Playboy, March 1967
The only thing I can think of is this must be some kind of buggery joke. I don't think it's just a dog in stocks, which is kind of funny in and of itself. And I don't think it's that he gave the dog a black eye. The joke must be that he had sex with the dog. Though during that time in cases of bestiality the animal would be punished in addition to the person, so this would be an illustration rather than a cartoon.
Punch October 26, 1915
Look at the date on that cartoon. Isn't that a weird coincidence? Wait a moment,
I did that same joke a few weeks ago when I posted a cartoon that was printed on the same date. Never mind.
Scamp, November 1957
Too bad this cartoon was done before the sexual revolution. If it were done in the 70's or afterwards they tied in the phrase “the captain goes down with his ship” with cunnilingus or depending on the time and kind of publication, the captain could be of either gender performing either kind of oral sex.
Playboy, March 1968
Bill Hoest
Is it that they're cartographers? Is it progressive for the time in that the woman is also one or is she just a secretary delivering a map? I would guess, considering it's by a guy most famous for doing
a strip about a “battle-axe” wife, it's the latter.
Esquire, June 1934
Syd Hoff
Hello Buddies, June 1952
My impression is that the long-extinct Dime-a-Dance business was always a front for prostitution. Maybe that guy is me.
Hello Buddies, Winter 1950
Bill Wenzel
Who's talking? The first rule of gag cartooning is that only the person who's talking has their mouth open. And why is one of the women topless?
Hi-Life, August 1964
Don Orehek
These next three are the trifecta of taboos. Cartoons that don't age well. Cartoons no magazine would print today.
First up, we have fat-shaming...
Good Humor, circa 1964
...pedophilia...
Jest, circa 1942
...and racism. At least I think this is supposed to be racist. But I don't get the glasses part. Is it just that the guy's an asshole?
Man, April 1966
Nugget, February 1956
It's questionable whether or not this is politically incorrect. It's still okay to make fun of homelessness in some contexts, I think. I think it's French, too. They have different standards about what can or can't be mocked.
Punch October 27,1915
A hole caused by warfare possibly?