As I’ve said before, there’s something about the music business that seems to create tortured performers, and a lot of them come to sad endings. Guys like Gary Stewart, who was an outstanding singer as well as a talented songwriter and multi-instrumentalist, but fought his demons for decades before finally taking his own life in 2003.
The Florida native first began to find some career traction in the late 1960s by taking the route followed by many — peddling songs in Nashville. After a few years of furnishing songs for 
country stars, he finally got a chance to hit the recording studio and employ his unusual singing voice. It was a tenor with vibrato — perfect for honky-tonk heartbreak songs.
Stewart sold some records but his breakout moment came when his album, Out Of Hand, was issued in 1975. It would become a classic. Filled with mostly hard-drinkin’ honky-tonk songs, it fit perfectly into the ‘outlaw country’ mood of the times. The big track on the album was a song that was also destined to become a classic — “She’s Actin’ Single (I’m Drinkin’ Doubles).”
For the rest of the decade Stewart continued to do well, but he was never really part of the Nashville establishment, and as the years passed he identified more and more with hard country rockers like the Allmans and others. He also fell prey to the lure of the lifestyle, and he often struggled with substance abuse. Meanwhile, his fans were confused by his musical efforts, and his popularity dissipated while he tried to find his niche.
By the 1980s, Stewart seemed to be into a pattern that saw intermittent down periods but also productive interludes during which he created some solid music. But it wasn’t a good recipe for rebuilding a career, and he gradually spiraled downward. By the turn of the millennium he was still performing, but when his wife died of natural causes in November of 2003 he took his own life a short time later.
Gary Stewart – “Flat Natural-Born Good-Timin’ Man”
Geezer Music Club 
Wayne Cochran and now Gary Stewart…love this site!
I produce archival releases for other labels & sometimes my own, Delmore Recordings. Recent projects have included Kris Kristofferson’s early publishing demos (“Please Don’t Tell Me How The Story Ends”), previously unreleased sessions / demos by Arthur Lee & Love from “71 (“Love-Lost”) and a pair of Karen Dalton releases of early 60s material. Thought you might be interested in our new release, GRANDMA’S ROADHOUSE, a 1971 “headneck” LP originally released in an edition of 500, featuring Gary 5 years before “She’s Acting Single…: Here’s a favorite review…more info and music samples at:
facebook.com/grandmasroadhouse
or delmorerecordings.com
Somewhere between the 1953 passing of Hank Williams and the circa-’57 rise of the Nashville Sound (prime architects Chet Atkins and Owen Bradley), questions about “purity” and “authenticity” in country music arose and, no matter how illegitimate, by and by had some hand in the emergence of such subgenres as “cosmic” country-rock (see Gram Parsons), outlaw country, and late-century alt-country (a/k/a No Depression a/k/a Y’Allternative). By now, the fusion of country with pop, rock, rhythm & blues, whatever, seems ubiquitous and seamless yet once there was a very real sonic and social divide — one in which long-lost 1971 gem Grandma’s Roadhouse made a brief splash then sank. Founded on the twangtrust of future “King of the Honky-Tonks” Gary Stewart and band namesake Riley Watkins (North Carolina native later transplanted to Michigan), Riley is the intriguing meeting of a Music Row maverick with a shitkicking bar band, Stewart’s eerie high lonesome tenor and guitars blending with Watkins’ gritty white chocolate soul tones and pickin’ to hollerback to then-dominant, exogamous rustic auteurs like John Fogerty and Robbie Robertson.
Grandma’s Roadhouse was cut in the belly of the beast as it were — at Owen Bradley’s famous Barn — but it’s significant that it was under the aegis of the younger generation — Owen’s son Jerry had signedGary Stewart to a publishing deal and facilitated his employ as an engineer’s assistant at the studio. Nowhere apparent is ’60s countrypolitan syrup; the three-way conversation between country, rock, and soul this group of players had first assayed at Muscle Shoals back in 1965 reaches its zenith herein. Often, Grandma’s Roadhouse sounds like what the Burritos might have been had they been formed in Nashville’s environs rather than Los Angeles, especially through the middle section when Stewart steps out on the Parsons-friendly “Love, Love You Lady” and the funky-fuzzy “You Been Cheatin’ on Me Honey.” Later in the 1970s, when Stewart hit with “She’s Actin’ Single (I’m Drinkin’ Doubles)” — after a stint in Charley Pride’s group — and became beloved of Alex Chilton (who covered Stewart’s bar blues masterpiece “Single Again” on Loose Shoes & Tight Pussy), the Allmans, and Mr. Nashville Skyline hisself, that peculiar crossover was complete.
However, thirty-odd years before Nashvegas got overly jiggy with rock (see Garth Brooks, Gretchen Wilson, Sugarland ad nauseam), it was still rarefied and its wilder shores commercially unsuccessful: folks forget today about Gram Parsons’ toil and trouble behind all that Keith Richards and Elvis Costello shine; Riley failed in lodging their LP with Berry Gordy at Motown (perhaps due to Watkins’ cannabis ode “Field of Green”?) and saw most of their 500 copies molder away. Grandma’s Roadhouse shines now as a fascinating artifact of the wide-open gap between such ornery lone stars as Johnny Cash, Gene Clark, Tony Joe White, and Stewart’s Kentuckian homeboy Jim Ford; and the imminent rise of southern rock, Waylon and his “Outlaw” bred’ren, and the superstardom of the Eagles. The current explosion of young bearded/mustachioed (unsigned) players worshipping at this altar of grease shows we ain’t nigh done mining that seam.
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Mark, I am almost numb (in a good way) after reading the info you’ve provided. I’m not sure we’ve ever received a comment this long and chock full of fascinating music history and opinion.
And thank you for filling in much of the background for my original piece, which is — like most of what I post — more of a brief overview of the artist.
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Gary Stewart is a particular favorite of mine. His was a music of dangerous, wild abandon, however, he was too rock for country, too honky tonk for rock. He wasn’t country rock. He was one of a kind. When he sang you held your breath, wondering if he’d get out of the song alive. We won’t see his like again.
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Well said, Peter.
I thought the song I posted — “Flat Natural-Born Good Timin’ Man” — was one of his best and it fit him like a glove.
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