“I never thought I’d last a half a hundred years,” bellows the smooth baritone of Ray Benson on Asleep at the Wheel’s “Half a Hundred Years” — not a lot of folks have had this kind of longevity in the music industry.
From behind a big white beard, Benson’s answer to his showbiz success is preceded by a deep, hearty chuckle: “Stubbornness, I guess. You know, whenever the time came where we’d go, ‘Well, are we going to keep doing this?’ I said, ‘Oh yeah, I love doing it.’ I love playing. I love touring. And I got a few more years. As long as my health holds up and people keep coming to the shows, I’ll keep doing it.”
As the autobiographical title track from his 2021 album — reportedly his 26th studio record with the outfit he founded in 1970 in Paw Paw, West Virginia — runs its course, Benson quips: “Might catch up to Willie one of these days.”
The Red Headed Stranger has been a friend of the band since the early days, encouraging the budding group to relocate to Austin in 1973, knowing they’d find more receptive audiences in Texas. In 1976, Asleep at the Wheel was the inaugural guest on the first official episode of “Austin City Limits” and has appeared 10 more times over the subsequent five decades.
In the early ’90s, Benson and Asleep at the Wheel decided to pay homage to Bob Wills, the godfather of Western swing music — the sound they’d been attempting to keep alive for the next generation.
“It was a hybrid form of music that was championed by many bands and singers and players from the ’20s, ’30s, ’40s and ’50s. Then in the ’60s, it really sort of disappeared,” Benson explains. “It was not mainstream music. Rock ‘n’ roll really kicked its butt, and then modern country music, too.”
So how’d Asleep at the Wheel make a living beating a dead horse during its nascent years? And how did Western swing become, as Benson puts it, “part of the fabric of American popular music”?
“We had a very small part in helping that, along with Merle Haggard and Willie Nelson and dozens of [others],” Benson says. That 1993 “Tribute to the Music of Bob Wills and the Texas Playboys” — which features Haggard and Nelson plus Dolly Parton, George Strait, Garth Brooks, Lyle Lovett, Huey Lewis, Brooks & Dunn and many more, including original Wheel players Lucky Oceans, Chris O’Connell and Floyd Domino — helped as well.
“I really have to credit Willie Nelson — and Merle Haggard — for really backing us with their endorsement, almost, you know?” Benson reflects. When putting that record together, “the first person I would go to is Willie — he’s my close friend. And so as soon as people heard, ‘Oh, you’re doing it with Willie,’ or Merle, then all these people jumped on board.”
They jumped again in 1999 on “Ride with Bob” — again featuring Haggard and Nelson plus Reba McEntire, Dwight Yoakam, The Chicks, Lee Ann Womack, Tim McGraw and more — before skipping forward to 2015’s celebration of Wills on “Still the King” with — you guessed it — Nelson and Haggard alongside The Avett Brothers, Amos Lee, Old Crow Medicine Show, Del McCoury, Brad Paisley, Shooter Jennings and then some.
Notable as these collaborations may be, they are just a small sampling of the Wheel’s incredible recorded output. Ten Grammy Awards may sound impressive, but this is a live band — one that’s seen more than 100 musicians attend the Benson school of Western swing. And maybe that’s how he’s kept the tradition alive.
“I’ve had the luxury of always having a band, between six piece and 12 piece. And right now, we’re usually seven or eight pieces,” Benson says. “When they [new players] join the band, we tell them a very simple thing: Here’s the tape, or here’s the file,” Benson chuckles, “of what went before. Learn the song, learn the way we’ve done it. And then add whatever personality and technical ability you have to that. That’s what works, because then they have something to build on, as opposed to something to just ape.”
As the Wheel rolls on, today’s touring band features steel guitarist Curtis Clogston, Jonathan Doyle on sax and clarinet, Radoslav Lorkovi on piano and accordion, bassist Michael Archer, drummer Russ Patterson and newcomer Ian Stewart on fiddle.
“When they join the band, I feature them. That’s the deal,” Benson adds, highlighting his innate ability to guide this group without ego throughout the years. “Sure, I’m the bandleader and I sing most of the songs,” he continues. “There are plenty of sideman gigs, but there are not a lot of gigs which enable him [Stewart] to sing the lead, write songs, be featured as a soloist, etc. And to me, that just makes the band that much better.”
From tributes stacked with icons of country music to more than 50 years of two-stepping originals, “the camaraderie among musicians is so important because that’s where great collaborations bring great music,” Benson sums up. It’s the reason Asleep at the Wheel still exists after all these years, and why “there’s a whole new crop of young folks that have taken the influences of Western swing. Although not playing Bob Wills’ music,” he continues, “still, the influence of Western swing music [is present] — i.e., the improvisational nature of the soloing. You look at acts like Sierra Ferrell or Billy Strings and some of these young folks, some of it’s based in bluegrass, but it’s also got a little foot in swing music and whatnot. So they’re taking all of the different influences and making new music based on older forms. And that’s what we always said we were doing.”
Asleep at the Wheel’s trajectory showcases a beautiful mashup of modern and bygone eras. Making an old style of music feel new again, there’s a line from the “Half a Hundred Years” track “There You Go Again” with Lyle Lovett that says: “There you go sending Venmos, to folks you barely know / There you go quoting Shakespeare, you never read him this I know!”
“Obviously I’ve had to adjust with the times or we would not be successful,” Benson says matter of factly. His sons, who he runs the business with, help him stay up to date. “If you don’t follow the technological changes that enable you to do things easier, faster, cheaper, you’re probably not going to be able to do it.”
“People ask me: What was the biggest change in your life from 1970 to the present? The first thing that was the biggest change was the fax machine,” Benson laughs. “The second thing was mobile phones, obviously. We got some of the first and it just changed our entire life. It was so amazing. It used to be you had a sack full of quarters and you’d use pay phones.”
Truth be told, life on the road hasn’t gotten simpler even with present-day advances — and, unsurprisingly, everything costs more money these days. “We’re coming up to Bend. To get from Austin, Texas — the first show will be in Portland — well, just to drive the bus up there costs thousands,” Benson says. (Not to mention the challenges of navigating our Central Oregon city: “The one thing I always say about Bend,” he pauses to laugh, “I’ve never seen a city build so many roundabouts. To take a 45-foot bus around those things is always a game.”)
“We have a Happy Trails plan that in a couple of years we’ll stop with the year-round touring, but we’ll never stop playing as long as I’m capable.”
When the Source Weekly spoke to Benson in late January, he was at home in Austin, “working on a new album” based around a concept that he calls “a pretty safe bet.”
“It’s an album of all Texas songs. We’ve been talking about doing this for about 15 years, and so I guess we finally got around to it.” More Texas standards — songs by Guy Clark, Peter Rowan, the Carter Family, Bob Wills and a Benson original.
When all is said and done, the legacy of Ray Benson may very well be right up there with the aforementioned. Too humble to say it himself, but it’s likely the ditties of Western swing would sound much softer without the torch-bearing efforts of Asleep at the Wheel for the last 55 years and counting.
Asleep at the Wheel
Wed., March 19; doors 6:30pm, show 7:30pm; all ages
Tower Theatre
835 NW Wall St., Bend
$44-$144
Get tickets
This article appears in The Source Weekly March 6, 2025.
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