Without Instructions: Lead Belly
Huddie William Ledbetter, best known by his stage name of Lead Belly, is easily the oldest artist I've ever played on The Enclosed Instruction Book (and is likely to remain so, unless I work up the bravery to play an Al Jolson song). He was born sometime in the late 1880s (exact date is unknown, and depending on who you ask the year varies from 1885 to 1889). He died in 1949. For perspective, the oldest non-Lead Belly song played on my show is Frank Zappa's "You're Probably Wonderin' Why I'm Here", from 1966.
When he was first recorded in 1934, folk music was horribly undocumented. The record industry was mostly based around New York, and most early pop music and classical music was written and sold on paper. Folk music, referred to at the time as "race music", was barely archived at all. It was only passed along by songsters, wandering musicians who learned their work from other songsters and whoever else knew the songs. Finally, working for the Library of Congress, John and Alan Lomax discovered Lead Belly (currently in jail for stabbing a guy). Accompanied by their somewhat primitive (and portable) recording equipment, they finally put on disc the first recordings of a great number of now-immortal folk songs. "Goodnight Irene", "Gallis Pole", "John Henry" (or at least a somewhat sexually charged variant thereof), and "Where Did You Sleep Last Night", "Pick A Bale Of Cotton", and perhaps most influentially, "Midnight Special" (a song written about the Sugar Land prison in which he stayed) were either first recorded or popularized by him.
To say nobody had instructions would be an understatement. When he started playing music, folk music was simply never written down and sold like piano music. (Even Tin Pan Alley did not yet exist.) Hardly anything had been recorded. He got an accordion from his uncle, and it isn't entirely clear how he learned or obtained his legendary 12-string guitar (which, by the way, ultimately found its way into the hands of one Kurt Cobain). He just went around, learning songs, sifting through variations of songs, and playing to whoever would listen. The pair of archivists who discovered him didn't have any precedent either; they had no idea what they were out to record, and field recordings themselves were very unusual in the days before tape. Nobody knew what they were doing, but somehow those recordings became part of the foundation of numerous artists from Lonnie Donnegan to Kurt Cobain.