Now, things seem to be falling apart between the couple that once seemed inseparable.
Here, we look at some of the biggest events that led to the current shaky position between the two A-list celebs.
Scroll through the gallery below to see the former couple's ups and downs.
September 20, 2016
Rumors swirled that Pitt had cheated on Jolie with a costar.
The same month, reports highlighted that authorities were investigating Pitt for child abuse as a result of what had happened between him and his son Maddox on a flight home from Nice, France.
Pitt, 56, wasn’t allowed near the kids amid the ongoing investigation. It was then that Jolie’s brother, James Haven, came in to help her with childcare duties.
November 16, 2016
Jolie, 45, appeared in public for the first time after the split. She taped a video for the International Criminal Court.
Rumors circulated that the pair got back together for the holidays. However, Pitt was only having supervised meetings with his kids.
December 22, 2016
Pitt moved to seal the court documents that could compromise the privacy of kids. He asserted that Jolie was not looking out for the best interest of the kids.
After receiving a call from Child Services, Pitt admitted to GQ Style that he “was really on my back and chained to a system.”
“We’re both doing our best," he said while talking about co-parenting their kids. "I heard one lawyer say, ‘No one wins in court — it’s just a matter of who gets hurt worse.'”
According to Us Weekly, an insider revealed that the pair hadn’t quite done anything to move their divorce along.
“No one thinks they are ever going to,” the source added.
Pitt and Jolie reached a custody agreement and avoided the trial. As per Jolie’s lawyer, Samantha Bley DeJean, the agreement was “signed by both parties and the judge” and “based on the recommendations of the child custody evaluator.”
The exes were said to have two in-person meetings at an L.A. office for the “ongoing process to work through things regarding the kids and the divorce.” They were said to have established a foundation that helped the entire process to “move forward in a much more thoughtful and peaceful manner.”
Jolie was seen at the premiere of the Netflix movie The Boy Who Harnessed the Wind. She attended the New York City event with all of her six kids.
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According to a court document obtained by Us Weekly, it revealed that the actress had legally become single despite the unfinalized divorce.
Pitt was said to have found a creative outlet in sculpting post-divorce. The actor said that the activity was quite therapeutic.
It was reported that Pitt was going to Alcoholic Anonymous after his split with Jolie. Pitt told The New York Times, “I had taken things as far as I could take it, so I removed my drinking privileges.”
Pitt was asked about how his split had affected his performance in Ad Astra in an interview with NPR. The actor said, “A breakup of a family is certainly an eye-opener that ... one needs to understand. I had to understand my own culpability in that, and what can I do better, because I don’t want to go on like this.”
“I would be exploring it whether there was a script that allowed that or not,” he explained.
A source had also revealed that Pitt got in touch with Jolie about reconnecting with Maddox who was studying in South Korea. The insider said, “Brad has talked to Angelina about visiting Maddox in Seoul. Angelina has been trying to heal the rift between father and son.”
It was also said that the Maddox wasn’t quite keen on that arrangement.
In the same month, Jolie spoke with the French magazine Madame Figaro and revealed that she felt a deep and genuine sadness about her separation from Pitt. She admitted that she lost herself a bit and felt “smaller, almost insignificant, even if it wasn’t necessarily obvious.”
By now, it had been more than three years since their marriage had ended. This is when an insider revealed that Jolie "still has a lot of resentment toward Brad."
The source added: "She wants him to be held accountable because she feels he turned her and the children's lives upside down."
The insider also said that Jolie hadn’t altogether shunned off the idea of meeting someone new, but that wasn’t “her main priority.”
Pitt opened up about his personal life after winning a trophy at the Golden Globes. Pitt responded to the attention he had received in a podcast with Marc Maron, saying that it was all a result of the “disaster” in his personal life.
Due to their children going through some “medical challenges," the Fight Club star skipped the 2020 BAFTAs in London. Instead, Pitt asked his costar Margot Robbie to attend the awards show.
Despite the messy split, the couple agreed that they would put their children through “traditional schooling."
"Brad wants the kids to be in a school setting, and not isolated being homeschooled," a source explained.
An insider revealed that things were getting better between Brad and Angelina.
"They're more cordial — they're aiming toward resolutions that work for each of them,” a source revealed.
It was also revealed that Jolie was quite happy with the way Pitt was approaching his sobriety.
Jolie revealed to Vogue that she separated with Pitt for the well-being of her family.
“It was the right decision. I continue to focus on their healing. Some have taken advantage of my silence, and the children see lies about themselves in the media, but I remind them that they know their own truth and their own minds,” she said.
Jolie filed a court document, which requested for the disqualification of Judge John W. Ouderkirk in the custody trial. She claimed that the judge had “failed to disclose” that he shared professional relations with Pitt.
Pitt’s legal team responded, saying that the accusations were just a “thinly veiled attempt” at delaying the trial.