You Can’t Take It With You: Unique Ways Rich Folks Cashed Out

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He made a fortune as co-creator of one of the most iconic television shows in history, and now he’s giving it all away.

Sam Simon, 58, announced in May that he only has months to live due to his ongoing battle with terminal colon cancer. With no wife or kids, and his family financially set, Simon’s donating his fortune – which he told The Hollywood Reporter amounts to “tens of millions” of dollars in Simpsons royalties each year – as well as his mansion to a variety of charities that benefit the homeless, including The Sam Simon Foundation, as well as children and animals (Simon is a staunch supporter of PETA).

Simon’s generosity in the face of a deadly illness is truly inspirational. And, it got us thinking – what have other rich and famous folks done with their wealth when their time came? We found seven creative examples:

William Shakespeare – A Bed for His Not-So-Beloved

It turns out the Bard, whose love sonnets are virtually intertwined with our modern notion of romance, actually wasn’t very fond of his wife. As one biographer wrote, “his removal from Stratford, the total omission of his wife’s name in the first draft of his will, and the bitter sarcasm of the bequest by which he remembers her afterwards, all prove beyond a doubt both his separation from the lady early in life, and his unfriendly feeling towards her at the close of it.” Et tu, William?

In his will, Shakespeare left, among other things, money to his relatives and children, a sword to a friend, and even £10 to “the Poor of Stratford.” To his wife, Anne Hathaway, he, in a note attached to the will, bequeathed his “second best bed” to her. Ouch. No word on who got his best bed. The family pet, perhaps?

Charles Vance Millar – The Great Stork Derby

Anyone born in Toronto between 1926 and 1936 might have Charles Vance Millar to thank. Millar, a local lawyer, also had a penchant for practical jokes. In his will, he stipulated that the Toronto woman who gave birth to the most children in the decade following his death would inherit a chunk of his estate. Four women, no doubt knee-deep in diaper duties, tied for the win with nine kids in 10 years, earning themselves $125,000 each. We’d hate to have been the person who managed to pop out eight kids during the contest period. At least they’d have the joys of motherhood to look forward to….right? Right?

Marilyn Monroe – Something’s Got to Give   

The late starlet left all of her worldly possessions to her famed acting coach Lee Strasberg, for the purpose of distributing them to her loved ones and also likely in part to make sure the general public didn’t get their hands on her unmentionables. Strasberg however, kept it all.

As Vanity Fair noted, “The Strasberg bequest would eventually net the heirs tens of millions of dollars from film royalties, the sale of her personal belongings, and the licensing of her image over the last 45 years. A fortune would accrue to a woman Monroe had barely known: Lee Strasberg’s third wife, Anna Mizrahi Strasberg.”

Still, in 2013, disputes over items Monroe left behind spill over into courtrooms. Sadly, even in death, Marilyn can’t seem to find any peace.

Jack Benny – A Flowery Farewell

This is one of the sweetest celebrity tales you’ll see. Comedian Jack Benny sent his wife a red rose every day for the rest of her life after he died. Benny passed away in 1974. His wife Sayde Marks died in 1983. That’s a lot of vases.

Leona Helmsley – One Pampered Pooch

The “Queen of Mean” made her share of enemies in life, and her loved ones couldn’t have been too happy with her in death. Sure, the infamous investor left a few million to her relatives, but it was her favourite four-legged friend who reaped the rewards of her demise. Helmsley’s Maltese terrier made out with a cool $12 million, though court proceedings later chopped it down to a fraction of that – still enough to buy all the kibble the little guy could eat.

Samuel Bratt – Put This In Your Cigar And Smoke It

Let’s just say that, in death, Bratt lived up to his name. In life, his wife had this annoying habit of not allowing him to enjoy his beloved cigars. You know, actually taking an interest in his health and well-being. Now Bratt was a wealthy man, and when he kicked the bucket he left his Mrs. Bratt a tidy sum of £330,000. All she had to do to collect: smoke five cigars each day, every day, for the rest of her life.

Warren Buffet/Bill and Melinda Gates – The Pledge

“Money has no utility to me beyond a certain point,” Microsoft billionaire Bill Gates told Britain’s Telegraph newspaper earlier this year. “Its utility is entirely in building an organization and getting the resources out to the poorest in the world.”

Gates and his wife, Melinda, are known for their charity work, especially through the Bill and Melinda Gates Foundation, “the largest transparently operated charitable foundation in the world,” which helps fight poverty and bring access to information and technology to those who go without. But it seems the duo, along with the world’s third wealthiest person, Warren Buffet, want to keep giving even after they’re gone.

As a result, they started The Giving Pledge – which, in a nutshell, is a promise (not legally binding) made by some of the world’s richest people to give away have of their fortune’s to charity by the time they die, or after death. So far, 113 really rich folks – we’re talking billionaires here – have signed on.

Side note: Gate’s tech-rival, Steve Jobs, co-founder of Apple Inc., faced criticism for not donating money to charities, despite a net worth in the billions of dollars. Following his passing in 2011, his wife and friends, such as U2 frontman Bono, spoke up about the millions of dollars he quietly donated toward researching and fighting AIDS.

“We’re really careful about amplifying the great work of others in every way that we can,” Jobs’ wife, Laurene Powell Jobs told the New York Times this year, “and we don’t like attaching our names to things.”