Asleep at the Wheel’s Ray Benson on Keeping the Texas Band Alive, Alert and Swinging for 50 Years

On April 16, Benson celebrates his 70th birthday (in conjunction with, as always, a fundraiser for the Health Alliance for Austin Musicians). Later in 2021, Asleep at the Wheel will throw itself a 50th anniversary party. He reminisces about the group's wild half-century ride.

50th anniversary western swing birthday haam
Mike Shore

“It’s just a number,” says Ray Benson, waxing modest about a couple of big ones that are arriving this year for himself and his group, “but as you know, being in the business, publicists need something to hang their hat on.” Then again, honoring significant round numbers feels appropriate for someone who invented the Wheel — Asleep at the Wheel, that is, the progressive Western-swing group that will be commemorating its 50th anniversary with an all-star show, God and vaccinations willing, in Austin in the fall of 2021.

Benson, meanwhile — seemingly a native Texan, but who really came to Austin by way of California, by way of his truly native Philly — will be celebrating his 70th birthday on March 16. For the last decade and a half or so, he’s always had a co-celebrant: HAAM, the Health Alliance for Austin Musicians, an organization he co-founded more than a decade ago to help provide health care for his adopted hometown’s indigent musicians… which, not to put too jokey a point on it, is most of ‘em. (Amid all the serious talk about health crises, he can’t help repeating the old joke: “What do you call a musician without a girlfriend? Homeless.”) In Austin, Benson’s birthday is nearly worthy of city holiday status, and the alliance always marks it with a South By Southwest-concurrent fundraiser, which will be a virtual one this month.

The fact that maybe Benson does take some pride in Asleep at the Wheel’s big milestone is reflected in the title of the album that the group has coming this fall: “Half a Hundred Years.” These five decades haven’t been all unerringly successful ones, as Benson made clear in his revealing and often hilarious memoir, “Comin’ Right at Ya: How a Jewish Yankee Hippie Went Country, or, the Often Outrageous History of Asleep at the Wheel.” The band leader could have used some health care assistance himself, he admits, in the down times between major- and minor-label record deals, or in moments anyone else might have guessed were triumphant. Benson has enough of a feel for humble absurdism to have opened his book with an ironic anecdote about how, in 1979, the band played to a crowd of eight customers at a club in Lubbock — the same night they were being awarded one of their many Grammys in absentia on the west coast.

Starting out at 19, Benson says, “I was hoping for 10 years, honestly. Especially for country musicians, if you were lucky enough to have a hit, you’d get on the road and do your thing,  then become a disc jockey or guitar teacher. Because the road is such a hard life. But I just loved it, and I don’t give up on anything. So that’s just part of my being. But I really loved seeing America and the world, and getting in that bus and going. To have a life and play the road like we did for the last 50 years is a real challenge and commitment. As one guy said who left the band said, ‘Listen, I gotta go. I’ve got to take control of my calendar.’ And I said, ‘Oh yeah.’ Because with us, if we’ve got a gig, we’re going. It doesn’t matter if it’s your kid’s soccer game — we’re gone.”

Gone and always going, even if part of the bus had been sheared off in an accident and snow and rain were coming in through the tarp on the side. “There were times when I collapsed on the floor, crying my eyes out: ‘What am I going to do now?’ But it was never ‘What can I do to get out of this?’ It was, ‘What am I going to do to fix this and keep going?’ That’s just who I am. My mom used to say, ‘I can’t win an argument with you because you just don’t stop,’” he laughs.

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Ray Benson of Asleep at the Wheel Courtesy Asleep at the Wheel

Having escaped the Vietnam draft, Benson and a few of his Philadelphia cohorts moved to rural West Virginia as the ‘60s turned to the ‘70s to live off the land in ramshackle cabins and literally woodshed their bizarre-to-their-friends interest in what Benson still calls “country-Western.” The Western-swing subgenre especially interested Benson because, like the jazz and blues he also loved, it was improvisational music. Asleep at the Wheel moved to Northern California and became part of a hippie-country scene with Commander Cody and His Lost Planet Airmen — a much more raucous one than the laid-back country-rock in SoCal. They toured as the backing outfit for Stoney Edwards, the Black country singer who never achieved Charley Pride’s success. (“It was 1971, and here was a Black Indian from Oklahoma with a hippie band!”) They relocated to Austin, for good, between their own first and second albums, while also continually dipping toes into Nashville’s mainstream country music.

“We were not Southern rednecks, but we wanted to be a country-Western band that had hit country-Western records, and we succeeded greatly with that,” Benson says. “But the interest in blues, Western swing and improvisational music was where it was at for us.” When it came to Nashville, “we revered the local players, the studios, the songwriters. And it was that love/hate thing: We love what you did. We don’t like what you’re doing,” he laughs. “It was the industry we knocked heads with. Because we had a top 10 in 1975 with ‘The Letter That Johnny Walker Read,’ a joke song we’d written with Porter and Dolly in mind, and all of a sudden they’re going, ‘Oh shit, we got a brand name — boom.’ They did what Nashville does, which was try to find us hit songs. But we went, ‘All right, let’s get crazy and let’s do all this stuff we really want to do!’”

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Asleep at the Wheel in the early days Courtesy Asleep at the Wheel

Willie Nelson and Doug Sahm had convinced them to move from Cali to Austin. “Willie said, ‘Yeah, you can open a show — a hundred dollars.’ ‘Oh shit, we’re there!’ Willie wasn’t the icon that he was; we were playing 200-, 300-seat honky-tonks with him then. But the Austin people who were our age, though they weren’t Western swing groups, were playing roots music, whether as singer-songwriters or doing Texas country. It was a lifestyle more than a musical style. There wasn’t any ‘Austin sound.’ And that’s why Nashville or the establishment didn’t like it, because they couldn’t automate it. But all of a sudden you had Willie, Waylon, Michael Murphy, Jerry Jeff Walker, Delbert McClinton, and later, the blues scene with my friends Jimmy and Stevie Vaughn and those guys. I got the Fabulous Thunderbirds their first record deal.

“It was just wonderful. I could do all my business walking around town or riding my motorcycle from one honky-tonk bar or eatery to another, all run by like-minded people. There were movies being written and books being written — and yet all these people hung out at all the clubs. Every night, it was like, ‘Where are we going?’ — when we weren’t on the road for those 200 days a year.” Nashville took another interest in Texas in the ‘80s. Benson reels off the names: “Lyle Lovett. k.d lang. Rodney Crowell. Roseanne Cash. The O’Kanes. Steve Earle. Mary Chapin Carpenter. And Asleep at the Wheel. There was an incredible renaissance of great music from ‘85 to 90 — until Garth Brooks, basically. And that was when Nashville and Austin got along beautifully.”

Cameron Duddy, bass player for the country band Midland, and an immigrant to Texas himself, is one of those who associates Benson’s band with the city. “We love Asleep at the Wheel,” says Duddy. “When you arrive here in Austin, you know whose town this is, just in the airport alone. This is a Willie Nelson town. This is a Dale Watson town. And this is an Asleep at the Wheel town. And if you want to make it, that’s the bar. You have to be that good. I’m not sure we ever made it that far, but that was our aspiration, and that’s why we moved from California. You know, it was like, ‘Oh, here, there’s a different level of commitment. And if you can’t cut it here, then you don’t deserve to be on stage.'”

Of the days when Austin could still be kept reliably weird: “Those days are gone. But it’s like how anybody who’s lived in Manhattan knows that it is a huge city, but it really is a bunch of small towns within the city. So there’s still that in Austin. But the do-it yourself, by the seat of your pants town, that’s over, just because of the financial strings of living here. Musicians, unfortunately, now, I just don’t know how they make it. We have a housing shortage. For $1,500 a month, you can barely get a 600-square-foot apartment. The California money has come in. Elon Musk and Joe Rogan and all these people, they’re not what Austin’s about. But they are what Austin is going to be.”

For those that find themselves indigent, “the town is so supportive of musicians with a bunch of nonprofits that help, including the Sims Foundation and, of course, the Health Alliance for Austin Musicians is incredible.” (More information on that below.)

When it comes to his own health, Benson was diagnoses with hepatitis when he was 50. Last year, he was one of the earliest boldfaced names to come down with COVID-19, and came through it OK. “I’m an early adopter,” he explains. “I tell people I’m Superman. I’m the king of viruses.” Benson had a whole section on viruses in his memoir, which seems prescient now. “My little brother, or not so little, is a genetic immunologist up in Northwestern med school, and we discuss how there are all these little beasties just waiting to get to us. These little bitty suckers are here to kill us. And antibiotics are probably on one of their last legs of effectiveness, within the next hundred years or less. It always interests me; I understand a little bit about public health. But I like to say: I’m not a scientist. I just stayed at a Holiday Inn the other night.”

Nowadays, one of Benson’s biggest champions is a guy who used to open for them: George Strait, for whom Asleep at the Wheel was opening in Texas stadiums at the time the pandemic hit. Strait is no Commander Cody, but Benson loves having him in command of keeping a Western-swing sound alive. “George is a Republican and I’m a Democrat, let’s put it as clearly as that. George is a matinee idol, whereas Asleep at the Wheel never could have fulfilled that role; we were renegades. But though we come from very different backgrounds, but we’re of the same generation and came to the same place.” Literally and otherwise. “We have similar musical tastes, and both believe in a Texas that is our home.”

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Asleep at the Wheel Courtesy Asleep at the Wheel

As integrated into both the mainstream country and Americana scenes as Asleep at the Wheel has been, Benson never loses sight of the things that still make him a happy interloper. “People had never met a Jew before,” he recalls of his early days. “I remember we were on a bus with Tammy Wynette, and the bus driver goes, ‘Yeah, it’s them damn Jews in New York who are keeping Tammy’s music down.’ I went, ‘Steve, I’m Jewish.’ He said, ‘You’re not — come on!’ Nobody knew. I was too tall to be a Jew,” Benson laughs. “I had red hair and I was 6-foot-7 and wore a cowboy hat and sang country music. So, no, it wasn’t until I basically made a point about it that people realized. And that was exactly how I wanted it, because I wanted them to love me first and go, ‘Holy shit!’”

Short of maybe a hero like Bob Wills, no one has ever gotten more deeply inside this music than Benson. “I always felt like I was one of those English guys, like Clapton, who discovered American blues and were able to turn America onto their own music. That’s the way I always felt: coming in from being an outsider was the best thing.”

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Asleep at the Wheel Andrew Bennett


Asleep at the Wheel and HAAM Keep an Austin Charitable Collaboration Going

Asleep at the Wheel’s Ray Benson has always been willing to ham it up for HAAM, the Health Alliance for Austin Musicians, which he helped co-found in 2005. “For about the last 10 years, Ray has used his birthday — which happens during South by Southwest — to help raise funds and awareness,” says HAAM CEO Reenie Collins. “He’s always used his contacts and friends nationwide to pull together a really diverse group of musicians that puts on a unique show for us. And his 70th (birthday) and their 50th (anniversary) is being tied into lots of things,” starting with an online invite celebrating the former on March 16. (Go to myhaam.org for details and to donate.)

HAAM’s local musician beneficiaries “keep trying to get back up off the ground,” Collins says, “especially now with live music being one of the first things to go and one of the last to come back. And I don’t think people really realize that often musicians are working two or three jobs” without full-time insurance, providing the engine that keeps the “live music capitol’s” cultural economy alive. Austin is home to an estimated 8,000 working musicians, and HAAM helps about 2,700 per year get access to care, on an operating budget of $3 million. “There really isn’t another city in the country that has something for musicians that does what we do.”

The org was founded pre-Obamacare, and helping musicians navigate that system to get access now is just one part of what HAAM does. “Having this to address these issues when I needed it would have been nice, but that’s why I do what I do,” says Benson. “Imagine a city where musicians get health care! It’s happening.”

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Fundraising for HAAM (the Health Alliance for Austin Musicians) Brenda Ladd