Even in the most amicable breakups, divorce is not easy. Meeting with lawyers, dividing assets, figuring out how to move on with your life are just a few things that make divorce stressful and unpleasant. Throw kids into the mix and what was already a difficult and unpleasant situation becomes about a hundred times worse.
While it seems that celebrities are more likely to divorce than their less-famous counterparts, their splits are often much trickier. Especially in relationships when there is a serious imbalance of earning potential — splitting with your partner doesn’t just mean a stress of going through with divorce proceedings, it means potentially throwing away large parts of your fortune at someone you really never want to see again. Whether it’s giving away assets or indefinite monthly payments, you might be financially on the hook for a long time.
That’s why it’s pretty standard that many of your favorite celebrities get a pretty intense prenup. We can’t really blame them, as much as you might love someone, the risk of separating and paying tens of thousands of dollars a month is just not worth it. For some of these celebrities, their mistake was believing that love was more powerful than the all-mighty dollar. In other cases though, some extra-marital dalliances is what led many stipulations of any prenup to be voided. In most cases the divorce payout is more than we’ve earned in our whole lives!
A lot can be learned from these mistakes, and while you might not be a millionaire, there may be an important takeaway from these celeb divorce disasters, to take with you on your own future committed relationship.
15. Britney Spears – Paid $1M + $20K Per Month
Britney Spears fans knew deep down in their hearts that Kevin Federline was nothing but bad news for the pop star. In the whole mess of her very public breakdown, Britney was also going through a divorce with a guy who looked like a low-scale scumbag and clearly never intended on making it work with the pop star. Bringing almost nothing to the table, he nonetheless got a big payday when the two split. Spears reportedly paid him 1 million dollars and he was also entitled to a monthly allowance for $20,000 to take care of the kids, of which they shared joint custody for.
14. Wiz Khalifa – Paid $1M + $15K Per Month
While it’s easy to look at the numbers involved in the Wiz Khalifa and Amber Rose divorce and wince, the pair is actually very amicable – something that will likely work out well for their kids. As per their prenup, Amber gets 1 million dollars and monthly child support payments of $14,800, according to TMZ. Khalifa gets to keep most of the assets though, including their home and ten of their cars. If there was any doubt that there aren’t any hard feelings between them, the pair celebrated their divorce settlement by going to the Ace of Diamonds strip club as one last final hurrah. Strangely enough, this is likely the happiest divorce on this list.
13. NAS – Paid $350K + $51K Per Month
When Kelis divorced NAS it was one of the biggest alimony and child support payment plans in the history of the music industry. Kelis of ‘Milkshake’ fame was pregnant with NAS’ child when they seemed to split very suddenly, and NAS end up paying very big for this breakup. He was ordered to pay $350,000 in missed back payments. In 2010 he was paying $51,000 a month (or $600,000 a year) to Kelis while also being responsible for her legal and accounting payments. No one would blame NAS for being a little bitter about love after that, but surprisingly NAS is pretty reflective over the whole situation. He doesn’t blame Kelis, saying it was never about the money but her wanting to hurt him like he hurt her (NAS had not only cheated on Kelis but had impregnated another girl, while Kelis was also pregnant).
In an interview with Complex he said shortly after divorce, “I can’t take it with me, so someone can take the money. Anyone that I’m married to, if I give you my life, I give you my heart, I love you—my money is nothing. You can have it all. It’s just sad that when you’re dealing with love and life and marriage, that marriage is a contract. It’s a business deal. That messes people up.”
12. Steven Spielberg – Paid Off $100M
Just because you’re one of the greatest directors alive, doesn’t mean you’re immune to problems with love. Steven Spielberg had married Amy Irving in 1985, right at the height of his rise from prodigy to all-time great. Irving was an actress best known for roles in Carrie and Amadeus, she was considered one of the better actors of her generation. Even before the pair got married they had a rocky relationship and had a big breakup that caused Irving to lose out a major role in an Indiana Jones film. By the time they broke up again in 1989, Irving received a pretty unprecedented 100,000,000 dollars – as Spielberg was valued at over 1 billion dollars at the time. Why did she receive so much? Well, Spielberg had drafted a prenup… on a napkin, and a judge ruled the document was not legally valid.
11. Janet Jackson – Paid Off $10M
While we often think of men as the ones who pay out big when it comes to expensive divorces, gender knows no bounds when it comes to money and fame. Janet Jackson had secretly married songwriter Rene’ Elizondo in 1991, so it was a pretty big shock for everyone when he filed for divorce in 1999. While many suspected the pair had been wed at some point, no one realized it was for that long and that it could fall apart also behind closed doors. He was always kinda around, producing some of her big hits, directing some of her music videos and it’s his hands cupping her breasts on her infamous Rolling Stone cover shot. The pair had a prenup but Elizondo filed to question its validity and ended up reportedly walking away from the marriage with a whopping $10 million.
10. Kelsey Grammer – Paid Off $30M
In some ways, the only thing that Kelsey Grammer seems to have in common with his uptight New England character Frasier, is trouble in love. His ex-wife Camille, earned $30 million when they split – let’s not forget he was at one point one of the highest paid actors on TV between Cheers and Frasier. Before you start calling foul though, Camille is maybe the only reason Kelsey Grammer had any money to part with. Apparently, when the pair got married in 1996, he was in financial ruin due to bad habits and an out of control drug problem. She worked hard to get him into rehab and to manage his remaining funds in order to save his fortune. Kelsey likely didn’t mind too much and had already remarried two weeks after this divorce settlement went through.
9. Jennifer Lopez – Paid Off $10M
Unfortunately for Jennifer Lopez, many of us could have predicted that her marriage to dancer Cris Judd was not going to last. Married for less than two years, their divorce was not a pleasurable one. Jennifer Lopez, who was valued at over 60 million dollars at the time, paid Judd over $10 million in the settlement – someone even did the math, considering the length of their marriage, it works out to being paid over $40,000 each day they were married. Apparently, the payout was so big because Cris Judd refused to sign a nondisclosure agreement about their relationship and Lopez was willing to dish out the extra cash to keep her ex silent about their bedroom secrets.
8. Harrison Ford – Paid $85M + Royalties
Once upon a time Harrison Ford and his wife Melissa Mathison, were held up as proof that Hollywood stars could stick it out and make a long and happy marriage work. But unfortunately, all good things come to an end. After 21 years of marriage, the pair filed for divorce – and Melissa walked away with not only $85 million, but a percentage of all future royalty earnings from films made during their marriage (including the Indiana Jones franchise). The pair had met in 1979 on the set of Apocalypse Now, where Melissa Mathison was working on a script and he had a small role. Mathison was a success in her own right and most famously wrote E.T. for Spielberg. Things were rocky in the last years of their relationship with a trial separation and a lot of late night bar hopping for Ford.
Melissa died in 2015 at the age of 65 years old and her last film, Spielberg’s BFG, was dedicated in her memory.
7. Paul McCartney – Paid $48.6M + $70K Per Year
The very messy divorce of Paul McCartney and Heather Mills ended with an enormous payout for Heather. Their divorce stretched over two very long years in which Mills made outlandish request after outlandish request. While the Judge for the divorce called into question her sincerity, writing, “I am driven to the conclusion that much of her evidence, both written and oral, was not just inconsistent and inaccurate but also less than candid,” he still awarded her $48.6 million! It’s likely that was part of Heather Mills’ plan all along though, as she had initially asked for $250 million from McCartney’s Beatles fortune, she still laughed all the way to the bank. She also receives $70,000 annually for child support and McCartney must pay for private school and a nanny.
6. James Cameron – Paid Off $50M
Linda Hamilton was James Cameron‘s fourth wife, and together they made two of the greatest films of all time: The Terminator and Terminator 2: Judgement Day. Cameron’s ability to turn just about anything into a cash cow has made him one of the richest people in all of Hollywood. It shouldn’t be a surprise that when it came time to divorce, Linda Hamilton got an estimated $50 million for her troubles – and troubles there were many. While Cameron never cheated, he was a driven workaholic who didn’t want to put in the time for a marriage. She said of their relationship, “It was terrible on every level. I wasn’t ready, he wasn’t ready. He was terribly insecure that I was going to ruin it for him somehow, which didn’t make sense since I am an actress in my own right and had been in front of the camera. It was dreadful.” James Cameron married his fifth wife just one month after his divorce from Linda Hamilton.
5. Michael Douglas – Paid Off $45M
Long before he met Catherine Zeta-Jones, Michael Douglas was in a very long-term marriage to Diandra Luker. The pair were together from 1977 to 1995, but only divorced in 2000. The divorce ended up costing Douglas a pretty heavy penny, as he paid his ex 45 million dollars. Douglas who has never been all that good about the line between his private and public life, has since spoken out about the marriage. While he has nothing against his ex-wife Diandra, he claims the biggest problem with that first marriage was that it went on as long as it did – ten years past its expiration date to be exact. His experience in divorce led him to put together a pretty iron clad prenup when he remarried Catherine Zeta-Jones, and while they had separated at one point, they’re now happily back together.
4. Madonna – Paid Off $85M
It’s not like Madonna‘s ex-husband, Guy Ritchie (responsible for Sherlock Holmes and Snatch) wasn’t successful – it’s just that he was never Madonna successful. So when the pair headed for divorce court, it shouldn’t be a big surprise that he asked and received a pretty huge sum of money. The pair had a rocky seven year marriage, during which Madonna has since reported feeling “incarcerated” by Ritchie. She felt that Ritchie was really interfering with her full potential as an artist and it was one of the reasons the marriage had to go down. She ended up paying Guy Ritchie a reported 85 million dollars in the divorce.
Who said freedom was cheap? In 2015 Ritchie end up remarrying, a beautiful British model named Jacqui Ainsley.
3. Tiger Woods – Paid Off $100M
A piece of advice: If you don’t’ want to pay your ex-wife a huge amount of money in divorce, then don’t cheat on her with multiple women, at least, don’t get caught. Tiger Woods‘ ex-wife Elin Nordegren, earned 100 million dollars in the divorce — apparently far more than what was agreed upon in the prenup, largely because of the circumstances of their separation. Since the pair had only been married for five years, that means she earned nearly $20 million for every year she stayed married to him! Talk about a comfortable yearly salary! Hopefully Woods has learned a very valuable lesson from this whole experience, namely, keep it in your pants if you don’t want to pay out (or don’t get married). So far so good, it’s been six years since his divorce and Tiger Woods has yet to remarry.
2. Michael Jordan – Paid Off $168M + Mansion
When Michael Jordan divorced his first wife, Juanita Vanoy, he paid one of the largest amounts we’ve ever seen someone pay in a divorce settlement. Shortly after the pair married in 1989, they signed a post-nuptial agreement that would grant Vanoy half of Jordan’s fortune in a divorce. When they split in 2006, that amount was a whopping $168 million! Juanita also got their Chicago mansion and custody of their kids. However, after that many years together there was clearly a lot of respect between the pair and no hard feelings. The divorce was clean and fair, with no dirty laundry aired to the press or public. Michael Jordan remarried in 2013 to Yvette Prieto in a larger than life and indecently expensive wedding.
1. Arnold Schwarzenegger – Paid Off Over $300M
It’s no big surprise that Maria Shriver called it quits on her marriage to Arnold Schwarzenegger when she found out not only that he was having an affair, but it was with the help and he had a child with her! Among the trickiest separations on this list, four years after she filed for divorce they were still officially married – according to sources, Arnold just kept delaying and delaying the inevitable. Maybe he knew that there was no way he wasn’t walking away from this divorce without paying big – and really, he would be right. Since the pair did not have a prenup according to California law, it meant that Maria was entitled to half his fortune – feeling bad about how the whole thing ended, Arnold reportedly threw in some extra as a good will gesture. The exact numbers have never officially been released but estimates put Arnold’s fortune at around $500 million and $750 million, which means that Maria likely got a divorce settlement around $250 and $375 million.