History of Playboy: The Current Years ("current" being 54 years ago)

Shel Silverstein
Playboy< March 1964

May 1964

June 1964

cartoons I don't get 5

Army-Navy Fun Parade, April 1953
Al Ross

Hello Buddies, c. 1951
The salesman is suggesting the young lovers get married, though the fact that he's printed in a different colored ink sort of lessens the joke and implies he's from another dimension or something.

Esquire, June 1934
Gregory D'Alessio

Punch September 11, 1927

Nugget, February 1956

Punch December 8, 1915

Stag, Fall 1941

The Dude, May 1959

I guess the joke here is that one guy's sawed the side of the makeshift raft the other male strandee is sleeping on so he can be alone with the girl. Somehow he has a saw with him and she's all dressed up like she's going out clubbing or something.

Playboy, January 1961
Phil Interlandi
Is he trying to look at her breasts instead of the baby? Is that what's going on? Is that the world we lived in fifty years ago? He was so desperate for a “peek” he couldn't wait a couple days for his wife to come back home or find a willing accomplice at work? If this happened now he could just look at porn on his phone. Even ten years from then he'd be helping and/or watching the delivery.

This Is It, Volume 22, number 29

Good Humor, c. 1964

Nugget, August 1963

Pad, June 1968