These Are The Weirdest And Most Expensive Divorce Settlements in Hollywood

Some say that love conquers all things, but we don’t think this is the case for the couples on this list. Instead of love, some of these celebrities chose money to foot the bill for their heartaches and expensive divorce settlements. Well, we can’t really blame them…

From high-ranking celebrities like Sean Penn, Angelina Jolie, and even business tycoons like Bill Gates and Jeff Bezos – it goes to show that money, not love, makes the world go ‘round. Let's see what are the weirdest and the most expensive divorces Hollywood has seen. 

Sean Penn and Robin Wright

It was said that Robin Wright was absolutely smitten with her ex-husband, Sean Penn – who wouldn’t? He is a talented artist in his own right. Although, even Robin’s love wasn’t enough to keep this relationship going.

In 2009, Robin and Sean finally divorced, and the former received nearly half of her ex-husband’s net worth. That’s around USD 150M which is a lot of money, but we think both of them would be just fine considering the wealth and talent they both have.

Bruce Willis and Demi Moore

Through the years, Demi Moore and Bruce Willis have become some of Hollywood's most famous celebrity couples. They’ve shared an impressive 11-year marriage, and they have three beautiful daughters, but trouble in paradise soon ensued…

In 2000, Demi and Bruce got divorced, then it was around this time when Demi moved in with Ashton Kutcher. In addition to her new beau, Demi also received an astounding USD 90M divorce settlement. It was a pretty sweet deal if you asked us – don’t you think so?

Chris Judd and Jennifer Lopez

It’s hard to imagine Jennifer Lopez without her high-profile lovers like Alex Rodriguez and Ben Affleck, but do you remember when she married Chris Judd? The latter was a backup dancer, and we don’t know what Jennifer thought when she married him.

In the end, they were only married for about nine months, and she ended up paying around USD 14M. That’s a lot of money for such a short time, but who are we to judge?

David Hasselhoff and Pamela Bach

If you’re trying to look for one of the strangest divorce settlements in Hollywood’s history, then just look at this one by David Hasselhoff and Pamela Bach. The couple thought that their marriage would last, but it wasn’t in the stars for them.

In 2006, David announced that he was going to file for a divorce, and it seemed like Pamela wasn’t even bothered by it. In the end, Pamela only got around USD 5M, which is nothing compared to what her ex-husband was probably worth. This next couple is another strange yet highly celebrated pair in Hollywood…

Kevin Federline and Britney Spears

If there’s one thing that Britney Spears knows how to do well, it’s how to get attention. We’ve all been a fan of Britney since her stint on The Mickey Mouse Club to her rise as one of Hollywood’s best pop stars, but her choice of husbands has always been quite problematic…

Since getting married to Kevin Federline, the couple has been in and out of the tabloids. Luckily for Britney, they divorced after two years, and Kevin only got USD 1M plus child support. Well, what about this next couple on our list?

Michael and Juanita Jordan

One of the NBA’s most celebrated couples is none other than Michael and Juanita Jordan. From the outside, it looks like this couple had everything: the money, the children, and the growing romance – although this was far from the truth.

After trying to work on their marriage for years, Michael and Juanita finally called it quits in 2002. Juanita then received an astounding USD 168M and the custody of their children, Jeffrey, Marcus, and Jasmine.

Phil Collins and Orianne Cevey

If you’re a fan of great music, then there’s a high chance that you know who Phil Collins is. Also, did you know that he’s the father of the great actress Lily Collins? Although, Phil had had a few ups and downs regarding his ex-wives.

After getting married in 1999, Phil and Orianne Cevey split up in 2008, but they married again in 2016. People said that Orianne hasn’t returned the money she received from Phil from their previous divorce settlement – what do you think about that?

Kenny and Marianne Rogers

Some people say that Kenny Rogers was one of the greatest musicians who has ever lived, and we’re not objecting. Although, his ex-wives, like Marianne Rogers, would agree that he was probably not one of the best husbands.

Marianne was Kenny’s fourth wife, but their marriage soon ended in divorce in 1993. She then bagged a whopping USD 60M, and Marianne said that she deserved every penny that she got from Kenny. Well, we don’t know about you, but that’s saying a lot about how he treated her – don’t you think?

Arnold Schwartzenegger and Maria Shriver

One of Hollywood’s most popular and controversial couples is Arnold Schwartzenegger and Maria Shriver. People thought this marriage was a match made in heaven, but it all fell apart after 25 years.

Maria filed for divorce when she found out that Arnold had impregnated their housekeeper. Due to his ex-wife’s familial status and since they never really signed a prenup, Arnold had to pay Maria around USD 375M in divorce settlements. Not only that, but Maria got custody of all their children.

Jeff and MacKenzie Bezos

Even one of the richest men on earth wasn’t exempted from undergoing a hefty divorce settlement. The love story of Jeff Bezos and MacKenzie Bezos started in 1992, but it would soon end in 2019.

Bezos owned Amazon, but since he had founded this company after he married MacKenzie, she was entitled to half of his fortune. So she got around USD 38B, which was a pretty good deal if you ask us! We wonder what MacKenzie would do with such a hefty sum…

Prince Charles and Princess Diana of Wales

Is there anyone alive right now who doesn’t know who Prince Charles and Princess Diana of Wales are? During their time, they were one of the most celebrated couples globally, and their marriage was seen as one of the crowning glories of the United Kingdom’s Royal Family.

However, their love story quickly turned sour, and they divorced in 1996. Princess Diana then gets an astounding GBP 17.5M, which isn’t bad – but then again, we all know how her tragic story ended…

Mick Jagger and Jerry Hall

As the lead singer of The Rolling Stones, it was no surprise that Mick Jagger had no problems attracting lovers of the opposite sex. While this was great for Mick, this was a problem for his then-wife, Jerry Hall.

About eight years after getting married in Indonesia, Jerry has had enough of Mick’s scandals, so she filed for divorce. We’re glad that Jerry stood up for herself – after all, she was probably one of the most beautiful of Mick’s wives.

Rupert Murdoch and Anna Maria Torv

One of the most controversial divorce proceedings of their time was none other than Rupert Murdoch and Anna Maria Torv’s. Sure, they’ve shared a great 32 years of marriage, but this wasn’t enough for Rupert to clean up his act.

In 1999, Anna Maria finally filed for divorce, and she took an impressive sum of USD 1.2B as her divorce settlement. Unfortunately, it would seem that Ruper didn’t learn his lesson because this wasn’t going to be the last time that one of his wives would take him to court for divorce…

Rupert Murdoc and Wendi Deng

A few days after Rupert Murdoc divorced his first wife, Anna Maria Torv, he then married Wendi Deng. This man doesn’t like to waste time, and he was married to Wendi for a good fourteen years.

However, he then filed for divorce in 2013 and settled for a good USD 1.8M. Some rumors spread that Wendi was in a relationship with Vladimir Putin, but these claims weren’t proven to be correct. Now, this next couple had shaken Hollywood to its core in the last few years…

Johnny Depp and Amber Heard

We’ve all probably heard of the whole debacle between Johnny Depp and Amber Heard. Their divorce and abusive claims towards each other really shook Hollywood to its core, and it had celebrities and their fans taking sides.

While many people took Amber’s side for years, it’s been slowly proven that the real victim was actually Johnny. We’re just glad that this is somewhat over for Johnny and that he can get his life back as quickly as possible.

Nick Cannon and Mariah Carey

It would seem that her fans were obsessed with Mariah Carey’s relationship with her ex-husband, Nick Cannon. After getting married in 2008, the pair welcomed their beautiful set of twins.

However, even Mariah’s marriage must come to an end because they divorced just six years later. In the end, Mariah got custody of their children, but Nick has been contributing a monthly sum that’s geared towards their children’s trust fund. How cool is that?

Dr. Phil McGraw and Debbie Higgins

We’ve probably all seen a single episode of Dr. Phil McGraw’s famous show, Dr. Phil, right? Although, did you know that he was once married to his high school sweetheart, Debbie Higgins?

While this seemed like such a cute thing to do, Debbie mentioned that Dr. Phil had a very domineering personality, and she didn’t enjoy being married to him as much as she thought she would. In the end, they divorced, and they settled for around USD 1M.

Steven Spielberg and Amy Irving

We think that we can all safely agree that Steven Spielberg is one of the best directors of his generation, but is he a great husband? While he shared a relatively short marriage with his ex-wife, Amy Irving, the latter still admires her ex-husband.

Amy got around USD 100M for their divorce settlement, but that wasn’t much considering that Steven was worth a whopping USD 3.6B! Now, what about the next couple on our list?

Lionel and Diane Richie

In 2004, Lionel Richie got divorced for the second time – he shared a great nine years with Diane Richie, but their marriage sadly had to end. Although Diane wasn’t going to go down without a fight…

For their divorce settlement, Diane demanded that Lionel pay her USD 300,000 per month and another USD 20,000 for plastic surgery. Lionel thought that this was crazy, but he gave her USD 20M and their USD 5M mansion in the end. Do you think that Diane deserved it?

Tom Cruise and Katie Holmes

We think that Tom Cruise is one of Hollywood’s most beloved leading men, which was probably why Katie Holmes fell for him. The couple got married, and they eventually welcomed their daughter, Suri, but trouble in paradise soon ensued.

In 2012, Katie filed for divorce because Tom was slightly obsessed with Scientology. Katie feared that this would impact their daughter, and so she deemed it best to part ways with her ex-husband. Unfortunately for Tom, this wasn’t the first time this happened to him…

Tom Cruise and Nicole Kidman

Before meeting Katie Holmes, Tom Cruise was actually married to another Hollywood legend. Nicole Kidman was Tom’s second wife, and they met while they were filming their movie, Days of Thunder – some say it was love at first sight.

Unfortunately, the pair soon divorced, but Tom and Nicole are still on relatively good terms. Now, let’s move on to this next couple on our list!

Mel Gibson and Robyn Moore

We all know Mel Gibson as a talented actor and director, but it would appear that he wasn’t that great of a husband. His then-wife, Robyn Moore, filed for divorce after 26 years of marriage because of all the scandals and scrutinies brought by Mel.

In 2006, Robyn had enough after Mel got arrested for DUI. It would take another five years for their divorce to finalize in 2011, and Robyn did receive around USD 850M as a divorce settlement.

Seal and Heidi Klum

One of Hollywood’s most iconic couples is none other than Seal and Heidi Klum. The pair had such great charisma together, and it appeared that they had a strong bond and connection.

However, the couple soon divorced after seven years of marriage. Although both Seal and Heidi still show their respect and admiration for their ex-partner, and this is more than we can say for most divorced pairs in Hollywood – don’t you think so?

Alec Baldwin and Kim Basinger

Before he was married to his current wife, Alec Baldwin had Kim Basinger by his side. Together they had a beautiful daughter, but even their daughter couldn’t stop Alec and Kim’s hurtful tirades towards one another.

After their divorce, Kim had blocked Alec’s visitation rights to see their daughter, but they both settled with a good USD 3M divorce settlement. It took a good decade for both Alec and Kim to clean up their act for their daughter and their fans. Now, this next couple is another controversial one…

Tiger Woods and Elin Nordergren

In 2004, it would appear that Tiger Woods had destroyed his reputation after it was revealed that he had been cheating on his wife with multiple women at a time. Throughout the whole scandal, Elin Nordegren has kept her head high, which earned her sympathy from fans and the press.

Though it wasn’t until 2010 that their divorce was finalized, and Tiger had to pay a whopping USD 750M to Elin. In the end, both Tiger and Elin agreed to share custody of their children.

Gavin Rossdale and Gwen Stefani

We don’t think that there could ever be another couple as unique and as beautiful as Gavin Rossdale and Gwen Stefani. After meeting in 1995, the pair decided to marry in 2002, and they both welcomed three beautiful children together.

Although even Gwen couldn’t keep her husband at bay because Gavin had an affair that caused their divorce in 2015. It was said that their settlement was around USD 2.5M. Honestly, we’re just glad that Gwen has finally got rid of Gavin – don’t you think so?

Bruce and Kris Jenner

Who doesn’t know of the very public life and relationship of Bruce and Kris Jenner? We’ve all seen them for quite some time after following their lives on their hit reality show, Keeping Up with the Kardashians. 

We honestly thought that Bruce and Kris would end up growing old together, but we were wrong… In 2015, Bruce came out as transgender, which might’ve shattered Kris’ whole world. While they divorced, they still managed to keep a relatively friendly relationship for the sake of their children, Kendall and Kylie. If that were you, what would you have done?

Sir Paul McCartney and Heather Mills

We don’t think we’d expect less than USD 3.2M for Sir Paul McCartney’s wedding, right? Unfortunately for this seasoned musician, his divorce settlement would cost him more…

In 2002, Paul married Heather Mills, but they soon divorced later in 2006. Some people thought that Heather only married Paul for his status and money, and we don’t think that’s entirely impossible. In the end, Heather got around USD 48M – do you think she did it for the money?

Harrison Ford and Melissa Mathison

After meeting on the set of their movie, Apocalypse Now, sparks flew all over for both Harrison Ford and Melissa Mathison. Then in 1983, the pair soon married and enjoyed the celebrity status that their stardom has given both of them.

Unfortunately, Harrison and Melissa’s marriage ended in divorce – this was something that wasn’t very shocking, as most celebrities get divorced a few years later. In the end, Melissa got an impressive USD 85M in the divorce settlement.

Brad Pitt and Angelina Jolie

Who can ever forget the whirlwind romance that swept Brad Pitt and Angelina Jolie off their feet? Between the two of them, they’re two of the highest-paid actors in Hollywood, and they do have six children together. Sadly, this wasn’t enough to keep Brangelina…

In 2016, Brad and Angelina started their divorce proceedings, which shattered the hopes and dreams of those who believed in the Brangelina love team. Nobody knows this for sure, but it was estimated that their divorce settlement would be somewhere around USD 400M – now this is small compared to this next couple’s settlement.

Bill and Melinda Gates

Another rich man who can’t keep his wife is none other than Bill Gates. The philanthropy and tech world’s most famous couple, Bill and Melinda Gates, have finally called it quits after 27 years of marriage. What went wrong between the two of them?

Nobody knows the reason behind Bill and Melinda’s divorce, but according to Forbes, this settlement could be the biggest ever to be recorded. According to sources, Melinda would gain around USD 60B after her divorce has been finalized. Now that’s a pretty good deal if you ask us…

Michael and Diandra Douglas

Before he was married to Catherine Zeta-Jones, Michael Douglas was actually married to his first wife, Diandra Douglas. It seemed like love at first sight, but the reality was far from that.

In 1995, both Michael and Diandra separated, but their divorce didn’t materialize until the year 2000. Diandra received a great USD 45M as her divorce settlement, which isn’t bad considering that Michael said that one of his greatest regrets is not divorcing Diandra sooner. Yikes.

Guy Ritchie and Madonna

The Queen of Pop’s divorce to her ex-husband, Guy Ritchie, has been controversial for so many reasons. Even though Madonna and Guy were only married for around seven years, they have shared some monumental moments.

Luckily for this couple, they didn’t sign a prenup, and they didn’t have to pay each other millions of dollars. Instead, the couple remained friendly towards each other, but the doors to reconciliation remained closed.

Love or Money: What Would You Choose?

Hollywood is such a strange place, especially for those of us who are considered as “outsiders.” While there may be couples out there who have stood the test of time, there are still those who chose money over love.

If that were you, what would you have chosen? Would you choose love or money? We guess it’s hard to tell unless you’re actually on the spot!