“Christmas Is All Around” - Billy Mack

This is the tune from the sappy, holiday flick Love, Actually, but the movie is loveably bad, and so is the song.

“Hanukkah Blessings” - Barenaked Ladies

Great song to include on the holiday playlist if you want to be inclusive. Even if you don’t have a diverse audience, it’s a bit of a toe-tapper :-)

“Warm Jamaican Christmas” - Wayne Wonder & Baby Cham

Here’s a good litmus test for how far someone’s willing to stray from holiday musical standards. Particularly apt if you spend the season with any weather wimps :-)

“Christmas Wrapping” - The Waitresses

Lest you thought they faded into Bolivian after the immortal “I Know What Boys Like”, here’s a reminder of the talent of The Waitresses.

The lyrics explain that they’d lost sight of the true meaning of Christmas, but it’s rediscovered by song’s end.

Mostly, I just wanted a song with a true 80’s feel on this list.

“The Little Drummer Boy” - Lou Rawls

This song is like the anchovies of holiday music. Even fans of the genre draw the line here.

If you share this problem, Lou Rawls is your solution. If the Drummer Boy is a pill you have to swallow, Lou is your sugar-coating.

“Donde Esta Santa Claus?” - Guster

I’m impressed by songs that successfully pull off a holiday feel without departing from their genre.

Even though Guster’s not a latin band (they’re from Boston, and met at Tuft’s), this song’s got a latin beat (and some Spanish lyrics), but is obviously a Christmas song.

“Another Christmas Song” - Stephen Colbert

Yes. That Stephen Colbert. He doesn’t sing much on this track (it’s more like speak/singing), but when he has to croon, it’s really not that bad, and the lyrics are a riot.

Seems worth mentioning that iTunes is currently giving away this and 21 other Christmas songs for free (in the cool, new LP format). Click this link to be redirected to the iTunes store to download them.

He’s got a full holiday album out at the moment, too, if you’re interested.

“Old Toy Trains” - Roger Miller

Sounds sad at first, but it’s actually a father singing a child to sleep on Christmas Eve.

The train reference may be a bit dated these days. A cover version could probably swap in “video games” without messing up the rhymes :-)

“No Christmas for Me” - Zee Avi

Great acoustic tune about missing your beau over the holidays, with a pleasant surprise.

“Santa Claus Goes To the Ghetto” - Nate Dogg & Snoop Dogg

What would a modern holiday music playlist be without Snoop? Not sure how well this ditty will age, but it’s a lot of fun in 2009.

“Christmas Feeling Ska” - Toots & The Maytals

This’ll sound way out there compared to the rest of your playlist, but after a few plays, it’ll fit right in.

“Cool Yule” - Louis Armstrong

This is now a staple in the Bain house. Even the cat likes it.

“Christmas Cookies” - The Oak Ridge Boys

I’m not saying that this is going to be your new favorite holiday tune, but it’s a fun, country-themed addition to your playlist.

A minute in, if you still don’t think you like it, stop the song, but I bet you’ll keep humming it.

“Up On the House Top” - Jackson 5

I’ve put together a holiday playlist of alternative tunes, or fun versions of traditional songs.

I can only post one a day (Tumblr rule), so it’ll be like a musical advent calendar. Here’s the link to the few from last year, and where this year’s will all go: http://maximumalexbain.com/tagged/☃♬