What Did Oprah Do To Michael Jackson That He Never Forgot?

the detail.
16 min readFeb 23, 2024

Just imagine, February 10th, 1993. It’s a Wednesday evening and at 9.30pm you sit down, like millions of others, to watch ‘Michael Jackson Talks… to Oprah’. ABC’s most anticipated interview special ever, and the world’s biggest entertainer’s first televised interview in over 14 years. The conversation promised to be candid, the revelations explosive, as Michael Jackson agreed to give the world a rare glimpse into the life and mind of pop’s most elusive superstar. Winfrey probed him on growing up famous, abuse, his changing appearance, tabloid rumours, relationships and even his sexuality. Before MTV cribs and social media made celebrity lives so much more accessible, Michael Jackson welcomed cameras into his private paradise for the first time, his lavish Neverland Valley ranch, which would soon become synonymous with the performer.

Oprah Winfrey and Michael Jackson, 1993

The short meeting forever changed the careers of both powerhouses, and Winfrey at least felt a close bond between the two during their short interaction. But why after so long of staying tight lipped, did Michael finally decide to speak out? How did Oprah Winfrey secure the scoop so many tried and failed at? And what did she ultimately do that taught Michael he could never trust her like that again?

Oprah Winfrey and her talk show had roots in A.M. Chicago, a half-hour morning show airing on WLS-TV, an ABC owned-and-operated station in Chicago. Winfrey took over as host in early 1984, and within a month, took the show from last place to first place in local Chicago ratings, beating out daytime powerhouse ‘Donahue’. Aside from her local talk show, Oprah was also pursuing a big-time career as an actress. A.M. Chicago granting her big break, and first Michael Jackson connection, when one faithful morning Quincy Jones saw Oprah on TV and contacted her saying she should audition for a film he was producing, the adaptation of Alice Walker’s ‘The Color Purple’. Winfrey was eventually cast as Sofia in the film to great acclaim, even receiving an Academy Award and Golden Globe nomination for her performance. Valuing her experience on set and working with the cast and crew on the movie, Winfrey struck up a tight bond with Quincy Jones in particular, and they became dear friends as a result.

Oprah Winfrey playing Sofia in The Color Purple, 1985

However, Oprah had to put her movie career on hold as she soon signed a big television syndication deal. Now expanded to a full hour and renamed ‘The Oprah Winfrey Show’, the first episode of her new talk show was broadcast nationwide on September 8th, 1986. The show immediately brought in double Donahue’s national audience, displacing ‘Donahue’ as the number-one daytime talk show in America. In the early years of ‘The Oprah Winfrey Show’, the program was classified as a tabloid talk show. Focusing on relationship dramas, celebrity gossip and combative debates on hot button talking points. However, Oprah’s unique relatable demeanour and compassionate interview style had its own charm. According to ‘Time’ magazine in August 1988, “What she lacks in journalistic toughness, she makes up for in plainspoken curiosity, robust humour and, above all empathy. Guests with sad stories to tell are apt to rouse a tear in Oprah’s eye … They, in turn, often find themselves revealing things they would not imagine telling anyone, much less a national TV audience. It is the talk show as a group therapy session.”

In 1988, Oprah Winfrey scored the interview of a lifetime and made her second Jackson connection, when Michael’s beloved friend and movie star Elizabeth Taylor agreed to an interview. However, although housewives up and down the country were more than happy to open up, and she was more than happy to listen, Oprah hadn’t yet developed an appropriate interview style for her often more jaded celebrity subjects. The two women were set up in armchairs at the Hotel Bel-Air, when Taylor gave Winfrey a last-minute stipulation, not to ask anything about her love life. Winfrey was caught off guard by the request and later said, “that’s kind of hard to do when you’re Elizabeth Taylor and you’ve been married seven times”. During the interview, Taylor didn’t give much of anything. Her responses were short, there were awkward silences, and Oprah was even given a tense “None of your business” as an answer to one of her questions. Winfrey later revealed that Taylor apologized for the interview and called the conversation “the worst interview of my life.”

The Oprah WInfrey Show, 1986

However, four years later Elizabeth Taylor gave Oprah another chance when the legendary star of the silver screen, celebrated her 60th birthday on ‘The Oprah Winfrey Show’ in 1992. Among the many stories she told about her glamorous life, Elizabeth shared one particularly vivid experience she had when, about 30 years before, doctors had declared her dead for five minutes. Elizabeth described her out-of-body experience as having been welcoming. When Elizabeth finally came to, she no longer feared death and always kept the experience close to her. The revealing conversation was a positive experience for both parties, and with friend Elizabeth Taylor now on good terms with the television host, Winfrey felt the timing was right to reach out to Michael Jackson in hopes he would agree to an exclusive interview.

For many months Oprah received nothing from the global entertainer, as he embarked on the first leg of his Dangerous World tour. All a while, the tight-lipped superstar saw the already unpleasant tabloid press become increasingly ferocious. With no explanation to his increasingly lightened skin and changing looks, they paraded unflattering photos of the artist as evidence of his mutilating addiction to plastic surgery and claimed that the superstar denied his race by casting a white child to play him in a Pepsi commercial. Jackson took legal action against those perpetuating lies and issued stern statements denouncing such claims, but the issue only seemed to be getting worse. Michael Jackson couldn’t ignore it anymore, he had to face up to his serious image problem. Having allowed the press to construct an increasingly bizarre ‘Wacko Jacko’ image of him for years now, it was seriously affecting his career.

Michael Jackson, 1992

Having already orchestrated press conferences, released open letters, and written an autobiography, the solution had to be even more radical. To stem the constant hostility being thrown his way and steer the press in a direction that would be more compassionate towards him and his efforts. Encouraged by Elizabeth Taylor, Michael needed to reveal himself to the world in a way he had for so many years avoided. Jackson boldly picked up the phone and called the television host. According to Oprah, she was dumbfounded that the elusive superstar would out-of-the-blue called her directly himself. Michael could have gone to Barbara Walters or any other primetime broadcast journalist to conduct the interview, but he likely chose Oprah because of their shared connection with Quincy and Elizabeth Taylor. The gloved one didn’t want to sit in a studio somewhere and be probed by a cynical interviewer he felt no connection to. If he was going to open up for the first time ever he wanted it to be at his home in California, broadcast live so his words can’t be manipulated, and conducted by a sympathetic ear who themselves revealed their inner most private details every day to millions.

The terms were agreed, and dates were set. Oprah had done countless interviews and met plenty of A-list celebrities before, but she remembers her excitement at going to the King of Pop’s home. “We are coming in the gates of Neverland, and it’s like a moment in The Wizard of Oz,” she said. “It was literally like going to see the wizard. We couldn’t believe it. I felt like a kid.” In early 1993, Oprah and her production crew visited Michael Jackson at his Neverland Ranch to shoot commercials for the interview special. One commercial was broadcast immediately after his record-breaking Super Bowl halftime show, just ten days before the live special was due to be broadcast. There was press speculation that Winfrey was told to only refer to Michael Jackson as ‘The King of Pop’, and that certain topics were off limits. Claims that were later denied, this was going to be the big moment where Michael Jackson was expected to finally open up about his private life.

Promo image for ‘Michael Jackson Talks… to Oprah’, 1993

On the night itself, Oprah Winfrey has since revealed that it was the most nervous she had ever felt. Stating that when she said the words, “live and around the world”, despite hosting a live talk-show watched by millions every day, she felt her knees immediately start to shake. By her own account, they were shaking in till she sat down with Michael and asked her first question, “well, how nervous are you right now?”. Jackson was surprisingly calm for someone not used to speaking publicly. Replying that he wasn’t nervous at all, which then put Winfrey at ease. During their interview, Michael spoke to Oprah about missing out on a normal childhood and

denied multiple tabloid rumours, including that he slept in a hyperbaric chamber or bought the bones of the ‘Elephant Man’, “Where am I gonna put some bones?”.

Michael’s relationship with his father, Joe Jackson, had made plenty of headlines throughout the years. When Michael spoke with Oprah, he was extremely open about the sensitive subject, saying his father called him ugly, beat him and frightened him. “I love my father, but I don’t know him… Sometimes I do get angry. I don’t know him the way I’d like to know him,” he said. Oprah said she was surprised that Michael was so candid in his revelations about his father. “Even in saying it, Michael tried to temper it by saying, ‘Please, don’t be mad at me, Joseph.’ So obviously you know that he still carried that fear and pain,” she says. “Look in his eyes when he starts to talk about his father. His eyes shift.”

Oprah Winfrey and Michael Jackson during the live interview, 1993

In 1993, controversy about Michael’s ghostly skin tone was at an all-time high. “He kept getting whiter and whiter and whiter, and nobody understood why,” Oprah said. “Anybody who knew Michael Jackson will tell you that when you are up close to him — he had absolutely no pigmentation in his skin — you are looking at his veins when you look at his hand. You are seeing through to the blue veins, and they’re very, very apparent… You’re looking at a person who is almost translucent.” In one of the most memorable moments of Oprah’s interview, Michael told her he had a skin disorder that destroyed the pigmentation of his skin. The disease, called vitiligo, was in his family. “It is something I cannot help. When people make up stories that I don’t want to be who I am, it hurts me,” he said. “It’s a problem for me. I can’t control it.” This was one of Michael’s most defensive moments of the interview, “You can see he got a little testy there about the skin issue. I think in 1993 nobody understood what it was. Nobody knew anything about vitiligo,” she said. “I could see that that was one of the areas that was very sensitive to him, obviously.”

Plastic surgery was another much talked about issue surrounding Michael Jackson in the early 1990s. His appearance had changed so much since he was a child star that there was much speculation about the work he’d had done. When Oprah broached the subject, Michael wouldn’t get into specifics but said he’d had less plastic surgery than people thought. “You can count them on two fingers,” he said. Admitting to having a nose job, but said most of the cosmetic surgery rumors were false. “I have never had my cheekbones done, never had my eyes done, never had my lips done,” he said. Regarding his appearance at the time, Michael said he wasn’t pleased. “I try not to look in the mirror,” he said. “I’m never happy with what I see.”

Oprah Winfrey in Michael Jackson’s theater during the live interview, 1993

In 1994, Michael married Lisa Marie Presley, but when he spoke with Oprah a year before his nuptials, everyone was wondering if — and who — he dated. Michael told Oprah that he was in a relationship with Brooke Shields. Oprah said she hadn’t been sure how, or if, she was going to ask Michael about sex, but she knew it was something audiences wanted to know. “There was this sort of mystery about him. At the same time, he’s holding his crotch and wants to rock with us all night, we don’t know who he’s rocking with. That’s what you really want to know,” she said. Oprah asked the question even admitting it was embarrassing: “Are you a virgin?” Michael never answered. “I’m a gentleman,” he said. “That’s something that’s private, that shouldn’t be spoken about openly. You can call me old-fashioned if you want, but to me that’s very personal.”

The interview then moved through Michael’s private amusement park and into his full-scale home theatre. It was here that Oprah got a private lesson in the gloved one’s signature move. “We all remember when we first saw the Motown 25 special, and Michael Jackson moonwalked. There are seminal moments in our life, and that’s one of them,” Oprah said. “So to be able to see him do that live and experience it, that was a little ‘thriller’ for me.” Towards the end of her interview, Oprah talked with him about his life’s purpose. “To give in the best way I can through song and through dance and through music,” Michael said. “I believe that all art has as its ultimate goal the union between the material and the spiritual, the spiritual and the divine. I believe that that’s the reason for the very existence of art, and I feel I was chosen as an instrument to give music and love and harmony to the world.”

Oprah Interview on the cover of Jet Magazine, February 1993

A.C. Nielsen reported that ‘Michael Jackson Talks… to Oprah’ was watched by an average of 90 million viewers, which at the time was the twentieth-largest audience for a U.S. television program ever and stands today as the largest audience ever for a television interview. The special, along with his recent appearances at the 1993 American Music Awards, and the Super Bowl halftime show just days earlier, were contributing factors in a resurgence in sales for his 1991 album ‘Dangerous’. After a further spike following an appearance at the Grammys to accept the Grammy Legend Award, ‘Dangerous’ eventually entered the top 10 on the Billboard 200. “It was the most exciting interview I had ever done,” Oprah said. “It certainly was going to be the most watched interview.”

After the live interview special was over, Oprah reflected on the experience and the time she spent with the superstar, “what I remember about Michael the most is that he was a person who was passionate about life. He was really passionate about his work … and passionate about his desire to try to be a good force in the world.” Looking back, Oprah says she realized in that moment that she had a fondness for Michael. “He’s very likable there, and I can tell you I really, really liked him,” she said. “After this interview, I thought I could be his friend, because I felt that he was really honest.” Despite speaking about their connection, the pair never became close friends. Within 6 months of the landmark interview, Michael Jackson was embroiled in another battle when allegations of child molestation hit news headlines in the summer of 1993. While in a fight to prove his innocence, save his colossal career and rectify his tattered public image, Oprah Winfrey, like many others in the public eye, steered clear of the controversy.

Michael Jackson live statement from Neverland, 1993

Having shared her own experience of being sexually abuse as a child while taping her talk show, Oprah Winfrey had become somewhat of an outspoken activist for change to protect children and exposing what she considered a “national epidemic”. She did countless shows on the taboo subject matter, urged Congress to establish a national system of background checks for child-care providers, donated thousands to child-abuse prevention groups and hosted the 1992 primetime special ‘Scared Silent: Exposing and Ending Child Abuse’. Having become an advocate for those to speak out about an issue that often has deep shame attached to it, Winfrey likely felt she would be a hypocrite if she spoke out herself in favour of Michael. Especially having only spent a brief period with the superstar, and when details of the case weren’t clear yet. Oprah instead distanced herself from the King of Pop and never publicly shared her opinions on the alleged claims in order to avoid backlash.

However, despite Oprah’s desire to disassociate herself from Michael Jackson, the groundbreaking interview did wonders for her career as the special gave Winfrey and her talk show much needed credibility. She set her sights on more high-profile interviews and wanted to tackle more serious subject matters. By the mid-1990s, Winfrey began to host shows on topics such as heart disease, geopolitics, spirituality, and meditation. She became the go-to interviewer for the famous who wanted to bare their soul in deep meaningful conversation. Giving space to address social issues they were directly affected by, such as certain health struggles, sexuality, or substance abuse.

Oprah Winfrey and John F Kennedy Jr, 1996

In 2003, after Martin Bashir’s documentary, ‘Living with Michael Jackson’, reignited controversy over the superstar’s perplexing relationship with young boys, Oprah Winfrey conducted an audience debate on the subject. Although the television personality never expressed an opinion on the singer’s innocence, she was visibly disturbed by Jackson’s warped perception of what is appropriate between a grown man and a child. Expressing that it was dangerous to justify such behaviours, such as sleeping in the same bed as a minor, as it permits others to leave children in vulnerable situations with potential predators. When Michael Jackson was in the throes of his high-profile trial for allegations of child molestation in 2005, and while the topic was in the public zeitgeist, Winfrey took the opportunity to discuss the impact of child abuse on several of her shows. His brother Randy revealed that the final straw for Michael was when the jury was deliberating on his fate, Oprah Winfrey chose to up her ratings by broadcasting a show on paedophilia. It was clear to Michael that Winfrey was just like any other clout chasing journalist looking for a story, and therefore she could not, and would not, be trusted again.

However, after Michael Jackson’s sudden death in 2009 and during a massive public outpouring for the artist, Oprah Winfrey paid tribute to the troubled superstar. Reflecting on their time spent together and their groundbreaking interview back in 1993, she dedicated a whole Oprah Winfrey show to the late artist. In 2010, Oprah was given access to Michael’s former home in Encino, after being granted an interview with Katherine and his three children. The Oprah show special, caused a dispute within the Jackson family, many of whom were aware of Michael’s distrust in Oprah Winfrey. They especially disapproved of Oprah being allowed to film inside his home and conduct his three children’s first interview ever. Especially for a father who had been so vigilant in protecting his children from the glare of the public eye. However, it appears that Paris Jackson, at least, found the experience positive, and therefore agreed to be interviewed by Oprah two years later, this time by herself, for OWN’s ‘Oprah’s Next Chapter’.

Oprah Winfrey during her interview with Michael Jackson’s mother, Katherine, 2010

However, having garnered rating success since the King of Pop’s death with sympathetic exclusives with those most dear to the artist. Oprah Winfrey caused widespread controversy among Jackson fans, when in 2019 she switched entirely by hosting ‘After Neverland’, a TV special starring Leaving Neverland’s James Safechuck, Wade Robson and its director, Dan Reed.

‘Leaving Neverland’ being a two-part documentary that sort to expose Michael Jackson through the explicit accounts of child abuse by Safechuck and Robson. Using the opportunity not to express her own convictions about Jackson, she said in the ‘After Neverland’ special, “The movie transcends Michael Jackson. If it gets you to see how sexual abuse happens, then some good would have come of it. This is a moment in time that allows us to see this societal corruption. It’s like a scourge on humanity.”

At the beginning of the special, Oprah Winfrey turned to the three men she was interviewing before saying, “We’re all gonna get it.” Meaning that they would become targets for his loyal fans and the Jackson estate, who had already filed a $100 million lawsuit to prevent the film from airing. During her interview, Winfrey reached out to Dan Reed and told him that he had done “in four hours what I tried to do in 217 episodes” dedicated to educating her audience about sexual abuse. “Don’t let anybody in your world make it about what Michael Jackson did or do not do,” Winfrey told the audience, which was made up predominately of child sexual abuse survivors. “It’s about this thing, this insidious pattern that’s happening in our culture that we refuse to look at… I hope we can get past Michael Jackson, the icon,” she added. “Stop staring into the sun and do what is necessary to heal our children and heal ourselves.”

Oprah Winfrey’s Leaving Neverland Special, ‘After Neverland’, 2019

As predicted, Oprah experienced an onslaught of criticism online for her alliance with Michael Jackson’s alleged victims. Those close to Michael claimed she was simply choosing to ignore facts and giving legitimacy to their claims through her association. With Michael’s brother Jermaine tweeting, “So many in media, including Oprah, blindly taking Leaving Neverland at face value, shaping a narrative uninterested in facts, proof, credibility…. We faced similar “graphic” claims + trial-by-media in 2005. Jury saw through it all. Trial-by-law proved Michael’s innocence long ago. Fact.”

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the detail.

Cut through the headlines and understand the man, the music and the magic behind Michael Jackson.