All the Feels, as Represented by Christmas Music

It’s hardly a novel idea that music has the power to inspire us and connect us through deep emotional resonance. But Christmas music exists in a category all its own when it comes to sparking nostalgia, joy, and a whole myriad of emotions. So I thought—what better time than now to reflect on the holiday and Christmas songs that have resonated most with me throughout my life and made me feel all the feels.

Before I begin, please know that this post is very tongue-in-cheek. I’m well aware that my opinions are exactly that: opinions. I don’t consider myself anything more than an appreciator of music. The beauty of art is that there truly is something for everyone. My favorite might make you scoff and roll your eyes. Your favorite might send me lunging for the “Skip” button. Or maybe, just maybe, we discover there’s an inherent joy and beauty in a song we both love.

And in the end, isn’t that what Christmas is really all about?

Again, please don’t take this too seriously. Have fun with it. I certainly am.

For Pure Melancholy

“Christmas Day” – Dido (1999)

When I was in middle school, I went through an Enya phase that persists to this day. I’m fairly certain my family was ready to scream in frustration as I played “Only Time” for the hundredth time in a single week. I knew every track by heart. That somber, ethereal folk sound connected to something deep within me.

So it should come as no surprise that I was immediately hooked when I first heard “Christmas Day” by Dido. Its gentle, melancholy rhythm paired with her dulcet tones captivated me as she told the story of young lovers meeting for the first time and hoping to meet again on, you guessed it, Christmas Day.

The song is filled with hope, yearning, and heartbreak. The young romantic in me was completely swept away by the story unfolding, while the older, wiser romantic can now appreciate its somber reality. Then and now, it remains a favorite, especially when I’m seeking something calm and reflective amid the hectic rush of the holiday season.

For Genuine Anxiety

“Carol of the Bells” – Popular arrangement by Mykola Leontovych (1916); lyrics by Peter Wilhousky (1936)

This song holds a special distinction for me because whether it’s purely instrumental or performed with vocals, I always feel anxious listening to it. Which is unfortunate, because I actually have fond associations with the song itself. I had an incredible music teacher as a teen, and my school chorus once performed it in what I believe was a fairly solid attempt at capturing its layered melodies.

More often than not, though, the rising tension within the music builds a feeling of mounting apprehension for me. It probably doesn’t help that the song is famously associated with a climactic scene in Home Alone (1990), emphasizing Kevin’s own anxiety as time runs out to protect his house.

For me, that unease is most clearly tied to a memory of being stuck in downtown traffic while trying to make it to college in time for a final exam. Naturally, this song came on during a Christmas playlist just as my hands tightened on the steering wheel and my eyes flicked desperately toward the clock. The tempo, the repetition, and the blasted bells counting down the passing of time were decidedly not soothing.

Now, whenever it comes on, I have to “nope” out of it immediately and move on to the next Christmas classic.

Which is a shame, really. It truly is a masterpiece.

For Sheer Annoyance and Utter Disdain

“Wonderful Christmastime” – Paul McCartney (1979)

Unlike my Christmas cookies, I’m not going to sugarcoat this: I hate this song. Plain and simple.

Paul McCartney is an incredible musician and artist, no argument there, but he also managed to craft the single most annoying Christmas song I’ve ever heard. Perhaps that, in itself, is a kind of crowning achievement?

Maybe it’s the relentless “ding-dong, ding-dong” repetition that triggers unpleasant associations with Carol of the Bells. Maybe it’s because, during my college job, this song seemed to blare over the speakers nonstop. Or maybe it’s the grating, tinny refrain that sets my teeth on edge.

Honestly, I can’t stand it. I couldn’t even bring myself to listen to it again while finding the video for this post. I simply refuse to subject myself to it willingly. I sincerely hope the video I linked is of decent quality.

All the best to you if this song is your favorite. “And that’s enough.”

For Comforting Nostalgia

“White Christmas” – The Drifters (1954)

This was a difficult category to narrow down. I grew up appreciating a wide range of music, and Christmas music was no exception. Choosing a song that immediately evokes fond holiday memories took some deliberation, but in the end, it had to be “White Christmas.”

I went back and forth between The Drifters’ version and Bing Crosby’s original (1942), trying to determine which resonated more. Sorry, Grandma, but as much as I love Bing, The Drifters take this one easily.

The soothing melodic tones of Bill Pinkney’s bass voice transport me every single time. Those opening notes instantly place me in the holiday spirit. Ironically, I’ve never actually experienced a “white Christmas,” since it rarely snows where I live, but that’s how powerful this song is. I’m nostalgic for an experience I’ve never even had.

For Pure Joy

“Hey Santa!” – Carnie & Wendy Wilson (1993)

I have to give full credit to my mom for introducing me to this one. Despite my deep love of music and endless exposure to Christmas playlists at work, I somehow missed this song entirely.

A few years ago, my mom asked if I could help her find a Christmas song she remembered loving but hadn’t heard in years. Thus began the search for “Hey Santa!” Thankfully, it was an easy enough quest in the digital age, and as fate would have it, I ended up loving it too.

The song begins with a solemn children’s choir before transforming into a joyful holiday bop (saxophone included) as the Wilson sisters ask Santa for the most important gift of all: bringing their love home. This song always has my mom and me dancing along.

I also have to give a quick shoutout to my runner-up for “Pure Joy.” Since I’ve already gushed at length about A Muppet Christmas Carol (1992) in a previous post, I restrained myself. But “It Feels Like Christmas” (1992) never fails to brighten my holiday spirit when it starts playing.

For Utter Hilarity

“Peace on Earth/Little Drummer Boy” – Bing Crosby & David Bowie (1977)

This one requires a bit of explanation, because in this case it’s not the song itself that’s hilarious, but rather the performance. And specifying the performance matters.

In 1977, Bing Crosby and David Bowie recorded a duet that became an unexpected Christmas classic. Vocally, it’s beautiful. Visually… it’s a bit awkward. Still, it rightfully earned its place in holiday history.

Then, in 2010, Will Ferrell and John C. Reilly created a near-perfect homage to the original. Their parody recreates the performance down to the smallest detail, only subtly amplifying moments here and there. The dedication to singing the song sincerely, rather than winking at the joke, makes the comedic beats land even harder.

Every December 1st, I send this video to friends with the message: “It’s that time again!” And I love that I can now share that joy and laughter with you as well.

In the end, I hope this holiday season brings you moments of joy, reflection, and laughter wherever you can find them. And remember: there’s absolutely no shame in pressing the skip button. Be kind to yourself.

Music and video links shared in this post are referenced for discussion and appreciation under fair use. All content belongs to its respective artists and rights holders.