The Austin-based Western swing institution wasn’t always an institution or a Western swing band.

Ray Benson is on tour celebrating 50 years of Asleep at the Wheel. Officially, that anniversary came in 2020, but thanks COVID. Their anniversary album, Half a Hundred Years, included tracks by the current lineup and guest appearances by Asleep alumni.

“On March 7, 2020, I was sitting right here,” Benson says, sitting in his house not quite an hour outside of Austin. “Had a film crew. Studio all set up. Everything stopped. People were coming in from Australia and California, Vermont, Nashville, and they said, We’re not getting on a plane. Everything got cancelled.”

But as a lifer with 50 years under his belt, Benson figured out what to do next. The band regrouped, made new plans, and in October 2021, Asleep was finally able to tour with some of the original members. “It was really incredible,” Benson says. “Chris [O’Connell], LeRoy [Preston], and myself—the parts were all there. Everybody just opened their mouths and sang. Same with Danny [Levin] on fiddle. It was amazing to realize that the musical bond you have with people is probably permanent.”

Asleep at the Wheel play Jazz Fest on Saturday (Sheraton New Orleans Fais-Do-Do Stage, 4:35p), and when the band started, it wasn’t a Western swing band. “We went out to discover the roots of American music,” Benson says. Western swing was one of the styles they picked up and discovered they had some facility for. “It became part of our repertoire, but we did country music and honky tonk music. We did Cajun music and country folk music. We had the instrumentation of a Western swing band, but it wasn’t until the late ‘80s that we morphed into a pure Western swing band.”

Today, it’s hard to imagine how a string band fit into 1970, but the Grateful Dead were inspired by bluegrass and Gram Parsons and The Byrds flirted with country on 1968’s Sweetheart of the Rodeo. Asleep at the Wheel found common spirits in The Lovin’ Spoonful and Commander Cody and His Lost Planet Airmen, whose guitarist Bill Kirchen will play Jazz Fest on Saturday, May 7.

Commander Cody leaned more on rockabilly than Asleep at the Wheel, but “they were quite an inspiration,” Benson says. “Also the Flying Burrito Brothers. We were doing similar things in a different vein.” He thinks about his generation as one that grew up on rock ’n’ roll “and a lot of other things.” Specifically, Benson also came of age listening to jazz. But he and his peers shared the idea that country music could speak to an audience beyond the southern, working class, conservative, Christian one it was associated with.  

When Asleep at the Wheel moved from West Virginia to Austin, Texas, they found their people. Before that point, the responses of their audiences were unpredictable. Some clearly got it; others definitely didn’t. It didn’t help that they were often opening for rock bands like Alice Cooper in the Washington, D.C. area. 

“That was why we came down to Austin and the Armadillo World Headquarters,” Benson says. “It was like home.” 

Austin welcomed them because older audiences liked hearing a band that loved the same music they did, and younger audiences appreciated how they conferred an element of cool on their parents’ record collections. 

“We were the only band that could play the ‘redneck’ dancehalls and the hippie rock joints,” he says. “That was our calling card.”

These days, they tour regularly, and record when they can, more to have vinyl to sell at the merch table than because albums sell like they once did. 

It’s to Benson’s credit that Asleep at the Wheel albums sound so consistent since he is the only original member left in the band. He half-jokes that his greatest talent is his ability to convince good musicians to join. “I’m 71 years old and convinced 30-something guys and gals to do the same thing,” he says. “It’s like joining the foreign legion or the circus. C’mon.” It helps that the Internet and changes in music distribution have helped a crop of great players develop overseas, including their Italian pedal steel player Flavio Pasquetto, who became interested in the instrument after seeing videos of it on YouTube.

Benson’s strategy has been to make limited edition, special recordings to create a little urgency, but he rejects the idea that including guest artists on Asleep at the Wheel’s albums is part of that concept. They have always been a part of Asleep albums—thought not in the same number, I’d argue—but more importantly, “I’ve always said—and I quote Willie Nelson on this—I got into this so I could play with folks I admire,” Benson says. “Collaboration’s what it’s all about.” On Half a Hundred Years, those include guest performances by Nelson, Lyle Lovett, George Strait, Lee Ann Womack, Emmylou Harris, and Bill Kirchen. 

Benson can be a raconteur, but he can also be more contemplative than his stage persona might suggest. Admittedly, there’s nothing like a 50-year anniversary to make you think seriously about your life’s work, and the band experiencing a collective bout with COVID a month ago added some gravity. “I’ve been doing this for 50-plus years and it’s always something,” he says. In print, that reads as a little facile, but when he says it, you can hear that it’s a realization born from good times and struggles. The band has had some dark times, but Benson declines to elaborate. His answer isn’t something said to avoid a hard question. It’s lived experience. 

“The pandemic. The weather. All you can do is soldier on.”

Asleep at the Wheel plays Jazz Fest on Saturday, April 30 at 4:35 p.m. on the Sheraton New Orleans Fais-Do-Do Stage.