Throwback: Brad Pitt challenging gender norms in Rolling Stone 1999

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.

Image: Rolling Stone – Mark Seliger

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.

Image: Rolling Stone – Mark Seliger

“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’t know what the hell I was doing. It just felt better than anything else,” he reflected.

The photo shoot was part of a broader effort by Pitt to redefine his public persona and demonstrate his versatility as an actor and an individual.

The public reaction to the shoot was mixed.

Traditional media mocked the photos, and many viewed it as a bold but confusing statement. The shoot was seen as controversial because it challenged conventional ideas about masculinity and femininity.

Image: Rolling Stone – Mark Seliger

At the time, gender fluidity and breaking gender norms were not widely discussed topics for people of Pitt’s social status in Hollywood.

Whilst there were obviously many before him who had made careers of challenging these gender ideals, for a straight man in his position, the appearance of Pitt in the shoot defied the social expectations of the actor.

Image: Rolling Stone – Mark Seliger

In the same Rolling Stone interview, he commented on the relentless media scrutiny he faced, especially regarding his relationship with Jennifer Aniston. “It’s just a weekly barrage… they create this whole scenario, and then they say we’re getting married, and because I did a movie about Tibet and because she’s Greek, we’re going to have a Tibetan-slash-Greek wedding, and we’re going to ride yaks into the sunset,” he said, venting his frustration with the tabloids.

The 1999 Rolling Stone cover remains a memorable moment in his career. By appearing in a dress on the cover of one of the most influential magazines, Pitt not only defied stereotypes but also paved the way for future discussions on gender and identity in the public sphere.

Image: Rolling Stone – Mark Seliger