Gary Coleman
Coleman was a childhood star who made around $70,000 per episode of his hit show "Diff'rent Strokes" that aired in the '80s. His show ended in '86, and that's when he found out that his family and financial manager were mismanaging his money. He struggled to find work and he lived in squalor for quite some time, but he eventually won a lawsuit against his family and financial advisor that returned a small amount of his money back to him. Unfortunately, that was not enough. Coleman filed bankruptcy in 1999.