Brad Pitt & Angelina Jolie: ~ $100 Million Settlement

Hollywood power couple Brad Pitt & Angelina Jolie first met in 2005, while shooting for their movie, Mr. & Mrs. Smith. And this is when he was already married to Friends actress Jennifer Aniston! Brad eventually adopted Jolie’s kids, and they had biological kids too.

After almost a decade of being with each other, they got married in 2014, but just two years later, Jolie filed for divorce citing irreconcilable differences. Media reports said that an altercation between her children and a drunk Pitt on a flight, led to this decision. He reportedly offered her a generous $100 million settlement, but the custody battle was messy.