Beyond fame, wealth, and iconic status, Oprah Winfrey and Angelina Jolie have one big trait in common: a passion for philanthropy. However, this wholesome passion became the root of a feud between the two women.

In 2006, upon opening an academy for girls in South Africa, Oprah hoped to work with Jolie to make an impact on young African girls. However, Jolie rejected the offer, and that made it "the last time [Oprah will] ask Angelina to help with any of her causes,” according to one source.

Jolie’s rejection happened because Oprah sided with Jennifer Aniston during the infamous Jennifer, Brad (Pitt), and Angelina love triangle of the 2000s. When Pitt left Aniston for Jolie, intense debate ensued over which woman was truly “right” for Brad, and Oprah favored Aniston.

In 2008, Aniston opened up about Pitt to Oprah, saying “He's done some amazing things in the last couple of years… I think he's doing great." While Oprah and Aniston have moved on from the “love triangle” debacle, it seems Angelina Jolie still feels cold on the matter.