Happy Holiday Season to all! I thought it would be fun to share with you some of my favorite tunes that are a little more obscure than the inevitable “Baby It’s Cold Outside” duets (is anyone else totally creeped out by that song?) or “All I Want for Christmas is You” – which amidst all the criticism of the recent tree lighting performance, is still stuck in my head. Here are some more original holiday songs to counteract all the deck-the-halls din.

1. Pearl Bailey “A Five Pound Box of Money”

What is funnier, more forthright or more swingin than this? None of that coy “Santa Baby” stuff here, just a straight up ask for a five – nah, make it 10 pound box of money,  Thanks John Baxter for this one, it’s the one tune on this list I would actually sing – but nobody could do it better than Pearl.

2. Treacherous Three “Xmas Rap” (from the film Beat Street)

“We’ll sing Silent Night and Jingle Bells and all those Christmas rhymes                                                                                                    Cause nobody gives a shit about your reindeer and hard times.”

I’ve been listening to this every years since I got the “Sugar Hill Records” set in my early teens…the strong language used towards Santa and the economic reality check might make this one not to share with the kids.

3. Tatsuro Yamashita “Christmas Eve”

This is simply a great pop song (the original is in Japanese, here’s the English version). To me this is on par with George Michael’s “Last Christmas”, and the vocal “Pachabel’s Cannon” on the bridge puts it on an even higher level. Thanks to Alvin Walker for passing this one along a few years back!



4. Don McLean  “Dreidel”

Okay, so perhaps this isn’t a Hanukkah tune perse; it’s simply a great sweeping song, as epic as his “American Pie” hit. It’s wild – when it’s over it’s hard to believe all that happened in just under four minutes. This song is especially fun to sing along to after a few cocktails, as my friend Uncle Shoe and I know well.

5. Steely Dan “Charlie Freak”

There’s some debate about this one being a Christmas song, but to my mind,once you put sleigh bells in the arrangement I feel it’s decided. And what is more heartwarming than the story of a man returning the ring he bought off a junkie after he ODs and dies from the fix? Happy Holidays indeed (you might need some Bing Crosby after this one).

Any favorites I missed? Would love your additions to the list in the comments.:)

Enjoy the season this week, and cheers!


8 Comments on “5 Unexpected Holiday Songs for the Season”

  1. Great list! I am going to send my husband this link as he loves to dj holiday evenings at home. A fave of ours is the Roches ‘Star of Wonder.’ Cheers and happy holidaying to a true STAR!

    • Oooh, I’m going to check that out! I made a little 10 song mix for the holidays – I’ll burn you one!:) Happy New Year to you – a woman who illuminates all around her. I can’t wait to see what you come up with in 2015!:) xxo

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