Playboy Number One. This issue features Marilyn Monroe in black-and-white on the front cover and nude and in color on page.19. As the centerfold for the premier issue of Playboy, Hugh Hefner purchased a previously unpublished photograph of Monroe from the John Baumgarth Calendar Company. Today it is synonymous with Playboy's early days. Monroe was the magazine's first "Sweetheart of the Month." The term "Playmate" was introduced in the second issue, but that term was applied to Monroe in several later issues.

This first issue of the magazine, a "handbook for the urban male," was printed without a date so that it could remain on newsstands indefinitely. It would sell more than 50,000 copies.