Jolie cited irreconcilable differences in her filing, and an attorney for the actress, Robert Offer, told the Associated Press at the time that the decision was made "for the health of the family." She also asked for physical custody of their kids -- 18-year-old Maddox, 16-year-old Pax, 15-year-old Zahara, 13-year-old Shiloh and 11-year-old twins Knox and Vivienne.
Since then, it's been anything but conscious uncoupling between the two, due to an intense custody battle, though things seemed to have cooled in recent months. From their legal fight to their dating lives, let's take a look at where 56-year-old Pitt and 44-year-old Jolie stand now since their separation in 2016.
Their court battle:
Shortly after Jolie filed for divorce, reports surfaced that Pitt was being investigated for child abuse after Maddox allegedly inserted himself into a fight between his parents during a flight home from Europe.
However, a source told ET at the time that it was "totally a child-parent disagreement," and any reports of inappropriate physical conduct are "exaggerated or untrue."
By November 2016, Pitt had been cleared of child abuse allegations by the Department of Child and Family Services. “It wasn’t clearly founded that there was any abuse by Pitt,” a source told ET at the time.
In a statement to ET, Jolie's team expressed relief that the investigation had concluded.
“The job of the DCFS is to make sure the children are in a safe and secure situation," the statement read. "As we said earlier this week, childcare professionals encouraged a legal agreement accepted and signed by both sides that was in the best interest of the children. Angelina said from the beginning that she felt she had to take action for the health of the family and is relieved that after their 8-week involvement, the DCFS is now satisfied the safeguards are put in place that will allow the children to heal.”
Later that month, the two agreed to a temporary custody arrangement. Jolie and Pitt each volunteered to participate in individual counseling, and Pitt also agreed to undergo drug and alcohol testing, though he was not required to, sources told ET. One month later, a judge approved a custody agreement between the two, granting Jolie physical custody of all six children. According to documents, Pitt would continue to have agreed-upon therapeutic visitations with the kids, as determined by the family's therapist who "shall at all times consider the best interests of the minor children."
Still, the two continued to be at odds when it came to their children, later engaging in a more complicated custody battle, as Pitt continued to request more time with the children.
In December 2016, Pitt's request for an emergency hearing to seal all documents related to his custody case with Jolie was denied. A source told ET that Pitt filed the motion to seal the documents "because he wants to keep this custody battle out of the public eye to protect his children." Meanwhile, another source told ET that contrary to some reports, Jolie was not trying to make Pitt "look bad" in court.
"Angelina's team is not opposed to sealing the documents," a source told ET at the time. "There have been many reports that Angelina wants to keep these documents public to make Brad look bad, that is false. As the document states, their custody agreement was already legally binding. The only reason to formally file it with a court would be to enforce the agreement because one of the parties was trying to change it and that is what was happening."
"Brad was attempting to set up his own schedule with the children," the source further claimed. "He was not relying on the advice of the healthcare professionals [as to] what should be done. In order to keep everything in line with the custody agreement, it had to be reinforced in court. Therefore that forced Angelina's side to file it within the courts."
"The parties and their counsel have signed agreements to preserve the privacy rights of their children and family by keeping all court documents confidential and engaging a private judge to make any necessary legal decisions and to facilitate the expeditious resolution of any remaining issues," the statement from the actors read. "The parents are committed to act as a united front to effectuate recovery and reunification."
But Jolie and Pitt's legal battle flared up again in June 2018. The court drama came after Jolie was ordered by a judge in June to help repair her children's relationship with Pitt. According to the court documents obtained by ET, the actor was given more time with five of his children over the summer, while Maddox, "because of his age and maturity," was able to determine how much time he wanted to spend with his father.
"Petitioner's Request is unnecessary, omits material information and is a thinly-veiled effort to manipulate media coverage," Pitt's court filing reads.
But in a statement to ET, Jolie's lawyer, Samantha Bley DeJean, said that Jolie's request for child support "was both legally appropriate and factually accurate in all respects." Jolie's spokesperson, Mindy Nyby, also told ET in a statement at the time that the actress actually just wanted to move the divorce process forward with her new court filing.
“The aim of Angelina’s routine court filing is to provide closure to the marriage in a way that clears a path toward the next stage of their lives and allows her and Brad to recommit as devoted co-parents to their children," the statement read.
"[Angelina's] main focus has always been to co-parent with Brad," the source said. “She gave up a year and a half of work to be with the children and is only now going back to work to pay off the house that she needed to buy because Brad kept their family home."
On the eve of the two-year anniversary of their split, a source told ET that the actress had recently reached out to Pitt to improve their co-parenting relationship.
"Brad and Angelina actually set up a secret meeting at her house," the source said. "It’s the first time they have truly gotten together to make things work since their group therapy with the children. Brad and Angie’s meeting was a success. They are going to stay with the plan set forth through the courts."
"Angelina decided it was time to try to make things work and Brad was relieved and very ready for the offer," the source continued. "Brad has been dedicated to making peace throughout the process and now it finally seems like they are at a point where they can create a calmer situation for the kids."
The source noted that the meeting between Jolie and Pitt was a "huge step" for the two.
"They both hope to continue to work together for the kids," the source said.
On April 12, 2019, a court ruled that both Jolie and Pitt were legally single, despite their divorce not yet being settled. A judge ruled that the former couple's marriage was officially over after Pitt and Jolie requested a bifurcated judgment, which would allow their single status to be restored while they continue finalize their divorce.
While a custody arrangement had been determined, the court's involvement in their divorce isn't over. According to court documents seen by ET in April 2020, Pitt filed a stipulation and order regarding "education and transitional support" for his children with Jolie on March 16.
According to a report from The Blast, the stipulation stated that the pair had come to an agreement regarding a "traditional" approach to their children's educations.
"I was really on my back and chained to a system when Child Services was called," Pitt said. "And you know, after that, we've [he and Jolie] been able to work together to sort this out. We're both doing our best. I heard one lawyer say, 'No one wins in court -- it's just a matter of who gets hurt worse.' And it seems to be true, you spend a year just focused on building a case to prove your point and why you're right and why they're wrong, and it's just an investment in vitriolic hatred."
"I just refuse," he continued. "And fortunately my partner in this agrees. It's just very, very jarring for the kids, to suddenly have their family ripped apart. If anyone can make sense of it, we have to with great care and delicacy, building everything around that."
"Our focus is that everyone come out stronger and better people -- there is no other outcome," he added.
He was also blunt about undergoing therapy and quitting drinking alcohol and smoking marijuana.
"I'm personally very retarded when it comes to taking inventory of my emotions," he said bluntly. "I'm much better at covering up. I grew up with a Father-knows-best/war mentality -- the father is all-powerful, super strong -- instead of really knowing the man and his own self-doubt and struggles. And it's hit me smack in the face with our divorce: I gotta be more. I gotta be more for them. I have to show them. And I haven't been great at it."
Vanity Fair described Jolie as "defensive" when addressing reports that Pitt wanting "a more stable, normal life for the whole family" was a catalyst for their breakup.
"[Our lifestyle] was not in any way a negative," Jolie replied. "That was not the problem. That is and will remain one of the wonderful opportunities we are able to give our children. ... They're six very strong-minded, thoughtful, worldly individuals. I'm very proud of them."
Jolie answered with a simple "no" when asked if she was surprised by Pitt's emotional GQ profile, and Vanity Fair describes her as looking "unmoved." Still, she said at the time that the two are keeping it amicable for the children.
“We care for each other and care about our family, and we are both working towards the same goal," she said.
She also suggested that their children were dealing with more than a divorce between their parents.
"They've been very brave. They were very brave. In times they needed to be," she said cryptically. "We're all just healing from the events that led to the filing. ... They're not healing from divorce. They’re healing from some ... from life, from things in life."
In April 2019, days after a judge ruled that their marriage was officially over, a source told ET that the former couple's relationship was "the best it's been since their split."
"Brad and Angelina have come a long way," the source said at the time. "To the surprise of many of their closest friends, their communication has improved tremendously and they're both dedicated to co-parenting. Their kids have a custody schedule and that's made a huge difference for the whole family. The schedule has alleviated any of the planning pressures Brad and Angelina have faced in the past. Now the kids spend time with both their parents and are happy and thriving."
The source added that, "While they don't agree about everything, they rarely argue now. Brad and Angelina are now at a point where they can discuss their children's plans calmly."
Their dating lives:
In January 2018, a source told ET that Pitt had been casually dating again more than a year after the split. The following April, he was linked to MIT professor Neri Oxman, though sources told ET at the time that the two were not romantically involved. One source said the pair were introduced through a friend who thought Oxman would be the perfect person to help Pitt with some of his architectural questions after the actor took up sculpting following his split from Jolie.
"They hit it off immediately and have been close for months," the source said of Oxman and Pitt. "They have so much in common intellectually and truly enjoy each other's company. [Pitt] is thrilled to be around someone who isn't all about Hollywood. He talks about her attitude toward fame and the A-list scene and he feels her apathetic view is refreshing.”
The source said Oxman was a hit with Pitt's pals.
"Brad's friends were secretly hoping he was ready to date and everyone loves Neri," the source said. "She is beautiful and smart and his friends feel he can't go wrong."
But in June, a source told ET that Pitt wasn't looking to jump into anything serious with anyone. “He has gone on dates but he’s not looking to leap into a serious relationship at the moment," the source shared. "He is content on his own and enjoys the quality time he spends with the children when he isn’t working."
"He isn't a celebrity or high profile in any way," the source said, adding that "it's not serious."
"Angie was in a very bad place after [her] split [from Brad]," the source further noted. "Just having another adult to spend time with has been helpful."
Their new projects:
Both Pitt and Jolie have been steadily working since their split. Pitt was photographed on the set of his 2019 sci-fi film, Ad Astra -- in which he plays an astronaut -- in October 2018, and a source told ET that the actor was the consummate professional on set.
"When he’s not on set filming, he hangs out in his trailer,” the source told ET. "He’s never late and he always arrives to set ready to work."
"Physically, he looks fantastic," the source added. "Brad is very friendly and genuine with everyone on set."
Jolie has also kept busy since the split with her humanitarian work as a United Nations Goodwill Ambassador and Special Envoy, most recently, visiting West Mosul in Iraq as part of her trip with UNHCR, the UN Refugee Agency.
"Right now I don't have anything to direct that I feel passionate about like this [First They Killed My Father], so I'll do some acting," she told The Hollywood Reporter. "I've taken over a year off now, because of my family situation, to take care of my kids."
True to her word, in May 2018, she reunited with Elle Fanning as production on Maleficent 2 began, posing for a playful photo which Fanning shared on Instagram.
Later that month, Variety reported that the actress and David Oyelowo were in negotiations to star in the live-action fantasy-drama Come Away, playing the parents of the brother and sister who became the protagonists of Alice in Wonderland and Peter Pan.
"You have your creative, and you have your work, and every day of your life is going to be about somehow growing as a person," she told Deadline Hollywood. "Somehow feeling you can contribute to the extent that you can get tribute."
"We’re all trying to find balance, as people," she continued. "I think to be a balanced person, you have to find those things that you just purely enjoy. But, of course, if you aren’t participating in the bigger picture of life, and in being somehow useful, and you aren’t doing something and growing, then really, you’ll find you’re not very happy. Really, you’ll have quite an empty life."
For more on Jolie and Pitt's split, watch the video below: