Top Ten Holiday Season Songs of All Time

I’ve been obsessed with Christmas music since I was forced to play an angel every year in the Nativity play.  My hyper dramatic show off side wanted to be the Virgin Mary. She was the star until the doll playing Jesus showed up. The angels would all stand near the altar and sing “Away in a Manger”. As a carol, I despise “Away in a Manger”, but it is particularly juvenile in melody, so the kids always sing it. (My daughters, angels all, also had to sing it during their Nativity plays, so things really never change in the Lutheran Church, even if your hip and sing folk songs every once in a while.) But I always found magic in the music. Some of the loveliest music ever written is Christmas music. Actually, some of the loveliest music ever written is religious music.

But there are also some gems from the secular world, from the mundane to the profane. I delight in it all, probably because Advent and Christmas were always my favourite time of year. At least, it was before I became an adult and started making giant feasts and having to budget for Christmas gifts for the children. Then it just became a lot of work. I was responsible for my mother’s last Christmas, which was the five of us plus my then two-year old daughter. I had never done the Christmas meal, it had always been my mother’s domain. The weird mix of Danish and North American food stuff were out the window as I had no idea how to make rødkål or brunede kartofler. Forget about julkage, or kransekage. I could barely make gravy then. Turns out that brunede kartofler is tricky because of the caramel sauce, kransekage is temperamental, and my kids don’t like julkage. Rødkål, though, was a jar of pickled red cabbage with a healthy shot of red currant jelly. Because why cook red cabbage in vinegar and red currant juice when you can take a shortcut?

That Christmas was dominated by Herman’s Hermit’s greatest hits, a gift from my brother to my mother. She still adored them after all these years. Within seven weeks she would no longer be with us. It was the last family event the five of us had, and I was in charge of the main event. And it didn’t go well in any way. I’ve since mastered a grand turkey dinner with the Danish touches. It was mostly for me, because I wanted to create the same atmosphere of that my mother did. Except for the stuffing. I can’t be arsed to create her sage stuffing when a box of Stovetop is what my kids will eat.

When I was little my mother, in her desire to encourage my piano playing, made multiple copies of a large book of Christmas sheet music. This wasn’t fake book material- it was full sheet music. I would play to my heart’s content for weeks. The last Christmas with her I didn’t play a note. The piano had been wrecked through many moves and repairing it was cost prohibitive then. I miss my piano. I miss my mother. I miss playing “What Child Is This?” for her.

So, here is my favourite holiday music of all time. Some of it is holy, some of it is not, and one of it is the Pogues.

You knew it would be there.


10. “Christmas (Baby Please Come Home)” Darlene Love

It’s a Phil Spector Christmas Miracle.  The great Darlene Love, forever a bridesmaid, got her greatest moment on the Phil Spector Christmas album. The music is utterly glorious, but it’s Love’s vocal that shines. The song has been covered numerous times (notably Mariah Carey and U2), but the original remains my absolute favourite.

9. “Gabriel’s Message” Sting

A thirteenth century Basque hymn Anglicized in the nineteenth century and made popular by a man who would record an entire album playing a lyre. It’s probably one of the rare times Sting as a solo artist will ever appear on this blog, so relish it while you can. The hymn references the story of Mary’s visit from Gabriel as told in the Gospel according to Luke. I’ve always found it beautifully haunting.

8. “Do They Know It’s Christmas?” Band-Aid

Always the original. Always. Yes, it’s condescending. Yes, it’s a tad empirical in it’s thinking. It doesn’t stop it from being a great pop song, and people’s hearts were in the right place. Bob Geldof and Midge Ure did shed a light on famine in Africa, and did try more than most to fight it. It’s easy in retrospect to be critical of the efforts made, but at least they tried to do something. This song just brings back so many memories from my childhood that it’s hard for me to hate on it for any reason.

7. ” Peace on Earth/ Little Drummer Boy” Bing Crosby and David Bowie

Nothing about this should work. But here it is, being all flawless. “Little Drummer Boy” is actually one of my least favourite carols, but as sung by Der Bingle and the Man Who Fell To Earth, it works beautifully, especially with the counterpoint of Bowie’s “Peace on Earth”. It would be one of the last songs Crosby would ever record, and I suspect that this year it will be especially touching as we all listen to the now much missed Mr. Bowie as well.

6. “Silent Night” by Sinead O’Connor

The highlight of every Christmas Eve candlelight service in Lutheranism is “Silent Night”. That’s when we light the candles and the lights go out and you end up with second degree burns. Those little paper wax catchers do nothing to actually catch wax. While know Bing’s version is the third biggest selling Christmas record of all time, my favourite is Sinead’s. That gorgeous voice just plays off the melody beautifully.

5. “All I Want For Christmas Is You” Mariah Carey

Again, this may be the only time she appears anywhere on this blog without some serious mocking happening. But the sheer joy of the song is infectious, it’s the most played Christmas song of the last decade, and one of the most covered. There is no flaw in this track, not a one.  I know it’s Christmas when I hear those opening chords.

4. “Have Yourself A Merry Little Christmas” Judy Garland

It’s set in stone. We watch White Christmas, Love Actually, The Holiday,  and Meet Me in St. Louis every December. while the last of these is not a Christmas movie per se, it does have Judy singing this song. My all time favourite version is actually Bert and Ernie from Christmas Eve on Sesame Street. I got that album when I was three and played it to death.  But then I heard Judy and knew that while Muppets may be the ones in my heart, no one sang it quite like Judy.


3. “White Christmas” Bing Crosby

Because it is iconic. And magical. And Bing.

2. “O Holy Night” by Celine Dion

Again, not someone who would typically discussed on this blog outside of the rare brilliant song choice.  I’ve never been one for over singers who refuse to learn how to judiciously use their voice. But this is a song meant for over singing. Enrico Caruso’s version from a century ago remains in print, so it says something that I went with Celine over the greatest tenor who ever lived. I just love her version. I love the difficulty of the song, as you can tell real singers from the “singers” with it. If you cannot reach those notes, a real singer can figure out how to evoke that soaring feeling without actually doing it. If you can hit those note, then you have a voice that can be used for miracles. Celine can hit those notes.


1.  “Fairytale of New York” the Pogues featuring Kirsty McColl

I just cannot imagine a Christmas with out Shane and Kirsty insulting each other.  A modern classic, rooted in reality (most of use view our childhood Christmas memories through rose-coloured glasses), the song plays off the Pogues shambolic reputation as a group of drunken folk punk terrors and place the Princess of English folk McColl as MacGowan’s equal, as feisty and angry as he was. The song is being pushed for U.K. Christmas number one on Facebook and I believe that it should have that honour. It’s different from everything else out there. I just love it.


Honorable mentions: Nat “King” Cole’s “The Christmas Song”; Wham!’s “Last Christmas”; The Pretender’s “2000 Miles”; The Ramones “Merry Christmas (I Don’t Want To Fight)”; John Lennon and Yoko Ono’s “Happy Xmas (War Is Over)”; Slade’s “Merry Christmas Everybody”; Wizzard’s “I Wish It Could Be Christmas Everyday”; Elvis Presley’s “Blue Christmas”; Greg Lake’s “I Believe in Father Christmas”; “Do You Hear What I Hear?” by Whitney Houston; Burl Ives’s “Holly Jolly Christmas”; Jose Feliciano’s “Feliz Navidad”; Bill Nighy as Billy Mack’s “Christmas is All Around”; anyone doing “Carol of the Bells”.