From Sarah Ferguson to Michael Jackson, why the rich and famous use Oprah Winfrey to tell all

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Oprah Winfrey interviews Sarah Ferguson - AP
Oprah Winfrey interviews Sarah Ferguson - AP

When the rich and famous are rocked by a scandal and need a sympathetic ear, who do they speed dial? Oprah. If you need to call out, come out or shed a public tear - without losing everything you have - no one else can deliver such favourable PR. The 67-year-old queen of American television is every nervous interviewee’s best friend. But why?

First, she has clout: worth a reported $2.7 billion, she owns her own entertainment company, Harpo Productions which includes the Oprah Winfrey Network and O, and has 19.3m Instagram followers. Aside from her reach, Winfrey, who was born in rural Mississippi, knows what it is to build a global empire from sod all. But the most alluring thing of all has to be the sense of safety even the most scandalous star experiences in Winfrey’s warm embrace. Paxman would surely roll his eyes at her faux-gritty line of questioning: hard enough to shock audiences yet cosy enough for her interviewees to feign discomfort while delivering the scripted answer.

The latest bottoms to snuggle into the seats in front of her belong to her friends and neighbours, the Duke and Duchess of Sussex. And they’ve enjoyed the classic Winfrey treatment, all from the comfort of their $14m Montecito home, where the sprawling gardens provide exquisite background foliage. It all begins with a dramatic trailer, heart racing music and a cinematic beat. It has the gusto of a Hollywood epic.

‘I don’t know how they could expect that after all this time we could just stay silent’, Meghan Markle says between the theatrical duh-dums. Then, in a blinding crescendo, Winfrey says, ‘you’ve said some pretty shocking things here’. The clip ends as Winfrey laughs, knowing that we’re already stocking up on family bags of popcorn, because nothing beats a royal scandal.

Read More: Oprah before Meghan and Harry, her most memorable and revealing interviews

Harry and Meghan
Harry and Meghan

The two-hour-long interview airs on CBS at 1am on Monday morning UK time, and will be broadcast on ITV at 7pm Monday evening. Ahead of the Sussexes' big moment, here are six other occasions when the rich and famous used Oprah to tell all - and get the public on side.

How to watch Harry and Meghan's interview with Oprah in the UK tonight

Sarah Ferguson: scorned Royal looking for sympathy

Meghan and Harry aren’t the first royals to scurry across the Atlantic hollering that life in a palace isn’t always their cup of tea. In 1996, Sarah Ferguson, aka Fergie, gave the first of many interviews with Winfrey after agreeing to divorce Prince Andrew - it came with the revelation that royal life is ‘no fairytale’.

‘The British press at the moment is completely and utterly cruel and abusive,’ she said, as the American audience marvelled over the surprisingly low bulb wattage permitted in the palace and oohed and ahhed about the fact that Fergie got to keep her tiara (pronounced ti-yeah-rah in American).

The broadcast was neatly timed to the release of her tell-all book, My Story, and the interview was larded with frequent mentions of Fergie’s good friend the recently divorced Princess Diana, calling her ‘the perfect princess,’ and explaining that, ‘we’re like rivers, we want to go around the next corner’. In a now ominously premonitory clip, she said, ‘the tabloids have literally tried to kill her.’

Like some Arabian Nights genie, Oprah opened the gigantic American market to a cash-strapped former Duchess to make a fortune from... if she could.

Lance Armstrong: the big reveal

In January 2013, the cycling world gasped a collective, ‘what the...’ Not because it emerged that the cycling star had doped to earn his seven Tour de France wins - a fact that he had viciously denied for decades - but because he chose Oprah as his interviewer. He flew her out to a hotel suite in Austin, Texas, for the occasion.

Nothing much was revealed in the 16-second teaser, complete, of course, with dramatic music, other than the fact that there were ‘no holds barred’. But the interview got straight to the point in the first heart-squelching minutes:

‘Did you ever take banned substances to enhance your cycling performances?’

‘Yes’

‘In all seven of your Tour de France victories did you ever take banned substances?’

‘Yes’

But the question asked by everyone, whether they were a ‘believer’ in Armstrong or not (I was, and this admission felt like a personal attack), was why was the interview not granted to a sports journalist, one of the many that he had lied to or sued over the years.

But rehabilitating Armstrong’s reputation was a step too far - even for Winfrey.

Michael Jackson: man on a knife-edge

In 1993, Winfrey was granted entry to Neverland, Michael Jackson’s infamous Santa Barbara estate, where it has since been alleged that he abused children.

It was Jackson’s first interview in 14 years, and remains the most-watched television interview in history, with 90 million viewers. ‘It was literally like going to see the wizard. We couldn't believe it. I felt like a kid,’ Winfrey reflected in a 2009 blog post.

The encounter took place as public interest in Jackson’s changing skin colour and plastic surgery addiction reached fever pitch, and he answered Winfrey’s questions on the topic defensively but got off unscathed.

In a now uncomfortably famous quote, he said: ‘People wonder why I always have children around; it's because I find the thing that I never had through them. Disneyland, amusement parks, arcade games – I adore all that stuff because when I was little, it was always work, work, work.’ It was one year before 13-year-old Jordan Chandler became the first child to accuse Jackson of assault at Neverland, a case which he later settled for $23m.

At the time, Winfrey seemed convinced by Jackson’s performance. In March 2019 the documentary Leaving Neverland aired. In it, Wade Robson and James Safechuck, alleged Michael Jackson sexually abused them when they were children. Winfrey presented the after show, After Neverland, interviewing Robson and Safechuck in front of an audience of over 100 men and women who say that they were sexually abused as children.

She described the documentary as an, ‘Intense and very emotional experience’ and said, ‘this moment transcends Michael Jackson.’

Whitney Houston: the downfall

In 2009, the 24th season of the Oprah Winfrey Show, which Winfrey had hinted could be her penultimate, premiered with a shocking Whitney Houston interview - one of the last before her death in 2012.

‘I was a little bit worried as to whether Whitney was going to bring it. To give up the truth. Or whether this was going to be a game of me asking questions and her artfully dodging those questions,’ Winfrey later said. But she described Houston as arriving early, looking ten million dollars, and appearing clear headed and thoughtful.

In the interview Houston spoke in shocking detail about her ‘crazy love’ for former husband Bobby Brown and how their descent into drug abuse led to the downfall of her career. For a short time, Winfrey presented the world with the possibility of a superstar reborn.

Upon the news of Houston’s death, Winfrey aired a special show dedicated to this last interview. She spoke of how excited she had been that ‘The Voice’ - the term she affectionately used for Houston - was going to be back, singing after seven years of silence. Alas, it wasn’t to last.

Ellen DeGeneres: coming out

Yet another Santa Barbara local is the subject of one of Winfrey’s biggest interviews ever. While Ellen DeGeneres’ reputation has been marred of late, many of the LGBTQ+ community remember the moment she came out as iconic.

In 1997, she appeared beaming on the cover of Time Magazine alongside the big red words, ‘Yep, I’m Gay’. This was followed up by what’s known as ‘The Coming Out Interview’ with Winfrey. She took DeGeneres’s hands as she walked on stage to the song, ‘I’m Coming Out’, and said, ‘you nervous or what?’

DeGeneres’ coming out and Winfrey are synonymous. First, because of the interview, which she introduced as ‘Ellen’s sexual identity strip tease’ and ‘Gay hoopla’. Second because, right after the interview aired, Ellen, the character DeGeneres played on her sitcom, also came out - making her the first openly gay character on prime-time US TV. Winfrey played the therapist in that same episode - a mark of support for her friend.

There was outcry: Winfrey remembers receiving hate mail, and the following year Ellen’s sitcom was cancelled. But over 20 years later, as public opinion continues to evolve on the topic of sexuality, The Coming Out interview remains a top YouTube hit and a landmark moment.

Tom Cruise and Katie Holmes: the interview nobody will ever understand

Oprah Winfrey and Tom Cruise - Getty
Oprah Winfrey and Tom Cruise - Getty

An audience of women jumped and screamed hysterically as Tom Cruise greeted Oprah on her yellow sofa in 2005. She started by high-fiving Cruise, perhaps the most famous actor in America at the time, for attending her Legends ball with new girlfriend Katie Holmes, because, you know - mates. But proceedings got crazier by the second.

Stuck on a loop, Cruise knelt on the ground, hugged Winfrey, cracked up in laughter and held her hands, on repeat. ‘Something happened to you,’ she exclaimed. ‘I’m in love!’, he cried out, flopping forward as if in a rapture. Such was his enthusiasm that he bounded onto the sofa and started jumping up and down. Winfrey leaned back and said, ‘you’re gone!’

Cruise proceeded to march backstage, cameras in tow, to drag Holmes out by the arms as Winfrey and the audience chanted her name. They kissed. The audience grew wilder. It was perhaps the most iconic interview that nobody will ever understand.

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