The rift started during the press tour and Oscar campaign for Precious back in 2009. Monique says Oprah, who was a producer on the film along with Lee Daniels and Tyler Perry, suggested she attend the Cannes Film Festival to support the movie. Monique wanted to spend her downtime with family or just relax, but faced pushback from the team, which led to her being labeled “difficult to work with”—a label she’s not happy about. But that’s not where her biggest issue with Oprah lies.

In 2010, just a month after Monique won the Oscar for Precious, Oprah had Monique’s brother Gerald on her talk show. Monique has had a troubled history with her brother, who molested her as a child. She’s been very open about this, and she shared that Oprah had called her to ask if it was okay to have Gerald on the show. Oprah reportedly said Gerald wanted to apologize and offer advice to parents on spotting predators, given his past actions against his own sister. Monique reluctantly agreed to let Gerald appear, even though she made it clear she didn’t want to be involved. She felt that Oprah’s framing of the situation, as Gerald wanting to help others, was not something she wanted to be part of.
It wasn’t just Monique’s brother causing her pain; it was her whole family. Monique was stunned as she watched her mother and other relatives brush off the abuse she suffered as a child. She never discussed her mom being involved, but seeing her defend Monique’s brother publicly, especially right after Monique’s big win with Oprah, was like a slap in the face. With Oprah’s spotlight, any family drama quickly became a huge deal.

Monique shared her feelings, saying, “I told Oprah that my relationship with my mom was in a really rough place and that I was hurting. I never expected Oprah to have my mom on the show. If I had known, I would have shut it down right away. I didn’t want the world seeing how my mother’s greed was affecting us.”

You can really feel Monique’s pain here. It’s a tough situation, and it reminds me of Oprah’s 1993 interview with Michael Jackson. That interview was supposed to help Michael clear up rumors and improve his image. Instead, some fans felt Oprah was too intrusive and challenging. Despite their past closeness, Michael’s trust in Oprah backfired, and he ended up feeling betrayed.
During her interview with Michael Jackson, Oprah delved into his personal life, asking about his romantic history, his virginity, and whether he was dating Brooke Shields. Michael chose not to discuss his virginity, calling it a private matter and saying he was old-fashioned. Oprah’s probing questions made it seem like she was suggesting he was hiding something, which put him on the defensive.

When Oprah turned to Michael’s appearance, she asked about any cosmetic surgery. Michael admitted to having a nose job but insisted he hadn’t made any other changes to his face, attributing his different look to vitiligo. Oprah seemed unconvinced and pushed for more details.

Oprah also questioned Michael about his friendships with children and why he enjoyed spending time with them. Michael explained that he found their innocence refreshing and felt he missed out on a normal childhood because of his fame. Oprah’s questions took a more accusatory tone, insinuating there was something inappropriate about his behavior and even asking if he had ever slept in the same bed with the children.

Michael’s fans were outraged by the interview, feeling that Oprah was being disrespectful and insensitive. They accused her of exploiting his vulnerability and contributing to the damaging allegations that would come up later. Some fans even boycotted her show and demanded an apology. Despite the backlash, the interview was a huge success for Oprah, bringing in new viewers and establishing her as a go-to interviewer for high-profile guests. But this wasn’t the last time Oprah would be involved with Michael Jackson.
Back in 2005, during the intense scrutiny of his molestation trial, Oprah Winfrey took the opportunity to discuss the effects of abuse on her shows. Michael Jackson’s brother, Randy, said that Michael was deeply disillusioned when the jury was deliberating his fate. Oprah seemed to capitalize on the situation, using it as a chance to boost her ratings with a show about liking children. To Michael, this move made it clear that Oprah was just another journalist chasing clout and couldn’t be trusted.

Oprah, who had opened up about her own childhood abuse on her show, had become a prominent advocate for child protection and addressing what she considered a widespread issue. Even after Michael’s death, she continued to spotlight him, producing a 2019 special titled After Neverland that focused on his alleged victims. It felt like a final blow.

It’s interesting to note that while Oprah has been eager to make and promote content about Michael Jackson, she hasn’t done the same for Harvey Weinstein. Weinstein, despite being found not guilty years ago, hasn’t been the subject of Oprah’s scrutiny. It makes you wonder why Oprah would choose to taint Michael Jackson’s legacy, especially when he’s no longer around to defend himself.

At the beginning of Oprah’s Neverland special, she told the three men she was interviewing, “We’re all going to get it,” meaning they’d face backlash from Michael Jackson’s loyal fans and the Jackson estate, who had already filed a $100 million lawsuit to stop the film from airing. As expected, Oprah faced a flood of criticism online for siding with Jackson’s accusers. Many claimed she was ignoring the facts and giving more credibility to their claims just because she had known Jackson before. They argued that Oprah’s support made the allegations seem more legitimate, unlike her stance on Harvey Weinstein’s victims, who had actual convictions against him.

The Jackson family has a complicated history with Oprah. They’ve said:

“In a sense, Oprah will say whatever she needs to get the interview, and she’s done that to our family many times. So, we have a different view of Oprah than most people because we’ve been hurt by her in the past.”

Thanks for tuning in to this clip from the “Let’s Get Into It” podcast. To watch the full episode, check out the link below.

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