Hugh Marston Hefner after graduating from High School, he studied art at the Chicago Art Institute. He then worked for various magazines, including Esquire, but when the magazine moved its offices to New York, Hefner remained in Chicago to start his own magazine.

The first issue, published in December 1953, was undated, as Hefner was unsure whether or not there would be a second issue. He produced it in his Hyde Park kitchen. The first centrefold was Marilyn Monroe, although the picture used originally was taken for a calendar, rather than for Playboy. The first issue was an immediate sensation; it sold out in weeks. Known circulation was 53,991 (Source: Playboy Collector's Association Playboy Magazine Price Guide). The cover price was 50¢. Copies of the first issue in mint to near mint condition sold for over $5,000 in 2002.

Nowadays the Company's three business groups are Publishing, Entertainment and Licensing.

Playboy's branded line of licensed fashion and consumer products has experienced exceptional growth at retail since its repositioning in 1999, with a product offering that includes men's and women's fashion apparel and accessories, underwear, leg wear, outerwear and footwear, as well as home furnishings and lifestyle and entertainment products. Playboy's licensed products business as a whole now generates in excess of $800 million in global retail sales in more than 130 countries and territories. Celebrities and fashion influencers spotted wearing Playboy fashions and accessories include Britney Spears, Jennifer Lopez, Janet Jackson, Jade Jagger, Snoop Dogg, and Lenny Kravitz.