From Marilyn Monroe on the first issue in 1953 to record-holder Pamela Anderson's debut in 1989More
The first issue of Playboy magazine, featuring Marilyn Monroe on the cover, was created by Hugh Hefner on the kitchen table of his South Side Chicago apartment. Financed with $600 of Hefner's money and less than $8,000 of raised capital, the magazine appeared on newsstands in December 1953 and sold more than 51,000 copies.
This wasn't the first bikini on a Playboy cover, but it was the first time the swimsuit was modelled in such a prominent fashion. (The first bikini cover was July 1954, but the swimsuit was washed ashore—the cover model wasn't wearing it.) The model on the beach towel is Janet Pilgrim, who also appeared as that issue's Playmate of the Month.