For Bob Dylan, 1968 was a year of withdrawal and rural domesticity. After the grueling world tour of 1966 and his motorcycle accident, the singer had gone underground at Hi Lo Ha, the rambling home he had bought in 1965 in rural upstate New York. Between the release of John Wesley Harding in December 1967 and Nashville Skyline in 1969, there wasn’t much in the way of writing or recording, and for one particularly good reason: Dylan and his wife Sara had three young children to bring up.
This was a headshop poster made by Richard Moffat in 1968. The poster, featuring several “Bobs” comes solidly out of the New York Pushpin Studios School of late 1960s graphic designers like Milton Glaser and Seymour Chwast, although the poster was printed by Tea Lautrec, a well-known San Francisco-based printer. The name, Bob on Bob was meant to reflect Blonde on Blonde, the 7th studio album released by Dylan in July, 1966.