However, the Friends actress has remained unbelievable reserved - at least publicly - over the years refusing to rake what they had through the dirt and took the high road over Brad's second marriage.
Now, years after that relationship also ended in divorce, Jennifer's unearthed comments about her ex reveal more about his personality.
Brad and Angelina's relationship has been contentious since their divorce in 2016, and yet he has maintained a close bond with his first wife, Jennifer Aniston.
That being said, Jennifer made an eye-opening revelation about her ex in an interview after they split and he began dating his Mrs. & Mrs. co-star.
It was very early in the couple's romance - they hadn't even confirmed they were dating - and the spread was entitled 'Domestic Bliss' as they played happily families.
When quizzed over whether she was hurt by how swiftly he moved on and if she thought the photoshoot was insensitive, she said: "I can imagine Brad having absolutely no clue why people would be appalled by it," Jennifer revealed of the shoot which was conceptualized by Brad too, but she added: "Brad is not mean-spirited; he would never intentionally try to rub something in my face. In hindsight, I can see him going, ‘Oh—I can see that that was inconsiderate.’ But I know Brad. Brad would say, ‘That’s art!'"
However, Jennifer then admitted that when it comes to her ex: "There's a sensitivity chip that's missing".
Jennifer's interview took place in 2006, a year after their breakup. He went on to marry Angelina in 2014 and they share six children. Maddox, 22, Pax, 19, Zahara, 18, Shiloh, 17 and twins Knox and Vivienne, 15.
Brad has come under fire from one of his six children whose previous claims against him on social media have resurfaced.
The private post was shared by Daily Mail and painted the actor in a terrible light as the upset teen added: "You will never understand the damage you’ve done because you are incapable of doing so."
Unfortunately, their marriage came to a bitter end following an incident involving Brad, Angelina, and two of their children on a private jet.
It was four years after the flight that Pax made the claims against Brad. His jarring greeting read: "Happy Father’s Day to this world class [expletive]!!”
He accused Brad of lacking empathy and consideration towards his younger siblings.The post highlighted the ongoing repercussions of the 2016 incident that led Angelina, 48, to file for divorce.
It also lead to an FBI investigation into Brad for alleged child abuse, although no criminal charges were pursued.
In October 2022, Angelina’s court documents surfaced, claiming that the children were "traumatized" by her ex-husband’s alleged behavior, which reportedly included physical and emotional abuse while under the influence of alcohol.
The allegations detailed Brad’s aggressive actions towards Angelina and their children, including physical assault and intimidation.
The relationship between Brad, now 59, and his children has remained visibly strained, as he has not been photographed with them since the 2016 incident.
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