Hugh Hefner (1926-2017) is internationally known for founding the successful Playboy brand. He started in publishing with a modest loan and went on to build an empire that came to be known for revolutionary eroticism, hedonism and glamour. The first issue of the magazine in 1953 featured the infamous Marilyn Monroe ‘Red Velvet’ photo shoot which caused a scandal early on in her Hollywood career, when it was revealed that as a budding model she had posed nude for cash to pay bills. In this portrait he is the image of suaveness and success; ensconced in a luxuriously appointed study; his initial professional ‘pipe dreams’ now reality as unlimited quantities of women, luxury, fame, and money swirl around him in expensive smoke. The Playboy brand branched out into merchandise, TV shows, and a nightclub chain which gave birth to the iconic ‘Playboy Bunny.’ Besides his philanthropic endeavors his greatest contribution was breaking boundaries not only for publishing but also for women.