2002 | 'Gangs of New York'

Martin Scorcese's period piece pegged Diaz as Jenny Everdeane, the love interest of Amsterdam Vallon (Leonardo DiCaprio), who goes to New York City seeking revenge against his father's killer, Bill the Butcher. Amsterdam falls for her but learns that Jenny, a pickpocket and con artist, was once Bill's ward and is still affectionate with him. The film, set in the 1800s, was nominated for 10 Oscars but infamously lost in all categories.
Mario Tursi / Miramax Films
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