every year i sincerely try: Janine Annett on Kacey Musgraves’ "Christmas Makes Me Cry"


It's all red and gold and Nat King Cole
And tinsel on the tree
It's all twinkle lights and snowy nights
And kids still believe
And I know that they say, "Have a happy holiday"
And every year I sincerely try
Oh but Christmas, it always makes me cry

It's the ones we miss, no one to kiss
Under the mistletoe
'nother year gone by, just one more that I
I couldn't make it home
And I know that they say, "Have a happy holiday"
And every year I swear I sincerely try
Oh but Christmas, it always makes me cry 

Always

Seems like everybody else is having fun
I wonder if I'm the only one
Whose broken heart still has broken parts
Just wrapped in pretty paper 

And it's always sad seeing mom and dad
Getting in a little greyer
And they always say, "Have a happy holiday"
And every year I sincerely try
Oh but Christmas, it always makes me cry

I love Kacey Musgraves. I’ve been a fan for years, ever since my friend and neighbor said to me one day, “Hey, have you ever listened to Kacey Musgraves? I think you’d really like her music.” I did. I do.
While Kacey Musgraves (rightfully) receives accolades for many of her songs and albums, I feel like A Very Kacey Christmas is often overlooked. A Very Kacey Christmas has a wonderful mix of brand-new holiday songs and covers of older ones (including one of my favorite Christmas songs, “Mele Kalikimaka”), leaning into the kitsch of the older songs where it’s warranted.
Similarly, don’t sleep on “The Kacey Musgraves Christmas Show,” a 2019 Amazon Prime Video holiday variety special that seems like it could have been made in 2019 or 1979. It features a variety of special guests, and Dan Levy (who is of half-Jewish, half-Christian heritage, like me!) narrates the show.
“Christmas Makes Me Cry” holds a special place in my heart. I mean, obviously I love Kacey Musgraves, but I also feel like there’s no other Christmas song that so accurately captures how I feel at Christmas. 

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My father’s birthday was on Christmas. He passed away in 2003, when he was only 55 years old. So every Christmas since he died, it’s been a double whammy of missing my dad during the holiday and missing him on his birthday. But I always felt like I had to put on a happy face (especially in situations like office holiday parties) and pretend I was having a great time so I didn’t bum everyone else out (“Happy holidays!” “Same to you, also, Christmas is my dead dad’s birthday!” isn’t really great party conversation).
I also wanted my son to be able to have a happy holiday without feeling like he needed to emotionally tend to me. That’s not his job. He’s a kid (although not a little one anymore; the jig has long been up on Santa). I want him to have fun on Christmas, which he does.

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Christmas was already a reminder of a big loss. Then, in 2022, my sister died unexpectedly, 3 days before Christmas. She was 45 years old. I had flown down to Nashville, where she lived, to see her in the hospital, even though she was on a ventilator and unresponsive. I was hoping for a Christmas miracle, a Hanukkah miracle, an interfaith miracle, or a non-denominational miracle. Any kind of miracle would have sufficed. 
For some reason, “Oh, What a World” by Kacey Musgraves kept running through my head when I was in Nashville (where Kacey Musgraves happens to live). I played the song for my sister through my smartphone, not knowing if she could hear it (especially over all the beeping machines and nurses coming in and out of the room), but hoping she would. “Oh, what a world, don't wanna leave, All kinds of magic all around us, it's hard to believe, Thank God it's not too good to be true, Oh, what a world, and then there is you,” Kacey sang as I sobbed. Maybe my sister would hear the song and think, “Wow. I don’t want to leave this world!” and would come back, as if she had a choice in the matter. But my sister died the next morning. I flew back to New York on Christmas Eve, crying the entire way. I waited until after Christmas to tell my son that his aunt had died. I didn’t want to ruin his Christmas. I had to pretend everything was fine.

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In 2024, Kacey Musgraves released the album Deeper Well, which contained the song “Cardinal,” about receiving signs from the beyond from someone she’d lost without warning. Later that year, she released extended tracks under the title Deeper Into the Well, which included the track "Little Sister." The first time I heard that song, I was driving in my car. I started to cry so much, I thought I was going to have to pull over.

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Recently, I saw Kacey Musgraves perform at Madison Square Garden as part of her tour for her latest album, Middle of Nowhere. It was not my first time seeing her, but it was my 15-year-old son’s first time. After years of him listening to Kacey Musgraves in the car while I drove him around to various activities, one day he said to me, “You know what, I decided I like Kacey Musgraves.”
I tried to play it cool. “Oh, really?” I asked. “You know she’s going on tour and Dad and I are going to get tickets to see her play. Do you want to come with us?” 
“Absolutely,” he said.
We saw Kacey Mugraves perform on the day that was my sister’s birthday (I didn’t remind anyone for fear of ruining everyone else’s good time). My son loved the show, and it made me happy, too.

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At Christmas time this year, and probably every year, I’m sure Christmas will still make me cry.
If it makes you cry, too, you should know that you’re not alone. And if you listen to the song “Christmas Makes Me Cry,” you might just feel like there is at least one other person who gets it. In fact, there are millions of us out there, crying on Christmas, remembering our loved ones and missing them.
Every year, I sincerely try. Oh but Christmas, it always makes me cry.


Janine Annett has previously written for March Shredness, March Vladness, and March Plaidness. She is the author of the humor book “I Am ‘Why Do I Need Venmo?’ Years Old.” She is working on a novel inspired by her late sister, which no one seems interested in. Learn more about her at www.janineannett.com.