YEAR: 2000
A kiss is just a kiss – unless it involves your brother. When Jolie – in Goth-inspired garb – planted one on the lips of bro James Haven during the Oscars pre-show, she cemented her reputation as a Hollywood wild card. Later, during her Best Supporting Actress acceptance speech for Girl, Interrupted, she went on to declare to him, "I'm so in love with you right now."

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