Did you ever wish you were born filthy rich? Then consider the following true-life tales of heiresses who might, in hindsight, have spit out their silver spoons.

Multimillionaires are not like everyone else, and Huguette Clark is a prime example of that difference. She owned mansions she never set foot in, spent time ordering splendiferous dollhouses and wrote her favorite nurse checks totaling over $36 million. Huguette was the daughter of copper king W.A. Clark, one of the original Robber Barons of the late 19th century. The section on W.A. Clark alone is an engrossing read. And Huguette, who passed away in 2011 at the age of 104, lived a long, odd, interesting life—ornate, imaginative, even artistic—but ultimately rather empty, too, like her many dwellings.

Born into the Guinness family, Ivana Lowell seemingly had every advantage and connection society could offer: her grandmother's parties were attended by the Queen Mum, her mother's husbands included artist Lucian Freud and poet Robert Lowell. And her mother was none nother than novelist Lady Caroline Blackwood. All privileges aside, genetics, absent parenting, and hiddden family truths resulted in Ms. Lowell's erratic upbringing and unfortuante abuse. The autobiography is a fierce patchwork of self-discovery.