Ray Benson’s Texas Christmas Playlist
Talking holiday songs (and Willie!) with the man behind Asleep at the Wheel

Perhaps no Texas singer-songwriter is as associated with Christmastime as Ray Benson. With his Western swing band, Asleep at the Wheel, he’s recorded three holiday albums1, each mixing traditional tunes with homespun originals, with guests including Willie Nelson and Dale Watson. They’re a staple this time of year around my house, and you can find Ray playing shows everywhere from Austin’s Armadillo Christmas Bazaar tonight (a solo engagement) to the legendary Gruene Hall down the road this Sunday with the full band.
I reached out to him to hear what he loves about a Texas Christmas, why Texans write great holiday songs, and, of course, to get a playlist of his favorite Christmas songs from the Lone Star State. Here’s what he told me — including his tips for recording with Willie — followed by that playlist with his liner notes. Merry Texas Christmas, y’all.
SES: What makes a Texas Christmas special?
RB: I've been living in Texas now for 52 years, and I always love that it’s not a white Christmas. [Laughs.] It’s also some of the traditions, especially the Mexican-American stuff — the tamales2. When my kids were small, we would go down to the municipal golf course, which they would close, but you could go play.
What are your favorite holiday rituals?
I grew up Jewish3, but my family celebrated Christmas, too. We always did Hanukkah-Christmas, so the kids always got more presents than they deserved.
Why do Texans write great Christmas songs?
That's the whole Texas thing. You can use Texas as the whatever. Whatever the relationship is, it's Texas with Christmas. So Santa’s riding a horse [laughs]. You can always put a Texas spin on it, which is a Western spin on it. That’s probably the most fun part of it. You can tie all of Texas — all of the mythologies, all of the realities — into the Christmas songs.
What makes a great Christmas song?
There's the gimmicky ones. “Baby, It's Cold Outside,” which is a very cool novelty tune. Same with “Rudolph,” same with “Frosty the Snowman.” And then you have the spiritual ones — “Little Town of Bethlehem,” etc. I guess, thinking about it, it breaks down into two things. You're either singing about Jesus, or singing about Santa Claus.
Those are the two big guys this time of year. Your Christmas album was recorded in summer. Did you do anything special to make it feel festive?
Katie4 would always string lights and Christmas stuff in the bus. We called her Christmas Katie, she would always make sure we did that.
Nice.
I’m staring at our Christmas tree, which my girlfriend makes me do every year. I told her, “No more live ones.” Back in the day, when I lived in the Hill Country, my nephew and niece would come, and we would go cut down a cedar tree, do a real Christmas. [Laughs].
Speaking of: What’s on your Christmas list this year — what do you hope to find under that tree?
I discourage gifts. I’m at the point in my life where I’m trying to get rid of stuff. [Laughs.]
No, I love the season. I love the singing of Christmas carols. I think that’s the greatest thing. If you can get people singing in public with a group, I think it's so important. I wish there were more carolers.
Any memorable Christmas gigs over the years?
Yeah, one time at Gruene Hall, it was a New Year's Eve gig. This might be about 10 years ago. New Year's Eve fell on a Monday or a Sunday, I can't remember. The town rules were, the bar is closed at 12 o'clock. And I'm sitting here, [saying], “You're going to close down this bar at midnight on New Year's Eve?” “Yes, we are.” “All right.”
And so I gathered the band and said, “Here's what we're gonna do. At 11:50, we're gonna get our acoustic instruments, and we're gonna start walking through the crowd, out the bar, playing ‘Auld Lang Syne.’ And the crowd will follow us out, and then we'll play a few songs on the sidewalk, and call it a night. At 12 midnight, we'll be outside.”
The entire place exited, and the guys at the bar went, “That was fucking brilliant, man. You know how hard it would have been to get those people out of here?” But the pied piper led them out, and so the cops didn't arrest nobody.
And then the same thing happened in Alpine! The guy said, “You’ll be shut down.” And we begged him, and he said [humorless police voice], “Okay. 12:15.”
And now, Ray Benson’s Texas Christmas playlist, along with his liner notes:
“When It’s Christmas on the Range”; “Santa’s on His Way,” Bob Wills & His Texas Playboys
Christmas music, I love. When we did the Christmas records, I started researching that. Going from the oldest to the newest, the oldest is the two from Bob Wills — “When it's Christmas on the Range,” and then “Santa's on His Way.” We recorded that one [on Santa Loves to Boogie5]. Those are the two oldest ones that I can think of, except…
“Merry Texas Christmas, Y’All,” Gene Autry
…of course, Gene Autry. Gene Autry was the original, and Ernest Tubb was the one I learned it from. We've recorded it, and done a commercial for H-E-B grocery store with it.
“Rudolph the Red-Nosed Reindeer,” Gene Autry
That’s as standard as you can get.
“White Christmas,” Bing Crosby
I always include Bing Crosby. People will say, “He’s not Texan,” but he did a whole album, Don’t Fence Me In, it’s a country-western album. I understand Bing is not from Texas, but he made those records so I consider him a Western artist — when he wanted to be.
“When It’s Christmas Time in Texas,” George Strait
We recorded this.
“Hot Texas Christmas Day,” Dale Watson
We did this with Dale. He wrote it. I love that one.
“Santa Got Busted by the Border Patrol,” Kevin Fowler and Ray Benson
[Laughs] I really like it.
“A Willie Nice Christmas,” Kacey Musgraves and Willie Nelson
I was there when they recorded Willie's part. They came down to Austin, and I helped them familiarize themselves with how to work with Willie: Make sure you roll your joints right, and don't tell him to do it again.
“Pretty Paper,” Willie Nelson and Asleep at the Wheel
It was a big hit for Roy Orbison, but there's so many versions — there's a hundred versions of it. We did a duet with Willie, so that's my favorite. I think we did it two different times, maybe, I'm not sure6. But what a great song.
How to work with Willie: Make sure you roll your joints right, and don't tell him to do it again.
“Merry Christmas from the Family,” Robert Earl Keen
I spent Christmas with Robert Earl Keen’s family one time, many years ago, and it was a whole lot like the damn song. His mother-in-law came in, and his wife had cooked the turkey and everything. And the mother-in-law came in with her own turkey, because she didn't trust the way that Kathleen was going to be cooking the turkey. It was hilarious. To me, in terms of the modern day, that is the quintessential Texas country-western Christmas song.
And, of course, every Christmas it’s like a bank account for him. He just does it to the max. One time I saw him, he was dressed up as one of the Magi, one of the gifts.
“Xmas in Jail,” Asleep at the Wheel
That was my favorite. The original group was an R & B group. I'm sorry I don't remember their name7, but that's where I learned it from. Our video on it is just fantastic. I hope YouTube hasn't scrubbed it yet8.
One last thing: Benson works with two important local nonprofit organizations, one of which he helped create: The Health Alliance for Austin Musicians (HAAM), which provides health coverage for local artists; and HOME, which provides housing assistance for aging musicians. Learn more, and consider donating if you can, at the links above.
Merry Texas Christmas, Y’all (1997); Santa Loves to Boogie (2007); Lone Star Christmas Night (2016)
I wish I could embed a recording of how Ray enunciates tamales. It’s enticing — no wonder H-E-B has him as a spokesperson.
Benson adds: ”My joke was you couldn't have Christmas without Jews. Because Jesus was Jewish [laughs]. And so many of the Christmas songs — Irving Berlin, etc — were written by Jews. I always thought it was hilarious.”
Shore, I think — the talented singer and fiddle player who sometimes joins Asleep at the Wheel, as she did for Lone Star Christmas Night.
Sadly, not on Spotify.
They did! On both the 1997 and 2007 holiday albums.
I had to look it up myself. It was The Youngsters, and they recorded it back in 1956.
Fear not, it’s still there!