Stanley Mouse & Alton Kelley, Zig-Zag Man Big Brother & The Holding Company, 1966 ‘Mouse and Kelley were also members of the San Francisco Five. They must have known that this poster, which carries the facade of the Zig-Zag rolling paper logo, constituted copyright infringement; the quote reads: “What you don’t know about copying and duplicating won’t hurt you.” Ironically, this poster was so popular that it became the first in the Family Dog series to be counterfeited. It is extremely rare in good condition, presumably because every hippie in San Francisco pinned it to their wall’

Photograph: Shapero Modern