Oprah Winfrey’s blunt question to Michael Jackson is still disturbing to watch years later: "Are you..."
Oprah Winfrey took the TV world by storm back in February 1993 when she interviewed the 'King of Pop' Michael Jackson at his Neverland ranch amid his child sexual abuse scandal. During the hour-long interview, Winfrey quizzed late Jackson about his childhood, health issues, and specifically his love life. At a point, it turned awkward when the topic veered toward the 'Thriller' hitmaker's dating life. Jackson admitted to dating and being in love with supermodel Brooke Shields at that time, and that is when Winfrey struck him with the most discomfiting question. “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?” Jackson grew visibly uncomfortable but maintained his composure and replied, “How could you ask me that question?” He avoided a direct response and said, “I’m a gentleman.”
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However, Winfrey did not end her curious questions targetting his love life, “Who satisfies your desire?” she prodded as per El Pais. "Brooke", Jackson shot back. “I’ve always been in love with Diana Ross," he quickly added. Kitty Kelley's 2010 book titled 'Oprah' revealed that the TV producer had pre-planned her questions to highlight his sexual life. Despite Jackson claiming to be in a serious relationship with Shields, the former model clarified during her 2023 documentary 'Pretty Baby: Brooke Shields' that their bond was 'platonic'. As per Entertainment Weekly, the 'Blue Lagoon' actress recalled being friends with the 'Smooth Criminal' singer since they were thirteen years old.
Shield called their connection 'childlike' and explained that they "both were quite juvenile in some ways and mature in others." "We had a bond," she said while honoring their friendship during his funeral in 2009. "Both of us needed to be adults very early, but when we were together, we were two little kids having fun." Shields even recalled Jackson wanting to adopt a child with her, "How can we make a difference, it's easier to adopt a child if you're two people. He never said, formally, 'Will you marry me,' it was never that for me, he never was that definitive," she confessed.
However, following Jackson's shocking 1993 interview with Winfrey, in which he publicly acknowledged dating her, they severed their relationship. The 'Mother of the Bride' actress was upset with her close pal because she was already in love with actor Dean Cain. In a 2001 interview with Rabbi Shmuley Boteach, Jackson admitted once again to be obsessed with Shields. "Her pictures were all over my wall, my mirror, everything." According to Oprah, millions of admirers were ready to unravel the enigma around Jackson and learn about his sexual life, the television queen justified herself when she recalled her famous inquiry years later.
"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 recounted. But Winfrey confessed that Jackson's answer blew her mind because he never entertained her thought, "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," he concluded.