It's hard to know what would have happened to Wynn Stewart if he had lived. It's tempting to think that his role as an architect of hard-driving, hard-bitten west coast country music would have been recognized and he could have renewed and sustained his career. It's likely, though, that he would have been put out to pasture in Branson or would still be touring smaller halls. Wynn Stewart never had a lot of luck. Many say he was the best, but that doesn't count for much if someone else gets the important breaks.
Wynn certainly had his successes. He darted in and out of the charts for thirty years, but the hits were fewer and smaller than they should have been. When people think of California country music these days, they think of Buck, Merle, and Dwight instead of Tommy Collins, Skeets McDonald, or Wynn Stewart. With those thoughts in mind, maybe it's time to readdress the balance, and give a pioneer his due.
The Challenge label was started by Gene Autry with some encouragement from Joe Johnson, a former law student at Vanderbilt University in Nashville. Autry had wanted to call the label Champion Records for his wonder horse, but Decca Records already owned the name, even though it had been retired.
"Challenge meant that we were going to challenge Decca and all the others", said Johnson, "and it was an answer to the challenge of not being able to use Champion". It began in March, 1957.
In October 1958, Gene Autry sold his controlling 56 per cent share to Johnson and Johnny Thompson. The record business wasn't enough of a sure thing for Autry.
After a year or so in the pop music business, Johnson decided to get back into country music. He started a new company with different distributors for his country releases. "I figured we'd have to be lucky to make it work, so we called the label, Jack-pot", said Johnson. After a few rough months, Johnson folded Jackpot into Challenge.
Wynn Stewart was one of the first country artists Johnson signed, whom he had met through Harlan Howard and his ex-wife, Jan. Johnson knew Harlan Howard through Johnny Bond, who was a guitar player for Gene Autry and was partners with Tex Ritter in Vidor Music. Wynn signed on June 9, 1958. He and Jan Howard signed as a duet in December, 1958.
Wynn's first record for Jackpot-Challenge was"Come On", a three-chord rockabilly bash. Johnson had nudged Wynn toward rock 'n' roll, telling him he had potential in both markets, but they found that only country stations played his music. So the next time they met in the studio, Wynn and Joe had decided to stand or fall with unadorned country music.
His second solo single was Harlan Howard's "Above and Beyond", cut on May 6, 1959. The record created enough of a stir for Buck Owens to re-record it in February, 1960. Buck had a hit with it, which Wynn seemed to take in stride. Wynn and Buck would play an occasional game of golf whenever he was in Bakersfield.
Wynn's first single for 1960 was "Wishful Thinking". His sister, Beverly, wrote a few lines of this one. It was his sister, Patty, who inspired it. She was out of town somewhere and wrote, "I wish I was home with you folks, but I guess that's just wishful thinking". Beverly also sang the soprano harmony. This record is everything you need to know about west coast country music circa 1960. Ralph Mooney played the steel guitar and Gordon Terry was on fiddle. It spent 22 weeks on the charts, peaking at number five. Sales of country music were very poor at this time, however, and it only sold thirty-five or forty thousand copies.
Wynn continued to record for Challenge until 1963. There were several more hits, including a duet with Jan Howard, "Wrong Company", which got up to number 26 on the charts. "Big, Big Love" got in the top twenty, and the blue collar anthem, "Another Day, Another Dollar", edged inside the top thirty. The last session for Challenge was held on April 30, 1963. Merle Haggard was playing bass, and they cut "I'm Not the Man I Used To Be" and "Slightly Used". After that, the Challenge label was history.
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