BIOGRAPHY of Wynn Stewart
The Challenge Years
Wynn then met up with Joe Johnson, who had started the Challenge label with Gene Autry. Wynn was one of their first country artists to sign, on June 9, 1958. Joe had met Wynn through songwriter, Harlan Howard. Wynn and Jan Howard were signed later as a duet. Wynn and Jan recorded several albums together. Jan Howard went on to become a Grand Ole Opry star (and still is) and had several successful albums of her own. Wynn lived in Baldwin Park, Los Angeles at the time.
The first record for the Jackpot label (which was part of Challenge records) was "Come-On", a rockabilly tune. Wynn was attempting to switch to rock 'n' roll, rather than fight it. But only country stations would play Wynn's records . There were a few other attempts at cross-over songs like "She Just Tears Me Up" and "Long Black Limousine", but in late 1958, Wynn decided to stick to hard-core country. It was what he felt most strongly about.
In May, 1959, he cut "Above and Beyond", on the Challenge label, which was later revived as a #1 hit for Rodney Crowell in the late 1980's.
Very often it was someone else who got the hit with one of Wynn's songs. Buck Owens also recorded "Above and Beyond" and scored higher on the charts. A British duo, Miki and Griff, had a U.K. hit with one of Wynn's early Capitol songs, "Hold Back Tomorrow". But his turn was coming.
On 12/28/59, he released "Wishful Thinking", which he co-wrote with his sister, Beverly. They got the idea from a line in a letter from their other sister, Patty, who was wishing she could be "home with the folks". Beverly also sang soprano harmony on the record. Ralph Mooney played steel guitar and Gordon Terry was on the fiddle. This recording is the ideal example of 60's west coast country music. It was Wynn's biggest hit so far, spending 22 weeks on the charts and peaking at #5.
On 5/30/60, a duet single with Jan Howard was released. "Wrong Company" spent just 2 weeks on the chart and peaked at #26.
Wynn was playing 6 nights a week at George's Roundup in Long Beach and appeared regularly on Cal's Corral, a Sunday afternoon TV show in L.A. He hosted a radio show 6 nights a week on KFOX as well.