Obray Ramsey is the banjo-picking cousin of old-time music instrumentalist Byard Ray, and the two worked regularly as a duo until they were "discovered" playing at an Asheville folk festival during the folk music revival of the '60s. From that point on, the two men's musical career took a strangely twisted path. Late-night television mongers who may have made it all the way through the strange psychedelic rock western Zachariah, may wonder who the two old-time musicians are that show up in one of this epic's many strange musical wonders, and the answer would be Ray and Ramsey. The same viewer may also wonder why they have become attached to their seat with cement, the only condition under which an intelligent human being would endure the length of the aforementioned film. In 1962, producer John Simon invited the duo to New York City, or "thawt New Yawk," as it is known south of the Mason-Dixon Line. The players were swept into experimental recording projects with a strange combination of players, although perhaps something a bit more threatening than a broom was needed to get these old-timers to pick alongside players such as avant garde classical guitarist Sam Brown, studio pro and funkmeister Chuck Rainey, rhythm and blues session drummer Herb Lovelle, sarcastic pianist Dave Frishberg, and even a black gospel group, the Wondrous Joy Clouds. File Under Rock was the name of the first album edited together from these sessions, the players collectively given the ad hoc group was given the name White Lightnin', at that time a slang term for a type of LSD as well as the traditional name for home-brewed liquor from the mountains. A second album entitled Fresh Air was also released, notable for a pleasant Bob Dylan cover version featuring the old-time musicians performing with the collegiate folkies Judy Collins and Eric Anderson, resulting in a memorable meeting of the old and new in folk music.
Ramsey has also recorded on his own, including an album of folk music for Prestige International. He is considered one of the finest banjoists for accompanying singing and has been compared favorably with Doc Boggs. In the late '50s, he was a member of fiddler Tommy Hunter's Carolina String Band with the leader's sister Nan Hunter and her husband George Fisher. The archival type Deadheads might have his name on the tip of their tongue (along with lord knows what else) via Grateful Dead's cover version of Ramsey's song "Cold Rain and Snow," one of many traditional Appalachian numbers this band used to jam out on. Ramsey and his music is also credited with having a large influence on the writer Manly Wade Wellman, a creator of science fiction, adventure, and mystery stories who once beat out William Faulkner in a writing contest. Through a friendship with folklorist Vance Randolf, Wellman met Ramsey during one of several collecting and recording trips in hillbilly territory. Ramsay is also a member of an elite club of musicians that have had songs written about them, in this case the ditty "Ballad of Obray Ramsey," recorded by Matthew's Southern Comfort on their 1970 album Second Spring. Ramsey also gave some music lessons to Mel Lyman, a musician who would eventually join the Jim Kweskin Jug Band as a replacement member and go on to supposedly form his own mind control cult in the Bay Area. Despite basically being a farmer and banjo picker, Ramsey just couldn't seem to avoid contacts with weird '60s stuff.