In 1993, Oprah Winfrey made history by conducting the most-watched interview in television history. It was an exclusive talk with Michael Jackson who had refused to be interviewed for 14 years. 90 million people tuned in for the sit-down chat at the King of Pop's Neverland Valley Ranch in Los Olivos, California. Winfrey called it "the most exciting interview" she'd ever done. After all, Jackson agreed to talk about anything. He didn't even discuss the questions with the host prior to the big moment. It was the candid conversation fans had been dying to see.

But at some point, they thought Winfrey had botched the interview. It started off as a friendly chat about Jackson's childhood and early music career. However, it quickly escalated into provocative inquiries about his controversies. The Billie Jean singer started to become emotional, seemingly frustrated about the questions. To this day, fans are calling out Winfrey for "lacking empathy" towards Jackson.

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Oprah Winfrey 'Lacked Empathy' During Michael Jackson's Vitiligo Confession

One of the first controversies Winfrey brought up was the color of Jackson's skin. "Are you bleaching your skin? Is your skin lighter because you don't like being black?" she asked the singer. The Thriller hitmaker seemed hurt about the accusations. "As I know of, there's no such thing as skin bleaching," he answered. "I have never seen it. I don't know what it is... This is the situation — I have a skin disorder that destroys the pigmentation of the skin. It's something I cannot help. But when people make up stories that I don't want to be who I am, it hurts me." Jackson's voice started to break.

"I can't control it," he added. "Let's reverse it, what about all the millions of people who sit out in the sun to become darker, to become other than what they are? Nobody says anything about that." Winfrey didn't stop to acknowledge how painful the question was for Jackson. A fan even tweeted: "Through woeful questioning, after suffering for years, Michael Jackson had the courage to tell Oprah & the world in 93 he had vitiligo. Did she show any empathy? Did the media ever pare back on the relentless attacks about him? No. It just became worse." Many fans agree.

"Not everybody has the gift of empathy," one wrote on Twitter. "But somebody like Oprah Winfrey, should be able to show some empathy, since people see her somehow as a role model. She kicked Michael in the back like anyone else. And that is very [shameful]." Another said the host was trying to "manipulate" the show. "What Oprah did here was to manipulate the audience and present Michael's response in a questionable way," they tweeted. "The way she responded was so skeptical, like 'you're not telling the truth' and it's exactly that attitude that leads to people who still believe he wanted to be white." Some also brought up the time Winfrey admitted in an interview that "when [she] was a little girl, she wanted to be [white]."

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Oprah Winfrey Asked Michael Jackson If He Was Still A Virgin

Back then, everyone was curious to know who Jackson was dating. The elusive star had always been private about his dating life. But for Winfrey's show, he confessed to dating Brooke Shields at that time. He also acknowledged other rumors about his love life, like his rumored proposal to Elizabeth Taylor who made a brief appearance in the show. It was what you'd call a "juicy" interview until the singer couldn't take it anymore. First, the host asked if Jackson had ever been in love. Then she asked, "Are you a virgin?"

"How could you [ask that]? I'm a gentleman," said the singer who quickly covered his face. He was laughing, but he also said he wasn't comfortable with such questions. Winfrey responded, saying that she'd "interpret" his being a gentleman as "you believe that a lady is a lady, therefore..." Jackson interrupted her and said: "It's something that's private. I mean, it shouldn't be spoken about openly. Call me old-fashioned if you want but for me, that's very personal. I'm embarrassed." Recently, fans reacted to the question, saying that Winfrey "got away with too much." A fan also tweeted that "[it's] very creepy [and] if a man asked her it would’ve been [an] uproar."

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Fans Called Out Oprah Winfrey For 'Destroying' Michael Jackson In 'Leaving Neverland'

In 2019, HBO released the controversial documentary Leaving Neverland where alleged sexual abuse victims of Jackson came out with their traumatic stories. Winfrey did an interview with the two accusers James Safechuck and Wade Robson, and expressed her support for them. Fans were quick to attack her, saying she was just making money off of Jackson's controversies. "Why did she profit off him by doing interviews with him?" a fan tweeted. "They were friends when he was alive. if she had heard the 'pattern and manipulation' she claimed why do light hearted interviews with the man. Makes her a bit shady."

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