The reasons why one-time Hollywood golden couple Angelina Jolie and Brad Pitt’s relationship turned sour.

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Angelina Jolie and Brad Pitt were once the most glamorous couple in Hollywood. But as they learned, you need more than impossibly good looks to make a marriage work. And after 12 years together, the pair dubbed by the tabloids as Brangelina went their separate ways. Later, in 2019, Jolie revealed why their relationship didn’t result in a happy ending.

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Jolie and Pitt first got together in the most tabloid-baiting way possible. The pair first met on the set of Mr. and Mrs. Smith, when the latter was married to Friends star Jennifer Aniston. Rumors soon surfaced that the action comedy’s two stars had embarked on an affair during filming, something Jolie furiously denied.

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But by October 2005 Pitt and Aniston had divorced. And just three months later, Jolie revealed that she had fallen pregnant with Pitt’s child. The pair would eventually have six children together, including three adoptees. They walked down the aisle at a ceremony in the French city of Correns back in 2014.

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Sadly, married life didn’t seem to suit the once-happy pair, and in 2016 they announced their separation. Jolie and Pitt officially divorced three years later, following lengthy and often fraught discussions about their custody arrangements. Here’s a look at their turbulent love story and how it all came crashing down.

As the daughter of Hollywood legend Jon Voight and occasional actress Marcheline Bertrand, Angelina Jolie was perhaps always destined to end up on the big screen. She first caught attention as a model, before honing her acting talents at NYU and the Lee Strasberg Theatre Institute. Jolie made her film debut in 1992 with a minor part in sci-fi sequel Cyborg 2.

Jolie’s big break came in 1995, when she starred opposite future husband Jonny Lee Miller in the cult classic Hackers. Over the next few years she won a Golden Globe for her portrayal as the titular president’s wife in George Wallace and picked up an Emmy nod for her leading role in Gia. Jolie then joined the all-star casts of both Playing by Heart and Pushing Tin.

In 2000 Jolie’s stock rose even higher when she was awarded Best Supporting Actress at the Oscars for her performance in Girl, Interrupted. Capitalizing on her success, she scored a box office hit with the fast and furious caper Gone in Sixty Seconds. And in 2001 Jolie took on the iconic role of Lara Craft in the first of two Tomb Raider adventures.

An in-demand Jolie then appeared alongside Colin Farrell in historical epic Alexander and Jude Law in war movie Sky Captain and the World of Tomorrow. Her prolific streak continued with Taking Lives and a voiceover role in the Dreamworks animation Shark Tale. And in 2005 Jolie landed a role in the film that would ultimately change her life. This, of course, was Mr. and Mrs. Smith.

After adding to her filmography with parts in The Good Shepherd and Beowulf, Jolie received further awards recognition for both A Mighty Heart and The Changeling. However, the likes of Wanted, The Tourist and Salt proved that she could still take on more popular fare. Likewise, Kung Fu Panda drew in audiences, with Jolie voicing Tigress in the animated hit.

In 2012 Jolie proved that her talents extended beyond acting. Indeed, she took the director’s chair for the first time on In the Land of Blood and Honey. The Bosnian war drama received positive reviews, as did her follow-up Unbroken. However, her third directorial effort By the Sea was given a critical drubbing upon its 2015 release.

Jolie got things back on track in 2017 with First They Killed My Father, a challenging Khmer Rouge-era drama which picked up nominations at the BAFTAs and Golden Globes. Two years later she once again played the eponymous wicked witch in Maleficent: Mistress of Evil. With a worldwide gross of roughly $600 million, its 2014 predecessor was the biggest commercial smash of Jolie’s career.

Of course, Jolie’s eventful love life has often taken the focus away from her considerable talents as an actress and director. Her first high-profile romance came in the mid-1990s, when she began dating her Hackers co-star Jonny Lee Miller. The pair said ‘I do’ at a ceremony in which Jolie sported a white T-shirt and black pants made of rubber. Bizarrely, she also used her blood to emblazon her shirt with Miller’s name.

Miller and Jolie separated just a year later and were officially divorced by 1999. And Jolie didn’t waste much time in moving on. Indeed, in the summer of 2000 Jolie walked down the aisle with another Hollywood actor. This time, it was the much older Billy Bob Thornton. The pair’s eccentric behavior – like carrying around each other’s blood in containers – provided the tabloids with countless stories.

In 2002 Jolie and Thornton revealed that they had adopted a Cambodian child. However, just a few months later, the unlikely pair decided to part company. By 2003 they’d officially divorced. Jolie later told Vogue, “It took me by surprise, too, because overnight, we totally changed. I think one day we had just nothing in common. And it’s scary but… I think it can happen when you get involved and you don’t know yourself yet.”

Things remained relatively quiet on the Jolie front until 2005. But that was the year in which she became a bigger tabloid name than ever. Indeed, while filming Mr. and Mrs. Smith, the actress was rumored to have become romantically involved with her male co-star. Of course, Brad Pitt was married to Friends favorite Jennifer Aniston at the time.

Jolie was soon keen to put all the gossip to bed. She told Marie Claire, “To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive. I could not look at myself in the morning if I did that. I wouldn’t be attracted to a man who would cheat on his wife.”

However, the rumor mill went further into overdrive when Pitt and Aniston separated shortly after Mr. and Mrs. Smith wrapped up. And in January 2006 Jolie announced that she and Pitt were expecting their first child. Shiloh Nouvel was born in the Namibian city of Swakopmund in May later that year.

Pitt and Jolie added to their family unit in 2008 with the birth of twins Knox Leon and Vivienne Marcheline. This took their brood to a total of six, as the pair had also adopted a Vietnamese three-year-old named Pax Thien in 2007. Jolie had previously adopted Maddox Chivan in 2002 and then Zahara Marley three years later.

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But the couple – dubbed by the world’s press as Brangelina – took their time in walking down the aisle. Indeed, they only became husband and wife in 2014, nine years after they first met. This happened at a ceremony staged on their French estate. Sadly, the wedding proved to be something of a curse.

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While Jolie and Pitt had sizzled up the screen in their previous big screen outing, they stunk it up in 2015’s By The Sea. Also directed by Jolie, the highly personal marital drama flopped with both critics and audiences alike. Stephanie Merry from The Washington Post wrote, “Peeling back layer upon layer of exquisite ennui reveals nothing but emptiness, sprinkled with stilted sentiments.”

Within a year of By the Sea’s release, its two stars announced that they were separating. Pitt and Jolie took a further two years to sort out the custody arrangements regarding their six children. And in 2019 the couple which had once widely regarded as Hollywood’s most glamorous were officially no more.

Jolie first discussed her separation from Pitt in an interview with Good Morning America’s George Stephanopoulos in 2017. The actress, who pointed to “irreconcilable differences” while filing for divorce, revealed the pair were still focused on her kids’ health. She said, “We will be stronger when we come out of this because that’s what we’re determined to do as a family.”

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Later that same year Jolie also opened up a bit further in a chat with Vanity Fair. She told the magazine, “It’s just been the hardest time, and we’re just kind of coming up for air.” Interestingly, Jolie also admitted, “Things got bad. I didn’t want to use that word… Things became ‘difficult.’”

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So, how bad exactly did things get? Well, in 2016 Pitt allegedly got into a massive row with Jolie on a plane. The pair’s eldest child Maddox even had to step in and act as peacemaker, according to reports. Pitt was then supposedly investigated by the FBI on child abuse grounds, but was then cleared of any wrongdoing.

Pitt’s heavy drinking habit was reportedly a major cause for concern in his relationship with Jolie. And the actor admitted to GQ in 2017 that he “could drink a Russian under the table with his own vodka.” However, Pitt was also keen to state that he no longer relies on alcohol, adding that he didn’t “want to live that way anymore.”

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However, things continued to get ugly between the pair. In 2018 Jolie argued in court documents that Pitt had been neglecting his child support payments since she filed for divorce. The actor’s legal team fought back, claiming that Jolie was both using her kids to “increase the conflict” and to “manipulate media coverage.”

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Pitt’s attorneys also asserted that the star had given Jolie over $1.3 million over the previous two years. This money was used for security, travel expenses and therapy for the couple’s six children. And Pitt also reportedly loaned his ex a whopping $8 million to help her purchase a brand new property in the U.K.

In 2018 Jolie further alluded to her problems in an interview with People magazine. Accompanied by her eldest Maddox, the Oscar winner revealed, “I have had my ups and downs. I guess I am a little bit stronger. We all have our difficult times, but as a mother you also have a responsibility first and foremost towards the kids.”

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A candid Jolie then added, “They are going through their formative years and everything else comes second to that. I haven’t worked for over a year now because they needed me home. We’ve all been a bit in lockdown. I think they’re itching to get out in the world again.”

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Jolie was just as happy to talk about her failed relationship with Pitt while promoting sequel Maleficent: Mistress of Evil in 2019. Speaking to Madame Figaro, the actress revealed that since her split, she’s been able to embrace her free-spirited side more often. “I feel like I’m coming full circle,” Jolie told the French publication.

During the chat translated by Lainey Gossip, Jolie also admitted that she felt slightly lost in the wake of her split with Pitt. She told Madame Figaro, “I do not know about destiny, but I’m certain that I’m in transition and this is a homecoming. I’m coming back to myself.”

When asked about when exactly she found things particularly hard to deal with, Jolie replied, “I think it was at the end of my relationship with Brad and then when we separated. It was complicated, I didn’t recognize myself anymore. And I’d become, how do I say this, smaller, insignificant, even if I didn’t show it.”

“I was profoundly, deeply sad. I was hurt,” Jolie continued. “On the other hand, it was interesting to tap into this humility and sense of insignificance. It’s a lesson I pass onto my children. The idea of renewal, and through it all, the possibility of joy. I had to rediscover the joy.”

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A month later Jolie discussed her private life once again in a chat with Harper’s Bazaar. She told the magazine that her children had been a huge source of support since her split with their father. “The part of us that is free, wild, open, curious, can get shut down by life,” Jolie revealed. “By pain or by harm. My children know my true self, and they have helped me to find it again and to embrace it.”

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Jolie then went on to add, “They have been through a lot. I learn from their strength. As parents, we encourage our kids to embrace all that they are, and all that they know in their hearts to be right. And they look back at us and want the same for us.”

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However, Jolie also seemed to imply that her ex-husband is still restricting her free spirited nature. The star told Harper’s Bazaar that she “would love to live abroad and will do so as soon as my children are 18. Right now, I’m having to base where their father chooses to live.”

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Pitt, of course, is still based in Los Angeles. And due to their custody arrangements, ex-wife Jolie can’t relocate outside the city with their six kids. But the Maleficent star revealed that she still wants her brood to develop the same sense of adventure as she has over the years.

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Jolie told Harper’s Bazaar, “My favorite place is somewhere I’ve never been. I like to be dropped into the middle of something new. I enjoy being out of my element. I want the children to grow up in the world. Not just learning about it, but living it and having friends around the world. Next year we break ground on a home in Africa.”

In fact, Jolie also challenged readers to break from their old routines, too. She advised, “Don’t just be comfortable with what is generally accepted, but find the new. Find your oxygen, your originality, your own voice. Live more fully. Rebel. Resist. Question. Be curious. Explore. Go outside what is comfortable to you. Say the thing you’ve been afraid to say. Put down this magazine, and go and do one thing today you’ve never done before.”

And Jolie appears to be taking her own advice when it comes to her career choices as well. She’s signed up to appear in her first superhero film with the role of Thena in The Eternals. But before that, Jolie will appear as a grieving mother in fantasy Come Away. And she’s also set to show up in the adaptation of Michael Koryta’s Those Who Wish Me Dead.