The Pinstriped Man.

I love stories about Western Swing pioneer Bob Wills. Living in Oklahoma, I run into a lot of people who heard Wills during his prime. They all have a good story to tell. Bob Wills and his Texas Playboys had a reputation for hard drinking, bare knuckle fighting, and being one of the best live bands ever. Bob Wills also had a reputation as a very honest and generous man.

My favorite Bob Wills story was told by guitar legend Eldon Shamblin, and the Playboy’s drummer Smokey Dacus. It was on a PBS documentary/tribute to Bob Wills aired few years ago. I’ll try to do the story justice.

Wills based his Texas Playboys out of Cain’s Ballroom in Tulsa, Oklahoma through much of the 1930s and 40s. They rehearsed there in the afternoon.

These were hard economic times all around. Every week or so a man wearing pinstripe overalls came into Cain’s. It was always a different person. But for some reason, he always wore pinstripe overalls. The man walked up to Wills and told his story. The story never varied. His mother was out in California. She’d taken ill and was expected to die. If Mr. Wills could just spare fifty dollars, the man could make it out to see his mother one last time. The amount asked for was always fifty dollars.

Bob Wills never hesitated. He reached into his pocket, pulled out a money clip, peeled off a hundred dollars and gave it to the man. Expressing his gratitude, money in hand, the pinstriped man quickly disappeared.

When Wills turned around, he saw the guys in the band shaking their heads and smirking. He always said the same thing: “Well . . . he was probably lying. But, I just couldn’t take the chance.”

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