These charcoal drawings are some of the oldest pieces in the entire collection. They were done between 1958-1961, when Ferlinghetti was 39-41 years old. Those dates put them right in there with the Howl trial in the summer of '57 and the publication of Coney of the Island of the Mind in '58. He would have started City Lights just a few years earlier in '53 and just bought his house at 706 Wisconsin Street in Potrero Hill. These gestural drawings even pre-date the arrival of his two children, who were born in 1961 and 1962.
The drawings in this batch vary in size from about 12" x 18" to 24" x 36". They are from when Ferlinghetti would attend drawing sessions at the former San Francisco Art Institute (which then was called the California School of Fine Arts). There are some interviews where he talks about attending drawing sessions there around that time frame. He mentions it in Part 2 of 4 of this interview.
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