My Top 5 Favourite Christmas Songs of All Time

Dust off those ornaments, put those gingerbreads in the oven, and slip on your ugliest Christmas sweater because it’s officially the most wonderful time of the year! That’s right, it’s December which means that the holiday season has officially started. Lights go up all over cities around the world, photos with Santa start popping up on everybody’s Insta, and all the music on the radio gets just a little more Holly Jolly. So, to celebrate the beginning of the season I thought I would countdown my top 5 favourite Christmas songs!

Now, I am purposefully leaving Mariah Carey’s ‘All I Want For Christmas Is You’ off of this list for two reasons:

1) This song is arguably the most played, most beloved, most universally Christmas-ie-est song of all time! So it’s a given that I, among many others, have it down as one of our favourites.

2) Because the only Christmas song I have ever recorded was a version of ‘All I Want For Christmas Is You’ which you can listen to here.

#5 WHAM! – ‘Last Christmas’

Wham! - Last Christmas (Official Video)

Coming in at number 5 on my list is definitely ‘Last Christmas’, by WHAM! The instrumentation on the song is very uplifting and hopeful which fits really well with the spirit of the season, and the story in the lyrics is very relatable. I mean, who doesn’t remember spending a Christmas with that special someone?

I love the idea of having a Christmas song that deals with finding love and working through past breakups. The idea of falling in and out of love over the holidays, and dealing with real-life situations over Christmas makes this track a very modern take on both classic Christmas and Love songs. It’s relatable, yet timeless at the same time plus, in the words of Wade Wilson, it’s “WHAM!”

Deadpool WHAM!

#4 Bing Crosby – ‘White Christmas’

Bing Crosby & Frank Sinatra - White Christmas

Irving Berlin wrote this song in 1938 and according to an interview Berlin did with Los Angeles Mirror writer Erskine Johnson, Berlin said,

“At the time I had no idea ‘White Christmas’ would be a perennial hit or that Paramount would add to its popularity with a movie of the same name…I took it off the shelf and polished the lyrics a little, and went to Bing’s dressing room at Paramount to get his okay on all the songs for the picture. I was nervous as a rabbit smelling stew. I sang several melodies and Bing nodded quiet approval. But when I did ‘White Christmas’ he came to life and said ‘Irving, you won’t have to worry about that one.’” – Irving Berlin, Erskine Johnson

I get all the warm fuzzies inside when I hear this song come onto the radio, and Bing Crosby’s version(s) of this song are arguably the most imitated and iconic to date. It’s one of those classic Christmas tunes that, every time I hear it, makes me think of Christmas lights, hot chocolate, and falling snow gently frosting the tops of buildings and trees. It paints a picture for me of what the ideal Holiday landscape looks like and, more importantly, reminds me of what the ideal holiday feels like when I’m sharing those moments with the people I love.

#3 Bruce Springsteen – ‘Santa Claus is Comin’ to Town’

Santa Claus Is Comin' to Town (Live at C.W. Post College, Greenvale, NY - December 1975)

It’s no secret that I am a huge fan of The Boss, so it’s not wrong to assume that when I’m making a Top 5 music list, he would appear somewhere on it. However, among Springsteen fans, this song is arguably one of his most iconic. Ever since I can remember my family and I would spend family time singing and dancing along to my parents’ favorite records, and my dad, being a massive Springsteen fan himself, would play this song every year leading up to Christmas morning. It’s a tradition that’s still alive and kicking to this day.

I love how playful Springsteen gets with this song because, to me, that’s what this song and Christmas, in general, is all about. It’s about putting away the adulting we all do and remembering what it’s like to believe in Santa and feel the magic that exists in the decorations and anticipation of the season.

#2 Bobby Helms – ‘Jingle Bell Rock’

Jingle Bell Rock / Bobby Helms 1957

This song has been featured in so many iconic movies and TV shows including, but not limited to, ‘South Park’, The Simpsons’, ‘It’s Always Sunny in Philadelphia’, ‘Home Alone 2’, and ‘Lethal Weapon’, that it’s become synonymous with this time of year!

Bobby Helms, the artist who first released the song, was already a pretty well-known Country Star with two #1 country hits that also made their way onto the Top 40 Pop charts at the time. According to even though ‘Jingle Bell Rock’ first came out 2 days before Christmas in 1957 it shot up the Pop Charts to #6. The same thing happened when the song was re-released in 1958 and again in 1960, it’s just that good a Christmas song!

There’s just something about the way the guitar lick comes in at the beginning of the song that reminds me of holiday parties with close family and friends, laughing and chatting, surrounded by decorations. It’s that energy, that light-heartedness, and fun that reminds me so much of the holidays, and always takes me back to this song.

#1 ‘Jingle Bells’

Every year around the holidays my grandparents move out to Colorado and my family joins them for Christmas vacation. I’m the oldest of 5, plus my parents and my grandparents make us a huge one family party everywhere we go. One year, my Dad decided that we were going to go for a horse-drawn sleigh ride on Christmas. The sun had just started to set, there was fresh, untracked snow everywhere you looked, and with the mountains on one side of us and a little stream on the other, my brother Zach starts singing “Jingle Bells”. It was one of those moments that felt so surreal, and magical. Before we knew it, the entire sleigh, including the driver, was singing along. It’s one of those memories that will last a lifetime and a song that, for me, will always remind me of Christmas!

For all of these and more amazing Christmas songs, check out my holiday Spotify playlist. Music touches all of our lives every day, so please enjoy these songs and make lasting memories with the ones you love this holiday season.

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