The whirlwind life of Hugh Hefner

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Perhaps one of the most famous people the world over is Hugh Hefner. Mention his name anywhere from Bangkok to Amsterdam, Rio de Janeiro to Los Angeles and everyone will know exactly who you are talking about.

He was the owner of Playboy and has the distinction of being the longest sitting editor in chief of a magazine anywhere in the world. He built up an empire based almost completely upon the vices of men young and old who wanted a little something more from the girl next door.

Hefner started a multi-media empire with Playboy. He had a satellite radio station, a pay per view television channel, and of course, a world wide magazine phenomenon.

One of the things that people always used to say about Playboy magazine is that they read the periodical for the articles, and not for the women. Well, that may not have been exactly true, but it was a big part in shaping society in the United States. With its willingness to publish even the raunchiest of jokes and short stories, it was the first place where America could really be free and express itself.

Writers such as Ronald Dahl, Ian Fleming (the guy who wrote James Bond), Norman Mailer, Ray Bradbury, Jack Kerouac, and Kurt Vonnegut all wrote for the magazine which would go on to become a bastion of liberation and counterculture in the 1960s and 1970s.

And yet, not all was as happy as it seemed at the Playboy Mansion. Hugh had several failed marriages, troubled children, and sometimes, even more troubled girlfriends (whom he would date seven or even eight at a time).

The multi millionaire had a whole bunch of twists and turns on his way to global super-stardom, some of which were not always as pretty as the girls he kept around him. For instance, it turns out that…

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Just a midwestern boy

Hugh Hefner was born in Chicago in 1926. Originally from Nebraska, his parents were strict Methodists who were all about keeping in line with sexual and social norms. This was one of the reasons why Hefner grew into the man he did and became such a counterculture hero.


Descendant of William Bradford

Hugh Hefner claims that he is a descendant of William Bradford from his father’s side. William Bradford was the governor of Plymouth colony in the 1620s. If true, that means that Hefner’s family have been in America for nearly 400 years.


In the army now

Hugh Hefner graduated from high school and drafted into the US Army in 1944. He won a marksmanship competition in basic training, but was then put to work as an Army clerk in Camp Adair in Oregon before being transferred to Camp Pickett in Virginia.


Studying psych

After starting his high school’s newspaper, Hugh Hefner went to the University of Illinois at Champaign-Urbana. It was there that he studied not writing or English as we would expect, but psychology. Well, he sure knew how to get into our heads, thats for sure.


The first marriage

Hugh Hefner got married to his college sweetheart Mildred Williams. Williams was actually Hefners first ever love and sexual partner. However, the things that she did would help to shape Hefner’s view and ideas on sexuality, eventually changing America’s as well.



Hugh Hefner and Mildred Williams ended up having two children together, Christie and David. Christie formerly acted as the head of Playboy Enterprises before she stepped down in 2009 in order to pursue more charitable interests.


Working for Esquire

After he graduated from The University of Illinois, Hugh Hefner went on to become a copy editor for Esquire magazine. He did this for several years until he decided to leave in 1952 in order to start something new.


Five dollars

Hugh Hefner decided to leave Esquire for one reason which, to us may seem a bit silly. Hefner wanted to have a five dollar salary raise, but the magazine was unwilling to give it to him. That would equal about $50 in today’s money.


Raising money

When he left, Hefner decided to start his own magazine where he could write what he wanted. So, he took out loans against his furnature, got a $600 loan from the bank, selling a nude pic of Marilyn Monroe, and raised another $8,000 from 45 different investors.


Free speech

Playboy quickly became a bastion of free speech. He had nudity in his magazine and also printed short stories deemed too raunchy for magazines like Esquire. In fact, his first ever published short story was a rejected Esquire piece.


No discrimination

The piece Esquire rejected was a story about heterosexual men who were discriminated against in a world where homosexuality was the norm. When angry letters came in, Hefner said that if you’re mad about hetero discrimination, you should also be worried about LGBT discrimination.


Sued for obscene literature

Ten years after the first ever Playboy issue was released it was quickly sued for being obscene over nude pictures of Jayne Mansfield In fact, Hefner was arrested over the pictures. However, in the end, the trial ended with a hung jury.

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The affair

One of the reasons that Hugh Hefner had such a different perspective on sexuality is due to his wife. It turns out that while he was away serving his country, his wife cheated on him. She felt horrible, and it was a huge blow for Hefner.



It was due to this immense guilt that Hugh Hefner’s wife Millie allowed him to have as many sexual partners as his heart desired in the hopes it would save the marriage. Hefner would go out and hook up with other women, but it didn’t help.



Despite allowing Hugh to be a playboy in his own right, the marriage reached its logical conclusion. Hefner divorced his wife Millie in 1959 and the two split ways. But Millie took the kids when she left.



Hugh Hefner had a lot of perks of being the owner of Playboy magazine. And one of the biggest ones is that he gets to sleep with any of the girls he wants. In the 1960s after his divorce, he was sleeping with 11 out of 12 monthly centerfolds.


Palimony suit

Due to him living with so many women without marrying them, it was inevitable that some would sue him in a palimony suit. He was sued for $35 million by eight different women who were all expecting to marry Hefner.


Buying the playboy mansion

In 1971 Hugh Hefner decided to move his entire base of operations for his men’s magazine to Los Angeles, California. It was then when he bought his now infamous Playboy Mansion for a cool $1.1 million from the son of the Broadway department store founder.


The digs

The mansion is giant. It has over twenty rooms, and includes such amenities as a wine cellar (accessed via a secret door installed in the Prohibition era), a tennis court, and a pool with a waterfall amongst other things. It is also a registered zoo.


In decay

A recent expose by a former star of the show Girls Next Door reveals that the interior of the eponymous mansion is in serious decay. The place does not look like it has been updated since the 1970s, there is a musty smell everywhere, and the playmates let their dogs pee on the drapes.


Bought out

Due to falling sales (part of which the online adult entertainment industry is to blame), Hugh Hefner had to sell off his world famous mansion. He asked for $200 million, but his next door neighbor bought the house for $100 million.


The second marriage

Hugh Hefner found love a second time in a woman named Kimberly Conrad, a woman who was named Playmate of the year back in 1989, the same year that the couple were married. This was despite Hugh being 36 years her senior.


More kids

Hugh Hefner and Kimberley Conrad ended up having two children together – Marston Glenn and Cooper Bradford. Marston has made a name for himself, having grown up in the mansion until the age of eight.



Hugh Hefner was partying like a rockstar at an age when a lot of people were becoming grandparents. However, in 1985 at the age of 89, Hefner suffered a stroke after an all night party. It was then he decided to slow things down.


Taking it easy

After deciding to be a bit more careful with his body, Hugh Hefner decided to take things a bit easier, something which included relinquishing the reins of his company to his daughter Christie. He was still involved but to a much lesser degree.



In 1998 Hugh Hefner decided to separate from his wife Kimberly despite him turning the mansion into a more family friendly environment. Hefner bought Kimberly the house next door so that he could be close to his children.


Acting roles

Hugh Hefner has played himself in a plethora of roles, including on the Simpsons, Robot Chicken, and several documentaries. He appeared as himself in the movie Miss March, a role which earned him the Razzie for worst supporting actor.


Girls next door

The Girls Next Door was a reality TV show which detailed the exploits of Hugh and his bunnies, most notably Holly Madison, the Shannon Twins, Kendra Wilkinson, and Bridget Marquardt. The show ran for six seasons.


Net worth

At one point in time at the peak of his career, Hugh Hefner was worth a staggering $200 million. He made his money from his Playboy Channel on both television as well as internet radio and also his magazine. He died with a measly $43 million.


Next to Monroe

Several decades ago Hugh Hefner decided that he wanted to be buried in the crypt next to Marilyn Monroe in the Westwood Village Memorial Park Cemetery. He bought the space in 1992 for an estimated $75,000.