In American pop culture, Oprah Winfrey is a towering figure. She is hailed as a media mogul, philanthropist, and one of the most influential women in the world. But behind the glossy veneer of success and empowerment lies a controversial undercurrent that has haunted her public perception for years: her complicated, often combative relationship with hip-hop culture—and more broadly, with some of the very Black artists her platform once promised to uplift.

While many Americans grew up with Oprah as a beacon of hope, a powerful Black woman who built an empire from nothing, some artists have questioned whether her influence has come at the expense of those she once claimed to represent. And few have been as vocal—or persistent—as Curtis “50 Cent” Jackson.

“If We Can’t Be Friends, Then Let’s Be Enemies”

The rapper-turned-entrepreneur has never minced words when it comes to Oprah. In interviews spanning over a decade, 50 Cent has repeatedly called out Winfrey for what he views as a pattern of demonizing hip-hop and the Black men who shape it. “Every time she made a mention to hip-hop culture, it was something that was wrong with it,” he once said. “You’re looking at me and saying that everything wrong with our culture is why I’m a success.”

50’s criticism of Oprah isn’t just about omission—it’s about rejection. Growing up in Jamaica, Queens, raised by his grandmother, 50 idolized Oprah. He hoped to one day sit on her stage, a moment of validation not just for him, but for the generation he represented. But according to him, the door was slammed shut.

“She was completely against everything that was in my music,” he told The Guardian. “So she ain’t never gonna have me on that show.”

In retaliation, 50 didn’t just speak out—he made it personal. He named his dog Oprah. He called her an “Oreo”—Black on the outside, white on the inside. But the most telling moment came when, years later, he finally did appear on her show. They talked, they laughed. It seemed like water under the bridge. But not for long.

The Selective Spotlight

In December 2019, as the #MeToo movement reshaped the entertainment landscape, Oprah was publicly backing a documentary focused on Russell Simmons, who faced sexual misconduct allegations. At the same time, she had already lent support to productions about Michael Jackson (Leaving Neverland) and R. Kelly (Surviving R. Kelly). For 50 Cent, this wasn’t activism—it was targeting.

He posted a photo collage of Oprah beside the Black men she’d supported documentaries about and wrote: “Why is Oprah going after Black men? No Harvey Weinstein, no Epstein, just Michael Jackson and Russell Simmons.”

In an appearance on Watch What Happens Live, 50 elaborated: “I just didn’t understand why certain people were being chosen. If you’re going to go after predators, go after all of them. Not just the ones that look like me.”

He wasn’t alone in this sentiment.

When Black Excellence Turns on Itself

Comedian Dave Chappelle once famously walked away from a $50 million deal with Comedy Central. When he reemerged, he chose The Oprah Winfrey Show to explain his decision. But the interview left many fans uneasy. Oprah, they claimed, tried to corner him into admitting he had a mental breakdown. Chappelle maintained it wasn’t mental illness—it was disillusionment with the industry’s manipulation.

Similarly, Oscar-winning actress Mo’Nique has long accused Oprah—and Tyler Perry—of blackballing her after she refused to promote Precious for free during awards season. According to Mo’Nique, she had fulfilled her contractual obligations. But her resistance to playing the Hollywood game branded her as “difficult.”

“Until that woman says, ‘Let me apologize to you publicly,’ it’ll be to the day I leave this earth,” Mo’Nique said in a viral interview. “What you did was malicious, and it was intentional.”

50 Cent publicly supported her, posting on Instagram: “I’m sure Oprah and Tyler Perry would not want to continue to allow their influence to damage Mo’Nique’s career… It’s time to apologize.”

More Than Coincidence?

Ludacris, too, had an awkward Oprah moment. Invited to her show to promote the Oscar-winning film Crash, he claimed Oprah used the platform to grill him about using the N-word in his music rather than celebrating the film’s message of racial healing. When the show aired, he found his rebuttals had been edited out, leaving a lopsided portrayal that humiliated him.

Kanye West has also been linked to Oprah—albeit indirectly. In 2016, after a breakdown that resulted in hospitalization, it was his former trainer, Harley Pasternak—a man reportedly close to Oprah—who called 911 and allegedly threatened to “send him back to Zombieland.” Kanye later ranted that “they can control LeBron James, they can control Jay-Z and Beyoncé, but they can’t control me.” For conspiracy theorists, the dots were too close not to connect.

And then there’s comedian Katt Williams, who, in an interview, spoke about the pressure placed on Black male artists to conform, even citing Hollywood’s so-called “dress ritual”—a theory that high-profile Black men are asked to wear dresses to emasculate them for the sake of mass entertainment. He included Oprah and Tyler Perry as part of this system.

Cultural Icon or Gatekeeper?

To be clear, Oprah Winfrey’s contributions to culture, education, and public discourse are staggering. She created a multi-billion-dollar empire, lifted millions through her book club, built schools in South Africa, and remains a beacon for philanthropy and self-help.

But her legacy—especially among certain circles in the Black creative community—is no longer so unassailable.

Critics argue that Oprah has leaned too far into assimilation and appeasement, creating a brand that is palatable to white America at the expense of unfiltered Black expression. They say she embraces trauma but only when it’s tidy enough for her audience. That she supports Blackness—but only a certain kind.

Of course, some of this criticism comes from artists who themselves are not without controversy. 50 Cent has been accused of misogyny and bullying. Kanye West’s actions have often bordered on the erratic. Mo’Nique’s refusal to play by the rules might rub industry insiders the wrong way, but does that make her wrong?

The Verdict—or the Beginning?

Oprah Winfrey has never directly responded to most of these accusations. She has, on occasion, acknowledged that she chooses her platform’s stories with intention. But intention does not negate impact. And in an age where Black artists are increasingly reclaiming their narrative, silence is no longer enough.

Whether one sees her as a media matriarch, a misunderstood figure, or a gatekeeper of selective progress, one thing is clear: the relationship between Oprah and hip-hop—or more broadly, Black creative culture—is far from resolved.

As 50 Cent once said: “If we can’t be friends, then let’s at least be enemies.”

For now, the jury is still out. But the conversation is louder than ever.