The first couple years of Playboy were basically put together in Hugh Hefner's kitchen with the photos bought from calendar companies and the other material was mostly reprints. The first issue was almost all black and white. Still, there are a lot of great cartoons to be found in those earlier issues.
Gardner Rea, from the second issue in January 1954
Virgil “VIP” Partch in February 1954
Arv Miller (March 1954) was one of the earlier contributors before he started his own imitation, Fling, from which I found a lot of the cartoons he used.
Sam Cobean (April 1954) was a long-time gag cartoonist that probably drew more variations on the now-established cartoon cliches of the unwed mother being turned away in the snow and the man imagining the passing young woman naked than anyone else.
William Steig, September 1954
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