One boast I can make without fear of hyperbole or contradiction is that I possess the world’s largest and most eclectic mix of Christmas music in these United States, if not the industrialized world. You’ll instantly agree with me if you’ve enjoyed any of the specialized playlists I’ve published here. It started with this post about underplayed Christmas classics and took off from there. Then I dredged up more undiscovered holiday gems and served up some Christmas Cocktails. Finally segue-waying into my Dance Party Christmas music playlist. And my Come To Jesus Christmas music playlist. But, surprisingly, one genre I haven’t adequately tackled on the Blogosphere is Cowboy Christmas. I’ll be correcting that oversight today.
First let me set the ground rules. As many of you may know, I draw a thick and distinct line between true Cowboy and just plain Country Music. While some Country Music can be Cowboy (hence, Country/Western) I demand that, to be truly Cowboy, the tune has to have some reference to the Cowboy experience. Or it has to be sung by a voice so distinctly Cowboy that, no matter what the words say, you imagine it being sung around the campfire out on the trail. I define the Cowboy Experience as including the Vaquero Experience and the experience of the estimated 10% of cowboys who were African Americans. I try to include the cowgirls. Yodeling is also a plus. So you’ll understand that I waded through — and rejected — a lot of my Country CDs before settling on this list which is presented in no particular order.
I hope these Christmas songs have you waving your Santa hat over your head and yelling a big Whooptie Ti Yi Yay, Pardner!
1. Rudolph the Red Nose Reindeer. Gene Autry. This is one of my least favorite Christmas songs ever. Yet, it has to be included, because the first recorded version was a big hit for that original of all media cowboys, Gene Autry. And when you listen to his straight-up Cowboy version, it’s not half bad. There are no references to cattle drives and, sadly, no yodeling, but I can imagine this being sung around the chuckwagon. At least in a Gene Autry movie. (And there’s an interesting backstory of how the song was created as an assignment for an employee of the Montgomery Ward Catalog Company. All of which has nothing to do with cowboys.)
2. Christmas Cowboy Style. Michael Martin Murphey. Since the first song had only tenuous links with the cowboy life, let’s turn to someone whose Cowboy Cred is impeccable. Some people maintain that Murphey single-handedly brought the Cowboy song back after it languished in obscurity for twenty years. He’s recorded, not one, but two Cowboy Christmas albums. This song is the title track from his first collection which, for my silver dollar, is the definitive Cowboy Christmas collection. With songs like The Creak of Leather, The Cowboy Christmas Ball, Ridin’ Home on Christmas Eve, and Merry Texas Christmas Y’all, this has enough roping, riding, horses and Christmas cheer to fill a whole corral. (His second Christmas CD, Cowboy Christmas II, is an accoustic Cowboy take on traditional carols.)
3. The Twelve Days of Cowboy Christmas. Riders in the Sky. Riding a close second is this Cowboy Christmas gem from everyone’s favorite cowboy trio. Their Christmas CD, Christmas the Cowboy Way, has it all — round-ups, roping, yodeling and Woody Paul (no relation), King of the Cowboy Fiddlers.
4. Two Step Around the Christmas Tree. Suzy Bogguss. Let’s get the cowgirls in here. And Suzy sashays in with a boot-scooting winner. This is from her Have Yourself a Merry Little Christmas CD, which is largely the traditional and the expected songs. But sung by Suzy Bogguss, all are kicked up a notch. Then hog-tied and branded.
5. Ding A Ling the Christmas Bell. Lynn Anderson. And speaking of cowgirls, I’ve declared loud and proud on this blog that Lynn Anderson is the All Time Greatest Cowgirl Singer — especially after she left the Nashville pap such as Rose Garden behind and turned her whiskey-tinged voice to bluegrass and cowgirl songs. In anyone else’s hands, this would be a song I would hate. It’s one of those come-from-behind hero teaches others the True Spirit of Christmas things like Rudolph or Little Drummer Boy. But Lynn puts it across. Lynn hasn’t made a Christmas album that I know of. I got this off Still Believing in Christmas which is a collection of songs sung by stars of the Grand Ol’ Opry. Whether you like this song or not, follow the link above and check out Lynn’s Cowgirl and Cowgirl II CDs.
6. Christmas in Mexico. T.G. Shepherd. I really wanted a Vaquero’s take on Christmas and I looked. Really I did. Maybe it’s still out there. A Christmas song about caballos and banditos and festively lit cantinas. But I couldn’t find it. In the meantime, from that same Still Believing in Christmas CD, is a song about yearning to get South of the Border for Christmas time.

Just in case you are getting too Holly Jolly, let Merle bring you down. At least you can rejoice in the fact that you’ll never have it tougher than Merle did.
7. When It’s Christmas Time in Texas. George Strait. You can always count on George. He’s put out at least three Christmas albums: Merry Christmas Strait to You, Classic Christmas and Merry Christmas Wherever You Are. This song comes from the first. All three are worthy of any Christmas collection. Even when he’s doing straight versions of Christmas songs, they’re Strait versions, if you know what I mean. Lots of Texas Cowboy feeling. In his take on We Three Kings, you have to keep reminding yourself that the kings weren’t riding on a Paint, a Pinto and an Appaloosa.
8. Pretty Paper. Willie Nelson. The Cowboy Experience isn’t all tinsel and wrapping. Sometimes it’s downright High Lonesome. What better voice to remind you of that than the Outlaw himself, The Red Headed Stranger. Willie can make even my most hated Christmas carol, Frosty the Snowman, worth listening to. Imagine what he does with a melancholy number like this one. Complete with that sad Cowboy harmonica. Perfect.
9. If We Make It Through December. Merle Haggard. As long as we’re crying in our beer, here’s the ultimate tearjerker. Merle sings, as only Merle can, about Dust Bowl type hardship during what should be a happy time. Want to count your blessings? Know that your life will never be tougher than a Merle Haggard song. Unless you’ve got prison, failed crops, faithless women and hard drinking in your future.
10. Honky Tonk Christmas. Alan Jackson. Okay, we’re turning Christmas on its head, but there’s no reason to end on a downer. In the album of the same name, Alan goes beyond Cowboy Christmas while avoiding all Christmas clichés. Of course, he includes Merle’s If We Make It Through December. As well as should-be classics such as Santa’s Gonna Come in a Pick-Up and Daddy (Please Don’t Get Drunk This Christmas). But to end this set, I’m choosing the upbeat title track.
That’s the list. Watch this space for more unconventional Christmas playlists. And, if you are keeping score during this Month of Crap and Culture, let’s file this post under Culture. On the Crap/Culture Meter, that’s two for the former, one for the latter. So I’m still more Crap than Cultured.
My husband could go toe to toe with you on the topic of Christmas music. He is driving us nuts already – even made up a special compilation CD for his truck.
Is this a veiled attempt do draw up some more eastern bloc support over the holidays??
I was askeared you was gon forget Alan Jackson.
Now please excuse me while I pop a top again. (And yes I know that’s really a Conway Twitty song.)