Brad Pitt and Angelina Jolie: The Way They Were

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Brad Pitt and Angelina Jolie: The Way They Were

From Mr. and Mrs. Smith to Mr. and Mrs. Pitt! Brad Pitt and Angelina Jolie have had quite the journey from costars, to parents, to spouses — and eventually, to exes. The A-list couple had a scandalous start to their romance when they met on the set of Mr. & Mrs. Smith in 2004, while Pitt was still married to Jennifer Aniston. The Friends alum split from Pitt in January 2005 after nearly five years of marriage. The Maleficent actress and the Oklahoma native were together for nearly 12 years after falling in love while working together on the action film. The costars tied the knot in August 2014 before splitting in September 2016 due to irreconcilable differences. After an initially messy custody battle, the exes are working to resolve issues about their kids, Maddox, Pax, Zahara, Shiloh and twins Knox and Vivienne — and have finally landed on good terms. "Things between Brad and Angelina are better than they have been," an insider told Us Weekly exclusively in May 2020. "They're more cordial — they’re aiming toward resolutions that work for each of them." [jwplayer i867TzJ4-l3ahXupL] While neither Pitt nor Jolie has officially moved on since becoming legally single in April 2019, the Troy star has found a sense of solace in his friendship with Alia Shawkat. The pair were rumored to be dating in November 2019, but Us later confirmed that they were just friends. "They have an incredibly tight bond and trust each other implicitly," a source explained in May. "Alia's been a wonderful help for Brad during this major transition." Jolie, for her part, had "been on a few dates" in November 2019, but didn’t settle on anything serious. “She's all about focusing on the kids, her job, and cleaning up her messy divorce,” another source told Us at the time. Scroll down to learn more about Jolie and Pitt's evolving relationship.

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2004

Sparks flew on the set of Mr. & Mrs. Smith (released the following year), despite the fact that Pitt was married to Jennifer Aniston at the time. "I think we were the last two people who were looking for a relationship. I certainly wasn't," Jolie later told Vogue. "We found this strange friendship and partnership that kind of just suddenly happened. I think a few months in I realized, 'God, I can't wait to get to work.'"

Related: Brad Pitt Praises Angelina's "Heroic" Mastectomy Decision

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July 2005

To promote Mr. & Mrs. Smith, the stars played house as a 1960s married couple in a 60-page portfolio for W magazine. The imagery upset Pitt's ex-wife Jennifer Aniston, who later told Vogue that "the world was shocked and I was shocked. . .There's a sensitivity chip that's missing."

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November 2006

The couple rode a motorcycle while visiting Ho Chi Minh City, Vietnam. The following year, they adopted 3-year-old Pax Thien from the same town. He was born Pham Quang Sang on November 29, 2003, where he was abandoned soon after birth. "Some of my kids are from countries that have seen conflict," Jolie has said. "I usually just explain to them that there are other families in the world that aren't as fortunate as ours and other kids."

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January 2007

Pitt and Jolie (in a St. John Couture gown) looked lovingly at one another at the 64th Annual Golden Globe Awards in L.A. "We've put down roots together," Pitt once told Parade of their relationship. "As Angie and I carve out our time as a couple, we carve out our lives as individuals."

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January 2007

While Pitt was shooting The Curious Case of Benjamin Button, he and Jolie dropped $3.5 million on an early-1830s masonry mansion in the French Quarter of New Orleans. Years later, Pitt let his Moneyball costar Jonah Hill crash at his luxe digs while filming 21 Jump Street. "I would go home every day from work and there'd be a tour outside and they'd be freaking out," Hill once said. "I'd get out of the car, and you could hear a collective audible sigh of annoyance when it wasn't Brad Pitt!"

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May 2007

The stars were open to adopting again, even with six kids. "There's a really nice balance in the house right now," Pitt told The Hollywood Reporter, "but if we see the need and get that lightning bolt that says, 'We can help this person; we could do something here.'"

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January 2008

With their kids at home, Jolie and Pitt couldn't keep their hands off each other at the 14th Annual Screen Actors Guild Awards in L.A. "I am very lucky with Brad," the Salt actress previously told The Telegraph. "He is a real gentleman, but he is also a real man's man."

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May 2008

Jolie — expecting twins Knox and Vivienne — gave birth just two months after hitting up the Kung Fu Panda premiere at the Cannes Film Festival.

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July 2008

The couple shared the first photos of twins Knox and Vivienne with Hello! for a reported $14 million — the most expensive celebrity pictures ever taken. "We felt we could handle more children, and we have a very happy, very full home," Jolie has said of her large brood.

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February 2009

The A-list duo managed to avoid a run-in with Pitt's ex-wife Jennifer Aniston at the 81st Annual Academy Awards in L.A. When Aniston presented an award alongside Jack Black, the cameras panned to Jolie — who flashed a smile at Pitt's ex.

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October 2009

Charity work is important to both stars, who visited Iraqi refugees in Damascus, Syria. Jolie, a Goodwill Ambassador for the UN, first visited the city in 2007. "Angie's heart is with Brad, her kids and her causes," a source previously told Us. "Their lives are complete."

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December 2009

The stars' son Maddox made his red carpet debut at the Invictus premiere in Beverly Hills. "He's just this little man that's very supportive of me," Jolie told Vogue of her eldest son. "It's like he's raised me a bit."

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January 2011

Considered to be the best-dressed couple of the night, Pitt (in Tom Ford) and Jolie (in Atelier Versace) glided down the red carpet at the 68th Annual Golden Globe Awards. Jolie was nominated for Best Performance in a Motion Picture — Musical or Comedy, but lost to The Kids Are All Right's Annette Bening.

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February 2012

Jolie put her best foot forward at the 84th Annual Academy Awards in Hollywood — and it quickly became one of the most-mocked moments of the show. "The people I surround myself with don't really talk about that kind of stuff," Jolie later said. "I heard something, but I didn't pay any attention. It's as simple as being a woman picking a dress you like and having a night, and not really thinking about anything else.

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April 2012

The Burn After Reading actor worked with jewelry designer Robert Procop to design the perfect engagement ring for his bride-to-be; Jolie flaunted it during a private viewing of the Los Angeles County Museum of Art's Chinese Galleries. Pitt's manager said their engagement was "a promise for the future, and their kids are very happy."

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June 2013

In an emotional op-ed for the New York Times, Jolie revealed she underwent a preventative double mastectomy in April 2013. Two months later she confidently hit the red carpet at the London premiere of Pitt’s film World War Z in a black gown, smiling on the arm of her then-fiance.

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November 2013

All grown up! Showing off their matured son Maddox on the red carpet, Jolie and Pitt happily attended the 5th Annual Governors Ball Awards in Hollywood, where the actress and activist was honored with the Humanitarian Award. “Mad, I’m not going to cry. I promise, and I won’t embarrass you,” she said in her speech. “You and your brothers and sisters are my happiness. And there is never a greater honor in this world than being your mom.”

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March 2014

With an Oscar of her own under her belt, Jolie attended the 2014 Academy Awards to lend her support to Pitt, who was nominated as a producer on 12 Years a Slave. Later in the evening the film took home the top prize of Best Picture, and the couple took part in host Ellen DeGeneres’ famous Internet-breaking selfie.

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May 2014

As the red-lipstick-wearing “evil” witch Maleficent, Jolie brought in her highest box office totals of all time. Pitt supported her on numerous red carpets for the Disney film, bringing along their six kids to the London private reception for the costumes and props. The pair’s then-4-year-old daughter Vivienne appeared in the film as a young Princess Aurora.

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August 2014

Surprise! After a two-year engagement, the couple tied the knot in a secret ceremony in Chateau Miraval, France. Jolie’s veil was decorated with drawings from her kids, who all played a special part in the big day. “It was important to us that the day was relaxed and full of laughter,” the couple told Hello! magazine. “It was such a special day to share with our children and a very happy time for our family.”

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November 2014

Introducing Mr. and Mrs. Jolie-Pitt! The newlyweds made their first official red carpet appearance together at the Sydney, Australia, premiere of Unbroken, the true story film adaptation directed by Jolie.

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January 2015

The married couple stepped out together at the 15th Annual AFI awards in Beverly Hills, Calif. on Jan. 9. The event followed the release of Jolie's sophomore directorial effort Unbroken.

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March 2015

Proud parents! Jolie and Pitt, who share six children, took in a soccer game in Los Angeles on March 14. They watched their daughters Zahara and Shiloh in the game, embracing as they cheered on the girls.

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May 2015

Dream team. Jolie and Pitt, who famously met on the set of the 2005 movie Mr. and Mrs. Smith, reunited on the big screen in By the Sea. The two starred in the film under Jolie's direction.

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September 2016

Jolie filed for divorce from Pitt after two years of marriage, attorney Robert Offer confirmed to the Associated Press on September 20. Offer said it was "for the health of the family." TMZ, meanwhile, reported that Jolie had requested physical custody of their six kids but was not seeking spousal support

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September 2016

Reports claimed that Pitt was being investigated by the LAPD for an alleged child abuse incident with Maddox. In a statement, the FBI stated that they were working “to gather facts and will evaluate whether an investigation at the federal level will be pursued.” The actor was cleared two months later.

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December 2016

After the investigation controversy concluded, multiple sources confirmed to Us that he saw his shared children with Jolie over Christmas weekend to participate in “a holiday gift exchange.”

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January 2017

The former couple released a joint statement in the new year, announcing their plans to seal their divorce documents. They said they intend to keep everything “confidential” and will work with a private judge “to make any necessary legal decisions and to facilitate the expeditious resolution of any remaining issues.”

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March 2017

Pitt touched base with his ex-wife, Jennifer Aniston, after obtaining her cell phone number again through “a tangled web” of contacts, a source told Us. “They started talking once he wished her a happy birthday,” the insider added.

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May 2017

Pitt admitted to GQ Style at the time that he “was really on my back and chained to a system” was after he received a call from Child Services. The Fight Club star then detailed how he and Jolie have worked together to coparent their six children. “After that, we’ve been able to work together to sort this out,” he continued. “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. And fortunately, my partner in this agrees. It’s just very, very jarring for the kids, to suddenly have their family ripped apart.”

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August 2017

An insider told Us that the pair have not “done anything” in months to help move their divorce along. “No one thinks they are ever going to,” the source added.

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December 2018

Pitt and Jolie avoided going to trial by reaching a custody agreement. The actress’ lawyer, Samantha Bley DeJean, told Us that the agreement was “signed by both parties and the judge”and “based on the recommendations of the child custody evaluator.”

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January 2019

A source told Us that the exes had two in-person meetings at an office in Los Angeles, which they said was part of the pair’s “ongoing process to work through things regarding the kids and the divorce.” A second insider added that Pitt and Jolie “have established a foundation … that is enabling the process to move forward in a much more thoughtful and peaceful manner.”

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February 2019

Jolie attended the New York City premiere of Netflix's movie The Boy Who Harnessed the Wind with all six of her kids.

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April 2019

According to court records obtained by Us, Pitt and Jolie became legally single despite their divorce not being finalized.

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June 2019

An insider told Us that Pitt has found a creative outlet post-split through sculpting. The source said that the activity is “very therapeutic” for the actor.

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September 2019

Pitt admitted to going to Alcoholics Anonymous after calling it quits with Jolie, telling The New York Times: “I had taken things as far as I could take it, so I removed my drinking privileges.”

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September 2019

Speaking with NPR, Pitt was asked whether the estranged pair’s split influenced his performance in Ad Astra. “I would be exploring it whether there was a script that allowed that or not,” he explained. “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.”

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October 2019

Jolie hit the London premiere of her film Maleficent with Zahara, Shiloh and twins Knox and Vivienne. Her shared children with Pitt joined her at the film’s premieres in other cities like Los Angeles.

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October 2019

A source told Us that Pitt contacted Jolie about reconnecting with Maddox while he is attending college in South Korea. “Brad has talked to Angelina about visiting Maddox in Seoul. Angelina has been trying to heal the rift between father and son,” an insider explained. Their eldest son, however, has not been “receptive.” 

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October 2019

Jolie spoke with the French magazine Madame Figaro about how she “felt a deep and genuine sadness” after her 2016 separation from Pitt. She admitted that she “had lost myself a bit,” adding that she felt “smaller, almost insignificant, even if it wasn’t necessarily obvious.”

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November 2019

An insider revealed to Us that the Salt star "still has a lot of resentment toward Brad," despite ending their marriage more than three years prior. "She wants him to be held accountable because she feels he turned her and the children's lives upside down," the source added. At the time, another source said that Jolie was back on the market. "She isn’t closed to the idea of meeting someone new, but it's not her main priority," the source added after noting that the actress had "been on a few dates." Pitt was rumored to be dating Alia Shawkat at the time, but Us later confirmed that the actors were just friends.

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January 2020

The Once Upon a Time in Hollywood star got candid about his personal life after taking home a big win at the 2020 Golden Globes. After gaining a lot of attention during awards season, Pitt teased that he’s a topic of conversation "because of my disaster of a personal life, probably, most likely," while speaking to Marc Maron on the "WTF" podcast.

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March 2020

Shortly after Jolie opened up about their daughters' "medical challenges," Us confirmed that the Fight Club star skipped the 2020 BAFTAs in London to be with his family during their difficult time. Pitt asked costar Margot Robbie to attend the awards show in his place.

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April 2020

Though their split was infamously messy, the former couple agreed on one major detail: "traditional schooling" for their kids. "Brad wants the kids to be in a school setting, and not isolated being homeschooled," a source explained at the time. Us confirmed one month earlier that their eldest child, Maddox, was taking virtual classes after his South Korea university closed due to the coronavirus pandemic.

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May 2020

Despite their many ups and downs, the coparents are starting to figure out a comfortable routine. "Things between Brad and Angelina are better than they have been," an insider told Us exclusively. "They're more cordial — they're aiming toward resolutions that work for each of them." Another source explained that Jolie was "impressed with Brad’s continued sobriety" and that he is typically able to see their youngest children every few days.

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June 2020

Jolie separated from Pitt “for the well-being of [her] family,” she told Vogue. “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.”

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August 2020

A source told Us that Jolie “has been advocating for a reconciliation” between Pitt and their oldest children Maddox, Pax and, “to a lesser extent,” Zahara. However, another insider stated that “there’s no sign this is true, but it would be great if [it] were.”

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August 2020

Jolie filed court documents requesting to disqualify Judge John W. Ouderkirk in her and Pitt’s custody trial, claiming Ouderkirk “failed to disclose” that he had a professional relationship with one of the Once Upon a Time in Hollywood star’s attorneys. Pitt’s legal team responded by slamming Jolie’s “thinly veiled attempt” at delaying the trial, noting that she had “hand-selected” Ouderkirk to preside over her and Pitt’s wedding and “never objected” to his involvement in the case before.

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March 2021

As the former couple continued their messy court battle, Jolie filed documents alleging incidents of domestic violence regarding her ex-husband. At the time, the actress stated that her kids were willing to offer "proof and authority in support" of the claims. Though many of the children would be testifying as minors, Maddox, the pair's eldest son, addressed the court as an adult.

"It wasn’t very flattering toward Brad," a source exclusively revealed in March 2021. "He doesn't use Pitt as his last name on documents that aren't legal and instead uses Jolie. Maddox wants to legally change his last name to Jolie, which Angelina has said she doesn't support."

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May 2021

After a lengthy court battle to determine custody of their six children, a judge ruled in favor of joint custody in May 2021, shortly after Jolie claimed the court refused to let the kids testify against Pitt regarding his alleged history of domestic violence.

Later that month, a source exclusively revealed that Jolie would "never forgive" Pitt for the way the arrangement ended up. "She maintains it's far from over and still believes that justice will prevail," the insider said at the time.