Dale McFeatters
Hello Buddies, circa 1951
Why is a child working for the company? Is it that his mother or father work there and they're off-camera?
Gilbert Wilkinson
The New Yorker May 16, 1925
This Is It, 1960s
Is the circus family his family, and if so, why would he have to beg in the street unless the circus doesn't pay anything? Or is the joke that the way he's sitting in front of the poster it looks like they're growing out of his head?
Erich Sokol
Playboy, October 1962
Another creepy cartoon nobody would publish today. I wonder if I should even be posting it in the context of "can you believe people thought this would be funny once?". If it's any consolation, I think after the cartoon he immediately put his clothes back on and brought her back home before anything could happen, never saw her again for at least a few more years, and went into counseling. He'd be in his seventies or eighties now.
For Laughing Out Loud, February 1960
Bill Ward
Fun House, February 1979
I think the joke has something to do with his bald head and her breasts, but like most other Humorama titles, they came up with captions for the same drawings over and over (this looks like at least a third-generation printing), and it looks like they didn't think the joke through this time.
Judge October 9, 1909
You just had to be there.
Eugene “Zim” Zimmerman
same issue of
Judge
Life January 5, 1905
Frederick Opper
Puck June 15, 1880
Ship-Bored
Punch January 28, 1920
Punch November 9, 1927