He moved to New York City after military service in the early 1960s, and began playing traditional folk songs in clubs before starting to write his own material.

[1][2] A close contemporary of Dave Van Ronk, Tom Paxton, Phil Ochs and others in the Greenwich Village folk boom, Sky released four well received albums from 1965 to 1969.

He played with many of the leading performers of the period, particularly Buffy Sainte-Marie, Eric Andersen and the blues singer Mississippi John Hurt (whose Vanguard albums Sky produced).

[1] This album featured the earliest known recorded version of the song "Luang Prabang", written by Sky's friend Dave Van Ronk.

The Adelphi Records website describes how the content was, indeed, shocking, yet how several critics encouraged the public to rush and buy these timely and brilliant "explicit lyrics" while it could.