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