Wynn Stewart was born in Morrisville, Missouri on June 7, 1934. He would become influential in the Bakersfield scene, inspiring Merle Haggard, Buck Owens and Dwight Yoakam among others.
Wynn's early life was steeped in the humble roots of a sharecropping family. He taught himself to play the guitar at the age of eight and by the time he was a teenager had already appeared on KWTO in Springfield.
The family moved to California during World War II, where Wynn’s father worked at a submarine base. They returned to Missouri briefly before settling in Los Angeles in 1948. Wynn, at 14, found himself immersed in the burgeoning music scene of the West Coast.
Despite an initial dream of becoming a professional baseball player he turned his focus entirely to music. While still in high school, Wynn formed a band and began playing in California clubs, with his father Cleo acting as his chaperone.
His first recording was a rendition of Eddy Arnold's hit, "Anytime." Wynn also frequented local talent shows hosted by Carl Moore, a DJ known as "Squeakin' Deacon," where he consistently won. It was at these shows that Wynn met Ralph Mooney, a future Steel Guitar Hall of Fame inductee, who would become a lifelong friend and collaborator.
In February 1954, at just 20 years old, Wynn signed his first recording contract with the independent label Intro, producing singles like "I've Waited a Lifetime" and "Strolling." His big break came when Skeets McDonald, a key figure in the West Coast hard country scene, introduced him to Ken Nelson of Capitol Records. Wynn's stint with Capitol produced notable records including "Waltz of the Angels" and "The Keeper of the Key," but commercial success remained just out of reach.
Frustrated with the pop direction many country artists were taking, Wynn left Capitol Records and joined the Challenge label in 1958. His rockabilly attempt "Come-On" marked a brief detour before he returned to his country roots with hits like "Above and Beyond" and "Wishful Thinking." Despite his moderate chart success, his influence was profound. His distinctive vocal style inspired legends such as Buck Owens, Merle Haggard and Dwight Yoakam.
In the mid-1960s, Wynn's career peaked with hits like "It's Such a Pretty World Today," which topped the charts and earned him the Academy of Country Music's Song of the Year award. He continued to produce a series of hits through the late 60s and into the 70s, maintaining a steady presence in the country music scene. His career, however, was marked by periodic moves and label changes, including stints with RCA and Playboy Records.
By the early 1980s, Wynn had largely stepped back from the spotlight, performing occasionally but not pursuing new recordings until he decided on a comeback in the mid-80s. Tragically, on July 17, 1985, at the age of 51, Wynn Stewart passed away from a heart attack just as he was preparing for a new album and tour. His untimely death came with a sense of unfulfilled potential.
His legacy is one of unrecognized greatness; a pioneer who shaped the sound and style of country music but never received the widespread acclaim he deserved. As Ralph Mooney aptly put it, Wynn was "the best singer who ever lived," and his profound influence continues to resonate in the music of those he inspired and listeners of Real Wild Radio.
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