Oprah Winfrey is no stranger to rubbing elbows with the biggest stars in Hollywood. From sitting down with influential figures like Prince Harry and Meghan Markle, to inviting A-listers onto her iconic talk show, Oprah has always been known for asking the most candid and revealing questions. Her platform has allowed celebrities to share deeply personal stories, creating unforgettable moments that resonate with millions of viewers worldwide. However, despite her undeniable influence, there is one huge Hollywood star who has reportedly refused to work with Oprah—Angelina Jolie.

While Oprah has had an extensive history of working with major figures in the entertainment industry, including numerous interviews with actors, musicians, and philanthropists, Jolie has remained an exception. Despite Oprah’s apparent desire to collaborate with the Academy Award-winning actress, Jolie has consistently steered clear of any association with Oprah, and the reasons behind this snub are more personal than professional.

The tension between the two first became apparent when Oprah launched the Oprah Winfrey Leadership Academy for Girls in South Africa in 2006. Oprah, who was passionate about giving back and empowering young women, had hoped that Jolie, who had spent time in Africa and was heavily involved in humanitarian efforts, would be the perfect person to partner with. Jolie, however, declined the offer, much to Oprah’s surprise. Sources close to the situation revealed that Oprah had expected Jolie to jump at the opportunity, given her own history of advocacy for children and young girls. But Jolie’s refusal marked a turning point in their relationship, and it reportedly became the last time Oprah would reach out to her for support on one of her philanthropic causes.

But what exactly led to Jolie’s refusal? The roots of this animosity are believed to stem from a more personal issue involving the infamous love triangle between Angelina Jolie, Brad Pitt, and Jennifer Aniston. Back in 2005, when Brad Pitt and Jennifer Aniston’s marriage ended, rumors swirled about the relationship between Pitt and Jolie, who met while filming Mr. & Mrs. Smith. Jolie and Pitt’s subsequent relationship, which led to their marriage and large family, was highly publicized, and the media had a field day comparing the two women who were linked to the same man.

Oprah, who had become close with Aniston over the years, seemed to take sides in the media frenzy surrounding the divorce. In 2005, Oprah invited Jennifer Aniston onto her show, and the two women shared an emotional conversation about moving on from the public scandal. However, when Jolie and Pitt’s relationship blossomed, Oprah’s support for Aniston seemed to have lingered. The media narrative surrounding Aniston’s heartbreak and Jolie’s “home-wrecking” image did not sit well with the actress.

According to sources, Jolie never truly forgave Oprah for her apparent loyalty to Aniston during that time. Despite the fact that Oprah never directly criticized Jolie, the way the media storm was handled left a lasting impact on the Maleficent star. Jolie, who has always been private about her personal life, reportedly took offense to the idea that Oprah was aligned with her ex-husband’s first wife, which may have led to her decision to distance herself from Oprah, both professionally and personally.

While Oprah has long moved on from the Pitt-Aniston-Jolie triangle, it appears that Jolie’s feelings toward Oprah remain unchanged. Despite Jolie’s willingness to work with various other charitable organizations and high-profile individuals, Oprah seems to remain a figure she chooses to avoid, especially given the history between them.

Interestingly, Oprah’s professional relationship with Brad Pitt has evolved in a more positive direction over time. In 2008, Pitt appeared on Oprah’s show and openly discussed his love for Jolie and their growing family. In more recent years, Oprah and Pitt even teamed up in 2020 to produce a film adaptation of Ta-Nehisi Coates’ The Water Dancer. This collaboration shows that despite their past, Pitt and Oprah have managed to move beyond the drama of their early years.

On the other hand, Jolie has never publicly commented on her strained relationship with Oprah, leaving fans to speculate about the reasons behind her refusal to work with the talk show host. Jolie’s stance seems to stem from her personal experiences and the very public fallout from her relationship with Brad Pitt. The media’s constant comparisons of the two women, coupled with Oprah’s public friendship with Aniston, undoubtedly played a significant role in creating a rift that continues to affect their relationship.

In the end, while Oprah’s career is filled with interviews, collaborations, and partnerships with Hollywood’s finest, Angelina Jolie remains one notable exception. The personal dynamics of Hollywood stars often shape their professional relationships, and in this case, the past media spectacle surrounding Jolie, Pitt, and Aniston appears to have overshadowed any potential collaboration between the two powerful women.