Hugh Hefner was working as a cartoonist for Esquire magazine in 1952. When he was turned down for a $5 raise, he quit his job at the publication and ventured out on his own.
In 1953, Hefner founded Playboy magazine using $600 of his own money and several thousand more he borrowed, including $1,000 from his devoutly religious mother. She wrote the check after her husband had said no.
On the front cover of the first edition of Playboy, Marilyn Monroe appeared waving her hand. Inside, Marilyn Monroe bared it all in the centerfold. Marilyn was its first cover girl, but she didn’t pose exclusively for the magazine. Instead, the Playboy mogul purchased nude photos of the star from a calendar company (for $500). The pictures were taken several years before by a pinup photographer named Tom Kelly (Marilyn was paid $50 at the time).
Through the decades, numerous celebrities would pose nude for Playboy including: Pamela Anderson, Madonna, Anna Nicole Smith, Carmen Electra, and Drew Barymore.