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Most men would probably say that he's the luckiest guy in the world - it's a title that Hugh Hefner still lives to at 83 years of age.
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caption="What do you want to ask Hugh Hefner?"]
Sometimes known simply as "Hef", the founder of Playboy Magazine and head of Playboy Enterprises has turned his love of women, politics and popular culture into a multi-million dollar company.
Hefner founded Playboy in 1953 and the first issue was produced from the kitchen of his mother's apartment in Chicago.
The first issue sold out in weeks and the magazine became an instant hit. Playboy peaked in 1972 with over 7 million copies sold.
The Playboy centerfold became synonymous with sex appeal and celebrities including Farrah Fawcett, Drew Barrymore and Kim Basinger all appeared in the magazine.
Although many people associate Hugh Hefner as the ultimate bachelor, he was actually married in 1949 and had two children. However, after an admission of infidelity by his wife, the couple divorced ten years later.
Today, Hefner is still enjoying his life as a bachelor and is notorious for dating many of his playboy playmates at a time.
Whether you agree with his lifestyle or not, Hugh Hefner has been the ultimate "playboy" for more than half a century.
Here's your chance to ask Hugh Hefner a question.
Do you want to know what life is really like inside the Playboy mansion? Maybe you want to know who his favorite playmate of all time is? What's the future of the magazine?
Please leave your questions below and tell us where you're writing from. Tune in on Thursday March 19 at 2100 GMT to see if we used your question.