But with his Jolie-Pitt marriage now over, the former couple are said to have become good friends and were even expected to reunite at the Golden Globe Awards on Monday.
Bosses are said to have seated the pair within metres of each other, and Mail Online claimed that neither star’s rep objected.
And their road to recovery is said to have started when Brad apparently reached out to Jen in 2017 to apologise for his behaviour.
“He’s been determined to apologise for everything he put her through, and that’s exactly what he did,” a source told the magazine at the time.
“It was the most intimate conversation Brad and Jen have ever had.”
However, his words apparently weren’t easy for Jen to hear.
In 2005 when a Vanity Fair interviewer asked her about Angelina’s then-rumoured pregnancy with her’s and Brad’s first born, Shiloh, she cried silently for several minutes and was unable to answer.
“I have to think there’s some reason I have called this into my life,” she said of their separation. “I have to believe that—otherwise it’s just cruel.”
So when Brad, 52, reportedly made his apologies, the source said it brought back a lot of that old hurt.
“Jen was overcome with emotion. All the hurt feelings and resentment she’d suppressed for years came flooding to the surface, and she broke down in tears.”
It wasn’t just the Angelina situation that he apparently wanted to make amends for.
Brad, who previously admitted to Parade magazine that he spent the nineties “sitting on a couch, holding a joint, hiding out,” is also said to have admitted that perhaps he wasn’t always the best partner.
“He apologized to Jen for being an absentee husband, for being stoned and bored much of the time. He also made amends for leaving her Angelina,” the source added.
Then married to Justin Theroux, according to the report Jen accepted Brad’s apology, although she “still resents Angelina.”