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Well before Playboy came along, men's magazines had a long tradition of providing risqué cartoons between the dirty pictures. They generally.
I have been watching adult cartoons for a few years now and this list is full of the best shows I have seen. I hope it can be of use to you.
25 retro cartoons that made the 80s & 90s awesome . is probably one of the first few cartoons we watched that had such, erm, adult themes.