Actor Robert De Niro and his wife Grace Hightower, who have two children, are divorcing after over two decades together
Credit: Cindy Ord/Getty

Robert De Niro and Grace Hightower are splitting up — but this isn’t the first time divorce has loomed for the couple.

The actor, 75, and the philanthropist and singer, 63, have had an epic drama’s worth of ups and downs over their 21-year marriage. They separated once before in the late ’90s and engaged in a heated custody battle over their son Elliot before reconciling and renewing their vows in a star-studded ceremony.

On Tuesday, a source close to the family confirmed to PEOPLE that the couple have separated and are living apart. Here’s a look back at their marriage.

A Catskills Wedding — and a Baby

De Niro and Hightower first met at a London nightclub in 1987, but didn’t wed for another decade. The two-time Oscar winner got a divorce from his first wife, Diahnne Abbott, in 1988 (they share son Raphael, 42, and daughter Drena, 47). He went to date model and restaurateur Toukie Smith and have twin sons Aaron and Julian, now 23, with her. After they split, he got serious with Hightower, and the two married at their home in Marbletown, N.Y. in June 1997. Among guests at the intimate, 11-person affair were De Niro’s actor pals Harvey Keitel and Joe Pesci.

Guests enjoyed on a five-course meal that featured wakame and lobster in rice paper and poussin breast with cranberry quince stuffing — and listened to Pesci crack jokes till past midnight. “There were congratulations all around,” a staffer told PEOPLE a the time.

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

A Custody Battle

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.

They amicably co-parented Elliot for more than a year until June 2001, when a custody battle erupted. Hightower accused De Niro of getting intimate with another woman on a family yacht trip (a source countered at the time that the woman “was helping him open and close the door to the bathroom”) and of 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.

The couple leaving dinner in N.Y.C. in November 2003.
| Credit: Arnaldo Magnani/Getty

RELATED VIDEO: Suspicious Package Sent to Robert De Niro at N.Y.C. Office After Pipe Bombs Mailed to Other Dems

Relationship Renewed

But the couple reconciled 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.

3rd Annual Tribeca Film Festival - Brotherhood Premiere
De Niro and Hightower at the 2004 Tribeca Film Festival in N.Y.C.
| Credit: Jim Spellman/WireImage

A New Baby

With their relationship back on solid ground, De Niro and Hightower welcomed a second child, daughter Helen, via surrogate in 2011. When he chatted with PEOPLE about a 2014 HBO documentary honoring his late dad, Robert De Niro Sr., the Goodfellas alum opened up about life as a dad of six.

“Sometimes you’re the last person they want to deal with,” he said of his kids. “It’s like when you walk your kids to school and they get older and they don’t want to hold your hand or kiss you goodbye.” He was thrilled to start the process over with his young daughter. “It’s good stuff now,” he said.

Another Split

De Niro remained largely private about his life with Hightower in the last few years, aside from revealing in 2016 that their son Elliot has autism. “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 amid controversy swirling around the planned but canceled screening of the anti-vaccination documentary Vaxxed at his Tribeca Film Festival.

Hightower and De Niro.
| Credit: Ronald Siemoneit/Sygma/Sygma/Getty

He and Hightower were last seen together publicly on the red carpet in June when they attended the 72nd Annual Tony Awards in New York City. Five months later, a family source confirmed to PEOPLE the two have separated and are living apart. “Sometimes things don’t work out the way you hope or want them to,” the insider said.