8. Amanda Lepore (Net Worth: $1.7 Million)
This singer/model/performance artist was born as Armand Lepore in Cedar Grove, New Jersey. She underwent gender reassignment surgery at the age of 19 and has undergone many additional surgeries to achieve the perfect female look. Lepore even had her ribs broken to appear thinner. Now a millionaire, she has appeared in fashion magazines, appeared in ads for big name companies like M.A.C. Cosmetics and Swatch, has a line of cosmetics in partnership with CAMP Cosmetics called “Collection Lepore,” and is considered a muse to many photographers including David LaChapelle and Terry Richardson.
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