Michael Jackson and Oprah Winfrey were two moguls that reached the pinnacle of their respective careers in entertainment by the 1990s. Their paths crossing only one time when the King of Pop agreed to be interviewed as part of a groundbreaking broadcast.

The conversation was revealing, an attempt to let audiences in the mind of Michael Jackson and his complicated world of superfame. Although Oprah allowed Jackson to open up, she eventually revealed herself to be untrustworthy after doing something to Michael Jackson that he would never forget!

‘Are you a virgin?’: The Oprah Winfrey-Michael Jackson interview 30 years later

In February 1993, the talk show host landed the first live, televised talk with the singer in 14 years. She asked the unthinkable in an hour-long television special, which portrayed an eccentric but vulnerable star. Mere months later, his public image would be tarnished forever

Michael Jackson and Oprah Winfrey during the high-profile interview at Neverland Ranch on February 10, 1993; according to some estimates, the broadcast drew nearly 100 million viewers worldwide.SAM EMERSON | REUTERS

To understand the enormous buzz that an interview with Michael Jackson (Indiana, 1958-Los Angeles, 2009) generated in February 1993, one needs to understand the context. Since the mid-1980s, people had speculated that Jackson wanted to become white, that he wanted to become a woman, that he had bought the Elephant Man’s remains, that he slept in an oxygen chamber, that he had married Elizabeth Taylor, that he suffered from anorexia, that his best friend was a monkey, that the monkey was telepathic, that Michael was a homosexual and that he was a virgin. Never had a celebrity provoked so much fascination or so many utterly bizarre headlines. Jackson had never responded to anything, except through his songs. For instance, Leave Me Alone, from his 1987 album Bad, was the first song in what became something of a subgenre in his musical oeuvre: Michael lamenting media harassment and responding to it with music.

Or at least that was how it went until February 10, 1993, when, sitting across from Oprah Winfrey in an ABC live special, he responded. According to Winfrey, the conversation was unscripted and uncensored. That was the first time Jackson had given a televised interview since 1979. Watching the two interviews back to back reveals an undeniable and astonishing fact: the biggest pop star the world had ever seen had become a completely different person in the intervening 14 years. It remains to be seen how the recently announced film about Michael Jackson’s life (which will star his nephew Jaafar and will be directed by Antoine Fuqua) will reflect this transformation.

Around 62 million viewers in the United States and 90 million worldwide watched the interview live, although some estimates, such as the one offered by Winfrey’s biographer, Kitty Kelley, claim it was higher at 100 million. The interview was one of those must-watch television events that stop everyone in their tracks; it presaged the massive viral video before the popularization of the internet: if one didn’t see the interview, there was nothing to talk about the next day. It was in the same league as David Frost’s interview with Richard Nixon in 1977, Barbara Walters’ interview with Monica Lewinsky in 1999 and, outside the United States, Martin Bashir’s interview with Princess Diana in 1995. Oprah is the queen of this format (her 2021 conversation with Prince Harry and Meghan Markle is the most recent great example of the show-interview).

According to television analyst Borja Terán, “Oprah really knows how to create an atmosphere. She arranges the interviews in advance, and they are very prefabricated, but then she has the [gift] of naturalness, of making herself seem like one more member of the audience, even though she is not. In the Michael Jackson interview, this is quite noticeable: she describes the artist’s disturbing environment with a naiveté that makes Michael himself not feel attacked. Oprah’s assumed naiveté achieves complicity with both Michael and the viewer, and on television complicity allows for everything. Thus, the most uncomfortable question was forgiven.” And Oprah posed a lot of difficult questions.

Michael Jackson, left, will be played in the film by his nephew Jaafar Jackson, right.MICHAEL PUTLAND / ARAYA DOHENY (GETTY)

The interview aired on February 10, 1993, and it coincided with a crucial moment in Jackson’s life. It was the last time the public viewed the artist not mired in disturbing allegations. Six months and 14 days later, in the summer of 1993, the first accusations of sexual abuse were made public, and his image was tarnished forever.

“That’s why I’m always surrounded by children now”

But in January of that year, Michael had just headlined the Super Bowl halftime show (the staging and format of which provided the template for today’s artists performing at the year’s biggest football game) and won three American Music Awards. In February, he received the Living Legend Award at the Grammys, an honor bestowed intermittently on the likes of Frank Sinatra and Aretha Franklin, which Jackson received at the age of 34.

The interview with Jackson took place at his huge Neverland Ranch, complete with its own amusement park and zoo. Oprah immediately connected with the artist and the audience by asking Michael if he was nervous. When he answered no, she commented that she wouldn’t be either. She began by asking softball questions. They talked about James Brown, Jackie Wilson, the Bee Gees and Motown. Eight minutes into the show, Oprah posed the question that would allow her to get to the meatier questions. “Were you as happy offstage as you were onstage?”

“Offstage I was very sad. I was always crying from loneliness.” With that, live in front of 62 million viewers, Jackson established the first great myth that would surround him from that moment on (and which his most diehard fans would use to justify his most outlandish behaviors): the kid whose childhood was stolen from him. “I was never able to enjoy the simplest things that a child takes for granted in his life. That’s why I’m always surrounded by children now.”

Michael Jackson, in 1993 in a hospital for sick children.GETTY IMAGES

After addressing how Michael felt going from an adorable child prodigy to a teenager, Winfrey laid the groundwork to address the singer’s controversial physical appearance; by then, the grown man had a pale complexion, a narrow, pointed nose, a Kirk Douglas-like dimple in his chin and he wore copious white makeup on his face. “I didn’t even want to look in the mirror, my father would tell me I was ugly and I would cry all the time,” he said of his adolescence. “Did he ever hit you?” “Yes.” “Why?” “He was very strict; just his look alone terrified me. Sometimes he would come to see me, and I would throw up.” “As an adult too?” “Yes.”

Then Oprah started to fire away. “Is it true that you sleep in an oxygen chamber to stay eternally young?” “Did you buy the Elephant Man’s remains?” “Is it true that you wanted a white actor to play Michael Jackson as a child in a Pepsi commercial?” Winfrey went through a litany of crazy headlines, all of which Jackson denied. At minute 24, Oprah posed the question that everyone was asking themselves in 1993: “Did you bleach your skin because you don’t like being Black?”

Here, for the first time in public, Michael mentioned that he suffered from vitiligo, an autoimmune disease that destroys pigment-producing cells. He defended himself somewhat crazily, but it did make some sense: “What about the millions of people who put themselves in the sun to make their skin darker, to become someone else? Nobody says anything about that!”

His physical appearance remained the focus of the conversation. “How many plastic surgery procedures have you undergone?” “Very, very few,” Michael replied. “You can count them on two fingers.” It doesn’t take a surgeon to know that Michael was lying; he maintained that falsehood in 2003, in his interview with Martin Bashir, when he responded sardonically to the same question: “I’ve had two operations…that I can remember.”

One of the last photographs that was taken of Michael Jackson while he was alive. He announced his farewell tour, “This Is it,” in a brief press conference on March 5, 2009, in London. He died three and a half months later.FOTO: GETTY IMAGES

But Oprah pressed the point, “You’ve had a nose job, that’s obvious.” “Yes, like a lot of people I know,” Michael responded “But I’ve never had my cheeks, eyes or lips done.” “Do you like the way you look now?” Oprah probed further. “I try not to look in the mirror too much, I’m never happy with what I see.”

“It’s embarrassing to ask you this, but I’m going to do it”

The interview was visually powerful; one could almost enjoy watching it on mute. Terán claims the visual aspect “very subtly [drew] Michael Jackson’s personality, that outdated mogul thing. The production was very skillful because the images told of all [Jackson’s] eccentricities. In that sense, the show [was] very ambiguous.” Despite the interview being filmed in his own home, one of the rooms served as a set. Michael entered the shot walking downstairs as Thriller played in the background, but no one was applauding. It is strange to see Michael in the absence of screaming and crowds; he seemed removed from his own celebrity. Every time a shot opens, we see behind him a huge, lonely room filled with expensive works of art. There’s one other person besides Michael: portraits of Michael Jackson, painted by Ralph Wolfe Cowan on a gigantic canvas showing him as a knight in armor accompanied by his monkey Bubbles, a parrot and a cherub. Terán notes that he believes “that Michael thought the interview would clean up his image, but instead it showed the grandiloquence of his fame, of having no childhood, which knocks a person off kilter forever.”

In the most awkward part of the interview, Oprah took up the topic of the singer’s love life and asked him a strange, naïve question that seemed more suited for a child than a 34-year-old man. “Do you go out and have fun, do you date?” “Yes,” Michael replied. “Who do you date?” “Right now, Brooke Shields.” Oprah nodded and murmured “Hmm.” “She comes to my house, or I go to hers,” Michael continued. “Have you ever been in love?” Oprah pressed on. “Yes.” “With Brooke Shields?” “Yes. And another girl.” The next question that followed was the most striking of the entire encounter, because it was asked of a 35-year-old man who had just claimed that he dated and had been in love.

“I’m going to ask you something and it’s embarrassing for me, but I’m going to ask it anyway. Are you a virgin?” Michael sighed, laughed and replied, “How could you ask me that question?” Ultimately, he sidestepped a direct answer with an odd response. “I’m a gentleman.” “Who satisfies your desire?” asked Oprah (in a nod to a line from the then newly released single Give in to Me). “Brooke.” Then he added, “I’ve always been in love with Diana Ross.” Oprah asked if he would propose to Elizabeth Taylor. “I’d like to,” Michael replied, apparently forgetting that he just implied that he was in a romantic relationship with Brooke Shields.

Michael Jackson and Brooke Shields at the 1993 Grammy Awards, a few days after the interview with Oprah Winfrey.JOHN T. BARR (GETTY)

According to Kitty Kelley’s biography Oprah, the host lied when she claimed at the beginning of the interview that nothing had been prearranged. The author claims that “Oprah promised not to ask him if he was gay.” She kept her promise. Of all the questions Oprah asked, none had to do with his sexual preferences.

The Oprah Effect

All the questioning that we have reviewed to this point occurred in just 30 minutes. In the second block of the interview, the tone changed completely. Michael showed Oprah his Neverland Ranch, and once they settled in the theater, he talked about his social work and his interest in helping children. He also sang and danced. Michael went from reacting to Oprah’s questions with some trepidation to carrying most of the conversation.

The interview had the intended effect (many considered it a promotional ploy by the two, rather than a real interview). Jackson’s album Dangerous, which had been falling down the charts in the two years after its release, became a top-10 bestseller again. “Oprah’s interview succeeded in reducing Jackson’s image from lunatic to simply eccentric,” wrote The Washington Post shortly thereafter. Time said, “Part soap opera, part show, the Michael Jackson interview was vivid, reckless and emotionally naked.” Life opined that “Oprah delivered as promised and accomplished something nearly impossible: bringing Peter Pan down from the clouds.”

Michael Jackson’s next two major interviews (with Diane Sawyer in 1995 and with Martin Bashir in 2003) would have even more disturbing questions. “Have you ever had suicidal tendencies?” “What’s a 36-year-old man doing sleeping with a 12-year-old boy?” “Have you ever had sexual intercourse with a child?” The rest of the story is familiar: Bashir’s 2003 interview, in which Jackson again claimed to share his bed with children, prompted an investigation and then a trial for the sexual abuse of a young boy who appeared with him on the show (Jackson was found not guilty).

Oprah’s 1993 interview closed with one of the last candid images we would see of Michael Jackson: Oprah and he walking toward the Neverland amusement park, as the camera pans up and music plays. But perhaps it’s not all that candid, Borja Terán argues. “If you look closely, in the sequence where they walk together to the amusement park all the rides are moving, but they’re completely empty,” he says. “It’s a magnetic, phantasmagoric ending. Wonderful.”

In this excerpt, we delve into the pivotal moment when Michael Jackson, facing a barrage of negative press and an increasingly bizarre public image, decided to confront his image problem head-on. Oprah Winfrey, a trusted and influential television host, became the chosen platform for this revelation. The decision to reach out to Oprah was a strategic one, based on their shared connections with Quincy Jones and Elizabeth Taylor, as well as a desire for a sympathetic interviewer with whom Jackson felt a personal connection.

The stage was set for a groundbreaking interview, which took place at Michael Jackson’s Neverland Ranch. Oprah recalls the surreal experience of entering Neverland, likening it to a moment in “The Wizard of Oz.” The interview aimed to address various controversies surrounding Jackson, including his changing appearance, plastic surgery rumors, and tabloid claims about his personal life.

During the interview, Jackson opened up about his childhood, revealing the impact of his relationship with his father, Joe Jackson. Oprah was surprised by the level of candidness, noting Michael’s fear and pain when discussing his father. This transparency was a departure from the carefully crafted public image Jackson had maintained for years.

One of the most significant revelations during the interview was Michael Jackson’s explanation of his skin disorder, vitiligo, which he said destroyed the pigmentation of his skin. This revelation aimed to dispel rumors and provide a medical explanation for his changing appearance. However, Oprah also notes the sensitivity surrounding this topic for Jackson.

The interview touched upon Michael’s encounters with plastic surgery rumors, with Jackson admitting to a nose job but denying other speculations about facial alterations. His dissatisfaction with his appearance was candidly expressed, emphasizing the toll the constant scrutiny took on him.

Michael’s relationships were also discussed, including his confirmation of a past relationship with Brooke Shields and his refusal to disclose details about his virginity, asserting his privacy on personal matters.

The interview showcased not only the vulnerabilities and challenges Michael Jackson faced but also his artistic purpose. He believed in the transformative power of art to unite the material and spiritual, striving to bring music, love, and harmony to the world. Overall, the interview marked a turning point in Michael Jackson’s public narrative, as he attempted to reclaim control over his image and share his authentic self with the world.

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