3. Hugh Hefner
Hugh Hefner was the founder of the Playboy Empire and the pioneer of the sexual revolution of the 1960s. He had an extravagant and controversial lifestyle, being the Playboy daddy for many Playmates over the years, some rumors claiming that he had up to 1,000 intimate girlfriends.
Unfortunately, after a long, full and happy life, Hefner died of a heart attack in 2017, at the age of 91, in his famous Playboy mansion in Los Angeles.
For Hugh Hefner, money was not an issue. Hefner founded Playboy in 1953 for $600 and over time turned the magazine into a multi-million dollar entertainment empire, which in the early 1970s included TV shows, a jazz festival, and a number of Playboy clubs whose waitresses wore bunny ears.
