Hugh Hefner, 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 and died on 27 September at his home, the Playboy Mansion, in the Holmby Hills area of Los Angeles. He was 91.

Discover 12 expensive things he previously owned.

The Original Chicago Playboy Mansion

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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. This luxury house boasted a brass plate on the door with a Latin inscription that translated to “If you don’t swing, don’t ring” and also had a large game room, a bowling alley, and Hef’s infamous round, rotating bed.

Mercedes-Benz 1969 600 Pullman Limo

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

What has been described as one of Hugh Hefner’s favorite 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-liter 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.

Playboy Mansion

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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

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.


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Stretch DC-9 Private Jet

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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 1960s and dined on Lobster and roast beef dinners, later throwing parties on the jet at 40,000 feet.

 Playboy Magazine

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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. 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.

Part of the Hollywood Sign

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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.

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.

1955 Cadillac Series 62 convertible

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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.


Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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

His wardrobe consisted of over 200 pairs of pajamas, 12 pairs of custom made velvet slippers and 35 custom-made Armani suits. His favorite outfit was a custom-made black smoking jacket and pajamas and you could often see him wearing his sailor hat in photo-shoots and ordinary day to day life.

Lamborghini Gallardo

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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 fiber used extensively inside and out to reduce weight to just 1,340 kg made it the lightest road-going Lamborghini in the range.

Wedding & Engagement Rings

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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.

 Mercedes-Benz 300SL Convertible

Hugh Hefner: Discover 12 Expensive Things He Previously Owned

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-liter engine, 4-speed manual transmission and had a top speed of 260 km/h.

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.

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.

The company also has a large online presence which includes 8 websites and a radio station while the licensing arm of the company handles Playboy trademarks on apparel, accessories, and collectibles 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.


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