My Kind of Country

Country music from a fan's point of view since 2008

Tag Archives: Gordon Terry

Country Heritage Redux: Wynn Stewart (1934-1985)

An updated version of an article originally published by The 9513:

Mention Bakersfield to a country music fan and the names Buck Owens and Merle Haggard immediately come to mind. That’s to be expected considering Buck and the Hag were the two most successful practitioners of the “Bakersfield Sound,” but there are several other artists just as important to the evolution of the sound. Chief among these is Wynn Stewart, a hard-core honky-tonk singer who arrived at a time when Nashville was distancing itself from the hard-core sounds.

Country music rapidly lost its audience after the arrival of Elvis Presley in 1956. In order to retain viability in the marketplace, Nashville producers attempted to broaden the appeal of the music by adding strings and background voices. As time went by, the background voices became choruses, the strings became entire string sections and (worst of all) fiddle and steel guitar became noticeably absent in the recordings of the likes of Jim Reeves and Eddy Arnold. Plus, the vocals themselves often became bland.

Wynn Stewart arrived in 1954 with his hard-core sound and distinctive tenor and phrasing, recording for a minor label out in California. He signed to major label Capitol in 1956 and had one hit, “Waltz of the Angels,” which reached #14, but he was unable to duplicate that success and was soon released.

He then signed to Jackpot / Challenge Records in 1958 where, after dabbling with a few rock and roll songs on the Jackpot label, he recorded a number of classic country songs, including “Wishful Thinking,” which hit #5 (Ralph Mooney on steel and Gordon Terry on fiddle), “Big Big Big Love (#18) and several duets with Jan Howard, including “Wrong Company” (#26). These records featured fiddle and steel guitar in a way that Nashville recordings of that era wouldn’t touch. My personal favorite of Stewart’s songs, “Playboy,” was recorded during this period. As was often the case for Stewart, some of his strongest material did not chart – this song being one of those cases.

While Stewart was signed to Challenge, one of his songs, “Above and Beyond,” was recorded by Buck Owens who took it to #3 in early 1960 (Buck’s second big hit). Years later Rodney Crowell finally got the song to #1. Before Buck formed the Buckaroos, you could clearly hear the Wynn Stewart influence in his vocals and sound.

In late 1963, Stewart’s bass player, a young ex-con named Merle Haggard, asked for his permission to record “Sing A Sad Song.” Always willing to help a fellow artist, Wynn gave the song to Merle who had his first chart record with the song (it reached #19).

Stewart re-signed with Capitol Records in 1964 but had little success until 1967, when his fifth single for the label, “It’s Such A Pretty World Today,” topped the charts. The recording found the classic Wynn Stewart sound softened with vocal choruses and string accompaniment. Three more top tens (“‘Cause I Have You,” “Love’s Gonna Happen To Me” and “Something Pretty”) followed, but the hits became smaller and smaller and after 1971 Stewart was dropped by Capitol. A stint with RCA produced no hits, although he did score one more top ten with “After The Storm” in 1976 on the Playboy label where he returned to his hard-core sound. Stewart’s last top 20 hit came in 1977 with “Sing A Sad Song,” which, ironically, was the song that launched Merle Haggard’s career; it too, got to #19.

Stewart formed his own label, Pretty World Records, named for his biggest hit, and seemed to be ready to get his career back into high gear when he was felled by a heart attack on July 17, 1985.

Both Buck Owens and Merle Haggard have cited Wynn Stewart as a major influence on their careers, yet somehow, he was never able to translate his enormous talent into extended and consistent success for himself. Possible reasons are several:

1. Poor timing. He was a hard country artist at a time when Nashville was going soft and attempting to co-opt the easy listening market.
2. A lack of self-discipline and some bouts with the bottle.
3. Lack of visual appeal. Like Haggard, Wynn Stewart was short in stature, probably shorter than Haggard. Unlike Haggard, who was very handsome and photogenic in his younger days, Wynn Stewart was just another guy, and not very photogenic (his daughters are all quite pretty, however.)

Wynn Stewart inspired tremendous loyalty among his fellow musicians and artists. For years after his death, legendary steel guitar player Ralph Mooney would identify himself as “Wynn Stewart’s steel player.” Roy Nichols, Haggard’s long-time guitar player, played for Wynn Stewart, and before that, for Lefty Frizzell. Roy regarded Stewart as a giant of the music.

Affordable CD collections of Wynn’s material are few. The crown jewel, of course, is Wishful Thinking, a massive ten CD box set. This set covers 279 recordings, from all labels, and is the only place to find all of Wynn’s Capitol hits. This set lists for $299 but can be found for less money if you look around.

Other than the Bear Box Set, the Ernest Tubb Record Shop has available only two other Wynn Stewart collections. There is a Best of Wynn Stewart 1958-1962 CD issued by Varese Sarabande available covering his years with Challenge Records. While this collection of nineteen songs misses his big hits on Capitol, it does include what I feel to be his best recordings: hard-core honky-tonk classics. Varese Sarabande also issued The Very Best of Wynn Stewart and Jan Howard which features eight Jan Howard songs from the Challenge years, six Wynn Stewart songs and the four duets they did together. Both of the Varese Sarabande sets are highly recommended. has available all three of the above titles plus Wynn Stewart- Greatest Country Hits. There is finally a CD available that contains some of Wynn’s recordings on Capitol. Titled Wynn Stewart – Greatest Country Hits, the CD, issued by Micro Werks (out of Los Angeles) contains his 13 biggest hits. The music is excellent, although I was hoping for a more comprehensive set (such as the other three Capitol singles to chart, plus some key album tracks), but at least it’s out there.

It’s out of print now, but in 1995 AVI released Wynn Stewart – The Best of The Challenge Years. This set contains sixteen of the nineteen songs on the Varese set plus an additional thirteen songs. With some effort, you may be able to find this CD.

Stewart’s daughter, Wren Stewart Tidwell, runs a very informative website and has some of Stewart’s vinyl LPs for sale. While I have hopes that someday Capitol / EMI comes to its senses and releases some of the songs on CD, I’m not holding my breath waiting for it to happen. The LPs are all worth owning and I’ve been buying them whenever I can find them. The official Wynn Stewart website is at

He recorded at least 58 of the 45 rpm singles–of which 31 charted. Used record stores may carry some of these records. Another place to search is . Happy hunting!

There is also available a tribute album available, recorded by Billy Keeble. This CD features 15 of Billy’s favorite Wynn Stewart songs, including a duet with Wren Stewart Tidwell on one of the selections. Billy isn’t Wynn Stewart, but his CD shows the breadth of the Wynn Stewart repertoire. This disc is available from CD Baby or from

Interestingly enough, Wynn experienced a bit of an upsurge in 2010 when Volkswagen used his 1962 recording of “Another Day, Another Dollar” in a commercial for the VW Jetta. This song can be found on the Bear Box Set and on the Varese Sarabande Best of Wynn Stewart 1958-1962 collection. While the song was not a giant hit (#18 Cashbox /#27 on Billboard), it is fondly remembered by those of us who recall hearing it the first time around.