Top 8 Hollywood Couples Who Had the Messiest Divorces That We Can't Get Over

Here Are 8 Most Dramatic Celebrity Divorces

Celebrity divorces might not shock us anymore, considering their busy work schedules, it's almost expected. However, what seems shocking is how messy things get when these relationships break. Heartbreak is already something very hard to deal with, but for these popular celebrities, divorce isn’t as simple as signing papers at the court. It is an entire drama played out under the watchful eyes of the world. This list highlights eight such celebrity couples who went through particularly tough and messy breakups.

1. Kevin Costner and Christine Baumgartner

After fighting several months of legal battle, celebrity couple Kevin Costner and Christine Baumgartner eventually finalized their divorce in February 2024. A major point of contention throughout their court battle was determining how much Costner should contribute each month for child support. During the official announcement, Costner's representative said, "It is with great sadness that circumstances beyond his control have transpired which have resulted in Mr. Costner having to participate in a dissolution of marriage action," as reported by People Magazine.

2. Kim Kardashian and Kanye West

Kim Kardashian and Kanye West officially filed for divorce in 2021, after years of tension, much of it stemming from West's unpredictable behavior in 2016. Talking about their divorce, an insider said, "Kim filing for divorce from Kanye is just a formal part of the process. The couple has been done for a while and have been amicable for a while. At the end of the day, Kanye and Kim love each other immensely, but knew it was time to call it quits." According to Pop Sugar, West and Kardashian agreed that neither would pay spousal support. Even after their divorce, the two have occasionally criticized each other in public.

3. Amber Heard and Johnny Depp

Johnny Depp and Amber Heard's relationship eventually turned into a toxic marriage. They got divorced in 2016 and later faced off in court over an op-ed Heard wrote about being a victim of domestic violence. Depp denied it and instead claimed that she was abusive to him. After the legal battle, the jury came in favor of Depp. During the divorce, a representative for Depp said, ​​"Given the brevity of this marriage and the most recent and tragic loss of his mother, Johnny will not respond to any of the salacious false stories, gossip, misinformation, and lies about his personal life. Hopefully, the dissolution of this short marriage will be resolved quickly," as reported by People Magazine.

4. Jennifer Aniston and Brad Pitt

In January 2005, Jennifer Aniston and Brad Pitt shocked the world by announcing their separation after more than four years of marriage. Talking about their divorce, Aniston said, "Sure, there were bumps, and not every moment felt fantastic, obviously, but at the end of it, this is our one life and I would not stay in a situation out of fear. Fear of being alone. Fear of not being able to survive," as reported by People Magazine. The real surprise came just a month after their divorce when Pitt was spotted vacationing in Kenya with Angelina Jolie.

5. Brangelina: Brad Pitt and Angelina Jolie 

Jolie and Pitt were entangled in a nearly decade-long divorce battle, complicated by child custody issues and ownership of their Chateau Miraval winery, according to Forbes. They were declared legally single on April 12, 2019. Meanwhile, talking about close relationships, Jolie recently said, "I don't really have those kinds of relationships. Maybe it's losing your parent young. Maybe it's working." As reported by HELLO Magazine, she added, "Maybe it's being somebody who's been betrayed a lot. I don't have a lot of those warm, close relationships as much that I lean on. But I have a few, and a few is enough."

6. Kris Jenner and Caitlyn Jenner

Kris Jenner and Caitlyn Jenner got divorced just two years before Caitlyn came out as transgender. During their divorce, Kris said, “We are living apart. But there is no animosity. We are united and committed to our family. We ended a marriage, but that’s not the end of our friendship. I will always love him, but we are no longer a couple in that way. We are happier this way," as reported by Us Weekly. Keeping Up With the Kardashians captured Kris’ feelings about her spouse’s transition. However, their relationship grew worse in 2017 when Caitlyn released her memoir, The Secrets of My Life.

7. Demi Moore and Ashton Kutcher

Demi Moore and Ashton Kutcher divorced after eight years of marriage. In her memoir, Moore claimed that Kutcher had been unfaithful. "Because we had brought in a third party into our relationship, Ashton said, that blurred the lines and, to some extent, justified what he's done," Moore said. She was referring to the cheating allegations. The age difference between them was also a major reason. She wrote, "Ashton's adult life was just beginning — both his personal life and his career. I didn't see all that because I was inside of it. I just felt like a fifteen-year-old girl hoping somebody liked me," as reported by Business Insider.

8. Sandra Bullock and Jesse James

The couple finalized their divorce in June 2012, and the Gravity actress adopted her son Louis later that year. Talking about the cheating allegations, James said, “Yeah, I did cheat on my wife, yeah. I stood up and took accountability for it and apologized. And that’s the end of story.” As reported by Us Weekly, he added, “In general, both women and men cheat. It’s part of life. It’s like people love to see you fall. And the farther you get, the higher you get, the more they love it." Speaking of their marriage, Bullock said, "It was not a thing I actually really wanted to do, but you know, it's cool. How do you let everybody down ... What's the fight? And when you have bosses telling you that you're the only person who gets a person to work on time, and 200 people either get to see their kids at night or they don't because our days start on time."