Playboy Jokes — Best Of

: Known for his "Travels with Shel" and quirky, often dark humor.

: This was the magazine's hallmark humor section, usually illustrated with small, colorful cartoons. The jokes often revolved around dating, marriage, office politics, and social faux pas. Best Of Playboy Jokes

: Provided macabre and surreal cartoons that became a staple of the magazine's "sophisticated" funny side. : Known for his "Travels with Shel" and

: While a comic strip, its satirical take on the 1960s and 70s culture often provided the "big laughs" for the magazine, mocking everything from politics to the sexual revolution. Famous Contributors usually illustrated with small

: Created the iconic "Females by Cole" illustrations that defined the visual style of Playboy humor in the early years. Why It Was Popular