A collection of never-before-seen photographs featuring Princess Diana and pop icon David Bowie has emerged nearly four decades after they were captured.
These candid images, taken during Bowie’s memorable 1987 concert at Wembley, reveal a joyful moment between two of the most celebrated figures of the time.
Photographer Denis O’Regan, the man behind the lens, recalled how the legendary promoter Harvey Goldsmith played a pivotal role in arranging the chance encounter between the Princess of Wales and the rock star.
O’Regan shared with MailOnline that he was working on Bowie’s Glass Spider tour and had just found a good spot for viewing, accompanied by his father and brother, when he learned that Diana was arriving.
O’Regan vividly remembers asking Goldsmith if he could snap a photo of Diana and Bowie together.
“Harvey suggested I should ask her directly,” he explained.
When 25-year-old Diana hesitantly inquired whether Bowie would be interested in the photo, O’Regan confidently assured her, “I think he would.”
However, the next day, Denis received a formal request from the royal palace asking him not to publish the photos.
The reasoning behind this media ban wasn’t due to the presence of Bowie, but rather because of Diana’s companion that night, Army Major James Hewitt – the man with whom she had a notorious affair that lasted from 1986 until 1991.
At the time, rumors about Diana and Hewitt’s relationship were circulating in the media, but there were no actual images to corroborate these claims.
O’Regan recalled how Hewitt purposely kept his distance from the cameras to prevent any potential captures alongside Diana.
Reflecting on the situation, he expressed no regrets about not photographing the pair—Hewitt was not a public figure, and the affair hadn’t been exposed yet.
This particular evening at Wembley has since been referenced in Andrew Morton’s explosive biography, Diana: Her True Story.
In it, Morton details that Diana was there with friends David Waterhouse and David Linley.
The Princess herself told Morton that she wore leather trousers, a choice she thought was fashionable, albeit inappropriate for someone destined for the throne.
This stylish choice, however, earned Diana a bit of a reprimand from palace courtiers, who felt that such attire was not fit for a future queen.
Morton noted that her fashion style at the concert was reminiscent of the then-Duchess of York, Sarah Ferguson, even if it wasn’t quite palace-approved.
Interestingly, this wasn’t Diana’s first encounter with Bowie; they previously met in 1985 during the iconic Live Aid concert, also held at Wembley.
Their paths would cross again in 1993 when Bowie hosted the Concert of Hope, a charity event organized partly by Diana to support awareness and fundraising for AIDS.
In O’Regan’s upcoming book, David Bowie by Denis, he reflects on his extensive career capturing musical legends.
The book features O’Regan’s stories and images of music icons from Freddie Mercury to Mick Jagger, showcasing his interactions with those who shaped the fabric of rock and pop history.
Diana’s very public struggle with her royal duties, alongside her personal affairs, paints a complex portrait of a woman caught between the expectations of her title and her true self.
After marrying Prince Charles in 1981 and experiencing a tumultuous separation in 1992, she confessed to the world about her affair with Hewitt during a landmark BBC Panorama interview in 1995.
As these long-hidden photographs resurface, they serve as a reminder of a different time; one filled with both joy and controversy—a snapshot of two icons, forever etched in history, frozen in a moment of laughter and connection amidst the storm of their tumultuous lives.
