It started when Leatha Pierce, a volunteer for LIFE Senior Services in Tulsa, asked Bob Wiles to put together a band for a big fundraising event. She knew Wiles was the man for the job. Not only had he been a founding member of the Red Dirt Rangers, that trailblazing Stillwater band; he also knew and regularly jammed with some of the best musicians around, including Leatha’s husband, guitarist/vocalist Anthony Pierce. 

“We’d just kind of sit around the campfire at bluegrass festivals, you know,” says Wiles about the music he and Anthony Pierce were making. “I don’t know that we’d ever played in public, just backyard barbecues and stuff like that.” 

Still, both were veteran musicians and songwriters who knew their way around a stage – which is just what Leatha Pierce’s event called for.  

“I asked her what it was, and she said it was a Sunday afternoon senior-citizens’ dance at the Cain’s Ballroom,” Wiles recalls. “And I said, ‘Oh. The Cain’s? Absolutely.’ I knew I’d have no problem getting people to come play at the Cain’s.”

With the commitment from Wiles, and the long-lived western-swing band the Round Up Boys already signed up as headliners, Leatha Pierce began working on promotion and publicity for the event. However, nothing could go out until Wiles took care of a little detail: Before the band could be promoted and publicized, it had to have a name.  

“I had just been to St. Louis, to the Cardinals’ museum,” he says. “And there was a left-handed pitcher on the team in 1899, the first year of the Cardinals’ existence. I would imagine he was the first ever left-handed Cardinals pitcher. And his name was Cowboy Jones. 

“I thought, ‘That’s kind of intriguing. We’ll call the band Cowboy Jones.’” 

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So when the time came for the Cain’s matinee, there was Wiles onstage, fronting a group that included Pierce on guitar, Kurt Nielsen on mandolin, Dana Hazzard on fiddle, Don Morris on bass, and Jim Karstein on drums. It was indeed, as Wiles notes, “a crackerjack band,” made up of top-flight area players with tons of experience and savvy. As good as it was, though, Wiles figured it was simply an ad hoc outfit, put together for this one event, with Cowboy Jones “a one-day name.”

Instead, it became a name that’s lasted 15 years – and counting.

As Wiles remembers it, “Somebody saw us at that gig and asked us to play at their company picnic. Then somebody saw us at the company picnic and wanted us to play a Christmas party. It just kept going. The next year, the people at LIFE Senior Services wanted us back, and we ended up doing that thing at the Cain’s on a Sunday afternoon for 15 years in a row. 

“I never knew if we were going to get to do it again, so every year, I treated it like a bucket-list opportunity – one year, we had 13 guys on stage,” he adds with a laugh. “The lineup sort of stayed the same every time, but then I’d think of somebody I knew who was a great musician but had never gotten to play the Cain’s, and I’d try to get him on the gig. There are so many great local musicians who’ve never gotten to grace that stage, and I don’t care if it’s your first time or thousandth time – it’s a thrill.” 

As much as anything else, it was the quality of the players he got to surround him that led Wiles to record a Cowboy Jones disc. Just released, it’s simply titled Bob Wiles and Cowboy Jones

“Every once in awhile, we’d be playing, and I’d look around and think, ‘Dang. These guys are good!’ he says. “When we were really hittin’ a stroke, it was like, ‘Man alive! We need to document this.’” 

Since, as Wiles notes, “All the guys in the band are in other bands, and it kind of took an act of God for all of us to have a hole in our calendars,” the album took a couple of years to develop. And as plans for the recording rolled along, the inevitable challenges cropped up. The saddest one was the unexpected death of Jim Paul Blair, the noted Muskogee-based musician who, says Wiles, “was going to be all over it” as a steel-guitarist and banjo player. 

“We had a few practices, and we didn’t try to reinvent the wheel,” recalls Wiles. “We just wanted to do something to represent a typical set of ours, adding a few new songs.

“So we booked some time at Dave Teegarden’s [Natura Digital Studios in Tulsa], and thought, ‘Boy, here it comes.’ But the first day we were supposed to be in the studio, we weren’t in the studio. We were at Jim Blair’s funeral.”

As heart-wrenching as Blair’s death was, it provided the impetus for Wiles to finish one of the standout songs on the new disc, one called “I’m Gonna Wake Up.” Without naming names, it stands as something of an elegy to Blair, as well as to Wiles’ late musician friends Bob Childers, who died in 2008; Tom Skinner (2015); and Brandon Jenkins (2018). 

“I started that song when Bob died,” says Wiles. “Any time a friend dies, it’s a wakeup call – or it should be. So I started it, but it was painful to keep writing it. Then when Tom died, I picked it up and wrote a little bit more. Then Brandon died, and I wrote a little bit more. But I never did finish it. In my mind, I never woke up. I never did answer the wakeup call. But when Jim died, I knew I needed to finish it. It wasn’t really done until we were going into the studio.” 

Songs written by both Skinner and Childers grace Bob Wiles and Cowboy Jones, which also features several new numbers from Wiles and a couple from Pierce. One of the two Skinner tunes on the disc is the Red Dirt classic “Used to Be,” written by Skinner and Wiles some years ago, which sounds like something that might’ve happened if the legendary rocker Doug Sahm – one of Wiles’ major influences – had ever collaborated with the Allman Brothers. Of the new tunes, such Wiles originals as “Fresh Cut Hay” and “Cock Robin” carry a strong element of personal nostalgia, deftly related.

“It’s funny, but when you’re writing something personal, you never know if anybody else is going to want to hear it or not,” he says, chuckling. “But that sort of became the theme of this whole record. Let’s make ourselves happy and let the chips fall where they may.

“You know, it’s taken me 60 years to find my own voice,” he adds. “Especially when I was in the [Red Dirt] Rangers, I was wanting to write what people wanted to hear on the radio. It always kind of bugged me that my songs seemed to appeal to senior citizens more than teenagers.”

He laughs again. “Now, I’m realizing that’s who I am. It’s really been liberating to finally just lean in and embrace that. I’m also realizing that there are a heck of a lot of baby boomers who still love live music. What I think the venue owners are finding out is that they don’t want to wait until 10 o’clock for the band to go on. So we’ve been pursuing early gigs, matinee gigs.

“There really are a lot of us who still love going out and hearing music,” he concludes. “We just don’t want to wait until our bedtimes for it to start.” 

Bob Wiles and Cowboy Jones is available online as a digital release, with physical copies at cowboyjones.com.