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One of Anne Hathaway's most daring films is "Havoc" (2005), where she plays a wealthy teenager who becomes involved in the gritty world of gang culture and drug dealing. The film showcases her willingness to take on challenging roles that contrast sharply with her more mainstream, family-friendly image. Hathaway's performance is both bold and provocative, highlighting her range as an actress. This film marked a significant departure from her typical roles and demonstrated her commitment to exploring complex characters.

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