Whether she’s a beleaguered astronaut, a tough football mom, or an undercover cop with a dirty mouth, Sandra Bullock can do it all! But at the height of her career, Sandra found out a horrible truth about her marriage that would lead her down a heartbreaking path. How did this Hollywood starlet get through one of the most difficult periods in her life?
Sandra and Jesse James met in an unlikely way. As it turned out, Sandra’s then 10-year-old godson was a big fan of Jesse. So as a birthday present, she arranged for the two of them to meet. This meeting would be the beginning of a seven year relationship.
Sandra and Jesse quickly became Hollywood’s hottest couple. Which meant that the tabloids were obsessed with them. And while constantly being followed was likely less than fun, the two were always photographed kissing and holding hands.
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Everyone remembers Jesse and Sandra. But not everyone remembers her relationship with Tate Donovan. The two met while filming Love Potion No. 9 and proceeded to date for a total of three years. After their break up, Sandra continued to date some of Hollywood’s most eligible bachelors.
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After she broke up with Tate, and before she married Jesse, Sandra dated some pretty high profile celebs, including football player Troy Aikman. And actors like Matthew McConaughey and Ryan Gosling. However, none of Sandra’s relationships really seemed to stick, that is until she met Jesse.
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Sandra and Jesse tied the knot in California on July 16, 2005. Sandra, of course, looked beautiful as she walked down the aisle wearing a custom wedding gown. The ceremony was intimate and romantic, including only close family and friends.
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Sandra and Jesse were a beautiful couple. There was absolutely no denying that. But things weren’t always perfect. The couple had to overcome quite a few obstacles from the very beginning of their marriage, especially considering Jesse’s tumultuous past.
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Jesse and his first wife had a tumultuous relationship, to say the least. Janine Lindemulder openly struggled with substance abuse and depression. Documentation of these issues exists in the form of emails between Lindemulder and James’ sister. It was even used during the custody battle.
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While Jesse and Sandra never had kids of their own, they were involved in a heated custody battle over Jesse’s then five-year-old daughter, Chandler. The battle involved Jesse’s ex-wife, whom Jesse felt was incapable of raising their daughter. The courts agreed, and Jesse won custody.
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After the ugly custody battle, Sandra became a stepmom to Jesse’s three kids: Jesse James Jr., Sunny, and Chandler. She and James were determined to give the children a stable and peaceful life. They appeared to do so until the cheating scandal in 2010.
It started out as a fantasy year. Sandra, raking in millions of dollars, was named the highest paid actress in the world. She was also included in Time’s 100 most influential people. But perhaps her biggest accomplishment came at the 82nd Academy Awards.
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At Oscars, Sandra received the award every actor wishes for. She won for her performance in portrayal of Leigh Anne Tuohy in the biographical drama, The Blind Side. The world was at her feet and nothing could go wrong — or so she thought.
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Bad news never has good timing, but this timing was especially bad. A week after her Oscar win, Jesse (allegedly) texted a woman saying, “Just think’n bout u this morning.” Shortly after, more women came forward claiming to have had affairs with him.
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Sandra moved out of the couple’s Southern California home right before the tabloid storm hit. That means it’s likely that the magazines reached out to the couple’s reps and tipped them off to the allegations, precipitating Sandra’s move.
As if the romantic fallout wasn’t enough, James’ and Sandra’s pup Cinnabun went missing on the same day that Sandra moved out. The irony here is that not only is Sandra not the first wife Jesse lost; this also wasn’t the first time that the dog went missing.
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Sandra (understandably) refused to take Jesse back, even after he checked into a rehab facility. So, on April 28, she filed for divorce, citing “conflict of personalities” as the reason. The divorce was finalized that June. Everyone wanted to know how Bullock was feeling.
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Sandra has been open about the pain she felt throughout this whole ordeal. She’s opened up about her heartbreak to several outlets, often mentioning that she didn’t think she was ever going to be able to get through it.
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One of the most complicated parts about the whole ordeal is that Sandra and Jesse were in the process of adopting a child together. While some thought Sandra would opt out of her application, she followed through and adopted two beautiful kids, Louis and Laila.
Instead of wallowing in self-pity, Sandra chose to focus on her own personal growth, well-being, and children. She wanted to give them a happy and calm life and successfully channeled all of her energy there.
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A few years after the messy divorce, and after she had had time to heal, Sandra met photographer Bryan Randall. The two fell in love and have been together for several years. He’s become a father figure for these kids, and as far as we can tell, all seems well!
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Sandra and Bryan sparked engagement rumors after stepping out with wedding bands. While her friends can’t wait for them to get married, some suspect the two may have had a secret wedding with just the two kids present. It was a tough chapter for Bullock, but at least she had good friends to lean on.
One of Sandra’s closest pals is none other than George Clooney, who kept up her spirits as she went through divorce hell. He’s the type of guy who’s in a million places at once, but is always around to do some good. He’s helped the world more than most of us realize.
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Who wouldn’t want to stare into the mirror each morning and see this handsome devil looking back at them? While George Clooney found a ton of success in life, he didn’t become an icon with just good looks and a few well-timed winks.
Still, it seemed as though Clooney was destined for Hollywood from the very beginning. His father, Nick, was a news anchor and popular television personality, and his aunt found success as a singer and actress.
After moving around a bunch due to Nick’s workload, the family eventually settled down in the small town of Augusta, Kentucky. This was where Clooney experienced his first taste of the entertainment industry.
At the age of five, Clooney starred as various sketch characters on the talk shows his father worked on. He enjoyed the stints, but once he entered school, his studies became his main priority.
He was a good student and even better baseball player, at one point trying out for the Cincinnati Reds. He didn’t make it into the big leagues, however, and worked odd jobs until his cousin called with a unique proposition.
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Miguel Ferrer, the son of Oscar-winner Jose Ferrer, told Clooney he and and his father were shooting a film about horse racing and offered him work. Clooney accepted, and this was when the acting bug bit hard.
Clooney fell in love with the craft immediately. He soon moved out to Hollywood and landed tiny roles in shows like Roseanne and The Facts of Life. Finally, in 1994, he felt like he’d finally hit the big time.
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He snagged the role of Dr. Doug Ross in the hit television medical drama E.R., and viewers immediately took to his looks and charm. Clooney was now on Hollywood’s radar, and he was only climbing higher up the ladder.
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He started receiving invites to celebrity events like California’s Annual Rock ‘n Jock Baseball games hosted by MTV. He was also brushing elbows with major stars who’d been in the industry for years and achieved major accolades of their own.
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Alongside megastar Arnold Schwarzenegger, he promoted their film Batman and Robin at London’s Planet Hollywood. By now Clooney had a solid cinematic resume under his belt, but it was the movie Syriana that earned him an incredible achievement.
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He managed to snag a Supporting Actor Oscar win as a government agent exploring corruption in the Middle East. Funny enough, with all the praise Clooney received over the years, he’s missing one crucial aspect of Hollywood.
He doesn’t have a star on the Hollywood Walk of Fame! Clooney simply never bothered to go through the intense application process, but he does have this cement print nearby. However, acting is far from his only venture.
He has his own brand of wildly successful tequila called Casamigos, which raked in hundreds of millions of dollars! But, he also holds another passion near and dear to his heart, and it’s nothing people would expect.
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Not only is Clooney passionate about politics and world events, but as a proud liberal he takes an active part in everything he can to help the cause, knowing full well his fame can bring much-needed attention to vital issues. His contributions over the years have been huge.
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Almost immediately after the September 11, 2001, terrorist attacks, Clooney banded together with dozens of fellow Hollywood stars in a fundraiser he organized. The event managed to donate over $129 million to the United Way!
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Of course, his caring doesn’t stop at the American borders. He and his father joined forces in 2006 to travel to the poorest areas of Sudan, specifically Darfur, to shed light on the genocide there.
The footage captured by the father-and-son team horrified the viewers who watched it air in the United States, and they managed to raise tons of money for support. Of course, George didn’t stop there.
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He was a huge proponent of funding a nationwide “2-1-1” hotline. The purpose was to provide a phone number to every single community that gave vital service information so people could stay connected and safe.
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Clooney and his wife also donated $500,000 to aid the March for Our Lives protests after the shooting at Marjory Stoneman Douglas High School in Parkland, Florida. They even got other celebs to offer massive assistance.
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In fact, one of Clooney’s closest friends in Hollywood has long been Brad Pitt. Pitt wouldn’t even sign on to star in Ocean’s Eleven until Clooney personally called and asked him to do it.
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And what would the last 30 years of cinema look like without Brad Pitt? The 55-year-old actor has spent his career rising through the ranks of the film industry one blockbuster at a time, but many would be surprised to learn that he wasn’t always Hollywood’s golden boy.
Before he was making millions of dollars on films like World War Z and Mr. & Mrs. Smith, Brad was your typical Missouri boy: the son of a business owner and school counselor, and brother to two younger siblings. Still, life wasn’t always so typical for Brad.
He was raised in a Southern Baptist household where he felt constant guilt about “what you can and cannot, should and shouldn’t do.” In an interview he said that he eventually “wanted to experience things religion said not to experience,” which led him down an unforeseen path in High School…
Wanting to shirk his conservative upbringing, Brad played multiple sports and was in the Key and Forensic clubs. He participated in school debates and, of course, he performed in school musicals. Still, the thought of acting on a bigger stage never seemed possible.
He’d always loved films and described them as being a “portal into different worlds,” but as a college student he focused on journalism. Still, as his college graduation loomed nearer, he couldn’t shake the feeling that something was wrong.
One thought kept popping into Brad’s mind: “I can leave.” He knew he had to make a career out of his passion. But the film industry was far away from the University of Missouri, so he took the chance of a lifetime.
He dropped out of college just two credits shy of graduation and moved to L.A. For seven months, he drove a limo for extra cash and tried to break into the acting world. Many aspiring actors would have quickly given up…
But after mere months of the acting grind, Brad secured an agent. Soon after came small TV roles, including on the family sitcom Growing Pains. As his success grew on the small screen, it was clear that a pattern was developing.
Many of his early characters fit the same mold: handsome, edgy loners from the other side of the tracks. Though it was definitely a departure from his religious Missouri upbringing, Brad wanted to prove himself as more than just a pretty face.
He thought back to his strict childhood to give him the confidence he needed. “One thing my folks always stressed was being capable, doing things for yourself,” Brad said. Ambition and a small ego, two things many aspiring actors fail to cultivate…
But early in his career, Brad seemed to have this balancing act down pat. His career finally seemed to be going somewhere with a role in 1991’s Thelma & Louise. However, this role also solidified his image for years to come.
His intense role made him the definitive “pretty face” in Hollywood. The recognition landed him roles in films like A River Runs Through It and Interview With The Vampire, which were successful, though they further pigeon-holed him.
At this point, many actors would have thrown in the towel, but not Brad. He was young, attractive, and talented, three attributes that mean everything in Hollywood. He started to accept his place as a “pretty boy” in Hollywood…in 1995, however, his luck changed.
Though his previous films had solidified him as a good-looking and capable actor, it was the film 12 Monkeys that earned him an Oscar nomination as well as a Golden Globe award. From here, his career skyrocketed.
Fight Club, Ocean’s 11, Moneyball: they were all movies that showcased Brad’s edgy and suave status among the Hollywood elite. Add in high-profile relationships with Jennifer Aniston and Angelina Jolie, Brad was truly among the best and brightest of Hollywood…
Living such a public lifestyle would be hard for anyone, and it took its toll. But every time he was in the news, he would remember what he learned growing up: he was capable of anything. So, he decided to do something unexpected…
Brad leaped into the role of producer, and it paid off: His films The Departed and 12 Years a Slave both won Oscars for Best Picture. Still, if there’s one constant about Hollywood, it’s change, and Brad could tell that something was shifting.
During an interview for the 2019 movie Once Upon a Time in Hollywood, Brad admitted that acting is now “a younger man’s game.” He’d always been Hollywood’s dependable “pretty boy” actor, but it seems he’s doubting his long-term role in the industry.
Many actors do whatever it takes to stay relevant in Hollywood, from taking corny blockbuster roles to doing reality TV. But Brad believes that everything will eventually come full-circle…including his own career. “There will be a natural selection to it all,” he said.
He’s even open to newer movie-making mediums, including streaming services. Still, he’s quick to underline his changing role in the industry. “But I could be a dinosaur and not even know it, man. And the comet could be on the way.”
Brad is seemingly at peace with the metaphorical comet that may be hurtling towards his career…though it’s hard to believe that the Missouri boy turned pretty boy turned Oscar winner could ever be anything other than front-page news. All you have to do is look at his love life for proof of that.
The world collectively gasped when the news broke that Angelina Jolie and Brad Pitt were splitting up. But what we didn’t see was the struggle the couple had endured for years — one that made Angelina desperate to figure a way out of their problems.
In her eyes, what would save their marriage was simpler than couple’s counseling. She had a plan, but it meant looking back to the past. And there were moments in her past that were especially painful to revisit…
After disastrous marriages to Jonny Lee Miller and Billy Bob Thornton, Angelina Jolie just wanted to raise her newly adopted son, Maddox, and move on with her life and career. But in 2005, she met someone who shook up her entire plan.
“Brangelina” famously began on the set of the film Mr. & Mrs. Smith, where they high-kicked their ways into each other’s hearts. Both of them were gorgeous, international movie stars, so they seemed like the perfect pair. There was just one problem.
Brad was already married to America’s sweetheart, Jennifer Aniston. The scandal forced them to keep their relationship private. But after a year, Brangelina had to let the world in on their romance, and for a very obvious reason…
Angelina was pregnant. The couple’s baby, Shiloh, ended up becoming one of the most famous babies in Hollywood history. By 2008, when Angelina again gave birth, this time to twins, it seemed like Brangelina was as happy as ever.
But all wasn’t as it seemed in the Jolie-Pitt household, as Angelina revealed a year after their divorce. Angelina opened up about how she felt as her marriage fell apart…and the plan she hoped would save their love.
Angelina’s only hope for their relationship was a shared project, the 2015 film By The Sea. “We had met working together and we worked together well,” she said. “I thought it would be a good way for us to communicate.”
But the reviews for By The Sea were not kind, with many critics calling Brad and Angelina, though “dazzlingly gorgeous,” totally devoid of any emotional weight. Their performance as a couple was called “empty,” an opinion that would soon prove to be ironic.
“There was a heaviness probably during that situation that carried on and it wasn’t because of the film,” she said. The couple couldn’t rekindle their love, despite Angelina’s strongest efforts. What’s worse, this “heaviness” didn’t seem to lighten over time.
In fact, the weight had been around for a while. “Over the span of that decade, I did lose my mother,” Angelina pointed out. It only got worse: during her decade-long relationship with Brad, she started contending with serious medical issues.
She found out she had an 87% chance of developing breast cancer…so she made a difficult decision. In 2013, Angelina underwent a double-mastectomy. But after such a life changing experience, Angelina did the opposite of what was expected of her.
She spoke candidly about her health, from her personal experience with a double-mastectomy to her 2015 ovarian cancer-prevention surgery that resulted in her inability to have biological children. Angelina’s frankness about her health is credited with redefining standards of beauty for women.
As she contended with serious, life-changing medical issues, she raised six children, focused on humanitarian issues, and maintained what the public saw as a happy relationship with Brad. But all the while, she knew things weren’t right.
“I did have my mastectomy, and I did then have an ovarian cancer scare and have that surgery as well,” she said, confirming her medical problems as relationship-stressors. Still, Angelina hoped that By The Sea, bad reviews and all, would keep them together…
And, though the movie itself was a flop, it did help them come to a decision. “A piece of art can be something that’s healing or something that’s difficult,” she said. “We did communicate something that needed to be communicated to each other.”
See, Angelina considers art to be a “common language,” one shared between people who both love the medium. Perhaps it’s the language she and Brad once shared, but somewhere along the way, things were lost in translation.
The making of By The Sea was a cathartic, but ultimately unsuccessful, experience for the couple, but there was one upside. By speaking this “common language,” Angelina has started to rebuild her relationship with another important man in her life…
Her father, actor Jon Voight. “Through art is a way we’ve been able to talk,” she said of their rocky relationship. And it seems to be doing them a world of good, as she says they’re finding “a new relationship.”
But what exactly she and Brad “communicated to each other,” we may never know. What’s sure is that the two will always hold a special place among Hollywood’s elite power couples. Their chemistry is what made their 2016 separation so unexpected — and so gut-wrenching.
Jolie and Pitt can take solace in the fact that the demise of their relationship was not out of the ordinary in Hollywood. Robert De Niro’s big-screen career has often overshadowed his personal life, and the 75-year-old’s life off camera has been no less eventful.
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.
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.
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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.
“[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.
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.
“[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.”
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.
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.
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.
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.
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“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.
“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.”
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.
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.”
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.
“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.”
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!
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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.
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.
“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.”
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.
“[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…
“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.”
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.
“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.”
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.
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.
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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.
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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.
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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.
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?
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.
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.
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