It was the “what?” heard around the world when Oprah Winfrey sat down recently with Prince Harry and Meghan Markle for a tell-all interview.
In an age where fewer people are watching live TV, over 17 million people tuned in for the explosive two-hour CBS special.
Oprah’s interview was the most-watched show in the UK this year. More eyeballs watched Oprah than the Emmys and Golden Globes put together, according to Deadline.
Perhaps, the most memorable moment was when Oprah reacted for all of us after Markle alleged her baby’s skin color was a topic of concern for a still-undisclosed royal. That’s when Oprah said it all with her expression and the one-liner, “What?”
During that interview, Diana revealed, “there were three of us” in her marriage to Charles, Prince of Wales.
Greatest Interviewer of All Time?
Following the latest Oprah Winfrey interview, the Washington Post called her “the greatest interviewer of all time” and a “Queen” in her own right.
Long-time Oprah bestie Gayle King said her interview was “perfection.” Certainly, Oprah is “famous for getting people to talk,” as the Evening Standard suggests.
“‘Oprahfication’ has come to mean public confession as a form of therapy. And when it comes to Oprah, no one gets away lightly – not even celebrities,” wrote Jessica Benjamin.
Despite a relentless focus on getting newsworthy information, she has remarkable compassion, respect, and understanding.
“With her relentless follow-up questions, compassionate demeanor, and focused skill in eliciting bombshell after bombshell, Oprah proved herself the best celebrity interviewer ever. This may not have been much in dispute, after her interviews with Michael Jackson, Kim Kardashian and Barack Obama, among many others,” wrote Margaret Sullivan.
On often-critical Twitter, journalism experts gave Oprah accolades for the interview. By refocusing the conversation on “newsmaking comments,” Oprah guided the couple toward specific answers. When dramatic, emotional moments happened, she didn’t interrupt.
A Shocking Moment with Meghan Markle
As noted, it was a shocking moment when Markle discussed her experience as a royal while carrying her child Archie. For some reason, he would not be afforded protection or a title. Oprah wanted to know why.
“You certainly must have had some conversations with Harry about it and had your own suspicions as to why they didn’t want to make Archie a prince. What are those thoughts? Why do you think that is? Do you think it’s because of his race?” said Oprah.
That’s when Markle dropped the bomb heard around the planet.
“In those months when I was pregnant, all around this same time… So we have in tandem the conversation of, he won’t be given security, he’s not going to be given a title, and also, concerns and conversations about how dark his skin might be when he’s born,” replied Meghan.
“What? Who is having THAT conversation?” replied Oprah.
“There is a conversation with you?” Oprah asked.
“With Harry,” clarified Markle.
Soon after the interview, Oprah revealed that Harry told her the comments didn’t come from the Queen or her husband.
Days later, the Queen finally broke her silence about the interview in a statement:
“The issues raised, particularly that of race, are concerning. Whilst some recollections may vary, they are taken very seriously and will be addressed by the family privately,” the Queen said.
“Harry, Meghan, and Archie will always be much-loved family members,” she added.
See the astonishing moment from NBC news below:
Recommended: Prince Harry – His Awakening and New Outspoken Voice
Interview with Michael Jackson, 1993
As jaw-dropping as the interview with Harry and Meghan was, Oprah’s most-watched live interview was February 10, 1993, with the King of Pop. Indeed, it was the most-watched television interview of all time with 90 million viewers.
After 14 years of avoiding interviews, the late singer Michael Jackson met Oprah at Neverland Ranch at age 35. It was before any allegations were made about sexual abuse.
As with Harry and Meghan, Oprah didn’t give Jackson the easy questions. For example, she zeroed in on subjects in many people’s minds at the time, why his skin appeared to have paled over the years, and allegations that his father beat him.
“Is your skin lighter because you don’t like being black?” Oprah asked.
A visibly upset Jackson revealed he suffered from a skin condition.
“When people make up stories that I don’t want to be who I am, it hurts me,” Jackson replied after claiming to have a skin disorder, vitiligo.
Jackson’s Lost Childhood
In another moment, she wanted to find out how hard it was for Jackson to grow up as a global star since he was 12 years old.
“I want to know how big a price it was, losing your childhood or having this kind of life?” Oprah asked.
Jackson replied with an answer that provided understanding.
“Well, you don’t get to do things that other children get to do, the simple things that they so much take for granted. Having friends and slumber parties, having buddies, and just hanging out. There was none of that for me. I didn’t have any friends when I was little. My brothers were my friends,” said Jackson.
Following the explanation, Oprah expertly continued, and Jackson opened up further.
“I think every child needs a place to escape into a child’s world, into a child’s imagination. Was there ever a time you could do that?” Oprah asked.
Jackson explained why he often surrounded himself with kids.
“No, and that is why I think now because I didn’t have it then, I compensate for that. People wonder why I always have children around because I find the thing that I never had through them,” said Jackson.
Oprah Goes to Neverland
Sixteen years later, Oprah reflected on the interview, saying, “He’s very likable there, and I can tell you I really, really liked him.”
“After this interview, I thought I could be his friend because I felt that he was really honest.”
She was genuinely excited about going to Neverland.
“We are coming in the gates of Neverland, and it’s like a moment in The Wizard of Oz,” she says. “It was literally like going to see the wizard. We couldn’t believe it. I felt like a kid.”
A Private Moonwalk Lesson
At one point, she got a private lesson in Jackson’s signature Moonwalk dance, saying the moment was a “thriller” for her.
“Where did the Moonwalk come from?” she asked.
Jackson revealed that his inspiration, once more, came from kids.
“The moonwalk came from these beautiful black kids who live in the ghettos in the inner cities, who are brilliant. They just have that natural talent for dancing any of the new, hot dances. They come up with these dances,” Michael said. “All I did was enhance the dance.”
Later in 2019, Winfrey hosted an HBO documentary about allegations of child sexual abuse against Jackson called Leaving Neverland. She felt it was important enough to merit taking the “hateration” of Jackson fans.
“The movie transcends Michael Jackson. If it gets you to see how [sexual abuse] happens, then some good would have come of it…” she said in the special.
Oprah believes the movie was more than a story about Jackson.
“The movie transcends Michael Jackson. If it gets you to see how [sexual abuse] happens, then some good would have come of it…
See the Oprah interview with Jackson below:
Interview with Donald Trump, 1988
Among Oprah’s most “iconic celebrity interviews” is her 1988 interview with Donald Trump on the Oprah Winfrey Show. Even then, you can see his trademark hand gestures and familiar rhetoric, such as when he claims American allies needed to “pay their fair share.”
Trump appeared to promote his new book, The Art of the Deal, promoting himself as a dealmaker with a facade of public success. Soon after release, it topped the New York Times’ list of best-sellers, though critics panned it as “a weapon in the continuing public relations war that is Donald Trump’s way of doing business.”
“Deals are my art form,” Trump had written in his book. “I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after.”
By 2016, the Times reported that Trump might have “lost more money than nearly any other individual American taxpayer.” Nevertheless, Trump took the presidency for one term.
Oprah on Trump’s Presidential Aspirations
During the interview, Oprah zeroed in with laser focus to find out if Trump was preparing to run for president. As with other interviews, she followed up as she sought to get to the truth of the matter.
“This sounds like political, presidential talk to me, and I know people have talked to you about whether or not you want to run. Would you ever?” she asked.
Trump suggested he wasn’t interested, but left the door open.
“Probably not, but I do get tired of seeing the country ripped off,” he replied.
Oprah pressed, “Why would you not?”
In response, Trump seemed aggrieved that he was not living like a king while others were.
“I do get tired of seeing what’s happening with this country. And, if it got so bad, I would never want to rule it out totally because I really am tired of seeing what’s happening with this country,” Trump continued.
“..How we’re really making other people live like kings, and we’re not”, he said.
Notably, at the time, Trump was complimentary of politicians of all parties, not yet a Republican himself.
“You’ve said, though, that if you did run for president, you believe you’d win,” Oprah pressed again.
That’s when Trump indicated he would be all in if he did run for the White House. It was perhaps not taken seriously so long ago, but the seed was planted.
“I don’t know; I think I’d win. I tell you what; I wouldn’t go in to lose. I’ve never gone in to lose in my life,” said Trump. “And, if I did decide to do it, I think I’d be inclined; I’d say I would have a hell of a chance of winning.”
Trump’s ‘Hate Tweet’ to Oprah
By 2020, President Trump was tweeting about Oprah, criticizing her for a 60 Minutes segment. The interview featured Trump’s critics and supporters, but he felt the show was biased.
“Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes. The questions were biased and slanted, the facts incorrect. Hope Oprah runs so she can be exposed and defeated just like all of the others!” President Trump tweeted.
As we know, Oprah did not run for the presidency and was confused by his tweet.
Good Morning America reported that the veteran journalist actually added a voice from a Trump supporter after she had seen the rough cut of the piece.
“So, I was working hard to do the opposite of what I was hate-tweeted about,” Oprah said.
In 1999, Trump considered Oprah as his running mate when he considered running as an Independent candidate. In a Larry King interview, Trump said, “She’s popular, she’s brilliant, she’s a wonderful woman. She would be sort of like me,” Trump said at the time.
Art of the Deal Co-Author’s Eery Prediction
In 2016, Tony Schwartz, co-author of Art of the Deal, predicted how Trump would react to losing the election to Hillary Clinton. Today, it eerily foreshadows what we saw after his 2020 election loss to President Biden.
After a speech at Oxford University, Schwartz warned that Trump would incite “that anger that’s sitting inside his supporters in any way he can to provide evidence that he was wronged, the election was rigged, and he didn’t really lose.”
“Trust me when I say this, when Trump loses the election, he will never acknowledge, he will not concede the election, and he will never acknowledge that he lost the election,” Schwartz added. “Because to do that is to feel obliterated, and he’s not going there. So it’s going to be a dangerous, tense time in America in the weeks after the election.”
Obviously, Schwartz’s words were prescient of what would come on January 6, 2021, the Capitol riot and insurrection. Maybe one day, Oprah Winfrey will interview Trump about that too?
See the interview from OWN below:
Featured images: Screenshots via YouTube