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30 Messiest Celebrity Divorces in Hollywood History

Sandra Bullock & Jesse James

Sandra Bullock & Jesse James

In 2010, Sandra Bullock blissfully walked the red carpet to all the award shows that season with her then-husband of five years - reality television star and biker Jesse James. It seemed all was perfect in the couple’s world in March when Bullock tearfully thanked James for “having her back” in her acceptance speech for her Oscar for her performance in The Blindside.

However, just a few short weeks later, a magazine interview with another woman surfaced claiming that she previously had an affair with James while Bullock was off shooting The Blindside. Bullock was publicly devastated, and by June of 2010, the couple divorced. 

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Brad Pitt & Jennifer Anniston

Brad Pitt & Jennifer Anniston

The world fell in love when Brad Pitt and Jennifer Anniston fell in love. One of the hottest movie stars of the 90s with America’s sitcom sweetheart, married!? It seemed the two were meant to be. Their managers were friends and set them up on a date in 1998 and the rest was history. Well, not quite.

In 2004, Anniston spoke about the prospect of slowing down when the show Friends ended and that after Pitt wrapped up the filming of Mr. & Mrs. Smith, she was planning on traveling with him while he filmed Oceans Twelve. Well, pretty soon rumors began circulating about Pitt and his Mr. & Mrs. Smith costar, Angelina Jolie and by January of 2005, Pitt and Anniston officially and publicly announced their separation.

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Tom Cruise & Nicole Kidman

Tom Cruise & Nicole Kidman

In Hollywood, these two A-listers are such powerhouses in their own right, that people often forget that they were the IT couple in the 90s. That’s right. The world barely had a chance to catch its collective breath after meeting Kidman for the first time in 1990’s Days of Thunder before we were digesting that the two had been married.

For a decade, the two acted in a few more feature films together, adopted and raised two children, and appeared to be the epitome of a happily married couple. Therefore, it was a shock to all of us when Tom Cruise filed for divorce in 2001, citing irreconcilable differences. Almost a decade later, and neither of the two actors will divulge what caused the split, although Tom’s interest in Scientology is rumored to be the blame.

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Charlie Sheen & Denise Richards

Charlie Sheen & Denise Richards

The '80s heartthrob actor Charlie Sheen met Denise Richards in the year 2000 while they were filming Good Advice. However, the two didn’t begin dating until Richards had appeared on an episode of Spin City in 2001. Richards has been known to say that by their second date, she knew Sheen was the one for her.

In March 2005, while pregnant with their second daughter, Richards filed for divorce. The couple briefly reconciled after the birth of Lola, but Richards filed for divorce again in 2006. It ended up being one of the messiest public divorces on record. During an intense custody battle, Richards filed for an order of protection against Sheen citing that he had threatened to murder her and watched “disturbing porn.”

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Britney Spears & Kevin Federline

Britney Spears & Kevin Federline

Not only was their divorce messy, but the whole marriage was a mess from the beginning. Mickey Mouse Club alum, Britney Spears and former backup dancer, Kevin Federline began making headlines the moment they announced their engagement in July of 2004—after just four months of dating. By September 18th, the two were married. Apparently, there was no fairy tale ending forthcoming for the pop princess.

After just two years and two babies together, Spears filed for divorce on November 7, 2006, citing irreconcilable differences. What followed was a pop princess public meltdown that would forever change pop culture. Once Britney began exhibiting unhinged behavior in public, Federline took her back to court to gain full custody of their children. What followed was a heated custody battle that lasted roughly two years and ended in Federline gaining 70% custody of their children.

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Johnny Depp & Amber Heard

Johnny Depp & Amber Heard

Speaking of messy divorces, this one may just take the win for messiest! The couple, who met on the set of Rum Diaries in 2009, dated under the radar until they made their red-carpet debut as a couple in 2014. They were married in 2015 and their divorce was finalized in 2016. We can’t believe it’s been four years and we’re STILL talking about it. But they are still in court battling out a $50 million defamation lawsuit that Depp filed against Heard when the Aquaman actress accused him of domestic abuse.

However, it may actually be the other way around. Depp has publicly accused Heard of being the abuser in the relationship. Many witnesses have come forward stating that Heard was the aggressor in the arguments most of the time. One witness even came forward stating that Heard called Depp “fat and washed up” and that she told him that his “career was over.” In addition, earlier in 2020, an audio recording of the actress admitting that she hit Depp had leaked to the press.

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Brad Pitt & Angelina Jolie

Brad Pitt & Angelina Jolie

Welp, we all know how this relationship started, and if you don’t, you should go back and read the first time we mention Pitt on this list. That’s right. In 2004, Pitt and Jolie met on the set filming Mr. & Mrs. Smith. Although both have always denied beginning their relationship at that point, they both admit that that is when they “fell in love,” Jolie told the New York Times in 2008. But the couple endured for more than a decade despite the scandal and the harsh media telescope that their relationship was under.

That’s why when the couple announced their decision to separate in 2016, the world was just shocked. Pitt filed for divorce in 2016 citing irreconcilable differences, but the real problems began on a private jet flight between Pitt and their oldest son Maddox, which ended in child services being called. The couple is still embroiled in a custody battle that just began in October of this year and started with Pitt calling an extensive 21 witnesses for his case.

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Tom Cruise & Katie Holmes

Tom Cruise & Katie Holmes

This is one relationship that ended as shocking as it began. Who doesn’t remember Tom Cruise’s infamous interview with Oprah where he broke the news of his and Katie Holmes’ relationship? Well, if you don’t let us remind you. On May 23, 2005, when Oprah asked the Mission Impossible star about his love life, he answered in a bizarre way. He jumped up and down on the couch on the stage and professed his love for Katie Holmes after dating the Dawson’s Creek alum for a few months.

By June of 2005, Holmes had converted to Scientology and Cruise was proposing to her atop the Eiffel Tower. By October, they were already expecting their first child together. In April of 2006, their daughter Suri was born, and the couple married in November of 2006. The couple spent six happy years together until 2012. The divorce surprised us all, none of us more than Tom Cruise who was apparently blindsided by the divorce. Holmes had made all of her divorce inquiries on a disposable phone and hired three law firms in three states. The divorce only took 11 days to complete.

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Jessica Simpson & Nick Lachey

Jessica Simpson & Nick Lachey

Jessica Simpson and Nick Lachey were both newcomers to the music scene in 1998 when their mutual manager introduced them at the Hollywood Christmas Parade. They ran into each other again at a party in 1999 and began dating soon after. Lachey proposed to Simpson in February of 2002 on a yacht in Hawaii once the couple reunited after a brief break up in 2001. From the beginning, because both had grown so popular, their relationship had been under a media microscope as it was. But soon, the Newlyweds: Nick & Jessica reality MTV show was born, and the world got to watch them navigate their first year of marriage.

Cameras followed the couple until early 2005, adding extra stress to an already stressful situation for normal, everyday people. A source close to the couple told Complex in 2017 that the couple really didn’t have anything in common but their music. So, no one was too surprised when Jessica filed for divorce in November 2005, citing irreconcilable differences. The divorce was as widely publicized as their marriage. The couple famously did not have a prenuptial agreement and Jessica effectively had to pay Nick $12 million in order to leave him.

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Sophia Bush & Chad Michael Murray

Sophia Bush & Chad Michael Murray

In 2003, One Tree Hill had made its debut on the CW and was an instant hit. Even better, two of the show’s biggest stars were dating in real life. Chad Michael Murray and Sophia Bush met on the set of the show and began dating almost immediately, putting them under a harsh media spotlight once word got out. By May of 2004, Murray had proposed and the two were married on April 16, 2005.

However, the marriage was short lived. They publicly announced their split in September of 2005, just five short months after their wedding. To this day both parties have remained pretty tight-lipped about what really went down, but there are rumors that Murray had been caught cheating with Paris Hilton on the set of the horror film House of Wax. Either way, Bush filed for an annulment citing fraud, but was denied and had to go through divorce court. The marriage was dissolved in December of 2006.

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Jennifer Garner & Ben Affleck

Jennifer Garner & Ben Affleck

In 2004 Garner and Affleck were spotted as a couple for the first time in October of 2004 at a Braves game. And although they mostly kept their relationship private, Affleck proposed to Garner publicly on her 33rd birthday in April of 2005, and the two were married in June of 2005. They were married for ten years and had three children together before the bottom dropped out. Rumors swirled about Affleck’s romance with the family nanny for a few weeks in 2015 and later that same month, the pair announced their divorce.

Although it certainly seemed like Affleck had been unfaithful, Garner told Vanity Fair in 2016 that they had already been separated for months before she heard the rumors of the nanny. Rumors swirled again in March of 2017 when an unnamed source said that the couple had called off their divorce and later that same month, Affleck admitted to completing treatment for alcohol addiction. However high fans’ hopes got for a reconciliation, in April of 2017 the couple officially filed for divorce and it was finalized in October of 2018.

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Reese Witherspoon & Ryan Phillippe

Reese Witherspoon & Ryan Phillippe

In the late 90s, Reese Witherspoon and Ryan Phillippe were relationship goals for teen hopefuls around the world. The two met at Witherspoon’s 21st birthday party and after a few too many Midori sours, she told Phillippe that she thought he might be her birthday present. In 1999, the two starred alongside one another in the teen cult classic film, Cruel Intentions. However, while teens everywhere were swooning over Sebastian and Annette’s romance, the real-life romance was alive and well.

One year after the couple met, Phillippe proposed. Before they got married, they discovered that Witherspoon was already pregnant with their first child, Ava. The two married three months after the Cruel Intentions premiere in 1999 while Reese was six months pregnant. Four years later the couple welcomed their second child, a son named Deacon. In 2006, they announced their separation, filing for divorce in October of the same year. Within a year, the marriage had been dissolved, but the pair have remained close friends ever since.

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Halle Berry & Olivier Martinez

Halle Berry & Olivier Martinez

If we have to pick just one of Berry’s messy divorces, we might as well go with the latest to French actor, Olivier Martinez. They met on the set of the film Dark Tide in July 2010, shortly after Berry had announced her split from then long-time beau, Canadian model Gabriel Aubrey. The two were dating by August, and in January of 2002, the news broke that the couple was engaged. Some could say that the couple’s troubles began because of the nasty custody battle Berry had been involved in with her baby daddy, Aubrey.

Berry and Martinez still trekked on, tying the knot at a French chateau in July of 2013, while Berry was pregnant with their first child - born in October of 2013. Just two short years later, the couple would announce their separation. Rumor has it that the fact that Olivier had to relocate to L.A. because of Halle’s custody agreement with Aubrey is what did the marriage in. Berry filed for divorce in October 2015 - although the two can legally claim single status, there are still some kinks left to work out in their custody agreement.  

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Paul McCartney & Heather Mills

Paul McCartney & Heather Mills

A fairly recently widowed Paul McCartney met former model Heather Mills at a charity event in May of 1999 and the two reportedly began dating a couple months later. They were married in June of 2002 in a romantic ceremony at a castle in Glasgow, Ireland. However, it wasn’t to be a fairy tale ending for the couple as they filed for divorce just four years later. The divorce proceedings started out friendly enough, for the sake of their two-year-old daughter Beatrice, but things soon took a turn for the worst.

Apparently, Mills had become rude and argumentative towards his staff, so Sir Paul filed proceedings to stop her behavior and the gloves came off. While Sir Paul stayed private in all of his other complaints, Mills told anyone who would listen that McCartney was abusive and that he was an alcoholic, among other things. The judge accused Mills of giving inconsistent and inaccurate evidence during the final ruling in the settlement. Still, although she attempted to get $150 million in the settlement, Mills did happily walk away with a cool $30 million.

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Madonna & Guy Ritchie

Madonna & Guy Ritchie

So, one night in 1999 Madonna attended a dinner at a friend’s house, when Sting and his wife (yeah, really), who were also guests at the dinner decided to play matchmaker. They introduced her to young film producer and director Guy Ritchie. They fell in love and Madge packed up and moved to the U.K., where their son Rocco was born in August of 2000. The pair married on December 22, 2000 in Scotland, in what has been called a lavish, fairy tale wedding. Sting and his wife were in attendance, of course.

Despite the flop that was their film Swept Away in 2002, the pair were still deliriously in love in 2004, if their vow renewal ceremony is anything to judge by. However, by 2008 eyebrows began to raise when Ritchie was absent the night that Madonna was inducted into the Rock N’ Roll Hall of Fame. Lo and behold, in December of 2008, the couple announced their intent to divorce. The divorce was very public because—well— because she’s Madge and we’ve always been fascinated by her. Ritchie won an astonishing $92 million in the settlement, but that included the cost of their U.K. residences and pub.

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Mariah Carey & Nick Cannon

Mariah Carey & Nick Cannon

Mariah Carey and Nick Cannon shocked the world when they got married on her Bahamian estate in April of 2008. They had only been dating for about six weeks when they tied the knot. The two were so dedicated, that in 2009, they proved their love to each other by getting tattoos of each other’s names. Two years later, on or near the couple’s anniversary, Mariah gave birth to the couple’s first children, twins—a boy and a girl.

In January of 2014, it seemed to the rest of the world that all was right in theirs when Nick Cannon told TMZ that his secret to keeping the marriage fresh was “lots of sex.” However, in December of 2014, Cannon filed for divorce from Carey. In a 2020 interview with Variety, Cannon said about their marriage, “It was more that whimsical fantasy idea of let’s have as much fun as we possibly can and when it no longer feels like fun, when it feels like a task and a job, we should amicably be able to move on.” And amicably move on they did, doing a fantastic job of co-parenting their twins.

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Gwen Stefani & Gavin Rossdale

Gwen Stefani & Gavin Rossdale

Back in the '90s, these two were THE coolest couple in Hollywood. They met in 1995 and dated all through the '90s, until in 2002, Rossdale finally asked for Stefani’s father’s permission to marry her. After a nine-month engagement, the two were married in London and then came home to get married two more times in ceremonies for friends and for family. In October of 2004, the world held its collective breath while waiting to see how Stefani would react to the news that Rossdale had a possible lovechild from back in 1989.

However, even when it was proven that Rossdale was indeed the father of a 15-year-old girl, the news didn’t shake the bond that the two shared. Instead, Stefani gave birth to the couple’s first child, a boy named Kingston in 2006. Which was followed by the birth of their second child, another boy, Zuma in 2008. In 2012 they celebrated their 10th anniversary and Stefani said, in an interview with Marie Claire that her marriage was her “biggest accomplishment.” In 2014, Gavin appeared as a judge alongside Gwen on a season of The Voice and the two appeared to have a lot of fun. However, they announced their split in August of 2015, ending their 20-year romance.

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Blake Shelton & Miranda Lambert

Blake Shelton & Miranda Lambert

Although this pair started out under questionable circumstances, the world was still pulling for them to succeed. Blake and Miranda met in 2005, when they sang a duet together. They both admit falling for each other then and there. But—Blake was married to someone else at the time! But by 2006, Shelton was divorced from then wife, Kaynette Gern, and was dating Lambert publicly. The pair dated for four years before Blake would ask her father’s permission before proposing. The two were married in 2011 on a Ranch in Texas in a rustic chic ceremony. That was the same year that Shelton took a job as voice coach on The Voice.

The two did their best to make it work while Miranda was on tour, making a rule to never spend more than two weeks apart from each other. At the same time, with all their time apart, despite being wide-open about their relationship with the media, rumors began to spread about trouble in the marriage. In an interview in 2013, Lambert said, “Divorce is not an option.” Unfortunately, it became one because the couple announced their split in 2015. Funny enough, that’s the same year Shelton began dating Gwen Stefani. Coincidence???

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Kim Kardashian & Kris Humphries

Kim Kardashian & Kris Humphries

Would this even be a list about messy celebrities without a Kardashian or two in the mix? This one is so messy, if we ranked them, it would be at the top. These two met on October 31, 2010, supposedly after she sat courtside at Kris Humphries’ basketball game. They were spotted out and about together a few days later. By April of 2011, Kris was welcomed into the Kardashian clan. In May, they were engaged. Humphries proposed to Kardashian by spelling out the words “Will you marry me” in rose petals in her bedroom and presented her with a 20.5-carat diamond engagement ring.

They were married on August 20, 2011, in a wedding so lavish it cost more than $10 million and the event was actually aired on television as a two-night four-hour special event. Shortly after the nuptials, rumors were already running amok about trouble in paradise for the newlyweds. And sure enough, just 72 days after the wedding and exactly one year to the date they met, Kim filed for divorce, citing irreconcilable differences. She said to MTV in a statement, “After careful consideration, I have decided to end my marriage. I hope everyone understands this was not an easy decision…”

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Tiger Woods & Elin Nordegren

Tiger Woods & Elin Nordegren

Tiger met Elin while she was working as a nanny for fellow golfer, Jesper Parnevik, who had required the nanny to move to the United States with the family. She was introduced to Tiger in 2001 at the U.S. Open, but she was dating someone else at the time. In 2003, though, they were spotted together at the Presidents Cup tournament in South Africa. Woods proposed to Nordegren on that trip while on safari at the Shamwari Game Reserve. The wedding took place on October 5, 2004 and was reported to be a lavish event worth about $2 million.

The messy part came on November 25th of that same year when the National Enquirer published a story alleging Woods was having an affair. November 27th of 2009, Woods crashed his Cadillac into a neighbor’s tree and afterwards, Nordegren is spotted using a golf club to smash out the windows. Come to find out, Woods had not one, or two affairs, but could be responsible for having more than 100 partners during the time they were married. The divorce was dissolved on August 23, 2010.

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Khloe Kardashian & Lamar Odom

Khloe Kardashian & Lamar Odom

Oh yeah. Another Kardashian. This time, the messy part was the marriage! Reality royalty, Khloe Kardashian, met NBA L.A. Laker Lamar Odom at a party for a mutual friend in August of 2009. The two were married three weeks later on September 27th at another mutual friend’s home. These two were considered so high-profile on the red carpet that they eventually were offered their own spin-off show called Khloe & Lamar. Everyone was surprised when two years later, the two seemed to still be going strong. That is—until Lamar was traded to the Dallas Mavericks and the couple moved to Texas in December of 2011.

However, Lamar had a pretty horrible few months in Dallas and relocated back to L.A. in the spring of 2012. They even cut ties with their reality show, citing that Odom needed to focus on his career. The rest of that year seemed to be a rocky one, as rumors swirled about Odom’s infidelity and he didn’t help matters when he received a DUI. In 2013, the news exploded that Lamar had been addicted to crack cocaine for at least two years just a couple of days after it was reported that Khloe had thrown him out of the house. It seemed the two might try to make it work for a while but Khloe ultimately filed for divorce the same year. However, the proceedings have never been finalized, so they are still legally married to this day.

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Leann Rimes & Dean Sheremet

Leann Rimes & Dean Sheremet

Country music and Hallmark actress, Leann Rimes met Dean Sheremet when he was chosen as a back up dancer for her 2001 Academy Country Music Awards performance. In an interview with In Style magazine Rimes said that after their first date she knew “This is the guy I want to marry.” She was just 19 years old at the time and he was just 21. The two announced their engagement at Elton John’s ‘The Concert’ for the Elton John AIDS Foundation and they were married on February 2, 2002 in Dallas, to be closer to Rimes family.

The two apparently had nine blissful years together while Sheremet quit his dancing career and switched instead to managing Rimes’ career. That is until 2009 when Rimes was filming a Hallmark film called Northern Lights. Her costar on the set was Eddie Cibrian, who also happened to be married to someone else. The Rimes and Cibrian began an affair on set that was soon leaked when the two went out to dinner and were photographed kissing. Dean filed for divorce in December of 2009 and it was finalized exactly six months later.

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Demi Moore & Ashton Kutcher

Demi Moore & Ashton Kutcher

In 2003, when Kutcher was just 25 years old, he met Moore—who was 40 at the time— at a dinner in New York City, and the two sat and talked long into the night. They announced their relationship in a very high-profile way—they attended Moore’s Charlie’s Angels premier together and stole the attention from the film. Two years later, in 2005, the two got hitched at a very private Kabballah ceremony by a Rabbi of the Kabballah Center.

While their wedding ceremony may have been extremely private, the couple allowed the world to witness most of their most private moments via Twitter. Five years into the marriage and adultery rumors started up, alleging Ashton had stepped out on Demi. While they both denied the rumors, in 2011, the couple stopped posting on Twitter and started spending more time apart. Another cheating scandal popped up for Kutcher, and a few months later Moore publicly announced her plans to leave him. The marriage was dissolved in November of 2013.

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Donald & Ivana Trump

Donald & Ivana Trump

Ivana Marie Trump (not to be confused with her daughter Ivanka) was born in Czechoslovakia and relocated to the United States in 1976. She was with a party of models at an Upper Eastside restaurant when Donald Trump offered to help them get a table. One year later the pair married on April 7, 1977. The couple had three children: Don Jr. in 1977, Ivanka in 1981, and Eric Trump in 1984. While married, Ivana had interests in Donald’s businesses and had executive status at the Trump Organization. The pair were recognizable faces in all the social elite circles until 1989 when the bottom seemed to drop out.

It seemed Ivana had found out about Donald’s extramarital affair with Marla Maples over the Christmas holidays. By February, the Chicago Tribune had reported that Trump had locked Ivana out of her office at the Plaza Hotel. Because there was trouble over the prenuptial agreement, the divorce dragged on and became fodder for the media. The divorce became final in 1992 when it was granted on the grounds of cruel and inhumane treatment by Mr. Trump

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Prince Charles & Princess Diana

Prince Charles & Princess Diana

If you really want to talk about messy divorces, this one definitely takes the cake. Diana and Charles met while Charles was actually dating her older sister. However, in 1978, Charles broke things off with Diana’s sister but still remained close to the pair. In July 1980, Diana and Charles met up again while at a friend’s estate party. The pair began dating under the radar until, in September, Diana was photographed on the Balmoral private family estate, and the world was abuzz with speculation. The couple was married at Westminster Abbey in London in July of 1981, while an estimated 750 million people watched live.

Prince Charles, and now Princess Diana welcomed their two children— Prince William in 1982, and Prince Harry in 1984. By 1986, both parties were having affairs and the rumors were feeding the media mills—and would until 1992 when Diana released a scandalous tell-all interview in May. In December of 1992, it was finally announced to the public that the pair would be separating. The divorce wouldn’t be finalized until August of 1996 with Diana receiving a financial settlement and retaining her rooms in the royal palaces for life. Tragically, that life was cut short just one year after the papers were signed.

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Demi Moore & Bruce Willis

Demi Moore & Bruce Willis

When Demi Moore met Bruce Willis in July of 1987, she was dating Emilio Estevez right after they had wrapped filming St. Elmo’s Fire. She was actually attending the premier of Estevez’s film Stakeout when Moore met Willis for the first time. In Demi Moore’s tell-all book, Inside Out, she remembers attending an afterparty with Willis the same night, and later when she was driving home, he pulled up alongside her car in a limo with all of his friends trying to get her attention. The pair began dating in November of 1987 and were married by November 21, 1987.

They welcomed their first child, daughter Rumer exactly nine months later. The two both kept making blockbuster, after blockbuster, becoming Hollywood’s Golden couple of the 90s. The couple had two more children and juggled super-successful Hollywood careers. Around 1992, rumors began circulating that there was trouble in the marriage because of their hectic lifestyles. But still, the couple held on until in 1996 when rumors about Willis having an affair arose. Unfortunately, two years later this “It” couple announced that they were calling it quits. Despite the media’s interference, Bruce and Demi were able to split amicably and are still friends to this day.

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Madonna & Sean Penn

Madonna & Sean Penn

Madonna and ANOTHER messy divorce? Oh yeah. Sean Penn and Madonna met in 1985 on the set of her video for the classic “Material Girl.” They had both just gotten out of relationships, so they began dating nonexclusively. But inevitably, just six months later in August, the pair were married. They were fodder for the tabloids almost immediately. It didn’t help that Penn attacked a songwriter he believed was kissing Madonna and was arrested for it nor when he had violent outbursts towards the press to the point of serving 33 days in jail for hitting a photographer.

Also, almost immediately, the couple began having marital issues. Penn had a jealous streak and soon accusations of infidelity began to fly and some close to the situation say that Penn became violent towards Madonna on occasion, although the undisputed Queen of Pop has vehemently stated otherwise. The actual reason behind the split was never revealed, but many thought it was the strain of their hectic schedules coupled with Penn’s outbursts that eventually did the couple in. Madonna filed for divorce in December of 1987 but withdrew the papers and they stayed together until she filed new papers in January of 1989, citing irreconcilable differences.

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Sonny & Cher

Sonny & Cher

Sonny and Cher were the power couple of the early '70s, with a hit comedy show, several Grammy awards and several hit songs. The two met when Cher was just 16 and Bono—who was separated from his then-wife at the time—was 27 in a coffee shop in L.A. in November of 1962. The two were just friends at first, and then roommates, and eventually lovers until they got married after the birth of their daughter Chasity. Early in their relationship Sonny had encouraged Cher to record backup on a few songs that turned out to be hits and then convinced her that she should perform on her own.

However, Cher was too shy to sing by herself, so Sonny began accompanying her. And thus, Sonny & Cher were born. They began the Sonny & Cher show in 1970, which quickly became a television staple. However, the marriage began to unravel around 1974 when Sonny’s extramarital affairs and high-handed ways began to affect the relationship. Cher asked to be cut into the finances 50/50 but Sonny refused and so she filed for divorce in 1974, citing “involuntary servitude.” The divorce was finalized in June of 1975.

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Alec Baldwin & Kim Basinger

Alec Baldwin & Kim Basinger

In 1991, Kim Bassinger was just freshly divorced after an eight-year marriage with her first husband, Ron Snyder so she wasn’t exactly eager for a new romance. However, she had accepted the lead in 1991's The Marrying Man alongside Alec Baldwin, and from the first moment they met, Baldwin was smitten. He did everything he could to change her mind, and by the time they were finished filming the movie, they were in a relationship. Alec proposed after they wrapped up filming their second film, The Getaway, in 1994 and Basinger accepted.

The two were married in August of 1993 at Baldwin’s Long Island home. The couple’s only child, Ireland, was born in 1995. After that, though, it seemed not all was perfect between the two. Reports of Baldwin’s temper filtered through the marriage’s cracks, and in 2000, Basinger filed for divorce. That wasn’t the messy part though. The messy part was the six-year custody battle that ensued afterward, which kept them in the tabloids constantly.

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Terrence Howard & All of His Exes

Terrence Howard & All of His Exes

Terrence Howard of Hollywood hits like Hustle & Flow and Crash, as well as the hit television drama Empire, has been married four times and is currently engaged to his third ex-wife. There is nothing about this man’s romantic history that isn’t messy. His first marriage occurred in 1993 to Lori McCommas. The couple had three children and a decade together before they divorced in 2003. However, in 2005, they rekindled their romance and remarried before ultimately divorcing again in 2008.

In 2010, Howard met and married Michelle Ghent. Their marriage was turbulent and constantly in the media, as Ghent accused Howard of becoming abusive and filed a restraining order against him. Ghent filed for divorce in 2011, but their nasty divorce dragged out until 2013 when Ghent was awarded alimony and a part of Howard’s future earnings. As soon as the ink was dry on that divorce, Howard married Mira Pak and the two did well until they ultimately divorced in 2015. In 2018, Howard posted on social media that he’d asked Pak to re-marry him and that she accepted! We’ll all just sit back and see how this one unfolds.

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