Whether he’s playing the cool casino executive Sam Rothstein in Casino or the revenge-driven Travis Bickle in Taxi Driver, Robert De Niro never fails to hit any tough-guy role out of the park. The Hollywood icon constantly dazzles audiences with passion, grit, and a little Irish spark.

So, as an actor known for playing violent mobsters and other tough-guy types, it’s not often we see him open up about his personal life. Yet in light of recent events and rumors, the legend has come forward with some heartbreaking news that’s guaranteed to bring fans to tears.

A Hollywood staple for over 40 years, Robert De Niro is widely considered to be one of the greatest actors of all time. But while his big-screen career has often overshadowed his personal life, the 75-year-old’s life off camera has been no less eventful.

New Statesman

While 1987 saw De Niro star in the critically acclaimed role of Al Capone in The Untouchables, this was also a significant year for the actor’s love life. Indeed, a chance encounter at a London eatery actually led him right into the arms of his future wife, Grace Hightower.

Entertainment Weekly

Unlike De Niro, Hightower spent most of her life working odd jobs to support her family. But when the opportunity to become a flight attendant presented itself, Hightower jumped at the chance to explore beyond her small Mississippi hometown.

Her frequent travels led her to settle in Paris and then eventually in London where she waitressed at the upscale Chinese restaurant Mr. Chow. A popular celebrity hangout, it was here that Hightower and De Niro met for the very first time.

Aaron Krieger / Flickr

But it wasn’t love at first sight, however, as at the time De Niro was still married to his first wife, Diahnne Abbott. And even after the couple divorced in 1988, it seemed the legendary actor had his eyes set on someone else.

Just several months after his divorce, De Niro began a longtime relationship with model and restauranteur Toukie Smith. The pair went on to have two sons together – Aaron and Julian – before divorcing in 1995.

Two years later – and ten years after their initial meeting – De Niro and Hightower wed at their home in Marbletown, New York. The ceremony was an intimate one and was attended by just 11 guests, including De Niro’s Goodfellas co-star Joe Pesci and his Mean Streets co-star Harvey Keitel.

The couple welcomed their first child, Elliot, in 1998, though it appeared that all was not well with the newlyweds. In 1999 – just two years after marrying – De Niro filed for divorce from Hightower.

Yahoo

“[De Niro] was just not working hard enough at his marriage to [Hightower],” a close friend told People magazine, yet that didn’t mean the couple was willing to shirk their parental responsibilities. They agreed to parent Elliot together, though in 2001, things got ugly.

After suing for custody, De Niro fell into a lengthy legal battle with Hightower. She accused the actor of infidelity and drug abuse, whereas De Niro turned around and cited his wife’s temper as the cause of their divorce.

Page Six

Surprisingly, these harsh words didn’t split them for good, as in 2004, De Niro and Hightower reconciled. In a ceremony attended by stars like Meryl Streep, Martin Scorcese, and Ben Stiller, the couple said “I do” for the second time in seven years.

Yet it appeared that things would be different this time around. De Niro and Hightower seemed closer than ever following their vow renewal, and in 2011, the couple welcomed their second child, Helen, via surrogate.

Things have since slowed down for De Niro and Hightower, and mention of the couple’s personal life has tapered off in recent years. However, in 2018, a rumor began to circulate that the tabloids simply couldn’t ignore.

After appearing together at the 72nd Annual Tony Awards, De Niro and Hightower weren’t spotted in public together for months. Additionally, De Niro began appearing solo at events he’d usually attend with his wife.

By the time November rolled around, things were not looking good for De Niro and Hightower. “They are not living together at this time,” one source told Page Six. “De Niro and [Hightower] are breaking up.”

As the rumors continued to swirl, it finally came time for the couple to address the truth behind their supposed split. Surprisingly, however, it was De Niro that came forward to deliver the shocking news.

Today Show

“[Hightower and I] are entering a period of transition in our relationship, which is a difficult but constructive process,” the actor relayed in a statement to CNN. “I honor Grace as a wonderful mother and ask for privacy and respect from all as we proceed to develop our roles as partners in parenting.”

Lipstick Alley

Since De Niro’s announcement, speculation as to why the couple has chosen to call it quits has run rampant. Some believe it was their political views that drove them apart, as Hightower is a fervent supporter of President Donald Trump while De Niro has openly spoken out against the Republican party.

CBS News

Others believe that it was the couple’s finances that caused their split, particularly Hightower’s excessive spending. “She was spending his money like there was an endless supply,” a source told Life & Style magazine. “[De Niro]’s definitely made some movies just to pay the bills.”

Whatever the reason, in 2019, it appeared that divorce proceedings would soon be underway. However, given the way their last legal battle turned out, we can only hope that their next visit to the courthouse will reunite them again rather than pull them apart.

Primetweets

Not everyone in Hollywood is lucky in love, yet celebrity marriages don’t always have to end in divorce. In fact, another Hollywood heavyweight recently spoke about his own marriage for the very first time, though his life as a married man has been nothing like he expected.

E! Online

Following his divorce from Talia Balsam in 1993, George Clooney was widely considered to be the most eligible bachelor in Hollywood. Many believed the award-winning actor would never settle down, but after meeting Amal Alamuddin in 2013, George’s life was never the same.

The pair first met at Italy’s Lake Como when a mutual friend dropped in on George at his lakeside home. Upon being introduced to Amal, the 52-year-old actor was undeniably smitten.

The Irish News

“I thought she was beautiful, and I thought she was funny and obviously smart,” George told The Hollywood Reporter in a 2017 interview. He then joked that Amal “probably thought I was old.”

But age was apparently just a number for Amal, as she and George – who is 17 years her senior – continued to keep in touch following their initial meeting. As the weeks progressed, the pair was talking almost every day.

“She sent some pictures from when she was here, and we were writing each other, emailing, talking, mostly about what was going on in each other’s lives,” George explained. “And over a period of time it became clear we were more than just friends.”

It appeared Amal felt the same way, too, as three months later, she visited George in London while he was overseeing the score for his 2014 film The Monuments Men. Following his studio session, the two went out on their first date.

Collider

“We went for dinner. [Amal] said, ‘Let’s go to this place.’ It was one of those places that was incredibly hip and chic,” recalled George. “And when we came out, there were 50 paparazzi there. But she handled it like a champ… Pretty quickly, things escalated.”

Yahoo

After a six-week stay in London and a trip to Cabo San Lucas for Christmas, the couple was spotted holding hands and engaging in plenty of PDA at the February premiere of The Monuments Men. From there, the rumors that George and Amal were dating only continued to heat up.

Bisnis

Later that month, George and Amal flew to Africa to go on safari in Kenya. Whatever went down there must’ve been significant, because as soon as he returned to L.A., George showed actor friend Ben Weiss a photo of Amal from the trip and said: “I think I’m going to ask her to marry me.”

Blog Baladi

And in April of 2014, he did just that. During a romantic, home-cooked candlelight dinner, George asked Amal to grab a lighter from the drawer so he could set out a few more candles. But when she reached into the drawer, she found no lighter — only a ring in its place.

M2Woman

“She just kept staring at the ring, going, ‘Oh, my God,'” George told The Hollywood Reporter. “It was 20 minutes of me on my knee, waiting for her to say yes, because she was so shocked.”

Page Six

A month later, Amal was spotted wearing her engagement ring for the first time. A 7-carat, emerald-cut diamond set in platinum, the ring was reportedly worth a whopping $750,000!

5 Star Wedding Directory

The couple tied the knot in September of that year in a private ceremony at the Aman Canal Luxury Resort in Venice, Italy. Among those who attended were a slew of big-name stars, including Matt Damon, John Krasinski, and Emily Blunt.

Yahoo Style

Shortly after the wedding, George and Amal were surprised to discover that they both wanted kids. “We just felt we’d gotten very lucky, both of us, and we should share whatever good luck we’ve got,” George said.

Popsugar

“We didn’t plan on it,” he went on to say. “We never talked about it until after we were married, which is funny. There was an assumption that we didn’t want them.”

Yahoo Entertainment

But want them they did, and on a February 2017 episode of The Talk, George announced to the world that he and Amal were expecting twins. Not only was this a pleasant surprise for the audience, but the fact they were having twins was a twist that not even George had anticipated.

Gala

“[The doctor] goes, ‘Well, there’s one.’ And I said, ‘Great,'” George shared with the audience. “And then he goes, ‘And there’s the second one.’ And I was like, ‘What?’ We just sat there, staring at that piece of paper they give you, and I kept thinking there was a mistake.”

Though it certainly wasn’t a mistake, as on June 6, 2017, George and Amal welcomed twins Ella and Alexander into the world. The couple was thrilled over the birth of their children, though the entire ordeal seemed to take a lot out of George…

Page Six

“This morning Amal and George welcomed Ella and Alexander Clooney into their lives,” said a statement the couple issued to People magazine. “Ella, Alexander, and Amal are all healthy, happy, and doing fine. George is sedated and should recover in a few days.”

Business Insider

The melodrama aside, George has never been shy about how much he admires Amal and how she and their children have completely changed his life. Once determined to be a lifelong bachelor, it’s safe to say George has taken to becoming a family man in stride.

fatherdrom

“Look, I’m 56 years old and I didn’t think it was going to happen for me,” he told Daily Mail in 2017. “And then I met Amal and I thought, ‘Well, I have this incredible relationship, this is wonderful.’ And then…all of a sudden we have these two knuckleheads around who make me laugh every day.”

Yahoo

George may have gotten his wish, but not everyone in Hollywood starts a family. Still, that doesn’t mean these actors are without love; in fact, one of George’s good friends found love from an unexpected source.

Leonardo DiCaprio has made headlines for partying with bikini-clad supermodels both on and off the camera. Still, there’s one woman who’s closer to his heart than any of them. Leo would likely call her the most important person in his life.

Variety

It all goes back to his earliest days. Leo was the only child of hippie parents George and Irmelin DiCaprio, who lived in a rough area of East Los Angeles. But before he even learned to walk, his mom and dad split up.

From then on, Leo spent more time with his mother, who was always a guiding influence. It was she who came up with his name during a visit to Florence. Awestruck by the Mona Lisa, Irmelin decided she’d name her son after the artist Leonardo Da Vinci.

Condé Nast Traveler

Growing up in the shadow of Hollywood, a precocious kid like Leo couldn’t help but try his hand at acting. But during his first gig, on the children’s show Romper Room, his bad behavior got him booted off the set.

Eastern Daily Press

Irmelin, though working multiple jobs at the time, knew she had to keep her son in line. At certain times she’d give him a respite from the excess of L.A. by sending him to her native Germany, where he stayed with his grandparents Wilheim and Helene.

Despite Leo’s early lack of professionalism, he soon settled into his role as a performer. He booked steady commercial work in advertisements for Bubble Yum and Kraft Singles. Still, a bigger break was just around the corner.

He joined the main cast of Growing Pains for its final season, though behind-the-scenes, he acted like anything but a bigshot. Co-star Alan Thicke recalled that the shy teenager asked him for advice on how to ask out girls!

Notwithstanding his low confidence with the ladies, Leo harbored dreams of becoming a bonafide movie star. Both parents encouraged him too, based on their watching habits with their son.

People / Scott Myers

Though divorced, both shared a love of culture and directed Leo toward real film. Robert De Niro, in particular, became a favorite subject. The parents would instruct him, “Son, watch closely because this is what great acting looks like.”

That made it all the more special when De Niro personally handpicked Leo from dozens of actors for his first major film role. They starred together in This Boy’s Life, which catapulted the teen into the inner echelon of Hollywood.

Leo announced himself as a serious actor with his role as the mentally handicapped brother in What’s Eating Gilbert Grape. After the part earned him an Academy Award nomination, Irmelin worried about whether the fame would go to his head.

Instead, she saw her son cling to normality, but not in the most conventional of ways. He made a point to goof off on his own rather than attend ritzy Hollywood parties. His oddball hobbies included doing celebrity impressions and tinkering with his car sound system.

GIPHY

Even though he mired himself in dorkdom, Leo soon found his heartthrob status inevitable. After leading parts in Romeo + Juliet and Titanic, Leo suddenly became a Hollywood hunk. But could he stay true to his roots?

Paramount Pictures

At first, he seemed like his same old self. After all, Leo brought both his mom and his grandmother as his dates to the big premieres. Reportedly, he wanted to treat them for always supporting him and driving him crazy distances for auditions.

But Leo also found himself attracted to the L.A. party scene for the first time. Not unlike Jay Gatsby — a role he was destined to play — the actor chased after the wildest festivities. However, drinks and music weren’t the biggest attraction.

Sipa / Patrick McMullan

Leo couldn’t get enough of beautiful women. He dated some of the biggest supermodels in the world, including Gisele Bündchen and Bar Rafaeli. Though the relationships lasted for years, they strangely never ended in marriage.

Sources close to Leo speculate that he might have chosen not to get married out of devotion to his mother. After she sacrificed so much for him, the A-lister made sure they spent time together. He also wanted to make her proud by achieving their shared dream.

In short, Leo decided he’d stop at nothing to develop into the greatest actor in the world. Leaving the fluffier roles behind, he focused on collaborating with genius filmmakers like Martin Scorsese. After multiple close calls, however, he still was without an Oscar.

Hindustan Times

He threw his all into 2015’s The Revenant, a brutal Western that saw Leo flirt with hypothermia and eat a raw bison liver. The actor went into the subsequent Academy Awards knowing he couldn’t have given anything more.

20th Century Fox

This time, fortunately, the hard work paid off. As he climbed behind the podium to accept his Oscar, he gazed at his loving mother and thanked her for making this dream come true. Irmelin could barely hold back her tears of joy.

The victory was especially moving when Irmelin considered all the chaos she and Leo endured on the road to success. Supporting him on the set of Titanic, for instance, she discovered full well that filmmaking is its own sort of disaster.