Evan Smith: Let’s do the most important question first: How tall are you, actually?

Ray Benson: I was six seven, but now I’m six six and a half. I shrunk.

ES: Who can tell?

RB: When I put on my cowboy hat and boots, I’m seven feet tall. That’s what really matters.

ES: Practically speaking, has your height ever been an issue for you?

RB: Absolutely. I did a movie of the week with Dolly Parton in 1991 called Wild Texas Wind. She’s five feet tall. They had a problem shooting us—you know, dig a hole for Ray or put Dolly on a box.

ES: Is it ever a problem for you from a music standpoint?

RB: Just hitting my head onstage.

ES: Were you tall as a kid?

RB: Yeah. I was a starting basketball player at a fancy Philadelphia prep school where most cowboy singers come from. I quit my senior year because I had broken four fingers and two thumbs—it was killing my guitar playing.

ES: Music was more important to you back then.

RB: I had been playing professionally since I was eleven. My sister and I had a folk group, the Four G’s. We played with the Philadelphia Orchestra. They had young people’s concerts, and they said, “Hey, folk music’s happening!”

ES: This would have been in . . .?

RB: Nineteen sixty-one. We did “This Land Is Your Land” and “On Top of Old Smokey”—those kinds of songs.

ES: Who taught you to play?

RB: I taught myself. My sister was taking guitar lessons, and she brought home this baritone ukulele—it’s a four-string guitar, basically. I picked it up. I played the song from the Ballantine beer commercial because it was on during the Phillies game.

ES: Are you still learning after all these years?

RB: Absolutely. I practice. I’m a personality and a singer—that’s how I make my living—but I’m always a guitar player.

ES: You make your living as a personality?

RB: My friend J. J. Cale once told me, “I was a really good guitar player, the best guitar player in Tulsa, and I was making two hundred bucks a week. Then I wrote my first song, for either Eric Clapton or Lynyrd Skynyrd, and my first royalty check was twenty-five grand or fifty grand. After that, every time I went to practice, I said, ‘I’m going to write a song.’ ” You have to be more than a guitar player. And when you recognize it, you go, “Okay, I can be that guy.” So I’m a quasi-celebrity. I go to these charity functions and help them out by being the entertainer or the emcee or the auctioneer. And I don’t enjoy it. I don’t like it. I’d rather be sitting there having a drink and talking about what an idiot the auctioneer is.

ES: But you’re so good onstage.

RB: I acted in high school and one year in college. I loved theater.

ES: Which is a good segue into talking about your play, A Ride With Bob, about the life of Bob Wills. How did it come together?

RB: I got the idea in July ’04. His hundredth birthday was coming up in March ’05. Mara Levy [a daughter of Texas Monthly founder and publisher Mike Levy] was working in [screenwriter and photographer] Bill Wittliff’s office, and she was trying to be a writer, so I said to her, “I need somebody to write a play with me. Do you want to help with this?” And she said, “No, I couldn’t do that. But my friend [screenwriter] Anne Rapp is wonderful.”

ES: Did you know Anne at that point?

RB: I knew who she was. Then [novelist] Bud Shrake said to me, “You know, there’s this screenwriter who loves your band.” So Anne and I met, and we called [Texas Monthly writer-at-large] Sarah Bird, who had once been out on a wild goose chase to do the Bob Wills story as a movie. The three of us had our first meeting, and we said, “Well, how are we going to do this? Are we just going to tell stories?” And Sarah said, “Tell me about meeting Bob.”

ES: You met him?

RB: I went up to Dallas to see him in 1973. He was making what would be his last record, which we had helped put together with United Artists, our label at the time. We drive up there, we go in, and he’s in a wheelchair. He’s kind of slumped over. They said, “Look, he’ll talk to you tomorrow. He’s very tired.” And they took him back to his room. That night he had a stroke and went into a coma, and he died eighteen months later. So I met Bob Wills, but I never got to talk to him. And Sarah says, “That’s your story: the conversation you never had with Bob Wills.” The next day, Sarah says, “Look, my mom is real sick. I don’t have time to do this.” She had to bail out, bless her heart. So Anne and I jumped on it. It was like that Bing Crosby movie Holiday Inn. Let’s go make a play!

ES: How did you get the thing funded? Plays cost a lot to produce.

RB: I went to my friend at H-E-B and said, “Hey, it’s your hundredth birthday this year. It’s Bob Wills’s hundredth birthday.” I sent him a proposal and he says, “How much do you want?” I say, “We want $37,500.” “Well, we’ll see.” It turns out that it was the end of their budget cycle, and they had too much money in their [anniversary] account. He came back and said, “What’s your total budget?” I said, “Our total budget is uh, uh, $100,000.” They gave us $50,000! We walked in on the right day.

ES: So you start working on the play . . .

RB: And all of a sudden I realize I’ve got expectations. I just took a bunch of money and I don’t have shit. So every day we’re writing. There’s drama, conflict, craziness. Having this money, we’re able to hire all these people. When you hire people, you’ve got problems, you know? I’m really stressed, and I don’t normally get like that. Screaming, yelling, crying—I’m screaming and yelling, they’re crying. Anyway, long story short, we do the thing [at the State Theatre in Austin]. And I was overwhelmed, because it was so good. I’ve never experienced anything like that before.

ES: The premiere was in March ’05. How many performances have you done since then?

RB: More than fifty—we did San Francisco, Tulsa, the Kennedy Center, in D.C.—and we’re going to do another twenty-some. [The show returns to Austin on October 4 and 5 at the Paramount Theatre.]

ES: Surely that’s not all on the original $50,000.

RB: No. At some point I had to raise more money. I was doing a benefit for the Austin Symphony, and we auctioned off a concert with me and [the Austin band] Tosca. Conoco bought it. So I say to a guy from Conoco, “You know, we’ve got this play. And you all are headquartered in Ponca City, Oklahoma. This play is perfect for Ponca City. There’s a nice old theater—I’ve played it before. We have to bring this play there. Do you know anyone at the company I can talk to?” And he said, “No, but if you want to raise money, this lady next to me is who you want to talk to.” It was Lisa Pollard, who’s the head of the oil-and-gas PAC in Austin. She’s a good ol’ girl from Alpine, and she loved our band. She said, “Okay, I want to talk to you about this thing.” It was the most fortuitous meeting of my life, because she got real involved in it and became a good friend. She went to Exxon, Chevron, BP—all the oil-and-gas companies—and AT&T and the Associated General Contractors of Texas.

ES: How much have you raised since that first run?

RB: Not including ticket sales? Probably half a million dollars.

ES: It’s amazing to think that enough people today still care about Bob Wills to get you that kind of underwriting.

RB: There are Bob Wills nuts all over the place. My friend Barry Rebo, in New York—he was the first HDTV guy. In L.A., David Steinberg, the writer, comedian, and director. And yet Bob Wills is one of the last iconic guys who’s not widely known. [National Public Radio reporter] John Burnett wanted to do a story. We went to his boss and said, “It’s Bob Wills’s hundredth birthday.” And he said, “Who the f— is Bob Wills?” But the appeal of his music is obvious. If you’re a music nut, you go, “Wow, man. This is amazing.” Because it’s funky, sophisticated, and Western. Bob Wills never made it past the eighth grade, but he had a sophistication about him and also an earthiness about him. There’s this earthy, funky, West Texas fiddle music, and all of a sudden it sounds like Glenn Miller walked in and Bessie Smith is singing.

ES: That amalgam of styles sounds like the thing Asleep at the Wheel does so well.

RB: The essence of western swing is the ability to do all kinds of music. We’ve done rockabilly. We’ve done straight-ahead country; we had a top-ten record in 1975, The Letter That Johnny Walker Read, which was as country as you could get. In the nineties I did two Bob Wills tribute albums.

ES: Why is Asleep at the Wheel still a band?

RB: Because I want it to be.

ES: You could just stop anytime you want, right? Mr. Vertically Integrated no longer needs the money.

RB: No, I need money to keep it going. I’m not wealthy. I only make a couple hundred thousand dollars a year, which is why I do other things. I do voice-overs for ads—you’ll hear my voice a lot and you won’t even know it. And we have two recording studios.

ES: Right. You produce albums for other people.

RB: Yeah, but that pays only a little bit. The studios break even. They didn’t used to, but my son took them over and now they do, which is really nice. The point is that I try to nurture other bands, because I wouldn’t be where I am without the people who helped us, people like Willie Nelson, Commander Cody, Van Morrison.

ES: How many dates does your band play on the road a year?

RB: About 150.

ES: Of those, how many are for the public and how many are corporate or private gigs for which you are handsomely compensated?

RB: About 30 percent are corporate. I’ll be sitting there saying to myself, “Why the hell are we playing for these people?” And a guy will come up and say, “Man, I went to college at so-and-so, and you played there in 1973.”

ES: You probably end up making more on the 30 percent than you do on the 70 percent.

RB: Absolutely. It’s been very fortunate, because how else would we make it?

ES: I know you to be a political person with a point of view on issues. Do you ever find yourself turning down corporate gigs when people you don’t like try to hire you?

RB: No. My mantra has always been that if I’m raising money, that’s one thing, but if I’m entertaining people, I don’t ask them who they voted for.

ES: A paying gig is a paying gig.

RB: Not just a paying gig. Entertainment. As an entertainer, I don’t preach from the bandstand. Take, for instance, the president of the United States, who I’ve played for at the White House. I knew him in Austin, and I disagree with 90 percent of what he’s done. But I have a lot of respect for the presidency, even though he’s screwed it all up. And this was before he really screwed it all up. We were supposed to play the White House on 9/11.

ES: You were?

RB: Oh, yeah. We were two blocks away. It was supposed to be a big deal.

ES: I’ve never heard this story.

RB: It was a joint party for the House and the Senate. George decided to throw a barbecue; he had Tom and Lisa Perini [of Perini Ranch Steakhouse, in Buffalo Gap] do the food. He wanted to have a big Texas do, right? So I’m laying in bed, because I’m kind of sick—I’d come down with hepatitis C—and my drummer calls up and says, “Turn on the television! Do you see what’s happening?” The world changed in two minutes. So, of course, we didn’t play.

ES: That’s incredible! But you eventually did play there.

RB: Yeah, a year and a half later. Laura Bush called and said, “We’re going to have that party we couldn’t have.” I said, “Well, okay. I’m there.”

ES: I’m sure they were very gracious.

RB: You know the Bushes. George Bush is the nicest guy. Should he have been president? No. I didn’t vote for him. I didn’t support him. But I’ve always felt that if a president asked, I’d come and play.

ES: So you’d play for him now?

RB: Maybe not. There’s a point at which you go, “How egregious is this?” Is there a line? Yeah, there’s a line. One time we played for Halliburton. They had rented Minute Maid Park. It was a gig. I really didn’t know about that one until we showed up. By then, it was too late.

ES: If the president knew that you’re getting ready today to play a benefit for the legalization of marijuana, do you think he’d have you back at the White House?

RB: Don’t know. But I just want to be honest about it. The numbers are ridiculous. A large percentage of federal prisoners are in for marijuana. We’re wasting billions of dollars. In big cities, marijuana is as expensive as gold—$400, $500, $600 an ounce. I was doing a panel one time with Michael Dell. Someone asked me, “Why did all those musicians move to Austin in the early seventies?” I said, “Well, rent was cheap and pot was cheap.” Dell looked at me like, “Ugh. Cross him off the list. If I need a minyan, maybe I’ll call him.”

ES: He must be crossing Willie off the list too.

RB: Willie, my best pal, has taken such heat on this, including being arrested a number of times. He said, “Will you do this [benefit]?” I said, “Yeah, of course.” I smoked marijuana off and on for forty years. My health is fabulous. My mental state is fabulous. I believe I’ve been a constructive father and community leader. I do not advocate the use of marijuana. All I’m saying is that the laws are ridiculous. Is it any worse than alcohol? No. So put it in the same category as alcohol. Tax it. Regulate it. And let’s get on with it.

ES: Obviously it hasn’t stunted your growth.

RB: That’s the other thing. Three years ago, the University of Massachusetts Amherst applied for a permit to study marijuana’s medicinal effects. And the government wouldn’t grant it. How are you supposed to know? I think it’s stupid. Prohibition didn’t work on alcohol; it ain’t going to work on marijuana. All it does is make criminals rich and put good people in jail.