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| June 19, 2018

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12 Expensive Things Previously Owned By Millionaire Hugh Hefner

  • On October 5, 2017

He was an american publisher, playboy and businessman, he was the editor-in-chief of Playboy magazine which he founded in 1953 and he had an estimated net worth of around £200 Million Dollars, he was Hugh Hefner and Vidello Productions is taking a look at 10 expensive things he previously owned.


12 – Original Chicago Playboy Mansion

The original Playboy Mansion was located in Chicago and featured 72 rooms and was a neo-classical French brick and limestone residence located in the Gold Coast historic district of the city.

Hefner owned the Chicago Mansion from 1959 until 1974 – when he moved into his new residence full-time after a string of unfortunate events with the law.

Many of the features in the L.A mansion could have been found here including the grotto with waterfall, an indoor pool with a bar underneath, accessible by descending a fireman’s pole and featuring a glass wall.

The Chicago mansion boasted a brass plate on the door with a Latin inscription that translated to “If you don’t swing, don’t ring”.

The mansion was located just 5 minutes walk from one of the Playboy Enterprises first nightclub’s.

The Chicago residence also had a large game room, a bowling alley, and Hef’s infamous round, rotating bed.



11 – Mercedes-Benz 1969 600 Pullman Limo

What has been described as one of Hugh Hefner’s favourite cars, he could often be seen riding in this car to and from the airport.

This six-door car was powered by a massive 6.3-litre V8 and had many famous owners including King Hussein, Mao Tse-Tung, Queen Elizabeth II and the Shah of Iran.

The car was sold at Barrett-Jackson for a reasonable $78,100 and other notable owners include Elvis Presley, the Pope, and Jeremy Clarkson.

Production on the cars began in 1964 and continued through to 1981, and production totalled 2,677 units, comprising 2,190 Saloons, 304 Pullmans, and 124 6-door Pullmans.


10 – Playboy Mansion

The crowning glory of the Playboy franchise, this massive mansion is located in the Holmby Hills area of Beverly Hills.

The mansion covers 21,987 square feet and has been described as of Gothic Tudor Architecture and sits on 5.3 acres of land.

It was designed by Arthur R. Kelly in 1927 and has 22 rooms including a wine cellar (with a Prohibition-era secret door.

Other features include a screening room with built-in pipe organ, a games room, three zoo and aviary buildings with pet cemetery, a tennis and basketball court, a waterfall and a swimming pool area which also including a patio and barbecue area.

There is a built in grotto, a basement gym with sauna below the bathhouse and landscaping includes a large Koi pond with artificial stream, a small citrus orchard and two well-established forests of tree ferns and redwoods.

On the western side of the mansion are Playboy’s publishing offices and the Master’s suite occupies several rooms on the second and third floors.

There is a separate mansion next door which is a mirror image of the Playboy Mansion layout, only smaller, and was purchased by Hefner in 1996 as the home for his separated wife Kimberley Conrad and their children.

The mansion was estimated to be worth $200 Million Dollars, but was later sold for $100 Million.


9 – Stretch DC-9 Private Jet

Not only does this jet have sleek black paint that had to get special permission from the government, it also has a light up Playboy Logo on the aircraft’s tail.

The whole jet had been designed by Hugh Hefner and included a large dining area, master bedroom suite and shower area.

He paid $5.5 million for the Private jet in the 1960’s and dined on Lobster and roast beef dinners, later throwing parties on the jet at 40,000 feet.

The plane featured a round bed covered in fur and even a disco area with the plane being called the Big Bunny.

There was bar and a cinema area, so the Playboy founder could be fully entertained for the duration of the journey and the girls were trained at the Continental Airlines’ stewardess school.


8 – Playboy Magazine

Founded in Chicago in 1953, by Hugh Hefner and his associates, and funded in part by a $1,000 loan from Hefner’s mother, this magazine became the global success story in the adult entertainment world and remains one of the best known.

The magazine is most famous for having nude pictures on its front cover, usually by famous celebrities and models.

The magazine has a long history of publishing short stories by notable novelists such as Arthur C. Clarke and Ian Fleming and a regular display of full-page colour cartoons from people such as Harvey Kurtzman and Jack Cole.

Playboy features monthly interviews of notable public figures, such as artists, architects, economists, composers, conductors, film directors, journalists, novelists, playwrights, religious figures, politicians, athletes and race car drivers.

After a year-long removal of most nude photos in Playboy magazine, the March-April 2017 issue brought back nudity.

The magazine celebrated its 50th anniversary with the January 2004 issue and celebrations were held at Las Vegas, Los Angeles, New York, and Moscow during the year to commemorate the milestone.


7 – Part of the Hollywood Sign

While not known by some people, Hugh Hefner actually owned part of the Hollywood sign.
Hefner acquired the letter after helping to pay for restorations to the sign and was reported to have raised a substantial amount threw a fundraising event held at the Playboy Mansion.

The sign originally read Hollywoodland and was in a state of severe dis-repair and was replaced in 1978 with the words Hollywood.

This was not the only time that Hugh Hefner has intervened in the sign however.

A group of Chicago investors bought the land in 2008 and there were fears that a major development could be built on the site.

Hefner contributed $900,000 to a fund that purchased the land and gifted it to the city… thus averting any construction plans near the sign.


6 – 1955 Cadillac Series 62 convertible

The Cadillac Series 62 was produced from 1940 through 1964 and was originally designed to replace the entry level Series 65.

The Series 62 included a lower sleeker body, a new cellular grille insert, and inverted gull wing front bumpers.

An Eldorado style wraparound windshield was seen on all models of the car.

Tubeless tires were a new standard Cadillac feature and sales reached a record 118,000 that accounted for nearly 84% of all Cadillac’s sold.


5 – Wardrobe

Known for his flamboyant style, you could often see Hugh Hefner dressed in his typical dressing gowns and pyjamas while residing at the playboy mansion.

His wardrobe consisted of over 200 pairs of pyjamas, 12 pairs of custom made velvet slippers and 35 custom-made Armani suits.

Its thought that when he moved into the playboy mansion, there were so many clothes for him to choose from that he never left the house for months at a time.

His favourite outfit was a custom made black smoking jacket and pyjamas and you could often see him wearing his sailor hat in photo-shoots and ordinary day to day life.


4 – Lamborghini Gallardo

The Lamborghini Gallardo is a sports car built by the Italian manufacturer Lamborghini from 2003 to 2013 and is Lamborghini’s best-selling model with 14,022 being built throughout its lifetime.

Hugh Hefner’s gallardo had a top speed of 325 km/h, and a 5.2L V10 engine while the carbon fibre used extensively inside and out to reduce weight to just 1,340 kg made it the lightest road-going Lamborghini in the range.

On 25 November 2013, the last Gallardo was rolled off the production line while production of the replacement for the Gallardo, the Huracán, began in 2014.


3 – Wedding & Engagement Rings

Hugh Hefner gave his wives several wedding and engagement rings throughout his life and one ring in particular is thought to have cost around $90,000 dollars.

The ring in question was an engagement present to then fiance, Crystal Harris, who later sold the 3.39-carat diamond ring for half the price.

She received a wedding ring after they married in 2012, however the price of that gift has never been revealed.

After his death, its been reported she was left a home in the Hollywood Hills and $5 Million dollars in cash in a pre-nuptial deal that was signed before the wedding.


2 – Mercedes-Benz 300SL Convertible

The Mercedes-Benz 300 SL was the first iteration of the SL-Class grand tourer and the fastest production car of its day.

The model was introduced in 1954 as a two-seat coupé with distinctive gull-wing doors and it was later offered as an open roadster.

The car featured a 3 litre engine, 4-speed manual transmission and had a top speed of 260 km/h.

The original coupé was available from March 1955 to 1957 and was introduced at the 1954 New York Auto Show with only 3,258 cars ever built.

If your looking to get hold of an original 1955 model then you can easily expect to pay somewhere around $1.5 Million dollars for good condition in today’s market.


1 – Playboy Enterprises

The global media and lifestyle company that featured the magazine of the same name was thought to be worth around $215 million dollars in 2017.

Sales of Playboy magazine peaked in 1972 at over 7 million copies however by 2015 the circulation had fallen to 800,000.

The company also had a select number of around 40 nightclubs on its books and ran casino’s in the United Kingdom during the mid-1960s to 1981.

From 1981 to 1984, the company was a partner in the Playboy Hotel and Casino in Atlantic City, New Jersey and the Playboy Club at the Palms Casino Resort in Las Vegas, which opened in 2006.

The company also has a large online presence which includes 8 websites and a radio station while the licencing arm of the company handles Playboy trademarks on apparel, accessories and collectables such as trading cards, toy cars, dolls and more.

The Playboy Entertainment Group is a division of Playboy Enterprises that includes Playboy TV and Playboy Online, which is the fastest growing revenue source for the company.

In 2005, the company began producing Playboy Digital which is an exact duplicate of the print version of the magazine and its initial launch started with 15,000 subscriptions.

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