When I go back to Ohio to visit my parents for Christmas, one my favorite personal traditions is staying up late after everyone falls asleep to make a cup of hot chocolate and listen to the saddest Christmas music I can find.

The lights on the tree cast warped shadows all around the darkened room, the tiny log house creaks in the wind, and occasionally I can hear coyotes laughing outside in the cold.

It’s every enneagram 4’s dream.

As a “4” there is nothing better than a melancholy Christmas song. It’s reflective, nostalgic, and somehow makes Christmas sweeter.

If you’re like me, and you love to cry along to Christmas music, here are 10 “sad” songs that will make your Christmas merry & bright.

1.) Have Yourself A Merry Little Christmas – Andrew Belle

There are so many renditions of “Have Yourself A Merry Little Christmas” but Andrew Belle’s is my favorite. I think you’ll love his modern take on this Christmas classic.

2.) Christmastime Is Here – Evan Wickham

When I first heard this song, I thought it was sung by Phil Wickham. Turns out, it’s actually his brother Evan. Evidently, the Wickham family can sing.

This song is already bittersweet with lyrics that paint a picture of warm Christmas memories, but Evan’s arrangement makes those memories feel faded, distant, and lost in the best way possible.

3.) I’ll Be Home for Christmas – Joy Williams

You might remember Joy Williams from the folk band The Civil Wars, but before she won the hearts of millennial hipsters everywhere she found success in Contemporary Christian Music back in the 90’s.

Joy Williams has an incredible way of bringing so much raw emotion to every song she sings, and her rendition of “I’ll Be Home for Christmas” is no exception. In 2020, this song feels timely and relevant.

4.) Glorious – for KING & COUNTRY

for KING & COUNTRY has created a lot of great Christmas music, but “Glorious” is one of their best.

5.) I Heard the Bells On Christmas Day – The Civil Wars

I find it really sad that The Civil Wars broke up, because I would love to hear a full Christmas album from them. Their version of “I Heard the Bells on Christmas Day” truly is folk perfection.

7.) O Come O Come Emmanuel – Casting Crowns & O Come O Come Emmanuel – Phil Wickham

“O Come O Come Emmanuel” is my favorite Christmas song, and I couldn’t choose just one version to share.

Casting Crown’s Instrumental rendition gives me chills every time I hear it, but because the lyrics to this song are so important you should hear Phil Wickham’s version as well.

When I listen to the words of this song I can almost envision the desperation of a pre-Christ world. A place that was stained with sin, filled with death, and the promise of a savior left unfulfilled. How abandoned the Jews must have felt. How fervently they must have mourned for a savior, and then one night everything changed. A savior had come.

Now all these years later, I too am longing for our Savior to come back, and my prayer is “O Come O Come Emmanuel.”

8.) Instrumental – Future of Forestry

I know there aren’t any lyrics to this song, but I love how it makes me feel.

The sound of footsteps, passing cars, and the crackling background noises paint a nostalgic picture of a lonely little town on Christmas Eve.

9.) The Secret of Christmas – Sleeping At Last

Sleeping At Last writes some of the most dreamy and beautiful music I have ever heard. Not only does this song hit all the right notes, but it’s a reminder that “The secret of Christmas is not the Christmas things you do at Christmas time, but the Christmas things you do all year through.”

10.) What Child Is This – Josh Garrels

Josh Garrels’ version of “What Child Is This” sounds like it should be featured in a Narnia movie. His haunting vocals and dreamlike instrumentals paint an almost mythical picture of Christ’s birth.

What are your favorite “sad” Christmas songs? Share yours in the comments below. I would love to hear them.

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