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Jessica Simpson

We've seen Jessica wear several hats over the years — singer, reality star, and, most recently, fashion designer at the helm of an empire reportedly worth billions of dollars. Life wasn't always so golden for the star, though. The gospel music label that represented Jessica went bankrupt when she was a kid, temporarily halting her platinum dreams. At 13, Jessica auditioned for Disney's Mickey Mouse Club, competing with Britney Spears and Christina Aguilera for a coveted spot on the show. Recalling her audition after watching Christina sing, Jessica later said, "I froze and forgot everything."

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