Playboy has been known for years as the king of nudie mags but actually had the tamest cartoons (relatively) and the least sexist. It might have something to do with them having being able to get better cartoonists the highest budget and production values and paying more. Recently while browsing the Heritage Auctions site, I ended up climbing down the rabbit hole (Playboy bunny, rabbit hole-- I just made a funny!) and this is what I found.
Erich Sokol, from the March 1965 issue.
J. B. Handelsman, March 1968
Paul Coker, Jr.. March 1965
Edmond Kiraz, March 1977
E. Simms Campbell, May 1962
Phil Interlandi, November 1966
Interesting that he used a ruler for the caption ever though he knew it would be replaced with a typeset one.
Shel Silverstein, October 1956
Jack Cole, October 1957
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