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.
May 1954
June 1954
July 1954
Hugh Hefner was an aspiring cartoonist himself but wisely quit for more more lucrative endeavors. I wonder what ever happened to him.
William Steig, September 1954
Same issue
October 1954
Candidate gets told they are an ideal match by a recruiter, then quickly
rejected by the hiring manager for not staying long enough in previous
jobs: ‘You’re told you’re a great match until you aren’t’
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You'd think a recruiter hyping you up would mean you nailed it, but this
job applicant discovered the age-old saying you shouldn't count your
chickens be...
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