A bright, energetic, and unusual talent in early bluegrass who doubled on upright bass and bass vocals, Estil Stewart's efforts as a bandleader proved that the one thing he wasn't very good at was simple math. His notable bluegrass outfit from the '50s, the 7 Flat Mountain Boys, never had seven members. Four, yes. Five, sometimes. Never seven. "I don't know. He made a misnomer there," was how one of these Flat Mountain Boys mandolinist and vocalist Cuddles Newsome explained the adding mistake. The bandleader himself was long gone from a heart attack before a new generation of bluegrass scholars began poking around into his background based on tracks reissued as part of the Rounder label's Early Days of Bluegrass series. Thus the Kentucky-born-and-bred Stewart was unable to offer a reason for the miscalculation, but perhaps the bandleader was trying to prevent any possible monkey business at gigs by giving the impression of a large, threatening group of people on the bandstand. Then again, the quartet or quintet version of the group could each easily sound like a larger group then it really was, based on the strength of some of the Flat Mountain Boys' instrumental talents.
The group included players such as fiddler Kenny Baker, driving rhythm guitarist Jack Cooke, and the powerful and fairly obscure banjoist Jimmy Braham. In the mid-'50s, this lineup cut several singles for a label known as Arrow, part of the legacy of independent regional releases created by bands mostly to sell at their own gigs, which eventually became something much bigger; a documentation of the entire development and growth of bluegrass out of old-time music in the first half of the '50s. The Arrow label operated out of Columbia, KY, and although the people who were actually behind this business have remained unaccounted for, the recording of the 7 Flat Mountain Boys came about as a result of the group's series of broadcasts over the Whitesburg station WTCW. For a short time, the Arrow releases and the band's gig activity in the region were something along the line of small phenomena feeding each other: the recording leading to gigs; the gigs attracting large crowds to shows held at venues such as drive-ins; the band building up an impressive fan base equally enamored with the hard-driving music as with the youth and exuberance of the members. It all must have looked pretty good to the Starday label, with a handful of talent scouts wandering Appalachia looking for new possibilities. Some of the Arrow releases were picked up and issued by Starday, meaning instant confusion as this was a record company that was legendary for multiple repackagings and compilation sets involving all manner of selections from its catalogue.
At any rate, the attention from Starday didn't exactly hurt. Attendance reports from the period show the 7 Flat Mountain Boys out-drawing popular country stars of the day such as Carl Story. The group's stage show also included comedy performed by both Stewart and banjoist Braham, the players alternating as each other's straight men. Yet, despite the success and potential of the group, the players drifted off into other ensembles in the type of implosion that has signaled the end of many a combo. Stewart eventually supported himself as a disc jockey in Virginia before his untimely death, making great use of his comedic talents over the air. Newsome continued trilling his mandolin in a variety of traditional bluegrass contexts; while fiddler Baker achieved the greatest success of all in the genre, going out with country singer Don Gibson and then eventually staying with Bill Monroe & his Bluegrass Boys for a long stretch before starting his own groups.