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9. Mark Twain
Of course, you’ve heard of Mark Twain. Everybody has heard of Mark Twain. America’s most famous original novelist, the man who wrote The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn, may not be someone you think about much these days (most of us probably haven’t thought of him much since high school), but he was once the most famous man in America. I’m talking easily — he was bigger than the president and richer, too. In fact, he actually owned the publishing company that released the best-selling memoirs of then-president Ulysses S. Grant, a memoir that made everyone involved millions of dollars. But by about 1880, the great author had lost boatloads of money investing in a newspaper typesetting machine that failed miserably, and his publishing house was floundering. By the time a depression hit in the 1890s, Twain was well and truly screwed and had to declare bankruptcy at the ripe old age of 60 — not a great way to finish one of the most famous entertainment careers in American history.
8. Kim Basinger – Thanks Alec
There was once upon a time when Kim Basinger was considered one of the sexiest and hottest leading ladies in Hollywood. The star of such steamy hits as 9 ½ Weeks, L.A. Confidential, as well as the first Batman, was an “It” girl for a while, even more so when she and Alec Baldwin tied the knot. Perhaps that’s why she tried to get out of her contract to star in the sexy yet oh-so-creepy artsy flick Boxing Helena. Whatever her motives, they steered her wrong. Main Line Pictures, the makers of the film, sued her for $7 million in 1993. She eventually had to pay off $3.8 million of that lawsuit and was forced to declare bankruptcy the same year. To make matters even worse for our girl Kim, she also had to face tremendous public scrutiny when she and Baldwin underwent a very nasty divorce in 2003.
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