“I put them together,” says Ray Benson of Willie Nelson and U.S. Senate hopeful Beto O’Rourke. To hear him tell it, Benson—the sole constant across Asleep at the Wheel’s 48-year run and a bona fide “FOW” (Friend Of Willie) since the early seventies—saw in O’Rourke a candidate Willie might want to get behind and, earlier this summer, cold-called Willie to run him through O’Rourke’s platform. “I don’t think I’ve ever asked Willie to do a political thing,” Benson says. “I’ve asked him to play benefits, to make records, and for help, but never a political thing.”

As it turned out, Willie liked what he heard—particularly about O’Rourke’s views on immigration and marijuana legalization—and asked if Benson might be able to arrange for Beto to come to his annual Fourth of July Picnic in Austin. O’Rourke accepted the invitation and huddled with Nelson and his wife Annie backstage before the show. At the end of the night, O’Rourke—who famously played bass in a series of El Paso post-hardcore rock bands in the nineties—shared the stage with Benson and Nelson. How’s O’Rourke’s guitar playing? “He has great enthusiasm,” Benson says. “Isn’t that the credo of punk music?”

Like Nelson—who will reinforce his endorsement by playing a rally for O’Rourke at Austin’s Auditorium Shores on September 29—Benson has performed for a variety of politicians of different political stripes over the years, although he says wading into the delicate intersection of music and politics is something he doesn’t enter into lightly. Our conversation for this week’s National Podcast of Texas explores that decision-making process and his relationships over the years with both Ann Richards and George W. Bush.

Also figuring prominently into our conversation is the future of Western Swing, the preservation of Texas dancehall culture, and the ever-changing state of the modern recording industry. And while Benson says Asleep at the Wheel is counting less than ever on album sales to pay the bills, they’re currently touring behind a brand-new release, New Routestheir first set of new material in over a decade.