Cassie’s Christmas Playlist

I feel like I am uniquely qualified to make a list of Christmas songs that should be on your playlist. Not only am I a musician, but I start listening to Christmas songs in about October. I have two reasons for this: I am a music teacher, and I have to make sure the kids are ready to sing/ play the Christmas songs by December, and I am a HUGE Christmas fan!


So here goes:


  1. John Legend’s “A Legendary Christmas”

First of all, I LOVE the play on words here. My favourite song from this album is What Christmas Means To Me – it’s got jingle bells, that festive spirit and a catchy, old school soul sound.


  1. Matthew West – Join The Angels

This song is about the story of Christmas but it’s told in such a festive way, you can’t not love it!!!!


  1. Pentatonix – Go Tell It On The Mountain

OH MY GOSH I LOVE THIS VERSION OF THIS SONG!!! I pretty much love anything Pentatonix does, but this song gives me such a happy heart!


  1. Glee – Deck The Rooftop

My friends introduced me to this song by doing a dance to it in a show we did. It gets so stuck in your head!! It’s basically a play on Deck The Halls, but more modern and vibey!


  1. Michael Bublé ft. The Puppinni Sisters – Jingle Bells

Think Andrews Sisters and Frank Sinatra. It’s got that jazzy flare from Michael, and such awesome harmonies from The Puppinni Sisters. I often skip to this one when I listen to the Bublé album.


  1. Stevie Wonder & Andra Day – Someday At Christmas

This is a proper soulful ballad, and even though the singing styles of these two singers are not my all-time favourite, the words are so beautiful, and somehow it captures the meaning of the song so much better than the original. Andra Day’s voice is so beautiful, and it has this edge to it that I just love. She just captures so much emotion in her voice.

  1. The Polar Express Soundtrack – When Christmas Comes To Town

Guys, I cry every time I hear this song. There’s something about a child’s voice that just expresses the sincerity, joy and sometimes sadness that the world knows at Christmas time. This song captures some of the reality of Christmas for some children. The music in the background makes your spirit full. Choir voices, strings, piano.


  1. Judy Garland – Have Yourself A Merry Little Christmas

Sometimes the original is the best. I’ve listened to a few versions, but the simplicity of Judy’s vocals is my favourite. Even then, I prefer less vibrato, but that’s just me. I’m not mad at Sam Smith’s version. The riffs he uses are pretty, but the original melody is so beautiful without any of the extra stuff!!! I do like the simplicity of the piano arrangement though.


  1. Sia – Santa’s Coming For Us

The chorus of this song is such a jam. Sia’s whole Christmas album is actually quite special, the only thing that irritates me is her terrible pronunciations. You can’t hear what she’s saying half the time! Luckily, the words come in the leaflet of the CD, and there’s google if you’re downloading the songs.


  1. Celine Dion – O Holy Night

I love this song anyway, I’ve grown up singing it in almost every choir. It’s such a pure, beautiful song. Celine Dion’s version is just beautiful without being too showy-offy.


My other favourite songs are:

  1. Eartha Kitt – Santa Baby
  2. Brenda Lee – Rockin’ Around The Christmas Tree
  3. Bobby Helms – Jingle Bell Rock
  4. Michael English – Mary Did You Know (the original has a kind of Toto feel to it, but any version is really beautiful)
  5. Burl Ives – Holly Jolly Christmas (Lady Antebellum’s version is quite lovely, but the original has that cheesy 50s feel which you can’t replace!)
  6. Nat King Cole – Chestnuts Roasting On An Open Fire
  7. Train – Shake Up Christmas
  8. Pentatonix – O Come O Come Emmanuel
  9. Sleigh Ride
  10. Joy To The World

I hope this has inspired your Christmas playlist a little bit. Go forth and be merry!!!



Cassie Rae

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