Grace Hightower and Robert De Niro separate—again

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Robert De Niro, one of our favorite actors, and his wife Grace Hightower, the  philanthropist and singer, are headed for splitsville.

De Niro, 75, and Hightower, 63, have experienced quite a few highs and lows over the course of their 21-year marriage. In the late 1990s, the pair separated and began a heated custody battle over their son Elliot before reconciling and renewing their vows in a star-studded ceremony, according to PEOPLE magazine.

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This week, a source close to the family confirmed to PEOPLE that De Niro and Hightower have separated and are living apart.

PEOPLE magazine took a trip down memory lane to look at their marriage.

De Niro and Hightower first met at a London nightclub in 1987. A year later, De Niro, a two-time Oscar winner, got a divorce from his first wife, Diahnne Abbott (they share son Raphael, 42, and daughter Drena, 47) and would then date model and restaurateur Toukie Smith and have twin sons Aaron and Julian, now 23, with her. After De Niro split with Smith, he got serious with Hightower, and the two married at their home in Marbletown, N.Y. in June 1997. Harvey Keitel and Joe Pesci were among the guests at the intimate affair.

That fall, it was revealed that the newlyweds were pregnant with their first child together, and in March 1998, they welcomed son Elliot.

In August 1999, De Niro filed for divorce from Hightower. “Bobby was just not working hard enough at his marriage to Grace,” a De Niro pal said at the time, according to PEOPLE.

The couple co-parented Elliot until June 2001, when a custody battle ensued. Hightower accused De Niro of infidelity, heavy drinking and drug use, which De Niro denied. He alleged Hightower had a violent temper.

At a closed 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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The couple would later reconcile and never finalized their divorce. In 2004, De Niro and Hightower renewed their vows at their upstate New York home in front of famous friends including Tom Brokaw, Martin Scorsese, Meryl Streep and Ben Stiller. Two judges were on hand to officiate as guests gathered around an indoor pool to watch the pair recommit to each other. “They can make sure this one sticks,” De Niro joked of the officiants, according to PEOPLE.

In 2011, De Niro and Hightower welcomed a second child, daughter Helen, via a surrogate PEOPLE reports..

Since then, De Niro has remained largely private about his life with Hightower, aside from revealing in 2016 that their son Elliot has autism, the report notes “Grace and I have a child with autism and we believe it is critical that all of the issues surrounding the causes of autism be openly discussed and examined,” De Niro said in a statement after controversy erupted after a screening of the anti-vaccination documentary Vaxxed at his Tribeca Film Festival was canceled, PEOPLE writes.