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I have over 270 Christmas and Holiday songs in my library.  Every year I seem to mine a new vein of artists and songs. I’ve whittled those down to a 129-song playlist of favorites. But which songs do I really, really love? If I were stuck in an elevator that played the same 10 Christmas and Holiday songs over and over which ones would I want them to be? That is the basis of this list.

There are some religious, some secular, some light-hearted and some very somber and melancholy. The rating is a combination of song and artist. For example, when I list “O, Little Town of Bethlehem” by Emmylou Harris, that is the specific version of the song that makes the rating. There may be other versions of the song but the one I list is the one that really grabs me.

Check my list and leave a comment about how I nailed it or nailed my thumb. What is on your “must listen to” list this season?

I’m listing these in divisions rather than in Top 10 Countdown format. Within the divisions the songs are listed more or less at random. Album names are in parenthesis

Reason for the Season Division

We wouldn’t have Christmas without Christ so our list has to start here.

1. O, Little Town of Bethlehem by Emmylou Harris.     (Light of the Stable)    

This came out in the 1979 Light of the Stable album. I’ve been listening to it for about 10 years now. There are a few songs in the list that I can’t sing without choking up a bit; the lyric that really grabs me is

How silently, how silently the wondrous gift is given
So God imparts to human hearts the blessings of his heaven
No ear may hear his coming but in this world of sin
Where meek souls will receive him, still the dear Christ enters in

That is a good description of God’s gifts. They are right here with us; we just have to open our hearts to them

2. O Holy Night by Bing Crosby. (Bing Crosby Christmas Classics)

I’m old, but not so old that I listened to Bing on the radio. I remember him from the Jack Benny show and various Christmas movies and specials. He has such a lovely baritone (I think it’s a baritone); his voice is like buttah.

3. God Rest Ye Merry Gentlemen / We Three Kings by the Barenaked Ladies & Sarah McLachlan. (A Winter’s Night)

This is the newest addition to my Christmas library. I first heard it when I had a Pandora Christmas list on. It grabbed me so much I had to pick up my guitar and learn to play along. It’s the most up tempo of the songs. It brings across the message in a happy way. I think my copy from the iTunes store is broken because it just abruptly stops 3;29 in.

I (Won’t) Be Home for Christmas Division

Christmas is a melancholy time for many. We have the expectations of joy and happiness with our families and loved ones blared out at us in Christmas specials, at the stores, and in radio ads. There is a sad side. I remember Carla and my first Christmas as young adults at our home in Caldwell, Idaho – 600 miles from home. As the years go by loved ones leave us and we look back with a misty eye.

4. I’ll Be  Home for Christmas by Bing Crosby. (Single from White Christmas)

Did I mention Bing’s voice is like buttah? He really hits the low notes in this song.

Christmas Eve will find me
Where the love light gleams
I’ll be home for Christmas 
If only in my dreams

Sometimes it’s only in our fondest dreams where we can be with our love ones.

5. Have Yourself a Merry Little Christmas by James Taylor (James Taylor at Christmas)

James Taylor has a number of songs in my list. This is another song that I try to sing but end up choking out some of the words.

I know that in a year we all will be together
If the fates allow (oh yeah)
Until then we’ll just have to muddle through somehow
Have ourselves a merry little Christmas now.

It’s that pesky little adjective “little” that lets us know our joy this Christmas will be diminished

6. In the Bleak Mid Winter by James Taylor (James Taylor at Christmas)

This song deftly crosses the divide between secular and religious. James Taylor reminds us that the Nativity was not a cozy little comfortable scene. Joseph and Mary were sleeping out with the animals. Who is going to rent a room to an unmarried couple, especially when the woman is pregnant. It was cold and miserable, yet God gave us the best gift possible. It shows just how powerful God is.

Fun Division

It’s not all cold and dreary; we can indeed enjoy some time with friends

7. Sleigh Ride by Amy Grant (A Christmas Album)

Another old classic. The Aloha High School band used to (and may still) invite alumni up to play this at the holiday concert. Trombone players would decorate their horns with Christmas lights. When I’m walking around feeling happy, maybe putting up the outdoor lights this song just jumps to my lips

We’re riding in a wonderland of snow
Giddy up, Giddy up, Giddy up it’s grand
Just holding your hand
We’re riding along with a song of a wintry fairy land
…
These wonderful things are the things we remember all through our lives

8. Baby It’s Cold Outside by James Taylor (with Natalie Cole) (James Taylor at Christmas)

Various versions of this song pop up on Pandora and iTunes radio but most leave me cold. This one nails it. There is a delicious, sassy, flirty give and take between the two.

What are you doing with your coat?
You don’t need your coat!
What are you  putting your coat on for?
It’s warm in here
You don’t understand ; I simply must go
Baby it’s cold outside
The answer is “no”

New Year’s Eve Division

9. What Are you Doing New Year’s Eve by The Head and the Heart
(Holidays Rule)

Love is blooming during the holidays and the couple wonder if it’s too early to ask for the big New Year’s Eve date.

Maybe it’s much too early in the game
Ah, but I thought I’d ask you just the same
What are you doing New Years, New Year’s Eve.
…
Wonder whose arms  will hold you good and tight
when it’s exactly twelve o’clock at night

I discovered the treasure “Holidays Rule” in 2012 and found some artists I’d never heard of before. For non-holiday enjoyment I recommend Lost in the Valley by this group.

10. Auld Lang Syne by James Taylor (James Taylor at Christmas)

I suppose it’s the English major in me that responds to this Robert Burns poem. The title translates loosely from Scottish to English as “Long, Long Ago” or “Old Long Since”. It is traditionally sung at midnight New Year’s Eve and at funerals as we look back on those we knew long ago.

We two have sported in the brook
From morning sun ’til night
But the seas between us have roared and swelled 
Since Auld Lang Syne

Runner Up Division

11.Christmas Island by Leon Redbone. (Christmas Island)

Leon Redbone is fun and this is a fun song reminding us that Santa isn’t just for the Europeans. The version by Jimmy Buffet is fun as well.

12. Mele Kalikimaka by Bing Crosby and the Andrews Sisters
(A Merry Christmas with Bing Crosby & The Andrews Sisters (Remastered))

Another song about Christmas in the South Sea Islands. Jimmy Buffet also has a version of this that is fun; but Bing and the background singers carry the day.

13. Señor Santa by Y la Bamba (Holidays Rule)

Kids asking Santa to bring them toys because they’ve been good. There is some nice accordian here and the killer line:

 Santa, we’ve been so good
We washed the dishes and done what we could
Made up our beds and [struck up our cozies?]
We used our hankies when we blowed our nosies

14. Linus and Lucy by Vince Guaraldi (A Charlie Brown Christmas)

The lovely play between the bass line and melody on the piano is instantly recognizable.

15. We Need A Little Christmas by Ages and Ages (Holidays Rule)

Sometimes we need to let Christmas in during the holidays to cheer us up.

As you can see I’ve centered in on a few artists – Bing Crosby and James Taylor especially – and a few killer albums. But there are lots of awesome songs out there. I didn’t even get to the Classical Music Division which would be devoted to André Previn and the London Symphony Orchestra performing Tchaikovsky’s “Nutcracker”. Please leave me a comment with your list.