Dave Chappelle, known for his sharp wit and controversial statements, has once again turned his attention to media mogul Oprah Winfrey. In his latest remarks, Chappelle accused Oprah of being a manipulative figure behind the scenes in Hollywood, drawing comparisons between her and rapper Diddy Combs. These accusations are not new, as Chappelle has raised suspicions about Oprah’s influence for years, and he is now delving deeper into what he believes are the darker sides of her public persona.

Chappelle claims that Oprah has a history of profiting from others’ suffering, working behind the scenes to maintain her image while allegedly perpetuating anti-Black stereotypes. He highlights incidents like her controversial interview with Michael Jackson’s accusers, which he argues was an unnecessary attack after Jackson’s death. Additionally, he brings up the public fallout between Oprah and comedian Mo’Nique, alleging that Oprah played a role in sabotaging Mo’Nique’s career. According to Chappelle, Oprah’s decision to invite Mo’Nique’s estranged brother, who had confessed to molesting her, onto her talk show without Mo’Nique’s consent was a deep betrayal.

Beyond these personal conflicts, Chappelle questions Oprah’s larger role in Hollywood. He accuses her of perpetuating harmful stereotypes, underpaying Black actors, and fostering toxic relationships with figures like Harvey Weinstein. While Oprah had distanced herself from Weinstein after his crimes became public, Chappelle points to her past connections with him and other problematic figures, including spiritual healer John of God, who was later convicted of sexual abuse and trafficking.

Chappelle’s critique doesn’t stop at Oprah’s alleged misdeeds in Hollywood. He also draws parallels between Oprah and Diddy, arguing that both use their influence to suppress their critics and control the narrative surrounding their empires. He suggests that, like Diddy, Oprah has connections to numerous scandals and that her public image hides a more ruthless approach to maintaining power.

Despite Chappelle’s claims, Oprah has remained relatively silent on many of these issues. While she has addressed some controversies, such as the rumors of her involvement with Harvey Weinstein, she has yet to respond directly to Chappelle’s latest accusations. Nevertheless, Chappelle’s remarks have sparked renewed discussions about Oprah’s legacy and her role in shaping the media landscape, particularly in relation to Black artists.