Caroline Bliss
It must have felt as though an eternity had gone by since their nuptials—14 months!—before Charles and Diana: A Royal Love Story premiered on ABC in 1982. But at least audiences got to watch the royal wedding of the century, held July 29, 1981, at St. Paul's Cathedral, all over again.
Playing Diana opposite David Robb as Prince Charles was Bliss' first role. She was still in drama school but, as a dancer who'd done some commercials, she had an agent who got her an audition.
"So I walked in and sat down, never for a minute thinking that I was anything like Diana," Bliss, who went on to be Miss Moneypenny to Timothy Dalton's James Bond in a couple of 007 films and act in British series such as The Paradise Club and Ruth Rendell Mysteries before becoming a spiritual teacher, recalled in a 2019 interview. "It just hadn't occurred to me. I don't think I look very much like her...and I could see them also thinking, 'Well, I'm not sure.' And halfway through the meeting, they said something and for some bizarre reason my reaction was, I went, 'Oh!'"
Reenacting the moment, Bliss put her hands on either side of her face in a gesture of astonishment, quite like the princess. "And they all went, 'Oh my god, she's done it naturally!'"
Nicola Formby
In 1992, the British tabloids were ablaze with headlines about Princess Diana and Duchess Sarah Ferguson's unraveling marriages. The Women of Windsor, which aired on CBS that October, tackled them both, with Jim Piddock as Charles and Sallyanne Law as Sarah.
Charles and Diana's separation was announced two months later.
Serena Scott Thomas
The 1993 NBC movie Diana: Her True Story was adapted from Andrew Morton's biography of the same name, which utilized tapes the princess made talking about the high and low points of her life as a royal. David Threlfall played Charles.
Julie Cox
A few months before Diana and Charles' divorce was finalized in August 1996 came the made-for-TV movie Princess in Love, co-starring Christopher Bowen as the Prince of Wales. The CBS movie was based on the 1994 book of the same name by Anna Pasternak, which told the purported inside story of Diana's affair with British Army officer James Hewitt, a captain in the Life Guards (which was first revealed in Morton's 1992 biography and which she admitted to during her 1995 Panorama interview).
Amy Seccombe
Airing in the U.K. in 1998, Diana: A Tribute to The People's Princess focused on the last year of Diana's life, including her relatively short romance with Harrods heir Dodi Fayed (George Jackos) that ended when the two of them were killed in a car crash in Paris on Aug. 31, 1997.
Genevieve O'Reilly
The 2007 TLC movie Diana: Last Days of a Princess was promoted as a documentary-style (with artistic license) account of her final days leading up to her death, incorporating real news footage and interviews with scripted dramatic scenes.
The additional inquest demanded by Mohamed Al-Fayed, Dodi's billionaire father, was still ongoing and wouldn't conclude until 2008 with the finding that the couple were unlawfully killed due to the "gross negligence" of their driver Henri Paul, who also died in the crash, and the paparazzi who gave chase to their car as they left the Hôtel Ritz in Paris.
Lesley Harcourt
The Scottish actress had a brief appearance as William's late mother as he's watching her in a television interview, setting the stage for the events covered in Hallmark Channel's William & Catherine: A Royal Romance.
The fairly pedigreed cable movie (Victor Garber as Charles, Jane Alexander as the queen and Jean Smart as Camilla) aired in August 2011, four months after Prince William and Kate Middleton's wedding, and was co-written, co-produced and directed by Linda Yellen, who had previously worked on Charles & Diana: A Royal Romance.
Naomi Watts
The 2013 film Diana focused on her complicated relationship with heart surgeon Hasnat Khan and subsequent coupling with Dodi Fayed, which wasn't as serious to Diana as the engagement ring on display at Harrods as a shrine to the ill-fated pair would have one believe.
Asked what compelled her to take on the role, Watts told reporters before the release, "Ultimately, the reason I wanted to say 'no' so much became the reason I wanted to do it as well. I was intrigued by the challenge. I mean, in the beginning I thought, how do you possibly take on the most famous woman of all time when everybody feels they know her so well? How do you take possession of that character? So that was daunting, to use a word of hers…"
Watts, who is originally from the U.K. but spent some formative years in Australia, said she didn't know much about Diana and Khan at all before she read the script, which was based on Kate Snell's 2001 book Diana: Her Last Love.
She also thought twice about accepting due to "the sensitivity of it—how will people feel about this?" Watts continued. "But I realized this story was bound to be told at some point, and how often do we stumble across such fascinating characters? They're quite hard to find as a woman, and one who embodies so many different things—the fragility, but also the great strength, unbelievable charisma, great beauty, wisdom, compassion and empathy. I thought about it and I thought, well I can't say no to this why not seize the opportunity?"
Reviews were not kind and the movie never received an American theatrical release, an experience Watts later shared with her dear friend Nicole Kidman, whose Cannes-to-Lifetime film Grace of Monaco received a royal share of ridicule, too.
Bonnie Soper
The New Zealander appeared in two Lifetime movies about Prince Harry's love life, 2018's Harry & Meghan: A Royal Romance, which aired about a week before the royal wedding, and 2019's Harry & Meghan: Becoming Royal, a melodramatization of the couple's first year of marriage.
Different actors played Harry and Meghan Markle in each, but their Diana was a constant.
"I didn't pay attention to the whole Royal scene—I was a little southern girl," Soper told New Zealand site Stuff in 2018. "However, I do very much recall seeing her in the magazines and seeing this woman hounded by the press. I remember being very interesting by her. Then of course, with the accident, I remember being shocked like the rest of the world and feeling sad, so sad."
Playing Diana was a "pretty amazing experience," she said, and she got an inkling that she might have nailed the audition when another actress there told her she just looked like the real deal.
"She looked at me and was like, 'oh my God, you're just like her. I'm going to read that you were cast,'" Soper recalled. "Then when I went into the room, they were like, 'wow, you're just like her.' Sure I was in character, but it was so nice to have that positive affirmation."
Jeanna de Waal
After two years of preparing, the Bavarian-born, Britain-raised daughter of a South African father and English mother was just beginning previews of the musical Diana at the Longacre Theater when their Broadway run was indefinitely postponed due to the COVID-19 pandemic. (The show had its world premiere at the La Jolla Playhouse in California in March 2019.)
"So, this show is about this once-upon-a-time princess called Diana," De Waal told Theater Mania at a cast event in February 2020, "and she met her fairy-tale prince, who was called Charles. But unbeknownst to her, he had a love on the side who was called Camilla. And the story is the workings of that relationship in a very public spotlight and what came to pass."
De Waal, who's 6 inches shorter than Diana's 5-foot-10, read Andrew Morton's 1992 biography of the Princess of Wales and spent hours studying YouTube videos to get her voice and mannerisms, including her finishing-school-caliber posture, just right.
"When you're trying to portray a painful moment at home, or nursing a baby, you don't want people to be, like, 'She looks like she's in stripper heels,'" De Waal quipped to the New Yorker in early 2020. As to what she observed watching the princess in action in old video footage, the actress noted, "She's fighting, she's surviving, but she's doing those things with her shoulders completely relaxed, and smiling for the cameras."
Asked why she felt Diana's story remained worth telling, De Waal, calling it a "dream role," told Broadway Inbound, "I think the reason people will want to see Diana is because she's still such a huge part of our zeitgeist and a part of our awareness. And I think we want to celebrate her."
Diana is re-headed for Broadway and Netflix in 2021.
Emma Corrin
The British actress, previously of the Bruce Wayne butler origin tale Pennyworth, took on the role for the fourth season of The Crown, starting with the earliest days of 19-year-old Lady Diana Spencer's romance with Charles.
"Initially I was very daunted, very much listened to the noise, heard all the voices and got quickly frustrated and quite scared about it," Corrin acknowledged her concerns to E! News. "I thought, this isn't actually giving me anything to work with, so then I very much had to kind of put blinkers on and just do my own thing. And then it massively helped, getting the script, because as soon as I had the script in front of me I realized, 'Oh, okay, this is a character I'm playing. This is The Crown's version of Diana. I can bring a lot of what I want to to this part.' It made it more manageable to do the role."
She enjoyed finding the precarious balance of strength and vulnerability that Diana projected, "and I think that's what The Crown does so well, is to show both sides of it."
Josh O'Connor, who plays Charles, told Harper's Bazaar in November 2019 when they were filming that "Emma's doing a brilliant job, and it's breathtakingly accurate; she looked the spitting image [of Diana], and it's kind of extraordinary. So that's kind of spooky."
Kristen Stewart
In Spencer, which aims to get beneath the surface and re-humanize the iconic People's Princess, Stewart may be the first actress to play Diana who actually has firsthand experience of the sort of paparazzi mob that the Princess of Wales faced off against regularly.
Addressing the question of how in the world do you get a thing like that right, Stewart said on Jimmy Kimmel Live in November, "I mean, everyone's perspective is different and there's no way to get anything right because what is fact in relation to personal experience? My movie takes place over, like, three days, and it's this, like, really poetic internal imagining of what that might have felt like rather than giving, like, new information. So, we kind of don't have a mark to hit. We just also love her."
Stewart was only 7 when Diana died, but she remembers seeing on TV the field of flowers that mourners left in front of Kensington Palace. "I've never seen so many in one place," the Twilight star recalled to Jimmy Kimmel. "I was really young, didn't really know what was going on. But now, it's hard not to feel protective over her."
Natalie Portman was nominated for an Oscar (and every other award) for her portrayal of Jacqueline Kennedy in Pablo Larraín's 2016 film Jackie, which focused on how the suddenly widowed first lady navigated the days immediately following her husband's assassination. Now, Stewart is the first to nab an Oscar nom for a Diana movie, none of them so far having been able to rise to the occasion that the late royal's hauntingly powerful—and, yes, inimitably scandalous—story remains to this day.
Elizabeth Debicki
The Paris-born, Melbourne-raised actress, whose resume includes The Night Manager, Widows and Tenet, will take over the role of Diana for The Crown's final two seasons.
"Princess Diana's spirit, her words and her actions live in the hearts of so many," Debicki said in a statement when the casting was announced in August. "It is my true privilege and honor to be joining this masterful series, which has had me absolutely hooked from episode one."