6. Cayetana Fitz-James Stuart (18th Duchess of Alba)
Besides being the recipient of horrifying plastic surgery, the Duchess is a testament to the power of true love. When the 85 year old Duchess, estimated to have been worth nearly $5 billion, decided to marry 61 year old Alfonso Diez Carabantes in 2011, there was a huge backlash from her family, as well as the King of Spain, Juan Carlos. To prove that wealth had nothing to do with their nuptials, the Duchess gave her six children their inheritance early—a vast fortune including estates, priceless artwork, and even the correspondence of Christopher Columbus—and completely renounced her wealth.
5. Howard Hughes
No list of the most eccentric millionaires and billionaires would be complete without crowning their king, Howard Hughes. The heir to an oil tool drilling fortune, Hughes first parlayed his wealth into movies, producing a string of blockbusters and bedding Hollywood starlets. He was also an aviation pioneer, a designer and test pilot who suffered a terrible accident when he crashed his experimental Hughes XF-11 into a Beverly Hills neighborhood. In the wake of the accident, what might have been called ‘eccentricities’ were amplified wildly—he spent months in a darkened screening room without bathing, relieving himself in bottles and subsisting on a diet of chocolate bars, chicken, and milk. He acquired RKO Studios the following year, but reportedly never visited as he descended into madness. He became a nomadic recluse, shuttering himself inside hotel rooms, often purchasing the properties when his demands became too outlandish for the owners. He suffered intensely from obsessive compulsive disorder and germophobia, and chronic pain from the accident left him with a crippling addiction to painkillers. He died in 1976, shriveled and unkempt. Fingerprints were required to positively identify the body.