Apparently, Oprah Winfrey was hopeful that she could work with Angelina Jolie when she opened her Oprah Winfrey Leadership Academy for Girls in South Africa back in 2006. After all, the Academy Award winner did spend a lot of time in Africa after the birth of her daughter, Shiloh, in Namibia. And Oprah hoped that, together, they could do something big for other girls of the continent. In theory, it sounded like a perfect fit: the biggest star in Hollywood working with the biggest star on television. But Jolie allegedly wanted no part of it — and the rejection felt like a sting to Oprah. One source close to the situation told Star (via Fox News) that, "Oprah thought Angelina would jump at the chance" — but Jolie's refusal apparently made it "the last time she'll ask Angelina to help with any of her causes."
But for Jolie, this was personal. If the Star insider is to be believed, "Angelina has never forgiven Oprah for siding with Jennifer Aniston after Brad Pitt split from Jen" during the late aughts. As fans remember, the actor was involved in a media-hyped love triangle between Brad Pitt and the "Friends" star. Pitt and Jolie met — and "fell in love" — on the set of their film "Mr. and Mrs. Smith" in 2004, when he was still married to Aniston. Of course, Pitt and Aniston would soon divorce, and he and Jolie would later marry and have six children (before going through their contentious divorce that began in 2016 and is still ongoing).
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