The Most Messy Celebrity Breakups Hollywood Has Ever Seen

From messy divorces to ugly break ups to calling off the wedding just one day before, Hollywood has seen its share of celebrity romances turn volatile quickly. From the 1960s to 2016 and every year in between, there’s never been at least one famous breakup that didn’t make headlines. Here’s a quick rundown of a few that were filled with tension, heartbreak, and anger.

Jennifer Aniston and Brad Pitt

Brad Pitt with Jennifer Aniston at a movie premiere.

This relationship was iconic. | Ucy Nicholson/AFP/Getty Images

Rumors swirled when Aniston and Pitt split up in 2005 after more than four years of marriage. Pitt was allegedly already involved with his future wife, Angelina Jolie, after the two filmed Mr. & Mrs. Smith together. Aniston told People, “I can’t say it was one of the highlights of my year,” referring to the photos published of Pitt and Jolie on a beach in Kenya. This seemingly perfect couple was one of the ugliest celebrity breakups to date.

Next: Pitt’s breakup with Aniston wasn’t the only messy one he had. 

Brad Pitt and Angelina Jolie

Brad Pitt and Angelina Jolie on a red carpet.

Hearts broke all over the world when this famous couple split up. | Jonathan Leibson/Getty Images

… And the Brad breakups don’t stop there. The iconic “Brangelina” started dating after they met in 2004. The two got extremely close during filming, which led many to think Pitt was cheating on Aniston. The couple dated for 10 years and had six children together, many of whom they adopted. They married secretly in 2014 and shocked the world when they announced their divorce just over two years later. Jolie asked for full custody of all of Brad’s children and wanted him to only have visitation rights. It led to a sloppy divorce, and Jolie claimed she was made to look like a bad person in the media.

Next: Everyone thought this Hollywood couple was doomed from the start.

Cameron Diaz and Justin Timberlake

Cameron Diaz and Justin Timberlake posing together.

Cameron Diaz and Justin Timberlake made a really great couple. | Stephen Lovekin/Getty Images

This couple met on the set of the Kids’ Choice Awards in 2003. The media thought they seemed like an “unlikely” couple, with Diaz being nine years older than Timberlake. Throughout their relationship, tabloids had accused both of them of having affairs; there were even lawsuits for libel. People also constantly spread rumors that the two were engaged. Finally, they chose to end their relationship in 2007, to the dismay of everyone who’d been rooting for them during their rumor-saturated years. Diaz reportedly had no interest in getting married, a source told People. It was never confirmed whether or not that was the reason for the breakup.

Next: The original “Bennifer” breakup left one of these two completely heartbroken.

Jennifer Lopez and Ben Affleck

Ben Affleck and Jennifer Lopez on a red carpet.

He moved on very quickly. | Kevin Winter/Getty Images

Lopez said, “It felt like my heart had been torn out of my chest,” when Affleck called off their engagement in 2004. She confessed in her memoir that she was heartbroken by the extremely public split. She feared being ridiculed about not being able to find love. The breakup didn’t seem as hard on Affleck, who began dating actress Jennifer Garner just a few months after the original “Bennifer” split.

Next: Bennifer 2.0 didn’t end well, either. 

Ben Affleck and Jennifer Garner

Ben Affleck and Jennifer Garner smiling on the red carpet together.

Ben Affleck and Jennifer Garner’s split involved a cheating allegation. | Pascal Le Segretain/Getty Images

This couple made headlines when it was discovered that Affleck was cheating on Garner with the family’s nanny, Christine Ouzounian. Garner fired Ouzounian once she heard that she had gone to Las Vegas with Affleck. A spokesperson for Affleck said that he and the nanny were not hiding anything, but the affair came out just days later. After a tumultuous separation, the two have since become more amicable and have been spotted together various times.

Next: Abuse allegations quickly put this breakup in the headlines. 

Johnny Depp and Amber Heard

Johnny Depp arrives at an airport in Tokyo with Amber Heard.

Their relationship was not as perfect as it seemed. | Yoshikazu Tsuno/AFP/Getty Images

The divorce between Depp and Heard rocked Hollywood when Heard filed for a restraining order against her estranged husband. She accused Depp of physical abuse and provided photos of her bruises. Heard claimed to have feared for her life and that Depp had a history of abuse with her. It shook fans and the public, as nobody wanted to believe that Depp’s abusive actions could be true. Depp’s lawyers fired back, saying Heard was only trying to secure a financial reward. The split repeatedly made national headlines in 2016.

Next: Excessive spending was one cause of this relationship’s end. 

Mariah Carey and James Packer

Mariah Carey posing with James Packer on a red carpet.

They put an end to their engagement. | Rob Kim/Getty Images

Multiple factors played into the queen of Christmas’ split with the Australian billionaire. Carey was allegedly spending too much of his money. Packer reportedly felt like there was no privacy in their relationship. Plus, he was supposedly jealous of Carey’s relationship with her backup dancer, Bryan Tanaka (the two are now dating). It only got more complicated when Carey’s former manager pushed her to do reality television. The couple had too many problems and called it quits in 2016.

Next: This split went down as one of the biggest cheating scandals of all time. 

Tiger Woods and Elin Nordegren

Tiger Woods and Elon Nordegren together at an outdoor event.

Tiger Woods and Elon Nordegren’s marriage was anything but perfect. | Harry How/Getty Images

It wasn’t just one cheating scandal that broke up this couple. It was many, many cheating scandals. Some estimates put it somewhere around 120 women. Nordegren supposedly chased Woods out of their home with a golf club the night she found out about his long-time affair with a New York City club hostess. Many women came forward after that, including the next door neighbor’s daughter. Needless to say, the marriage didn’t last.

Next: A surprise baby made us cringe at this messy breakup. 

Tom Brady and Bridget Moynihan

Tom Brady and Bridget Moynihan pose together on a red carpet.

Things got complicated after their split. | Mark Mainz/Getty Images

Things got rocky between Brady and Moynihan when she announced that she was pregnant with his child just after their breakup in 2006. Brady began dating his now-wife Gisele Bundchen shortly after he split with Moynihan, which thickened the pregnancy plot even more. Moynihan broke her silence a few years later, saying she wished she wasn’t a single mom. Today, the two seem to co-parent pretty well, even though the pregnancy initially came as a huge shock to both of them.

Next: Rumors of infidelity brought this marriage to a halt. 

Demi Moore and Ashton Kutcher

Demi Moore and Ashton Kutcher together at an awards show.

Their relationship ended due to rumors of infidelity. | Alberto E. Rodriguez/Getty Images

The split between these two spawned from reports of Kutcher’s infidelity. Moore tried to get past the rumors but couldn’t. She filed for divorce in 2011. In 2017, Kutcher accepted an award for his good character and commented that the cheating scandal helped shape him into who he is. Kutcher never admitted to cheating. He began dating Mila Kunis in 2012, and the two are now married with two children.

Next: “All I can say is it’s been awful,” is how this actress described her divorce. 

Tom Cruise and Nicole Kidman

Nicole Kidman and Tom Cruise on a red carpet.

They eventually dated other celebrities. | Torsten Blackwood/AFP/Getty Images

When Cruise filed for divorce from Kidman in 2001, she reportedly begged him to stay. She asked to go to marriage counseling, but he refused. At the time, she was pregnant with his child but ultimately had a miscarriage. Kidman wrote that she was stunned when he filed — just as stunned as the public, it turned out. She told Oprah Winfrey, “All I can say is it’s been awful.” Today, Kidman is married to country singer Keith Urban.

Next: This actress called off the wedding 24 hours before. 

Keifer Sutherland and Julia Roberts

Julia Roberts and Keifer Sutherland posing together.

Julia called off their wedding. | Sara Elyoumni via YouTube

Roberts and Sutherland met on the set of Flatliners, and were set to wed in 1991. Roberts called off the wedding the day before the ceremony was supposed to happen. It was a shock to fans, and Sutherland, too. He claimed that Roberts’ fame ended up taking over her life, which made it too difficult for her to get married at the time. Roberts reportedly ran off with one of Sutherland’s friends after cancelling the wedding, sending shockwaves through Hollywood.

Next: This man claims to have no regrets about cheating on his wife with multiple women.

Jesse James and Sandra Bullock

Sandra Bullock and Jesse James at an awards show.

Jesse James choked into rehab after the divorce. | Jason Merritt/Getty Images

In March 2010, a scandal hit James and Bullock’s five-year marriage. Multiple women came forward and claimed to have had affairs with James, prompting Bullock to file for divorce. James admitted to the affairs and reportedly checked into rehab to work on his personal problems. In an interview in 2017, James said he doesn’t regret cheating on Bullock and that cheating is a part of life.

Next: This actress refused to obey her famous husband, which led to their divorce. 

Frank Sinatra and Mia Farrow

Frank Sinatra and Mia Farrow hugging on a boat.

Frank Sinatra did not want Mia Farrow to work. | Marmar via YouTube

Sinatra and Farrow surprised fans when they decided to get married in 1966 — she was 21 and he was 50. Just two years later, he filed for divorce because he did not want farrow to star in Rosemary’s Baby, but she refused. He had the divorce papers sent to her film set, allegedly because he told her that if they got married, she would have to quit her career. The two divorced but were rumored to have had affairs throughout the years. In 2013, a Vanity Fair interview with Farrow made headlines when she admitted that her son Ronan — thought to be the son of Woody Allen — might “possibly” be Sinatra’s.

Next: This couple’s daughter played a huge role in their ugly split. 

Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger attend a red carpet together.

A very messy divorce. | Hal Garb/Getty Images

This breakup might be one of the messiest divorces Hollywood has ever seen. Baldwin and Basinger’s daughter, Ireland, was in the middle of it, too. A voicemail leaked from 2007, where Baldwin called his daughter a “rude, thoughtless little pig.”  Basinger referred to the divorce as “nasty.” Things took a turn for the worse when the couple fought in a long custody battle over their daughter. Baldwin was forced to attend anger management, and reportedly admitted to wanting to kill Basinger’s lawyers. Basinger claims the two are “cool” now.

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