Actress Angelina Jolie has filed for a divorce from actor Brad Pitt after 12 years together including two years of marriage, the end for one of Hollywood's most glamorous and powerful couples.
Below is a timeline of key moments in the A-list couple's relationship over the years:
January 2005: Brad Pitt and "Friends" star Jennifer Aniston separate amid rumours that he and Jolie had an affair while filming the upcoming spy action thriller "Mr and Mrs Smith." Neither party confirmed the rumors. April 2005: Photos appear in media of Pitt with Jolie and her adopted Cambodian son Maddox, vacationing together in Kenya.
January 2006: Representatives for Jolie and Pitt confirm to People magazine the actress is pregnant with Pitt's child, the first time the couple acknowledge their relationship publicly.
A Los Angeles judge grants Jolie's request for Pitt to become the adoptive father of Maddox and daughter Zahara, changing their last names to Jolie-Pitt. May 2006: The couple's first biological child, a girl named Shiloh Nouvel, is born in Namibia. July 2008: Jolie gives birth to the couple's twins Vivienne Marcheline and Knox Leon in southern France.
September 2011: Pitt appeared on Ellen DeGeneres' show while promoting "Moneyball" to discuss marriage plans with Jolie. "I've said that we would not be getting married until everyone in this country had the right to get married," he said. April 2012: Jolie and Pitt announce their engagement after she is spotted wearing a large diamond ring designed by Pitt.
May 2013: Jolie reveals in a New York Times op-ed that she underwent a double mastectomy after learning she had inherited a high risk of breast cancer. She said she made the decision in part to reassure her children that she would not die young from cancer, as her own mother Marcheline Bertrand did at age 56 in 2007. August 2014: Jolie and Pitt quietly marry in a small ceremony at their Chateau Miraval estate in France. All six children took part and Jolie wore an Atelier Versace white dress featuring colourful designs drawn by her children.
November 2015: Jolie and Pitt appear at the premiere of "By The Sea," a drama directed and written by Jolie in which they play a married couple drifting apart. September 2016: Jolie files for divorce from Pitt in Los Angeles court, citing irreconcilable differences and requesting sole physical custody of the children. Pitt responded with a statement to People magazine saying he was "very saddened."