50s Playboy

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

up the cerebral cortex

from ESQUIRE, January 1971

Apologies in advance for the upcoming racial stereotypes.


from ESQUIRE, February 1971






from PLAYBOY, January 1954

from PLAYBOY, December 1958

Shaft, January 1954

College humor anthologies always have "before they were famous" mentions, and Mark Newgarden once compiled a list for Comics Comics of people who initially wanted to be cartoonists, but were more successful at what they became better known for. Here's one...