Oprah with Meghan and Harry: masterstroke or disaster? | Oprah Winfrey

You could have forgiven the British royal family for giving primetime, tell-all interviews a wide berth for the foreseeable. The evisceration of Prince Andrew by the BBC’s Emily Maitlis in 2019 managed to achieve the near-impossible: making the Duke of York appear more dubious and less sympathetic.

But if we have learned one thing about the Sussexes, Harry and Meghan, it’s that they are intent on doing pretty much the opposite of what the other royals want them to do. So next Sunday, 7 March, a 90-minute special, Oprah with Meghan and Harry, will air on the US network CBS. There is also understood to be a bidding war between UK broadcasters – though not the BBC – for the interview, which, it is promised, will be “intimate” and “wide-ranging”.

“Most royal interviews are horrible car crashes,” says Jonny Dymond, the royal correspondent for BBC News. “Princess Diana garnered an enormous amount of sympathy, but actually did it work out as she thought it would do? Arguably not. Prince Charles and Jonathan Dimbleby, Prince Andrew and Emily Maitlis. Now, Meghan is going to get an easier ride from Oprah, I don’t think there’s any doubt about it. But you have to wonder how this will play.”

The bulk of the programme will be a conversation between Oprah Winfrey and Meghan; Harry is expected to join only for a concluding, future-oriented segment. And it seems clear the reason it is happening is because of a growing closeness between the two women. They met for the first time in March 2018, when Winfrey was visiting London and was invited to Kensington Palace. Two months later, she was a guest at the Sussexes’wedding at Windsor Castle. Winfrey wrote afterwards in her magazine, O: “All mature beings recognised it as the beginning it was.”

If it has been a courtship, it has been a mutual one, sometimes played out on social media. The 67-year-old Winfrey dispatched “welcome to the world” gifts for the couple’s baby son, Archie. In December, Meghan, 39, sent Winfrey a hamper from Clevr Blends, a company she has invested in that makes vegan “superlattes”. “My new drink of choice for the morning and night,” Winfrey told her 19.3 million Instagram faithful. Last summer, the Sussexes moved to a $14m house in Montecito, California, not far from Winfrey’s $100m mega-ranch, Promised Land.

“We now have the great benefit of hindsight, but quite why you would have someone at your wedding who you’ve met precisely once is a curiosity,” says Dymond. “Maybe they really, really got on well, but this does appear to have been a relationship that has certainly thrived in a fairly short space of time. Now [with the interview] it comes off to their mutual benefit: Oprah is a great platform for Meghan, and Meghan is a fantastic get for Oprah.”

For Kitty Kelley, an American author who published a controversial unauthorised biography of Winfrey in 2010, and has also written extensively on the royal family, the friendship makes sense. “Both have much in common: they know what it takes for a woman of colour to excel in a racist society,” says Kelley. “Yet each has achieved the American dream of global success and Midas wealth. Both women exude immense charisma, and know how to bedazzle the media, not unlike the late Princess of Wales. Both Oprah and Meghan have had to contend with fathers giving embarrassing interviews to the media.”

Kelley speaks from experience. Winfrey is famously guarded, and many of the most salacious sections of Kelley’s book came from a three-hour chat she had with Oprah’s father, Vernon Winfrey, in his barber’s shop in Nashville. “Each sees herself in the other,” Kelley says. “Oprah always wanted to be an actress, and listed ‘dramatic interpretation’ as her talent when she ran for Miss Black Nashville in 1971. In their personal lives, each woman seems to be the driving force: Meghan the push behind Harry as Oprah is with [long-term partner] Stedman Graham.”

For Meghan, endorsement from Winfrey could have some powerful (and lucrative) benefits. Winfrey has made unknown books into bestsellers, turned diets into overnight sensations, and her support of Barack Obama from 2006 onwards may even have swung the balance for him to become president. “Oprah might see herself becoming to Meghan what Maya Angelou was to her: a mentor and best friend,” says Kelley. Winfrey, of course, has considerable previous form when it comes to global scoops. In 1993, Michael Jackson gave her a tour of his Neverland ranch and his first interview for 14 years. The programme was watched by 90 million: a record for TV interviews that still stands. Tom Cruise jumped on her sofa in 2005 to proclaim his infatuation with his new girlfriend Katie Holmes.