Welcome to the beautiful intersection of country music and the holiday season. The punch has a bit too much brandy in it. The vibe borders on melancholy, but by God the songs are classics. The country genre has this way of tapping into the best parts of Christmas, reveling in them for just about three minutes, and then leaving your heart wide open for the rest of the year.
For our selection, we tried to choose an assortment that highlighted both the happy and the not-so-happy without just listing a whole bunch of covers of tunes you already know. We already know that the unimpeachable rendition of “Have Yourself a Merry Little Christmas” belongs to Judy Garland, so we let that one be. What you’ll find here is a collection of cuts that will enhance your holiday playlist without having nineteen versions of “Jingle Bells.”
So get your spiked cider and some cookies and hit play. And if you’re on the hunt for more groovy festive fare, check out our list of the best new-ish Christmas albums.
“Hard Candy Christmas,” Dolly Parton
Arguably, the Christmas bop, the song wasn’t initially intended to be a Christmas anthem (believe it or not). It was first used in The Best Little Whorehouse in Texas and then was adopted by the sad Christmas souls that needed a song full of suggestions on how to overcome the holiday blues.
“Tennessee Christmas,” Alabama
You might think of “Christmas in Dixie” when you think of Alabama’s holiday offerings, but “Tennessee Christmas” is the tender cousin to the former.
“If We Make It Through December,” Merle Haggard
This isn’t a Christmas song exactly, but we’d be remiss not to include it here. The woful track cuts into one of the hallmarks of country music in the most beautiful way that it simply makes sense.
“It’s Christmas Eve,” LeAnn Rimes
Is this from a Hallmark movie? Sure. But it’s also a reminder that LeAnn Rimes has one of the most textured voices in country music. Heartfelt and understated, “It’s Christmas Eve” is sincere enough to overcome its kitsch.
“Country Christmas,” Loretta Lynn
Sweet, Loretta. “Country Christmas” is an underrated holiday gem, but to put together a list of country must-listens and not include a track from Loretta is to not understand country or the holiday season.
“Christmas Without You,” Dolly Parton & Kenny Rogers
The only artist who received double inclusion on the list! Dolly understands what makes the holiday so emotional, and she’s all the better for having the late, great Kenny Rogers in tow. If “Hard Candy Christmas” is the lament of the single person throwing their hands up, “Christmas Without You” is the upbeat 80s twist on missing the one you love on the celebratory day.
“I’ll Be Home for Christmas,” Rascal Flatts
This is included (and will always be included), if for no other reason than Gary LeVox’s a capella opening lines. The rest is great too, but my God, the opening!
“Christmas Makes Me Cry,” Kacey Musgraves
It’s heartbreak from start to finish, which makes it perfect. Tapping into the undercurrent that the holiday season can be quite difficult for more people than not, Musgraves doesn’t lean into any gimmicks or quick punches. “Christmas Makes Me Cry” is a thoughtful, honest look at the bluer parts of festive season.
“Snow Globe,” Pistol Annies
The most recent release on the list, Pistol Annies have entered the Christmas song arena with a playful take on the holiday anthem. This is the first drop from their upcoming themed album, but it makes you wonder why Miranda Lambert, Ashley Monroe, and Angaleena Presley haven’t gotten around to this project sooner.
“All I Want for Christmas is a Real Good Tan,” Kenny Chesney
This would sound like a parody song if it were sung by anyone else but Kenny Chesney, but considering that it’s the permanently shirtless beach bum of country, you know this is less of a joke and more of a legitimate wish. No bells or kitschy instruments here: just cool beach boy vibes.
“O Holy Night,” Brandi Carlile
It’s Brandi Carlile. And Christmas. We need the whole album, but until then, this will get us through.
“The Angels Cried,” Alan Jackson ft. Alison Krauss
Country music, perhaps more than any other genre, really leans into the religious side of day, resulting in some of the most beautiful tracks played during the season. Here, Alison Krauss lends her vocals to an Alan Jackson classic. The results are a reminder that when Krauss has a mic, you’re already halfway to angel status.
“Where Are You Christmas?,” Faith Hill
It’s the holiday epic of the modern country music genre. The Whitney Houston of Christmas songs. Released at the height of Faith Hill’s career, this one is for belting in the car or with your family, together, perhaps after one too many mugs of mulled wine.
“Pretty Paper,” Willie Nelson
In all of Nelson’s offerings, of which there are many, “Pretty Paper” may be one of his greatest contributions. There’s something about WIllie’s vulnerable, familiar voice that makes “Pretty Paper” one of those songs that may be replicated, never duplicated.
“O Come, O Come, Emmanuel,” Sugarland
Leave it to Jennifer Nettles and Kristian Bush to put a beautifully haunting, banjo-fied twist on what many write off as a boring traditional Christmas song. Actually, Sugarland’s whole Gold and Green album is woefully underrated.
Justin Kirkland Justin Kirkland is a writer for Esquire, where he focuses on entertainment, television, and pop culture.
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