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Brad Pitt and Angelina Jolie: Timeline of Hollywood’s Favorite Power Couple

From ‘Mr. & Mrs. Smith’ to a large family and global reach, a look back at the Brangelina romance over the years

As Hollywood's most popular power couple, Brad Pitt and Angelina Jolie transformed into an exemplar of an unconventional romance – resisting legal marriage, adopting and raising their children and weathering whatever life threw at them with ease.

On Monday, September 19th, the Academy Award-winning actress, 41, filed divorce documents, citing irreconcilable differences. The pair married in 2014 and Jolie Pitt is seeking physical custody of the their six children – Maddox, 15, Pax, 12, Zahara, 11, Shiloh, 10, and twins Knox and Vivienne, 8 – and she requested that the Fight Club actor, 52, only get joint legal custody. She is not asking for spousal support.

"This decision was made for the health of the family," attorney Robert Offer said in a statement to Reuters. "She will not be commenting and asks that the family be given its privacy at this time."

Pitt is currently starring in Allied, a World War II drama co-starring Marion Cotillard (who has been dragged into the tabloid fray). Pitt told People in a statement: "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."

Here's a look back at the Brangelina romance, as it has played on and off screen.

Angelina Jolie, Brad Pitt

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October 2006: Pitt Says They Won’t Marry Until Legal for Everyone

Once their romance and launch of their family seemed settled, tabloid focus shifted to just when the pair would marry one another. In an interview with Esquire, Pitt revealed that the couple had chosen to not get married until all couples could legally wed. Even so, the pair still got married in 2014, nearly a year before same-sex marriage was declared legal in all 50 states.

Angelina Jolie, Brad Pitt, engaged

Pascal Le Segretain/Getty

April 2012: Jolie, Pitt Confirm They Are Engaged

Representatives for Pitt and Jolie confirmed that the couple was planning, at long last, to tie the knot. "It is a promise for the future and their kids are very happy," Pitt's manager, Cynthia Pett-Dante, told People, adding, "There's no date set at this time." The ring, which Pitt designed with Jeweler Robert Procop, features 16-carats of emerald-cut diamonds. Early reports pegged its value at $1million; that figure was later revised downward to half a million dollars and finally a reported $250,000.

double mastectomy, Angelina Jolie

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May 2013: Jolie Reveals Her Preventive Double Mastectomy

At age 37, Jolie chose to undergo a double mastectomy after finding out that she carried a defective BRCA1 gene which gave her an 87-percent chance of developing breast cancer. Both her mother and grandmother died of ovarian cancer while her mother also suffered from breast cancer. Her maternal aunt also died from breast cancer. "Once I knew this was my reality, I decided to be proactive and minimize the risk as much as I could," she wrote in a much-read (and debated) New York Times op-ed. "I am writing about it now because I hope that other women can benefit from my experience." In the piece she thanked Pit for being "so loving and supportive" during her procedure.                                    

Angelina Jolie, Brad Pitt, wedding

August 23rd, 2014: Pitt, Jolie Marry in France

Though it came before same-sex marriage was legalized across the United States, Brangelina wed after roughly a decade together. The couple had announced an engagement two years prior, and their quiet wedding took place at their Châueau Miraval estate in Correns, France. According to People, the pair only invited 20 guests. Jolie's dress featured artwork from their six children who were also involved in the ceremony, with Maddox and Pax walking their mom down the aisle, Zahara and Vivienne serving as flower girls and Shiloh and Knox being the ring-bearers.

Angelina Jolie, Brad Pitt, By the Sea

Universal Pictures/Everett

November 2014: Couple in Malta for ‘By the Sea’ Filming

A few months after marrying, Jolie Pitt discussed the nuptials for the first time with the press during the promotional ramp-up to the release of Unbroken, which she had directed. "We got married with our [six] children, and they were part of the ceremony," she said on Today. "It was all of us agreeing to be together and to just commit to this life together. Not because we had to … because we were absolutely sure we felt that much of a family." 

The couple then filmed By the Sea, which starred both Pitt and Jolie, and she directed. "The tricky thing is directing myself and directing Brad. It's hard, dramatic material, and we're balancing," she told DuJour magazine while taking a break from directing in Malta. "It's a heavy film, and it's not easy for us. But even as you struggle through it, you're in the trenches together and you don't expect it to be easy. We're challenging each other and that's a really good thing." Jolie also predicted she would retire from acting and dedicate herself to directing and raising her family.

Angelina Jolie, Brad Pitt

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November 2015: ‘Brad and I Have Our Issues’

While promoting By the Sea, a film that was written and directed by Jolie Pitt and that starred the couple together, she spoke generally of tensions within the marriage. "Brad and I have our issues, but if the characters were even remotely close to our problems we couldn't have made the film," she told The Telegraph. "To be clear: We have fights and problems like any other couple. We have days when we drive each other absolutely mad and want space, but the problems in the movie aren't our specific problems."