He wrote and illustrated his own comic book titled School Daze when he was in high school.
He was born in Chicago, Illinois on April 9, 1926. He describes his parents Grace Caroline and Glenn Lucius as "conservative, Midwestern, Methodist."
Hugh married his college sweetheart Mildred Williams in 1949.
Mildred confessed to cheating on Hugh prior to their wedding. He describes the confession as the "most devastating moment of my life."
Despite always having multiple girlfriends with him, Hugh has been married three times. He has four children from the first two marriages.
He took out a $600 bank loan and borrowed $8,000 from his mother to start the magazine. He said his mom did not believe in the business but had faith in him.
He has two Guinness World Records; the longest editor-in-chief position for the same magazine and owning the largest collection of personal scrapbooks.
His IQ is 152, although he was not an astounding student academically.
He quit his job as copy writer for Esquire magazine when they turned down his request for a $5 raise.
The first issue of Playboy was released on December 1953, although there was no date on the magazine because Hugh was unsure there would be second issue.
Hugh claims he did not lose his virginity until he was 22 years old.
The first issue of Playboy to feature a nude calendar of Marilyn Monroe. 50,000 copies were sold.
In 1992, he purchased the crypt situated beside Marilyn Monroe in Westwood Village Memorial Park cemetery. He paid $75,000 for the spot.
In 2010, Hugh donated the remaining $900,000 required to preserve the 138 acres where the Hollywood sign stands.
The girls in the mansion are forbidden to use drugs and will be fired if found using them. They also have a 9:00PM curfew.
The Playboy mansion is one of the few residences in L.A. with a zoo license.
Hugh is a distance cousin to former President George W. Bush as well as Secretary of State John Kerry.
He loves movies; he watches new and classic films every week.
Hugh does not know the exact number of women he has slept with but he estimates it to be around 2,000.
He is not ashamed to admit he uses Viagra.
He was voted as "the most likely to succeed" in high school.
He has admitted to having a homosexual encounter in the past.
The Playboy mansion is on sale for $200 million but it comes with a catch; Hugh will continue to live there. He bought the mansion in 1971 for $1 million.
John Lennon was almost banned from the Playboy mansion after he drunkenly extinguished his cigarette butt on a priceless Matisse painting.
In 2011, it was found that the grotto at the mansion had legionella pneumophila, a bacteria that can develop into pneumonia and H1N1.
During WWII he was enlisted in the army as an infantry clerk. He wrote and illustrated cartoons for the Army newspaper.
The Playboy mansion is the only residence in Los Angeles that has a pyrotechnic license. The giant fireworks every 4th of July can be seen miles away.
Playboy magazine is banned in most of Asian countries like India, Myanmar, Thailand, Singapore, and Bruinei. Muslim countries also ban the sale and distribution of the magazine.
Hugh has famously said, "the major civilizing force in the world is not religion, it's sex."
A rabbit found in the Lower Keys marsh is named, Sylvilagus palustris hefneri, after the publishing mogul.
The playboy rabbit was chosen by Hugh for its "humorous sexual connotations." It is said all people have to do is draw the rabbit on an envelope and it will arrive at the correct destination.
Since 1970, the magazine has been publishing a braille edition for the blind. The Library of Congress funds the special edition.
There is no succession plan in place in case Hugh Hefner passes away. The businessman hopes one of his kids like Cooper (pictured) will step in.
The original Playboy mansion was a 70-room brick house in Chicago.
Hugh owns over 200 silk pajamas in 20 colors, he always wears black during the day for work. He started wearing his night clothes in the 1950's when he was working around the clock.