While many jokes were submitted by readers (who were famously paid for their contributions), the magazine's humor was elevated by legendary cartoonists and writers:

: Provided macabre and surreal cartoons that became a staple of the magazine's "sophisticated" funny side.

: 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

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

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

: 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.

: Many jokes leaned into the "Playboy lifestyle," featuring suave bachelors, glamorous dates, and the humorous misunderstandings that occur in high-society settings.