While the Whiskeyhill Singers only survived on the folk scene for a short time during the early '60s, the group's sole album nonetheless represents an interesting footnote to the era. Unlike so many forgotten trios and quartets of the period, the group simultaneously served as a proving ground for ex-Kingston Trio leader Dave Guard and as a launching pad for Judy Henske's solo career. Henske's departure following the first album and Capital's impatience, however, assured that the quartet would never get a chance to fully develop Guard's ideas.
In 1961, Guard decided to leave the Kingston Trio, the most popular folk band of its day. In many ways, he was a casualty of the criticisms offered by traditionalists who condemned the commercial folk that spurred the revival on. Although he was the acknowledged leader of the Kingston Trio, the other members balked when he suggested changing the band's repertoire. "I wasn't convinced my associates were doing the best they could," Guard told Show Business Illustrated. Guard left the trio and began auditioning potential players with the idea of radically departing from the Kingston Trio's sound. The final lineup included Heinze, then an unknown singer working on the West Coast, Cyrus Faryar, a high-school chum of Guard's, and David "Buck" Wheat, a bassist who'd played on many Kingston Trio sessions. With the choice of a woman singer, the Whiskeyhill Singers would more clearly resemble the Weavers than the Kingston Trio, with a notable difference: Heinze's style of belting the blues had more in common with Bessie Smith than Ronnie Gilbert.
The zany quality of the newly formed group was captured in a photo of the group for Life in December of 1962. In a fictionalized version of the folk song "Railroad Bill," Wheat and his bass have been tied up on the railroad track while Henske, revolver in hand, pursues an animated Guard and Faryar. "When the Whiskeyhill Singers performed," Faryar later told Richie Unterberger, "we really frightened people as much as entertained them. Buck Wheat was years-plus older than all the rest of us, about my height, five-foot six. David [was] six-foot-four, and Judy, in her heels, [was] six-foot four." The group soon entered the studio and cut Dave Guard & the Whiskeyhill Singers. Although it failed to completely sever Guard from his popular folk past, it did offer a product quite unlike anything of its time. Overall, however, the album seemed to be going in several directions at once, incorporating smooth harmony, tradition, and raunchy blues.
The Whiskeyhill Singers returned to the studio to record a second album, but Capital chose to leave the material in its vaults (where it still remains). Henske had departed before the sessions were over, and the other members soon scattered in different directions. Faryar joined the Modern Folk Quartet and worked as a session player, while Guard basically disappeared from the music business for a number of years. Dave Guard & the Whiskeyhill Singers was re-released in 2001 on Collectors' Choice Music.