For years, I didn’t like Oprah Winfrey. She’s not the kind of person you’d want to have a problem with—tough, smart, and powerful. But when it came to hip-hop, Oprah had a history of criticism, and it felt personal. Every time she spoke out against the genre, calling it misogynistic and damaging to America’s youth, I felt like she was talking about my music. Her comments seemed aimed directly at albums like mine, which is why I, 50 Cent, felt conflicted.

In the early 2000s, Oprah’s critique of hip-hop’s lyrics struck a nerve with me. After the success of my 2003 album Get Rich or Die Tryin’, I wanted to appear on her show to make my grandmother proud. But it didn’t seem like Oprah was eager to have me on. I later shared in an interview that I felt shut out because of my music’s harsh content. It was a difficult moment for me, especially when I realized that Oprah’s audience—a demographic largely made up of middle-aged white women—found me and my lyrics unsettling.

Despite my respect for her success, there was undeniable tension. Oprah’s public stance against hip-hop, particularly calling out its themes of violence and misogyny, created a divide between us. I felt misunderstood. My lyrics, while gritty, were a reflection of my real-life experiences, including surviving being shot nine times. I wasn’t promoting negativity, just sharing my truth. But Oprah didn’t seem to see it that way.

Over time, though, things changed. We finally met, and the distance between us began to shrink. Oprah even invited me and my grandmother onto her show, a moment I had long dreamed of. It was a major turning point, showing that we could move past our differences. Yet, during that appearance, we avoided discussing the negative themes in my music. I respected that decision—it wasn’t the time to delve into deeper debates.

Still, I wasn’t the only one who had issues with Oprah. In 2020, when Oprah got involved in a documentary about a woman accusing Russell Simmons of misconduct, I felt uneasy. While I support holding people accountable, there was something about Oprah’s involvement that rubbed me the wrong way, particularly given her history with the Black community and the entertainment industry.

Oprah’s complicated relationships with Black artists in Hollywood didn’t stop with me. Taraji P. Henson, for instance, faced challenges while working on The Color Purple, a project produced by Oprah. Taraji revealed that she was paid far less than expected, sparking conversations about the underpayment of Black women in Hollywood. Oprah, according to rumors, blamed Taraji for the movie’s poor box office performance and was reportedly upset about Taraji’s complaints regarding pay and working conditions.

But Taraji wasn’t the first actress to clash with Oprah. Monique faced similar issues after her role in Precious. She was paid just $50,000 and was later asked to promote the film without additional compensation. When Monique refused, it led to her being blacklisted in Hollywood. Oprah was a major player in that fallout, alongside Tyler Perry and Lee Daniels. Monique’s career took a significant hit, with many in the industry afraid to work with her for fear of crossing Oprah.

I, however, stood by Monique and Taraji. I’ve always been outspoken about the mistreatment of Black people in entertainment. When I saw Monique perform during Super Bowl weekend, I publicly voiced my support for her comeback, urging the industry to give her the respect she deserves. I did the same for Taraji, showing my solidarity and even offering her work on fair terms.

This long-standing tension between Oprah and various figures in the Black community highlights the complex power dynamics in Hollywood. Oprah has incredible influence, and when she takes a stance, it has consequences—both positive and negative. My own journey with her shows how misunderstandings can turn into friendship, but also how unresolved issues can linger in the public eye.

As for the future, only time will tell how these relationships evolve. But one thing is clear: the conversation around race, gender, and fair treatment in the entertainment industry is far from over.