17. Nicky Hilton wore a young and fun embellished mini from alice + olivia, which skimmed her body to perfection. 2. Soulful Ruben Studdard edged out Clay Aiken to win the show’s second season crown, and received a 2004 Grammy nomination, but his finances have made for quite the sad song. Despite having accounted for more than $2.2 million in album sales, his credit was so bad at one point that he could not get financed for a house. In 2006, Studdard won $2 million in his lawsuit against his ex-manager for misappropriating the singer’s money and credit cards.
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