Oprah Winfrey is someone who has rubbed elbows with most of the elite stars in Hollywood.
After all, she is someone who has always asked all the important questions — perhaps, in
particular, in her seismic interview with Prince Harry and Meghan Markle, a no-holds-barred
conversation that rocked the world with its revelations about what royal life is like
behind closed doors.
"My father and my brother, they are trapped."
During her run as a talk show host, almost every A-lister in the entertainment industry
sat on Oprah's couch and spoke about some of their most personal experiences and life-changing
moments.
"I was angry for a long time."
And for Oprah, every single episode was as important to her as the next.
During her commencement speech at Harvard University, Oprah said,
"The goal of my shows, my interviews, my business, my philanthropy, all of it, whatever ventures
I might pursue, would be to make clear that what unites us is ultimately far more redeeming
and compelling than anything that separates me."
And while there were a lot of people who were willing to sit down and answer some of the
most personal questions ever asked to them, there was one huge movie star who allegedly
refused to even be in the same room as Oprah — Angelina Jolie. Sure, she has gotten very
candid in other interviews throughout her career, but Jolie's lips have remained sealed
when it comes to the big O. Here's why.
Oprah Winfrey was apparently 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,
"Oprah thought Angelina would jump at the chance."
Jolie's refusal apparently made it the last time Oprah would ask her to help with one
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."
"Let me ask you this. Are you ready to start the whole dating thing again?"
"Yeah!"
As fans remember, Angelina was involved in a media-hyped love triangle between Brad Pitt
and Aniston. 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 own contentious divorce.
For more than a decade, fans and critics alike simply could not choose between who they preferred
to see by Brad Pitt's side: his first wife, Jennifer Aniston, or his second wife, Angelina
Jolie. The tabloid magazines and gossip blogs had a field day whenever they felt Jolie threw
subtle shade towards Aniston or vice versa. Pitt, on the other hand, did appear on The
Oprah Winfrey Show back in 1998 and 2004. In 2008, he appeared on the show again and
talked about his love for Jolie and their family.
"It's the greatest thing I've ever taken on. I can't imagine life without her."
More recently though, Pitt and the queen of daytime talk have initiated a different sort
of collaboration. Oprah and Pitt teamed up in 2020 to produce a new film called The Water
Dancer. Their production companies will tackle Ta-Nehisi Coates' debut fiction novel.
And while Jolie allegedly could not get over the fact that she was not as popular with
Oprah as Aniston was, Aniston played it cool and casual when Oprah asked her about her
ex-husband and his new wife in 2008. Aniston revealed she was proud of her ex — and the
family he had built.
"He's done some amazing things in the last couple of years. So I just think he's, I think
he's doing great."
While much has changed in the years since Aniston's interview, Jolie's opinion of Oprah
seemingly has yet to thaw.
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