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15 Actors Whose Relationships Were Too Messy To Clean Up

Divorces are not uncommon in Hollywood. Many actors have had several ex-spouses, but some of their previous relationships have been incredibly messy.

Sometimes relationships don’t go as we expect. It takes two for a commitment, but even for these actors, relationships are never easy. Sometimes relationships can be even harder for celebrities, since they have to deal with so much fame and popularity on top of their responsibilities and commitments.

Because of this, many celebrities go through relationships as quickly as one might go through a bag of chips. Thus divorces are not at all uncommon in Hollywood. Many actors have more than a few ex-spouses.

However, the press doesn't always get everything right. In fact, many couples who fans believed were perfect turned out to have terrible relationships with one another.

It's time to take a look at some of the most famous actor couples who had incredibly messy relationships. Though these relationships may have looked good on the outside, on the inside they were rotting and eventually became so broken that they were beyond repair.

With that said, here are the 15 Actors Whose Relationships Were Too Messy To Clean Up.

15 Mel Gibson and Oksana Grigorieva

During Gibson’s early years, he met Oksana Grigorieva, a successful Russian singer-songwriter and pianist. The two began a relationship in 2007 and in 2009, the two had a daughter, named Lucia, together.

The couple later separated in 2010, with Grigorieva obtaining a restraining order against Gibson a few months later.

Grigorieva thought Gibson would harm her, alleging that Gibson had physically attacked her. During their custody dispute over their daughter Lucia, copies of tape recordings that Gibson had sent to his wife, which were incredibly abusive and offensive, were leaked to the public and quickly went viral.

Grigorieva denied that she had released the recordings to the public. Gibson then agreed to provide Gigorieva with $15 million in order to keep the tapes private, but Grigorieva refused to accept this amount.

Eventually, in 2011, Gibson was sentenced to three years of probation, counseling, and community service.

14 Jennifer Lopez and Ben Affleck

When Jennifer Lopez and Ben Affleck got together, "Bennifer" fans emerged from every corner of the world. The two actors were seen as a super couple and were looked up to by many fans as perfect.

Lopez and Affleck met on the set of Gigli and eventually began dating. The two became engaged shortly after. However, Gigli ultimately turned out to be a box office flop and created a tense atmosphere for both Lopez and Affleck. Affleck ultimately decided to call things off in 2004 just before their wedding, which plastered the power couple's faces all over the tabloids.

According to Lopez, their relationship "self-destructed in front of the entire world."

Affleck and Lopez later managed to move on and kept in touch as colleagues. Lopez has since reflected back on the relationship, stating that she never regretted the time she spent with Affleck, despite how messy their relationship was for a time.

13 Kristen Stewart and Robert Pattinson

Kristen Stewart and Robert Pattison were another couple that fans instantly fell in love with, particularly because they were lovers not only just off-screen, but on-screen as well.

Though the two allegedly dated from 2008 to 2012, they tried to keep most of their relationship a secret. Their relationship was talked about a lot, though, due to Twilight fans who saw the two as a perfect couple.

However, things fell apart when Stewart was caught on camera kissing Snow White and the Woodsman director Rupert Sanders. After the huge scandal, both Sanders, who was married at the time, as well as Stewart, publicly apologized for their behaviour.

Unfortunately, it was too late and Stewart and Pattison's relationship never fully recovered. Twilight fans were immediately angered over the break up, upset that Stewart and ruined it.

12 Demi Moore and Ashton Kutcher

Demi Moore and Ashton Kutcher quickly started appearing in tabloids when they began dating. The two met in 2003 at a casual dinner with friends and instantly hit it off. Though there was a large age gap between the two, with Moore being 41 and Kutcher being 25 when they first met, the two didn't let it get in the way.

The two went on to marry in 2005. However, things eventually took a turn for the worst and the two decided to separate in 2009, later divorcing in 2011.

Their separation was due to Kutcher allegedly cheating on Moore with another woman.

In the end, there was no point in repairing the messy relationship, which was flooded with rumors and allegations of Kutcher's infidelity.

11 Josh Brolin and Diane Lane

Josh Brolin and Diane Lane met in 2003 and married a year later. The two remained married from 2004 and 2013. During this time, Brolin and Lane had an extremely rocky relationship. Their relationship was not easy, as Brolin often became physical-- a few domestic disputes eventually made the headlines.

In 2004, Brolin was charged for spousal battery after Lane called the police, claiming that he had harmed her.

However, Lane did not want to press charges and Brolin was later bailed out of jail.

From there, Brolin continued to get in trouble with the law-- Brolin was arrested again for intoxication in 2013. In the same year, the couple decided to end their marriage. Brolin went on to marry Kathyrn Boyd.

10 Liza Minnelli and David Gest

Liza Minnelli and David Gest were introduced to each other by Michael Jackson in 2001. Though many fans thought them an unlikely couple, since Gest was severn years younger than Minnelli, the two instantly hit it off, marrying in 2002.

Minnelli, who had struggled with health problems and substance abuse issues, believed that Gest had restarted her career. However, the happy days didn't last for long. Though many believed that Minnelli had stopped drinking, Gest allegedly stated that Minnelli was still drinking and had assaulted him.

Things quickly became even uglier, as the two tried to sue each other for damages. Eventually, the Minnelli and Gest started spreading rumors about each other-- Minnelli allegedly stated that Gest had stolen from her and that he had poisoned her, while Gest allegedly stated that she had given him herpes.

Their divorce proceedings lasted until 2007, when the two finally settled on a no-fault divorce.

9 Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger met in 1990 on the set of The Marrying Man and instantly hit it off. The two married a few years later, in 1993. They remained together until Basinger filed for divorce in 2001.

They fought for custody over their daughter, Ireland Baldwin, who was 7 years old at the time, and eventually reached an agreement and finalized their divorce a year later.

Part of the agreement included Baldwin attending anger therapy. He was also only allowed 90-minute phone calls to his daughter.

In 2007, a voicemail that Baldwin had left for Ireland, who was 11 at the time, was leaked to the public and went viral. In it, he called his daughter a "thoughtless pig" for not answering his call. Baldwin later issued a public apology.

In recent years, Basinger has stated that she and Badlwin are at peace with their past.

8 Brad Pitt and Jennifer Aniston

Jennifer Aniston and Brad Pitt started dated in 1998 and got married in Malibu in 2000. The marriage lasted for five years until both decided to separate in 2005. Pitt allegedly left Aniston after he met Angelina Jolie on the set of Mr. and Mrs. Smith in 2004.

Two months after the separation, Pitt posed with Jolie for magazine in a shoot where they were both dressed as a married couple in the '60s surrounded by children.

Pitt and Jolie were seen together by paparazzi for most of 2005, which caused a huge stir in the media.

In 2006, Jolie became pregnant with their first child. The two eventually went on to marry in 2014 after spending several years together.

 

7 Pamela Anderson and Tommy Lee

From the beginning of their relationship, Pamela Anderson and Tommy Lee’s lives consisted of one hot mess after another. The two met in 1995 when Anderson ordered a drink for Lee. According to Lee, he was smitten immediately.

Their relationship took off from there, and four days later they were married. Though fans around the world believed that their relationship wouldn't last, they remained together for three years and had two children. They eventually divorced in 1998. At the time, scandal was abound-- various accusations of Lee assaulting Anderson were floating around tabloids and a copy of a tape from their night together during their honeymoon had gone viral.

Anderson accused Lee of subjecting both her and their two sons to physical and mental abuse. However, the two continued to see each other after their divorce.

 

6 Lindsay Lohan and Sam Ronson

Lindsay Lohan and Samantha Ronson dated for one year from 2008 to 2009. During this time, Lohan accompanied DJ Ronson to various events.

Since then, Lohan has called their relationship "toxic."

She stated that, at the time, both she and Ronson were toxic people, and thus their relationship was bound to eventually fail. She also said that they were both lonely at the time and were thus both searching for something more.

Before they began dating, Lohan and Ronson were friends. "Samantha Ronson was my best friend," she told News. She went on to say that Ronson was "a really good friend to me when I really needed one." Lohan has struggled with substance abuse issues and was arrested several times.

Thankfully, Lohan and Ronson have remained friends years after the breakup, despite the toll it took on the two of them.

 

5 Charlie Sheen and Brooke Mueller

Charlie Sheen and Brooke Mueller married in 2008 and had two twin boys in 2009. They were together for a few years until they divorced in 2010. During their divorce, Mueller stated that Sheen was drinking and abusing substances, occasionally becoming violent.

In 2009, Sheen was arrest for domestic abuse charges. Mueller told police that Sheen had threatened her with a knife. However, Sheen stated that Mueller had actually been the aggressor.

The couple checked into rehab after the event. 

Later, Sheen was hospitalized in 2011 after police were called to respond to an "emotionally disturbed person," as Sheen had gone into a rage. A few months after this, the couple filed for divorce, with Sheen stating that they had separated in 2009.

4 Sandra Bullock and Jesse James

Jesse James and Sandra Bullock got married in 2005. The two had met on the site of James' Discovery Channel show, Monster Garage. In 2009, James faced a custody battle with his previous wife, Janine Lindemulder, with whom he had a daughter. James and Bullock won the case.

However, in 2010 a huge scandal broke out-- several women publicly spoke out, voicing that they had had affairs with James while he was married to Bullock. During the same year, James publicly apologized to Bullock for his infidelity.

James and Bullock finalized their divorce in 2012. "A lot of good happened out of [the end of my marriage] because it helped me focus on being a dad more," James said in an interview. "It helped me focus on doing the right thing and being myself, and getting out of L.A. and getting a better life for my kids."

3 Sean Penn and Madonna

Sean Penn and Madonna met in 1985 and married the same year. However, their relationship was never easy and was constantly all over the tabloids. This was mostly due to Penn's violent outbursts. In one instance, Penn was arrested for assaulting a photographer on set.

In 1989, Madonna filed for divorce against Penn, citing "irreconcilable differences" as the reason. The same year, Penn had been arrested for domestic assault and battery.

There were many allegations that stated that Penn had physically and verbally assaulted Madonna, threatening to shave her head and beating her with a baseball bat. 

However, both Penn and Madonna have denied that Penn ever physically harmed Madonna. Madonna went on to state that while they "certainly had more than one heated argument during our marriage, Sean has never struck me, 'tied me up,' or physically assaulted me." Either way, their relationship was incredibly toxic.

2 Tom Cruise and Katie Holmes

Tom Cruise and Katie Holmes began dating in 2005 and got engaged later that year, only seven weeks after meeting. They were married in a Scientologist ceremony. Holmes, who had been raised Catholic, began studying Scientology. Cruise had become a member of Scientology in 1990 though Mimi Rogers, his first wife.

The couple had a daughter, named Suri, in 2006. Holmes filed for divorce after five years of marriage in 2012. At the time, Holmes was allegedly scared that Suri would be abducted by Cruise and forced to become a member of Scientology.

During the pregnancy, Holmes underwent strange rules that were enforced by Cruise.

She was told to remain completely silent while she gave birth, since according to Scientology, labouring women should avoid making any noise to prevent their newborn from being traumatized.

Additionally, members of Scientology hd moved into Cruise and Holme's home in order to cater to Cruise, which allegedly freaked Holmes out.

1 Johnny Depp and Amber Heard

Johnny Depp and Amber Heard met on the set of The Rum Diaries in 2011. They moved in together the following year and married in 2015. That same year, the couple failed to declare their Yorkshire terriers to the Australian Customs Service when they flew into the country. Tabloids went wild. The two later released a video apology. However, this was only the beginning of their rocky relationship.

In 2016, Heard filed for a divorce and obtained a temporary restraining order against Depp. She stated that Depp had been both physically and verbally abusive during their relationship. Despite images of a bruised Heard and a leaked video of an argument between the two appearing online and going viral, many fans and celebrities defended Depp against the claims.

The two eventually reached a settlement and their divorce was finalized in 2017.

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Can you think of any other actors who had messy relationships? Sound off in the comment section!

 

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15 Actors Whose Relationships Were Too Messy To Clean Up