New York Post

As an up and coming young entrepreneur, Hugh Hefner needed as much recognition as he could get. Newspapers such as the New York Post belonged in the upper echelon of agencies that could propel Hefner’s dream into super-stardom; and photographs like this one most definitely contributed to his overall success. Captured here with a plethora of women, the vivacious Hefner captivates us with an endless smile, thick wavy hair, and that signature cunning stare that was so commonly used as a weapon against all of us. As a young man trying to emerge himself in a relatively unknown market, he ultimately catapulted his business to the top almost overnight. The always smooth Hefner could almost always be caught in an advantageous pose such as this one, a style we would become all too familiar with.