Brad Pitt and Angelina Jolie were one of Hollywood’s most iconic “it” couples.

The former pair first met in 2003 while portraying the role of husband and wife in the film Mr. & Mrs. Smith. Jolie was enjoying being a single mother, and Pitt was still married to Jennifer Aniston (the two later split in 2005). Looking back, Jolie recalled to Vogue that it wasn’t really love at first sight; she and Pitt just made a good team.

“Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened,” Jolie told the publication in 2007.

She continued, “I think a few months in I realized, ‘God, I can’t wait to get to work.’ … Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork.”

The former couple shares six children together: sons Maddox and Pax Thien, daughters Zahara Marley and Shiloh Nouvel and twins Knox Léon and Vivienne Marcheline.

Brad Pitt & Angelina Jolie’s Judge Disqualified from Case, Pitt Says ‘Facts Haven’t Changed’

While the former couple shared a lot of happy moments, they also had hard times. On Sept. 20, 2016, Jolie filed for divorce from Pitt, citing irreconcilable differences.

From their joint movie projects to their top-secret wedding in France, here’s a look back at Brad Pitt and Angelina Jolie‘s relationship.

2003: Brad Pitt and Angelina Jolie meet on the set of Mr. & Mrs. Smith

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The actors first crossed paths while filming the spy thriller Mr. & Mrs. Smith, in which they play married assassins. At the time, Pitt was still married to Aniston while Jolie had recently separated from ex-husband Billy Bob Thorton.

“I didn’t know much about exactly where Brad was in his personal life,” Jolie recalled in a January 2007 Vogue interview. “But it was clear he was with his best friend, someone he loves and respects.” Jolie and Pitt remained friends throughout filming.

January 7, 2005: Brad Pitt and Jennifer Aniston separate

On Jan. 7, 2005, Pitt and Aniston announced their separation. “We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration,” Pitt and Aniston said in a joint statement to PEOPLE.

Aniston officially filed for divorce in March of that year, which was finalized on October 2.

2005: Angelina Jolie travels to Ethiopia to adopt daughter Zahara Marley

While Angelina Jolie adopted her first son, Maddox, in 2002 from Cambodia, in the summer of 2005, Jolie became a mother of two after adopting newborn Zahara in Ethiopia. The Eternals actress wasn’t sharing too many details at the time, but she did tell PEOPLE that she and Maddox were “happy to have a new addition to our family.” Pitt accompanied Jolie to Ethiopia.

“Angie’s over the moon,” a source close to Jolie told PEOPLE. “It’s a dream come true. She’s always wanted to extend her family.”

January 2006: The last names of Angelina Jolie’s children are changed to Jolie-Pitt

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In January 2006, the couple hit a milestone in Pitt’s journey to legally adopting Jolie’s two children, Maddox and Zahara. A Los Angeles judge approved the couple’s name-change petition, which requested that Maddox and Zahara’s last names be legally changed to Jolie-Pitt.

“It’s the idea that you love one another and you want to create a family together,” a friend of the couple told PEOPLE at the time. “What’s beautiful is you can do it by birth (or) by adoption.”

May 27, 2006: Brad Pitt and Angelina Jolie welcome daughter Shiloh Nouvel

Jolie and Pitt welcomed their first child together on May 27, 2006, a daughter named Shiloh. She was born in Cottage Hospital in Swakopmund, in the African country of Namibia. The name Shiloh is biblical and translates to “the peaceful one.”

Representatives of both actors had confirmed to PEOPLE on Jan. 11, 2006 that Jolie was expecting. Jolie first revealed the baby news at a charity center in Santo Domingo, Dominican Republic.

September 2006: Brad Pitt says he and Angelina Jolie will marry when everyone can

In a 2006 Esquire interview, Pitt told the outlet that wedding bells will be in his and Jolie’s future once every couple is legal to do the same. “Angie and I will consider tying the knot when everyone else in the country who wants to be married is legally able,” Pitt said.

He also touched on their growing family, including newborn Shiloh, and the process of legally adopting Maddox and Zahara. “They’re as much of my blood as any natural born, and I’m theirs. That’s all I can say about it. I can’t live without them. So: Anyone considering (adoption), that’s my vote,” Pitt said.

December 2006: Brad Pitt and Angelina Jolie make their red carpet couple debut

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The New York City premiere of The Good Shepherd marked the pair’s first red carpet appearance as an official couple.

January 2007: Angelina Jolie publicly addresses their relationship for the first time

Jolie got extremely candid about her relationship with Pitt and how it started in Vogue‘s January 2007 issue.

“It took until, really, the end of the [shooting Mr. and Mrs. Smith] for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration,” she said.

The pair was all about taking things slow, but it was Maddox who helped nudge them along. “[Maddox] just out of the blue called him Dad,” Jolie recalled. “It was amazing. We were playing with cars on the floor of a hotel room, and we both heard it and didn’t say anything and just looked at each other. So that was probably the most defining moment, when he decided that we would all be a family.”

March 2007: Angelina Jolie travels to Vietnam to adopt son Pax Thien

Jolie adopted 3-year-old Pax — whose name means peaceful sky — from Tam Binh orphanage in Vietnam in March 2007. Big brother Maddox accompanied his mom; Pitt was not in attendance due to a scheduling contract with a film he was working on.

Jolie’s name was the only one to appear on the adoption application as she and Pitt weren’t married at the time, and it’s harder for an unmarried couple to adopt under Vietnamese law. But in February 2008, an L.A. County Children’s Court judge approved Pax’s adoption, and consequently, legally changed Pax’s last name to Jolie-Pitt.

“You can imagine what courage it takes to be in all new surroundings, with new people and a new language. He is very strong,” Jolie told PEOPLE following the adoption.

February 23, 2008: Angelina Jolie debuts a baby bump at the Independent Spirit Awards

Though the couple hadn’t publicly confirmed Jolie’s pregnancy, Pitt and Jolie walked the red carpet together at the 2008 Film Independent Spirit Awards, where the actress debuted her growing baby bump.

May 27, 2008: Brad Pitt and Angelina Jolie rent a French chateau

With four children and two on the way, Pitt and Jolie signed a three-year lease for Château Miraval, an 880-acre estate in Correns, France. Reportedly valued at $70 million in 2008, the property came with its own private vineyard, olive groves, lake, moat, fountains and a forest.

Jolie told reporters at the 2008 Cannes International Film Festival that French is a “second language” in her family’s home and she was considering giving birth to her impending twins in France.

Pitt and Jolie officially purchased the property in 2012 and launched the wine business Miraval Wines.

July 2008: Angelina Jolie says humanitarianism and philanthropy brought her and Brad Pitt closer

Jolie has been an outspoken humanitarian all her life, but in Vanity Fair‘s July 2008 issue, she explained it was the philanthropic work Pitt did privately that really brought their worlds together.

“Though he wasn’t as publicly active, I found him to be very aware of the world, very curious, very compassionate,” Jolie told the publication. “In his private way, he had been doing a lot. When we met, we realized our common goals were that we both wanted to be involved in the world and see what we could do.”

She continued, “We have similar interests but different approaches. He’s more involved in rebuilding New Orleans, environmental issues, green sustainability. I am more refugees. But when it comes to common goals — orphans, orphans’ rights, children — we support each other. It brings us together and makes our relationship work.”

July 12, 2008: Brad Pitt and Angelina Jolie welcome twins Knox Léon and Vivienne Marcheline

Jolie and Pitt’s fraternal twins, son Knox and daughter Vivienne, came into the world on July 12, 2008, in Nice, France. Knox arrived just one minute before his sister.

“It is chaos, but we are managing it and having a wonderful time,” Jolie told PEOPLE in her July cover story. The couple and their four other children relocated to Château Miraval for the summer ahead of the twins’ arrival.

“[Shiloh] and Z pick out [the twins’] clothes and help change and hold them,” Jolie continued. “It’s sweet – they are little mommies.”

July 2010: Angelina Jolie reveals how she and Brad Pitt juggle their busy schedules

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In a 2018 Parade interview, Jolie explained that she and Pitt never take on projects at the same time so that one of them is always available for their six children.

“He takes the kids to school; he visits me on set with the kids. I’m home for dinner, or I’m there for breakfast. We’re together all the time. We plan,” Jolie said.

“There’s never a period when Brad and I are pulled apart. We are not separated for more than three days, ever,” she continued. “We’re very homebound. We’re very much Mommy and Daddy in our pajamas.”

January 29, 2012: Brad Pitt says their kids are eager for them to get engaged

While speaking with CBS News, Pitt revealed that he and Jolie were “getting a lot of pressure from the kids” to get engaged.

“It means something to them and they’re, you know, they have questions when their friends’ parents are married and why is that?” Pitt said. “We will someday. We will. … [But the kids say], ‘Get mommy a ring!’ Okay, I will, I will.”

April 2012: Brad Pitt and Angelina Jolie confirm they’re engaged

Brad Pitt and Angelina Jolie in March 2014. ETHAN MILLER/WIREIMAGE

On April 12, 2012, Pitt’s manager Cynthia Pett-Dante confirmed to PEOPLE that the couple was officially engaged.

“Yes, it’s confirmed,” Pett-Dante said. “It is a promise for the future and their kids are very happy. There is no date set at this time.”

A day earlier, the bride-to-be had privately debuted her new engagement ring while attending a function at the L.A. County Museum of Art. An independent expert told PEOPLE at the time that the ring potentially weighed more than 10 carats, with a price tag of $1 million, though the couple never confirmed the sparkler’s details.

May 14, 2013: Angelina Jolie shares she had a preventative double mastectomy

In a New York Times op-ed piece called “My Medical Choice,” Jolie shared that in February 2013, she elected to have a double mastectomy after genetic tests revealed she had BRCA1. She was told there was an 87 percent chance that she could develop breast cancer. Jolie’s mother, actress Marcheline Bertrand, died from breast cancer in 2007.

Jolie also publicly thanked Pitt for his support. “I am fortunate to have a partner, Brad Pitt, who is so loving and supportive,” she wrote. “So to anyone who has a wife or girlfriend going through this, know that you are a very important part of the transition.”

“We knew this was the right thing to do for our family and that it would bring us closer. And it has,” she penned.

August 23, 2014: Brad Pitt and Angelina Jolie tie the knot in an intimate destination wedding

Surrounded by 20 of their closest friends and relatives, including their six children, Pitt and Jolie said “I do” on August 23, 2014. The very private wedding ceremony took place in the chapel of Château Miraval, the family’s estate in the French village of Correns.

PEOPLE reported that Jolie walked down the aisle with her eldest sons Maddox and Pax, while Zahara and Vivienne served as flower girls and Shiloh and Knox as ring bearers. The couple tapped a very special baker for their wedding cake: Pax. The Jolie-Pitt clan even helped their parents write their vows.

“It was important to us that the day was relaxed and full of laughter,” the couple told PEOPLE. “It was such a special day to share with our children and a very happy time for our family.”

Jolie shared that her wedding gown was designed by Atelier Versace tailor Luigi Massi, in conjunction with her children. The dress and veil were embellished with the kids’ art drawings.

“Luigi is like family to me and I couldn’t imagine anyone else making this dress,” Jolie said. “He knows and cares for the children and it was great fun putting it together.”

August 29, 2014: Brad Pitt and Angelina Jolie film By the Sea on their honeymoon

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Pitt and Jolie mixed business with pleasure while honeymooning in Malta. The newlyweds spent much of their vacation filming By the Sea, in which they portray a married couple who develop a sexual fascination with their neighbors. The sexy drama marked the first time Pitt and Jolie had worked together onscreen since Mr. & Mrs. Smith in 2005. Even more special, Jolie wrote and directed the film.

“I wrote something a few years ago for Brad and me,” Jolie told PEOPLE in May 2014. “Just for fun. Just an independent little art piece. Because we don’t get to do those as much as we’d like. But it’s something really small and experimental.”

March 24, 2015: Angelina Jolie reveals she had her ovaries removed to reduce her risk of cancer

After a blood test revealed possible detections of early cancer, Jolie scheduled a consultation with a surgeon to undergo tumor testing. In a New York Times op-ed, Jolie explained that although those test results came back negative, it was still possible that she had early-stage cancer. To reduce her risk, she decided to undergo surgery to remove her ovaries and fallopian tubes.

Jolie said Pitt immediately boarded a plane after she phoned him with the initial blood test results. “The beautiful thing about such moments in life is that there is so much clarity. You know what you live for and what matters. It is polarizing, and it is peaceful,” the mother of six wrote.

November 5, 2015: Brad Pitt and Angelina Jolie walk the red carpet at the By the Sea premiere

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At the L.A. premiere of By the Sea, Pitt and Jolie walked the red carpet hand in hand. He wore a black suit while she donned a strapless white dress embellished with jewels.

September 20, 2016: Angelina Jolie files for divorce from Brad Pitt

Shortly after their second wedding anniversary, Jolie filed for divorce from Pitt on Sept. 20, 2016. She cited irreconcilable differences and requested physical custody of their six children and visitation for Pitt. Jolie did not request child or spousal support.

“Angelina Jolie Pitt has filed for dissolution of the marriage. This decision was made for the health of the family. She will not be commenting at this time, and asks that the family be given their privacy during this difficult time,” Jolie’s attorney told PEOPLE.

In a statement to PEOPLE, Pitt said, “I am very saddened by this, but what matters most now is the well being of our kids. I kindly ask the press to give them the space they deserve during this challenging time.”

April 13, 2019: Brad Pitt and Angelina Jolie are legally single

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Nearly three years after Jolie first filed for divorce, she and Pitt were ruled legally single by a judge. The former couple was in the midst of finalizing their divorce settlement. Over the last few years, Pitt and Jolie had been in ongoing negotiations regarding custody of their children and the divvying of their finances.

July 23, 2021: Brad Pitt loses previously awarded time with kids amid custody case with Angelina Jolie

In May 2021, Judge John Ouderkirk awarded Pitt more time with his and Jolie’s five minor children. However, just two months later, that decision was reversed after a three-judge panel disqualified Ouderkirk from the case due to a violation of “his ethical obligations,” PEOPLE reported.

Ouderkirk, who was serving as the couple’s temporary judge, did not disclose his business relationships with Pitt’s attorney, and Jolie argued that this could make his rulings biased.

A source close to the actor told PEOPLE, “Brad believes there is overwhelming evidence that the current situation isn’t good for the kids. This just sets things back for everyone.”

September 4, 2021: Angelina Jolie speaks about her split from Brad Pitt

Five years after filing for divorce from Pitt, Jolie spoke to The Guardian‘s Weekend magazine about her decision to end their marriage. “I’m not the kind of person who makes decisions like the decisions I had to make lightly. It took a lot for me to be in a position where I felt I had to separate from the father of my children,” she said.

The publication also asked the Oscar-winning actress how the last five years have impacted her, to which she replied, “I mean, in some ways, it’s been the last decade. There’s a lot I can’t say.”

October 6, 2021: Angelina Jolie sells her stake in the winery she shared with Brad Pitt

The actress sold her stake in the $164 million French estate and winery she bought with Pitt to Tenute del Mondo, the wine division of the Stoli Group. According to court documents obtained by PEOPLE, Jolie was cleared to sell her shares a month prior to the deal. Jolie had previously run into issues when trying to sell her shares due to her and Pitt’s ongoing divorce.

Tenute del Mondo purchased 50 percent Château Miraval estate from Jolie for an undisclosed amount.

2022: Brad Pitt sues Angelina Jolie for selling her stake in the wine business and accuses her of harming the company’s reputation

Angelina Jolie; Brad Pitt. STEFAN ROUSSEAU – WPA POOL/GETTY IMAGES; KEVIN WINTER/GETTY IMAGES

Pitt and Jolie’s former business venture has been at the center of the ex-couple’s legal battles. In response to Jolie selling her stake in Château Miraval in 2021, Pitt sued his ex-wife in February 2022, claiming she violated a previous agreement.

According to legal documents obtained by PEOPLE, Pitt alleged that Jolie failed to receive his permission before selling her shares to the Stoli Group, despite their agreement that neither would do so without the other person’s approval.

In a new court filing on June 6, 2022, Pitt further accused Jolie of damaging the reputation of the wine business by selling her shares to a “stranger.” The Lost City actor claimed that Jolie intentionally “sought to inflict harm on” him by selling her half of the business.

“Jolie pursued and then consummated the purported sale in secret, purposely keeping Pitt in the dark, and knowingly violating Pitt’s contractual rights,” read the filing.

Pitt’s legal team also wrote that Miraval is the actor’s “passion” project that grew “into a multimillion-dollar global business and one of the world’s most highly regarded producers of rosé wine” through his work. Pitt also accused Jolie of contributing “nothing to Miraval’s success.”

August 2022: PEOPLE obtains FBI documents regarding Angelina Jolie and Brad Pitt’s 2016 airplane incident

Amid an ongoing custody battle with Pitt, Jolie, under the anonymous “Jane Doe,” requested that FBI documents about her family’s 2016 private plane incident be released to her under the Freedom of Information Act.

PEOPLE obtained the highly redacted documents, which gave new details of the alleged Sept. 14, 2016 conflict, days before Jolie filed for divorce.

According to the FBI report, Pitt allegedly grabbed and shook Jolie during a private flight from France to Los Angeles, pushed her into a wall and punched the plane’s ceiling. She also claimed Pitt “poured beer on” her at one point. When she said it seemed “like he was going to attack” one of their children for calling him a “prick” during the dispute, Jolie recounted wrapping her arms around Pitt’s neck in a chokehold-style.

Jolie said Pitt was “becoming a monster” as he “ranted” and “mimicked the behavior of a monster and screamed at them.” She added that she and the kids were “shell-shocked,” saying she was “frozen, scared and didn’t know what to do.” Jolie also claimed that his actions made her feel “like a hostage” on the plane.

The Los Angeles Department of Child and Family Services concluded its investigation into the incident in November 2016 with no findings of abuse. The FBI also closed its investigation that month with no charges. Pitt denied any abuse.

August 17, 2022: A source says Angelina Jolie is “trying to Inflict the most amount of pain” by reviving plane incident with Brad Pitt

After the FBI documents that Jolie requested were made public, a source close to Pitt told PEOPLE that the actor thinks Jolie is set out to hurt him.

The insider claimed that both Pitt and Jolie have had the documents in question for six years, and Jolie likely meant to “revive an issue that was painful for everybody and was resolved six years ago.”

The source added, “They investigated it. They prepared materials, reviewed it together and decided not to charge him.”

“What are the motivations of a person to take up court time and public resources in filing an anonymous FOIA request for material they have had for years? There’s only one: to inflict the most amount of pain on her ex,” the source continued. “There is no benefit to this. It is harmful to the children and the entire family for this to be made public.”

September 7, 2022: Angelina Jolie claims Brad Pitt “masterminded” plan to “seize control” of their winery

After Pitt sued Jolie in February 2022 over her sale of her Château Miraval stake, the Tomb Raider star filed a countersuit in which she accused her ex of “waging a vindictive war against” her.

The lawsuit was filed by Nouvel — a business founded by Jolie. The company is seeking more than $250 million in damages, claiming that Pitt “masterminded a so-far-successful plan to seize control” of Château Miraval following the couple’s divorce in 2016.

Of the countersuit, a source close to Pitt told PEOPLE, “This is just the latest in a series of deliberate efforts to misdirect, recycle and reposition the truth of what has happened over the last six years, thinking that reasonable people would be duped by these obvious misrepresentations.”

October 13, 2022: Brad Pitt says sculpting was a “flame of joy” amid split from Angelina Jolie

Pitt is now an artist in every sense of the word. The Fight Club star picked up sculpting — a creative outlet that has helped him through tough times, including his divorce from Jolie.

“Out of this misery came a flame of joy in my life,” he told the Financial Times. “I always wanted to be a sculptor; I’d always wanted to try it.”

Pitt went on to talk about one particular piece called “Aiming At You I Saw Me But It Was Too Late This Time,” which depicts a gunfight between eight figures.

“It’s all about self-reflection,” he told the publication. “I was looking at my own life and really concentrating on owning my own s—: where was I complicit in failures in my relationships, where have I misstepped.”

The actor added: “For me, it was born out of ownership of what I call a radical inventory of self, getting really brutally honest with me, and taking account of those I may have hurt.”

December 1, 2022: Angelia Jolie calls Brad Pitt’s winery lawsuit “part of a problematic pattern”

In a case management statement, Jolie called Pitt’s legal actions “frivolous, malicious and part of a problematic pattern.” The actress is holding firm that she and Pitt did not have “a secret, unwritten, unspoken contract” that required them to ask for consent before selling their shares of Château Miraval.

The statement also read that Jolie has requested a jury trial lasting 10 to 15 days and has agreed to participate in a settlement conference or mediation session as a form of alternative dispute resolution. In his case management statement from Nov. 23, Pitt also agreed to mediation.

June 2, 2023: Source says Brad Pitt decided to sue Angelina Jolie after she refused to sign an NDA

A source close to Jolie told PEOPLE that Pitt decided to pursue legal action regarding the sale of Château Miraval as a retaliation.

“The reality is that Pitt refused to complete the Miraval sale with Jolie unless she agreed to being silenced about the abuse as he demanded that $8.5 million be held back to force her to keep quiet,” the insider claimed. “Ms. Jolie had no interest in speaking about what happened. In fact, she has not done so even once, and instead, she devoted her life to helping the children heal.”

The source continued: “Mr. Pitt saying that he is suing his ex-wife to protect his family is hard to understand because he is well aware the children have not felt able to return to the house in France for almost seven years now due to the events that led to Ms. Jolie filing for divorce.”