Princess Diana Shined on the Red Carpet—See Rare ’80s and ’90s Photos With Hollywood’s Biggest Stars

James Bond is a British institution, so it’s only fitting that Diana met Roger Moore and his wife, actress Luisa Mattioli, at the premiere of Octopussy.

Diana met Steven Spielberg and his then-wife, actress Amy Irving, at the premiere of the ’80s classic Back to the Future, while Phil Collins, who produced an Eric Clapton song featured on the soundtrack, looked on. Spielberg was an executive producer of the film and served as a mentor to its director, Robert Zemeckis. The legendary director met Diana multiple times, and attended her funeral.

Diana and a teenage Jennifer Connelly looked quite amused by Ludo, a furry creature from Jim Henson’s David Bowie-starring cult classic Labyrinth. In a 2022 Stephen Colbert interview, Connelly, who had her breakthrough role in the film, recalled, “You can see how pink my cheeks are. I was so overwhelmed meeting her. She was impeccable. She was lovely.”

Diana and Michael Douglas showed off their surprisingly similar hairstyles at the premiere of Wall Street while Douglas’s costar, veteran British actor Terence Stamp, stood between them. At the time, Douglas admitted he felt sheepish about seeing the Princess, saying, “I'm nervous about sitting next to her because of some of the language I use in the film.”

Diana met Bob Hoskins, the human star of Who Framed Roger Rabbit, at the film’s premiere, and she managed to look like the epitome of class even while standing by a person in a Roger Rabbit suit.

Diana met Uma Thurman, John Malkovich and Glenn Close, the stars of the sexy period piece Dangerous Liaisons, at the film’s premiere, and dressed the part in a strapless black velvet dress with matching opera gloves. Diana and Close had a connection that went beyond just meeting on the red carpet: In a 2024 episode of Finding Your Roots, she discovered that the Princess was her eighth cousin. She said the revelation, “Makes me feel stronger,” and joked about a possible resemblance during their fateful meeting.

Meg Ryan, accompanied by her then-husband, Dennis Quaid, and costar, Billy Crystal, leaned in to admire Diana’s gorgeous red Bruce Oldfield evening dress at the premiere of her beloved rom-com When Harry Met Sally . . . In a 2021 Andy Cohen interview, Crystal recalled that when the film’s infamous fake orgasm scene happened, everyone turned around to see how the Princess would react, saying, “She started laughing so hard . . . she had one of those kind of laughs that if it was a date, I don’t think I’d see her again, just because of the laugh, but she was so wonderful and loved the movie.”

Sean Connery, accompanied by his wife, artist Micheline Roquebrune, met Diana at the premiere of his spy thriller The Hunt for Red October. At the time, he was recovering from surgery, but he wasn’t going to miss his chance to meet the Princess.

Diana met Bob Hoskins, Robin Williams and Phil Collins, the stars of Hook, at the premiere of the Steven Spielberg film. Williams had performed for Diana and Prince Charles in the ’80s, and during a Johnny Carson interview, he joked about the Prince’s big ears, then exclaimed, “I guess I’m not going back to England!” Charles must’ve not been too offended, as the comedian returned just a few years later.

Diana smiled at Kurt Russell and his costar, William Baldwin, at the premiere of their action blockbuster Backdraft. In a 2016 interview with James Corden, Russell said that during the premiere, Diana opened up to him about the struggles of dealing with the paparazzi, and he invited her to his ranch in Colorado as a getaway. Years later, Diana took him up on the offer, and visited the ranch with her sons and got some much-needed privacy. Russell recalled, “They came and stayed for 10 days at the ranch, and they had a great time.” While there, Diana struck up a friendship with Russell’s housekeeper, and she went on to send her Royal Christmas cards every year.

Diana may have been a literal Princess, but that didn’t mean that she had an unlimited supply of gowns. At the premiere of the Top Gun parody film Hot Shots!, she met Charlie Sheen while wearing the same sparkling red dress she’d worn at the When Harry Met Sally . . . premiere just a few years earlier.

The Liza Minnelli musical Stepping Out was a box office flop, earning just $246,000 on a $12 million budget, but that didn’t stop her from having a fun time with Diana at the film’s premiere. Given the fact that she came from a famous family, Minnelli felt that Diana was a kindred spirit, and said, “I was lucky enough to count Princess Di as a friend . . . we’d bump into each other at premieres or events where she’d be the guest of honor. We’d fall into conversation then we’d meet for tea. Later on, she’d come to my hotel and we’d have lunch, just the two of us . . . My instinct was to protect her. We talked about everything under the sun. She loved music. All my life I’ve had people bowing and scraping . . . Well, Princess Di got used to people bowing and scraping. So it was a relief to both of us that we could just be ourselves around each other.”

Diana met Prince of Tides director and star Barbra Streisand and her costar, Nick Nolte, at the film’s premiere. In her 2023 memoir, My Name Is Barbra, Streisand remembered how Diana helped her avoid a fashion faux pas when she noticed her skirt was unzipped, and she wrote, “She was warm and friendly, and it was fun to sit next to her in the balcony of the theater at Leicester Square, watching the film . . . Diana turned to me and asked, 'Do you know how wonderful you are?' . . . I thought Diana was wonderful. I wonder if she knew how wonderful she was."

Diana met Hollywood power couple Tom Cruise and Nicole Kidman at the premiere of their film Far and Away. Diana’s personal chef, Darren McGrady, recalled that after she met Cruise again during the filming of Mission Impossible, she joked, “That’s another one off the list. He’s too short!”

Jurassic Park director Steven Spielberg, his wife, Kate Capshaw, and the film’s stars, Sam Neill, Jeff Goldblum and Richard Attenborough met Diana at the premiere of the mega-hit. In a 2022 GQ interview, Neill recalled, “I'd seen it three or four times by then. So it was really half an eye on the screen, and half an eye on her, looking at how she was reacting, and sometimes she would have her hands in front of her eyes. I mean, she really loved it.”

Diana chatted with Apollo 13 director Ron Howard, the film’s star, Tom Hanks, and his wife, actress Rita Wilson, at the premiere of the space-travel drama. In 2017, Wilson shared the picture on Instagram, writing, “She could not have been more gracious, charming, funny and kind. I was expecting our second son at the time and she kept asking me if I was comfortable, and if I needed anything. She was a gregarious dinner partner, laughing and engaged. I think she felt like a ‘normal’ person. It was when she got up from the table it became so noticeable that she wasn't ‘normal.’ The entire restaurant went silent and watched her as she made her way through the tables to go to the ladies room.”

Diana met Chris O’Donnell, who played Ernest Hemingway in In Love and War, at the film’s premiere. In a 2018 interview with Stephen Colbert, O’Donnell said, “She couldn’t have been more friendly. She was letting my mom try on her jewelry. She was unbelievable.”