Why I Hated Christmas Songs In my 20s & Love Them Again In my 30s

or, How Holidays Change Their Meaning As We Age

I created my All-Time Greatest (secular) Christmas Songs Playlist, in order of greatness (1st song is best, 2nd song is 2nd best, etc.) heavily influenced by Soul renditions, Rock n’ Roll originals, and of course, Home Alone. Click here to listen on Spotify.

I was a lucky kid. My family was able to get together for every major holiday, both on my mom’s side and my dad’s.

On my mom’s side we had 4 older male cousins we called “The Big Boys”, (the way a 6 year old would say it not the way a 21-year-old sassy twink would say it, which for some reason is how my mind now reads that phrase). 

Every get-together the games changed depending on which aunt and uncle’s house we were at but it all rotated around Nerf wars, video games and shooting pool.

On my dad’s side we’d cavort with our cousins, turning old liquor bottles into secret potions, spending all night at sleepovers learning every Weird Al lyric and watching The Ghost & The Darkness which my parents would have never let me watch at that age. Thanks cousins!

Much luck, and much privilege, is imbued with ignorance. Not only was I lucky, I didn’t realize I was lucky.

I thought everyone had a bunch of cousins they could have fun with at every holiday.

It only took a year or two out of high school to realize my mistake, to realize I had missed an opportunity to appreciate the rare camaraderie I shared with my cousins due to the efforts of our parents.

The time and attention my parents and piblings put into ensuring we all had cousins is something I took for granted as a kid, resented in my 20s, and have an overwhelming appreciation for in my 30s.

Let me explain.

Roaring Twenties

The death of summer and winter breaks is truly a milestone in becoming an adult: a poop covered, poop flavored milestone that smells exactly like it tastes, like poop.

Sure I worked at Miller Park throughout much of High School but it wasn’t until my sophomore year of college that this lack of a break really sunk in.

Beginning that year I would have I would have year-round jobs (also known as “jobs”) for the rest of my life.

That’s where the resentment started.

Suddenly, it seemed, I was driving 6 hours back to Milwaukee on Christmas Eve, hoping to get there in time for shrimp and jokes at the kids table, stressed by the snow, knowing I’d need to drive back in 2 days.

Long gone were the weeks of winter free time.

Weeks of free time that left with a suddenness only adulthood is capable of inflicting.

It took a decade to process that loss.

It was during my 20s that I began to hate Christmas songs.

I worked security at the University of Minnesota bookstore. At least 2/3rds of every shift was spent on the bookstore floor where they pumped in Christmas music, around the clock, for the full 30 days leading up to Christmas (the remaining 1/3rd was spent behind a bank of 9 video screens with a joystick, moving the cameras around as much as possible and trying not to fall asleep). 

Christmas music seeped into every open pore of my body.

Retail workers understand this in their bones, in a way that induces shudders.

Not only did this result in listening to hundreds of hours of Christmas music, it associated Christmas songs with work and a school career I was barely clinging onto by my Junior year.

Not only was I associating Christmas music with the dreaded, adult “Work”,  I was grieving the recent death of my own Christmas.

All the fun and carefree anticipation of Christmas-As-A-Kid was being replaced with stressful travel plans, having to actually buy things for people with the zero-budget of a college kid, and the creeping realization that Christmas-As-An-Adult would be my reality for the rest of my life.

CHRISTMAS AS A KID

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All of this combined to equal a detached resentment for everything Christmas. Unbeknownst to me this would only be the beginning of my disdain for holidays.

CHRISTMAS AS AN ADULT

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Fast forward a few years.

I’m just getting hired as a contractor. Contractors, in my role at the time, were paid $15/hr with no paid time off. $15/hr without PTO was not enough to take time off, so I would be stuck in the office on holidays like Memorial Day, Labor Day, and even the days surrounding the 4th of July because I simply couldn’t afford to take that time off.

Again, not working = not getting paid. This is the reality for far too much of America.

I was living on my own in a studio apartment, putting groceries on my Target credit card at the end of most months, and doing what a lot my generation has done: replacing lack of income due to generationally stagnant American wages with recklessly available credit.

Nothing was sacred in my world anymore.

And even with that, I was lucky to have held onto any sense of sacredness for as long as I did.

Holidays became a nuisance to be planned around. I would say they were a nuisance to be budgeted around but there really was no way to budget for them. I just had less money than I needed to live on when the most important holidays (i.e., the holidays I couldn’t work through) arrived.

There is an aspect of the collective consciousness you only notice when you have to go into a big, fluorescent-lit, empty building full of cubicles on a day you know everyone else is outside in the sun, relaxing.

You feel it.

Sure, the drive into work is remarkably breezy, and having a completely empty office is actually preferable for me most of the time, but something in you dies a little having to work on a holiday.

On paper it doesn’t seem like that big of a deal, Memorial Day is just a monday in May.

But what dies inside of you is any remaining sense that sanctity exists in our modern world, any sense that some things in life are more important than money, any sense that you as a person with a full-time job are getting ahead.

You’re not, you don’t live in a country that cares about that. 

You live in a country where you can’t even afford to not work when everyone around you is not working.

With that real world, real American, slap in the face – which again, I count myself as lucky to wait so long to experience – I began to resent everything I saw as bullshit holiday stuff.

This is the way unfettered capitalism works: it breaks you, then it forces you to resent the parts of you it broke. In order to survive, to avoid breaking down completely, you have to discard the things you’ve lost, including your own sense of loss. 

Anything that people celebrated about holidays I took as a challenge to resent.

BBQ and beers? Fuck you, I have to work.

The night before Thanksgiving with your hometown friends? I’d be lucky to get in town before 10pm.

That week between Christmas and NYE? Better travel back to a town devoid of friends to work until New Years Eve because I can only afford to take off New Years Day.

And so I hated Christmas songs.

It was an easy thing to do, a lot of people seemed to agree with me.

There also happen to be a lot of annoying Christmas songs. Even the good ones have slews of subpar versions that make the rounds every year. 

Most classic, secular Christmas songs carry a sense of nostalgia and cheer that only seem capable in bygone American eras.

For this reason, it seems, most of our most popular Christmas songs seemed to have been written and recorded between 1935 and 1965. With the 60s came the evolution of the modern age into the post-modern (hot take?), and irony – which would be the language of pop-culture for the next 50 years – snuffed out the oxygen of sincerity that Christmas songs survived on.

It is also for this reason, this unbridled earnestness, that Christmas songs are easier to hate in your 20s.

You’re a kid who thinks they’re an adult, a kid who thinks they’re invincible and doesn’t see what all the fuss is about when it comes to things like, “dealing with your issues responsibly” or “allowing yourself to feel and process your emotions”. You don’t need that shit, you have poker on Wednesday, Beer Pong tournaments every Thursday, Jager for the rest of the weekend, and weed all the time. What the fuck is a “Have Yourself A Merry Little Christmas?”

So when Christmas songs met the death of my own innocence met Corporate America’s cynical ploy to play Christmas songs 24/7 starting Black Friday morning in order to keep us all shopping, I had had enough.

I was done with magic, I was done with snow globes, I was done with being the person who looked forward to the holidays. I was going to watch The Sopranos and drink whiskey and bah humbug the still-sentimental souls of this world.

And then…

ThirtySomething

I burrowed so far down the cynicism hole I came out the other side.

That said, the better paying job and successful relationship with a woman I loved were probably more influential factors in my return to Christmas music than anything else.

In your 30s you start to pick up the parts of yourself you needed to discard in your 20s to survive.

Now, because you only have a few days off (and you get paid for them, again, if you’re a lucky American or if you’re just any person born in Europe) you know you need to appreciate every moment of egg nog and present wrapping that you ever come across.

Because the outside world is so brutish and cold, any time you can spend doing anything remotely reminiscent of the highlights of your childhood is sacred because you carve out that time and declare it sacred.

Uncle pushing drinks on you?

You feel awkward making small talk?

Need to wrap presents for your nephews at the last minute?

So what.

Real life has real stressors and having an aunt make food for you while you drink beer and eat as many snacks as you can fit in your face is a blessed reprieve. 

In your 30s, the nostalgia from all the memories you buried in your 20s starts to rise up again. Or at least it did for me.

Memories I buried because I felt too alone to deal with the idea that “you once had a home and now you don’t”.

Living in a small, shitty room in a house shared with your unsuccessful bandmates does not a home make.

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In your 30s you start to build your home, your nest, and you invite back in the small, delicate things that radiate warmth. The things that the coldness of another 20-something life-failure mocked. Or, at least, this is your path if you’re the kind of person who doesn’t like paths, throws them out the window, tries to make it in the wild, gets beaten down by the wild and comes back to the warm light of the collective holiday shining from across the snow covered field, beckoning you inside for bailey’s and hot chocolate, welcoming you with a familiar tune you told yourself you hated but now hear again with the older ears of a much younger self, a tune sadly, slowly lamenting:

Here we are as in olden days

Happy golden days of yore

Faithful friends who are dear to us

Gather near to us once more

Through the years we all will be together

If the fates allow

Hang a shining star upon the highest place

So have yourself a merry little Christmas

Maybe others didn’t go through this journey, maybe it took them longer or ended sooner, but this has been mine, and I’m glad I made it back home.

As I found my way back to Christmas songs, I put together the definitive list of them. All the best versions of the best secular pop Christmas magic.