Hidden Photos Of Princess Diana And David Bowie Finally Surface After Nearly 40 Years
By Chukwudi Onyewuchi on May 13, 2025 at 4:15 PM EDT

A long-lost photo of Princess Diana and David Bowie, taken backstage at a 1987 Wembley concert, has finally been unearthed.
However, the reason it stayed hidden for decades is even more fascinating than the photo itself.
Princess Diana And David Bowie Shared A Backstage Moment

Backstage at Bowie's 1987 Glass Spider concert at Wembley Stadium, a quiet yet captivating moment unfolded.
Photographer Denis O'Regan took a photo that remained unseen for nearly four decades. The snapshot showed Princess Diana smiling beside Bowie. It was a rare, candid image of two of the most recognizable figures in the world, captured just before the musician took the stage.
O'Regan, who worked with Bowie during the tour, was with his father and brother in the crowd when he heard that a very special guest was on her way.
"I was working with David on the Glass Spider concert," he recalled in a recent interview with the Daily Mail. "I was helping my father and brother find a good place to watch when I was told Diana was coming backstage."
Music promoter Harvey Goldsmith arranged the meeting, introducing the late Princess of Wales to the music legend. When O'Regan asked if he could take a photo, Goldsmith simply told him to ask Diana herself.
The Princess, ever humble, hesitated. “Would he even want a picture with me?” she asked shyly. O'Regan reassured her: “I think he would.”
Why the Palace Wanted the Princess Diana Photo Buried

The next day, O'Regan received a call from the palace requesting that the image not be published. At first glance, it seemed the royal aides were trying to protect Diana’s image by limiting photos with celebrities. However, the real reason was far more personal and secret.
Diana had attended the concert with Army Major James Hewitt, who was, at the time, her lover. Their five-year affair, which began in 1986, didn't become public knowledge until years later. In 1987, their relationship was still a closely guarded secret.
“James kept his distance from photographers all night to avoid being photographed with Diana,” O'Regan said. “At the time, I had no idea who he was. There was no buzz or speculation about him yet, so I didn’t even think to photograph him.”
Still, the palace was cautious. Any evidence of Diana’s outings with Hewitt, especially at such a high-profile event, could spark a scandal. Hence, to avoid any chance of exposure, they quietly asked O'Regan not to release the photos.
Princess Diana’s Bold Concert Outfit Sparked Palace Whispers

The photos weren’t the only thing that caught the attention of royal aides. Diana’s outfit choice that night, a pair of black leather trousers, also made waves.
To the average concertgoer, her look was stylish and fun. However, the ensemble raised more than a few eyebrows behind palace walls.
In "Diana: Her True Story," author Andrew Morton revealed that the Princess received “slapped wrists” for the daring outfit.
Diana later admitted she didn’t give the look much thought. “I went in leather trousers, which I thought was the right thing to do,” she said. “Completely putting out of mind that I was the future Queen, and future Queens don’t wear leather like that in public.”
Morton explained that Diana was trying to be more relatable and fun, like her sister-in-law, Sarah Ferguson. But the palace courtiers weren’t amused. “Once again, she was trying to behave like Fergie,” he wrote, “but courtiers did not feel her apparel was suitable for a future Queen.”
Still, the outfit became an iconic part of her style legacy and another example of how Diana balanced her royal duties with her desire to be her own person.
Princess Diana And David Bowie’s Unexpected Friendship

Though the 1987 photo has only now surfaced, it wasn’t the only time Diana and Bowie interacted.
Their first known meeting happened in 1985 during the historic Live Aid concert at Wembley Stadium.
Two years later, their brief but warm backstage meeting added another chapter to their connection.
In 1993, Princess Diana once again supported Bowie by attending his Concert of Hope. The event was held to raise money and awareness for AIDS charities, a cause that she championed passionately throughout her life.
Her appearance helped spotlight the event's importance, and her connection to Bowie reflected their mutual respect.
Lost Photo To Appear In Denis O’Regan’s New Bowie Book

Nearly 40 years later, the long-lost image of Princess Diana and Bowie will finally be published in Denis O’Regan’s upcoming book, "David Bowie by Denis."
The book chronicles O’Regan’s two-decade journey with the legendary artist, capturing candid and iconic moments from 1974 to 1994.
O’Regan’s archive includes images of musical greats like Freddie Mercury, Mick Jagger, Keith Richards, and Bob Marley.
However, the Diana and Bowie photo stands apart, not just because of who is in the frame but also because of its hidden story.