10 of the Messiest Breakups in Pop Culture History

It seems that no matter how much you love a celebrity couple, breakups and arguments are always waiting for them at the end of the rainbow.

Celebrities should really learn to either keep their relationships private, or not have so many breakups. Don’t get me wrong, I love the drama and the messiness that comes with a breakup, I just wish some couples would stay together. It seems like every time I look at my phone, another couple is breaking up. There is no way the amount of breakups in Hollywood match what you would find in everyday life. Anyways, from Britney and Justin to Brad and Jennifer, we have learned that splitting up is not always an easy transition. Let’s take a look at the 10 messiest breakups Hollywood has ever seen.

Brad Pitt & Jennifer Aniston

Brad and Jen who had one of the worst breakups in history.
Brad and Jen

You can’t talk about bad breakups and not mention the demise of Jennifer Aniston and Brad Pitt’s marriage. Things got messy fast in this divorce, mostly because of why it ended. Fans speculate they got divorced because Brad fell for Angelina Jolie while filming Mr. and Mrs. Smith. It’s hard not to believe she wasn’t a factor considering he spend the next 12 years of his life in a relationship with her. Jennifer famously called Brad out on missing a sensitivity chip and said she was shocked to see pictures of Brad and Angelina together in Africa with their son. This breakup is the definition of messy because it had everything.

Brad Pitt & Angelina Jolie

Angelina Jolie and Brad Pitt.
Angelina Jolie and Brad Pitt

This man really can’t catch a break when it comes to relationships can he? The relationship he left Jennifer Aniston to pursue went up in flames after 12 years. This time around however, Brad was looked at as the victim and Angelina was once again looked at as the bitch. She accused him of abusing their oldest son, drinking too much and losing his temper. Once investigations into her claims came back bogus she began grasping at straws and made everything public. A nasty custody battle ensued and their oldest son still doesn’t talk to Brad. Jolie had to do major damage control and is finally back in some people’s good graces after years of being looked at as the bad guy.

Johnny Depp & Amber Heard

Mandatory Credit: Photo by Rich Fury/Invision/AP/Shutterstock (9123547a) Amber Heard, left, and Johnny Depp arrive at The Art of Elysium's Ninth annual Heaven Gala.
Mandatory Credit: Photo by Rich Fury/Invision/AP/Shutterstock (9123547a) Amber Heard, left, and Johnny Depp arrive at The Art of Elysium’s Ninth annual Heaven Gala.

This is probably the saddest example, because a man’s career and reputation were ruined in the process. Heard accused Johnny, in a sworn declaration, of throwing a cellphone at her during a fight, bruising her cheek and eye. She accused him of abusing her throughout the course of their marriage, and because of this, Depp had to pay her $7 million in their divorce. He lost movie roles and sponsorships, ultimately leading to his bankruptcy. Turns out the public turned on Johnny over a lie. In 2019 he sued Amber for defamation, claiming she was the one abusing him during their relationship. This mess was not fun to watch unfold.

Nick Young & Iggy Azalea

Iggy and Nick at the 2014 Billboard Music Awards.
Iggy and Nick at the 2014 Billboard Music Awards.

Iggy thought she had found the man of her dreams and was all set to marry basketball player Nick Young. Turns out he was a player in a whole different meaning of the word. It wasn’t long before word, and video, got out that Nick was cheating on Iggy. If I learned one thing from this scandal, it is never cheat on Iggy Azalea. She told Andy Cohen on “Watch What Happens Live” that when she heard the news, she burned all of Nick’s stuff. Not someone I really want to mess with.

Justin Timberlake & Britney Spears

The it couple of the 90s and 2000s broke millions of hearts when they went their separate ways after three years of dating. While the true reason for their breakup has never been revealed, we can assume it wasn’t as amicable as they would like us to believe. Justin reportedly wrote Cry Me A River two hours after their breakup, a song many believe to be about the end of their relationship. Also, they have yet to reunite in any capacity, which can also point to a bad break. This could add some credibility to the Britney cheating rumors. I guess we’ll never know.

Jay Cutler & Kristen Cavallari

Kristen and Jay
Kristen and Jay

Their divorce was just announced but things are already not looking too good. Right after the announcement rumors started swirling about Jay possibly having had an affair with Kristen’s best friend. They deny it but maybe it just wasn’t with her. Fans of their show Very Cavallari were not surprised by their split, saying they never liked how he treated her on the show. In the divorce filing Kristen stated Jay engaged in “inappropriate marital conduct.” What does that mean? Things got even nastier when it came to custody. Jay wanted joint custody while Kristen wanted sole custody to go to her. Then he wasn’t allowing her to move out, I don’t know. They worked it out in the end but word is they hate each other and there is no hope for a reconciliation.

Tiger Woods & Elin Nordegren

This was the breakup of the century. It played out in the headlines and each update was more scandalous than the last. When Elin found out about one of Tiger’s affairs she allegedly charged him with a golf club and chased him out of the house. If you have any doubts about whether or not that was an overreaction, just wait. Turns out there wasn’t just one woman, but many, 11 to be exact. I think the golf club incident was well deserved on Tiger’s end, just a little premature.

Robert Pattinson & Kristen Stewart

Teenagers mourned the loss of their it couple in July 2012 when Kristen Stewart cheated on Robert Pattinson. Edward and Bella broke up and the world was officially ending. Kristen was spotted making out with Rupert Sanders, the director of her film Snow White and the Huntsman. They both claim there was no long term affair, just a brief lapse in judgement. Not only did this break up Edward and Bella, but also caused Rupert to split with his wife, whom he shares children with. She quickly moved out of the house they shared and that was that. In a 2019 Howard Stern interview, Kristen said if Rob had asked, she would have married him. Too bad, so sad.

Jim Edmonds & Meghan King Edmonds

Meghan and Jim before their breakups.
Meghan and Jim

This is one of those breakups where you saw it coming a mile away. It was a matter of when not if. The way Jim spoke to Meghan on the Real Housewives of Orange County was not very nice and fans instantly hated him. Me being one of them. As if he wanted to make us all hate him more, Jim had an affair with their nanny. He thinks it makes it better that noting physical happened, and that all he did was sext with the girl. The scariest part of this split was that Meghan’s former housewives co-star Vicki Gunvalson accurately predicted that their marriage would only last five more years.

Olivier Sarkosy & Mary Kate Olsen

Not much was known about the relationship between these two and not much is really known about their breakup. Sources say it was cause by Mary Kate changing her mind about having kids, and Olivier not wanting any more. He already has two from a previous marriage. Olsen was forced to file an emergency petition to file for divorce because Sarkosy terminated the lease on the apartment they shared and she had only weeks to find a new place. Due to COVID, this proved to be difficult. I mean kicking her out was not the best move for his image.

There you have it. My picks for the top 10 worst breakups in pop culture history. What do you think of these, and any other breakups I may have missed? Let me know in the comments!

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