February 22, 2009 - Frazer Harrison/Getty Images North America more pics like this »
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18. Penelope Cruz

Penelope Cruz won twice on Academy Awards night: once for Best Supporting Actress in Vicky Cristina Barcelona, and again for the billowing, vintage Pierre Balmain gown she wore on the red carpet. She saw the dress eight years before she decided to wear it, and we'd say she picked the right night.