Hugh Hefner, Playboy founder and American icon breathed his last on September 27 (Wednesday). Aged 91, he passed away peacefully, surrounded by his loved ones. While he started off as a writer for a military newspaper during the World War II, it is as the flamboyant Editor-In-Chief of Playboy magazine that he became more popular as. The iconic American men' lifestyle and health magazine is popular for its bold and artistic features, which includes a combination of nude photography, fiction and in-depth interviews with world icons. Published in December, 1953, the first issue of the magazine featured the beautiful Marilyn Monroe on the cover and got many talking. Click through to see some of the most iconic covers of the magazine.