in your own way and let me keep it in mine.

Here’s what you should add to your holiday season playlist, post-haste.

Rudolph the Red Nosed Reindeer by The Cadillacs: Let’s start things off with a popular standard that’s improved dramatically just by adding several dashes of bop. The Cadillacs were a doo-wop group, perhaps best known for their hit record Speedo. They bring that same energy to Gene Autry’s tepid ballad about a reindeer whose bright and shiny nose prevented him from participating in reindeer games and deliver a song that your kids will still like, and that you can sing along to unabashedly without feeling like you’ve been transported back to some horrible elementary school Christmas pageant.

Do They Know It’s (Snoopy’s) Christmas? by The Kustard Kings: No matter how noble its intentions, “Do They Know It’s Christmas” is a tepid blend of patronizing lyrics and forced sentiment. And that goes for all its incarnations, from the original version to the latest mutation. At least “Do They Know It’s Christmas” wants to raise money, though; the only thing Snoopy’s Christmas wants to raise is fat royalty checks for one-trick-ponies The Royal Guardsmen and the massive Snoopy industrial complex. But smash these two terrible songs together as the instrumental band The Kustard Kings have done, and you’ve got something peppy and seasonal and fun — proof that on occasion, two wrongs actually do make a right.

The Little Drummer Boy by Los Straitjackets and Mele Kalikimaka by Chris Isaak: This will be my 42nd Christmas on this planet, and it will be the 41st in which snow is but a rumor¹. As a consequence, I have no truck for songs about winter wonderlands. No, I appreciate songs that recognize that some of us celebrate Christmas in more temperate zones, which is why I have Chris Isaak singing about Hawaiian holidays and Los Straightjackets playing a surf guitar version of a holiday standard on constant rotation this time of year. That Los Straightjackets perform in lucha libre masks is only the bow on this particular present.

Santa Isn’t Here by The Crystalairs: You have to appreciate any musical enterprise that takes the tune from the old German Christmas carol O How Joyfully — or “O du fröhliche,” if you sprechen the ol’ Deutsch — and turns it into a do-wop song about Santa getting stuck in a chimney and ruining Christmas.

Jingle Bells by Duke Ellington: Look, if everyone and their brother is going to record a version of this song, they should at least try to put their own stamp on it. That’s what Duke Ellington does, with a version of “Jingle Bells” so jazzy and distinctive, you’ll think it’s an original composition. And since it’s an instrumental, you can still fill in the lyrics about Batman smelling and the Joker escaping and the Batmobile losing its wheel. And you’ll sound like you should be headlining at The Cotton Club while you do it.

How I Hate to See Xmas Come Around by Jimmy Witherspoon: This one probably isn’t for all tastes. You really have to enjoy the blues to like this number — the “friend, I’ve got troubles” school of blues in particular. In this particular song, our put-upon narrator has no money for Christmas presents and can’t raise any additional funds, not even through pawn shops and loan sharks. I will concede that this is not particularly festive, but somehow, it’s effective background music for me, particularly as I’m shopping online for presents².

I Won’t Be Home for Christmas by Blink 182: A remarkable number of songs tackle the topic of Christmas in jail, and I find nearly all of them delightful. But rather than try your patience with yet another blues number, let’s go with a song written and recorded within the last two decades. As much as I personally enjoy the anarchist guitar-playing in this number, I would not advise playing it at family get-togethers, unless your matronly aunt regales you with tales about how she once got kicked out of CBGB for hassling the Patti Smith Group.

Silent Night by Dinah Washington: I sense I am in danger of losing the room, so let’s go with another classic — this one impeccably performed and beautifully arranged. Too many modern takes on holiday standards have attended to the Loud Is the New Good school of vocals — looking in your direction, cast of Glee — and what you wind up with is a lot of soulless caterwauling. This is not a risk with Dinah Washington, who has pipes to carry off this song and the good sense to know how to best deploy them.

Trim Your Tree by Jimmy Butler: Somehow, when Jimmy Butler sings “I’m going to bring along my hatchet/My beautiful Christmas balls/I’ll sprinkle my snow upon your tree/And hang a mistletoe on your wall,” I get the feeling that he is not merely talking about holiday decorations.

You’re A Mean One Mr. Grinch by The Asylum Street Spankers: You will find multiple versions of the only tolerable musical number from How the Grinch Stole Christmas all over the iTunes Music Store. While you’re well within your rights to beat a path to the original version by the wonderfully named Thurl Ravenscroft, I like the live version The Asylum Street Spankers cranked out because it’s playful and unique — loyal to the source material but confident enough to put its own spin on the tune.

A Cold, Cold Christmas by Stephen Colbert: I enjoyed Stephen Colbert’s 2008 Christmas special, which has apparently been dropped from the Comedy Central rotation because I guess the world needs more South Park and Tosh.0 reruns. No matter — A Colbert Christmas is a really fun half-hour of TV that calls back to the awkward holiday TV specials of my youth. (Why, it’s David Bowie dropping by Bing Crosby’s house! This isn’t awkward at all!) “A Cold, Cold Christmas” never actually appeared on the special, but it’s the best cut off the album, and it’s a pretty good indicator that Colbert is going to do a fine job replacing David Letterman, even if he makes job offers to the wrong TeeVee.org writers.

Father Christmas by The Kinks: As mentioned roughly 8,000 words ago, certain elements of the holiday season bring me down. So if you want to sing angrily about commercialism and how not everyone is feeling particularly jolly this time of year for reasons other than getting some flashy new present, then I’m not one to stop you. The drumming by Mick Avory also helps.

This is my favorite holiday song. That probably explains why I don’t attend many Christmas parties.

May Every Day Be Christmas by Louis Jordan & His Orchestra: Let’s end things on a more upbeat note, shall we? Louis Jordan’s tune about the more positive aspects of the holiday is simple and charming — some might argue a little too sappy, though if they do around me, there may be fisticuffs — and really the perfect song to wrap up a holiday get-together. Assuming you haven’t already driven everyone away by playing The Kinks and Blink 182, that is.

[Here’s the entire playlist on Spotify.]

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