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In 1999, Brad Pitt graced the cover of Rolling Stone in a series of daring photographs that featured the Hollywood heartthrob in various dresses. This bold move, captured by the renowned photographer Mark Seliger, was a significant departure from Pitt’s usual roles and image, challenging traditional gender norms long before gender became cannon fodder for conservatives. Brad Pitt: Challenging The Norm The cover image itself was striking: Pitt, smoking a cigarette, donned a boldly printed dress.

Inside the magazine, additional photos showed him in a variety of feminine attire, juxtaposing his rugged masculinity against delicate, often brightly coloured dresses. The contrast was not just about fashion but was intended to provoke thought and conversation about identity and societal expectations at the time. Pitt’s decision to participate in the shoot stemmed from a desire to break free from the heartthrob mold that had defined much of his career.



At the time, he was known for his roles in critically acclaimed films like “Fight Club,” “Se7en,” and “12 Monkeys,” yet he was often typecast as merely a handsome face. Coupled with this Pitt was at the centre of attention for his budding romance with Jennifer Aniston, garnering attention worldwide. “It just felt better than anything else” “There’s nothing to talk about.

I couldn’t just sit there and be pretty guy again...

I think that dress looked pretty damn good” he said of the shoot. “Truthfully, I don�.

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