Robert De Niro and Grace Hightower are separating, but this is not the first time the divorce is approaching for the couple.
The actor, 75, and the philanthropist and singer, 63, had ups and downs in an epic drama during their marriage of 21 years. They separated once before in the late 1990s and faced a heated battle for their son Elliot before reconciling and renewing their vows in a ceremony full of stars.
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On Tuesday, a source close to the family confirmed to PEOPLE that the couple had separated and lived separately. Here is a retrospective look at their marriage.
A Catskills wedding – and a baby
De Niro and Hightower met in a London nightclub in 1987, but they did not get married for another decade. The two-time Oscar winner divorced his first wife, Diahnne Abbott, in 1988 (they share the son of Rafael, 42, and the daughter of Drena, 47). He left with model and restaurateur Toukie Smith and has two sons, Aaron and Julian, now 23, with her. After they separated, he became serious with Hightower, and the two were married at his home in Marbletown, New York, in June 1997. Among the guests to the intimate affair, 11 people were the friends of De Niro actor Harvey Keitel and Joe Pesci
The guests enjoyed a five-course meal that included wakame and lobster on rice paper and poussin with cranberry quince filling, and listened to Pesci jokes until after midnight. "There were congratulations everywhere," one staff member told PEOPLE at the same time.
That fall, it was revealed that the newlyweds were pregnant with their first child together, and in March of 1998, they welcomed their son Elliot.
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A custody battle
In August 1999, De Niro filed for divorce from Hightower. "Bobby just was not working enough on his marriage to Grace," said a friend of De Niro at the time.
In a friendly way, they co-created Elliot for more than a year until June 2001, when a custody battle broke out. Hightower accused De Niro of intimacy with another woman on a family yacht trip (a source responded at the time the woman was "helping him open and close the bathroom door") and excessive drinking and drugs, that De Niro denied He claimed that Hightower had a violent temper.
At a closed-door hearing in July, a judge ordered a mental health expert to evaluate De Niro and Hightower before their next court date.
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But the couple reconciled and never finalized their divorce. In 2004, De Niro and Hightower renewed their vows at their home in New York State, in front of famous friends such as Tom Brokaw, Martin Scorsese, Meryl Streep and Ben Stiller. Two judges were present to officiate while the guests gathered around an indoor pool to watch the two re-engage each other. "They can make sure it sticks," de Niro joked of the officiants.
A new baby
With their relationship back on the mainland, De Niro and Hightower welcomed a second son, their daughter Helen, through a surrogate mother in 2011. When he spoke with PEOPLE about a 2014 HBO documentary in honor of his late father , Robert De Niro Sr., Goodfellas Alum opened up about life as a father of six.
"Sometimes you're the last person you want to deal with," he said of his children. "It's like when you take your children to school and they get older and do not want to take your hand or kiss you to say goodbye." He was excited to start the process again with his little daughter. "It's good now," he said.
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De Niro remained largely private about his life with Hightower in recent years, in addition to revealing in 2016 that his son Elliot has autism. "Grace and I have a child with autism and we believe that it is critical that all issues related to the causes of autism be discussed and openly examined," De Niro said in a statement amid controversy surrounding the planned but canceled projection of the anti-vaccination documentary Vaxxed at its Tribeca Film Festival.
He and Hightower were last seen publicly on the red carpet in June when they attended the 72nd Tony Awards in New York City. Five months later, a family source confirmed to PEOPLE that the two have separated and live separately. "Sometimes things do not work the way you expect or want them to," said the initiate.