Everything in Hollywood is glamorous, even the divorces. Billion-dollar settlements, million-dollar homes, and everything from expensive jewelry to private islands is up for grabs as the lawyers divvy up the lifestyles of the rich and famous. Okay, maybe the legal battles aren’t exactly glamorous, but the spoils of these divorce wars are certainly extravagant. So, we just had to know — between all the glitz and glam, drama and intrigue, who actually walked away from their marriages with the biggest settlement claim from fame? We dug deep to find out. Here are the most expensive celebrity divorce settlements to date.
From public showdowns to private legal battles and everything in between, these celebrity couples have done it all. While some had very public displays of non-affection, others settled their marital troubles fairly quietly and privately, which in Hollywood especially, is surprising. Don’t worry because we were able to get all the dirty details on these celebrity divorces, including how much these marital mistakes cost them. Check it out.
Paul McCartney and Heather Mills — $50 Million
For a man who made his millions singing songs about love, it’s surprising that even Paul McCartney still seems to have a thing or two to learn about it. Paul McCartney and Heather Mills had something of a whirlwind romance. They met in 1999 when Mills was engaged to Chris Terrill, but she quickly broke off her relationship with him to be with the former Beatles frontman. McCartney and Mills began their relationship in 2000, and by 2002, the couple was married. By 2003, they had a daughter together, whom they named Beatrice.
Yet by 2006, the couple was separated, and by 2008, the nasty and very public divorce was finally settled. All sorts of rumors flew as to why the couple’s marriage disintegrated so quickly, including everything from difficult family dynamics with McCartney’s teenage daughter Stella to accusations the pair had gotten together too soon after McCartney’s first wife, Linda’s, untimely death. Regardless of the reason, the divorce, even by Hollywood standards, was dramatic. In fact, according to People, McCartney called his marriage to Mills “one of the biggest mistakes” of his life. Ouch.
When all was said and done, the four-year marriage cost Mr. McCartney a grand total of $50 million. We can see why he might not view the marriage so fondly. The immense final settlement made the McCartney divorce one of the most expensive (and dramatic) in Hollywood history.
Kevin Costner and Cindy Silva — $80 Million
Kevin Costner and Cindy Silva had, by Hollywood standards, a very long relationship. By all initial accounts, their marriage seemed destined for happily ever after. Yet, after 16 years of marriage and three children together, the couple finally called it quits.
Costner and Silva met in 1975 at USC, and within three years, they were married. As time went on and Costner’s career took off, rumors of infidelity plagued the couple, and Costner’s romantic and often sexual love scenes in movies supposedly did not help the couple’s cause. There were rumors that Silva even issued Costner an ultimatum, demanding he either quit the amorous movie scenes or the marriage. As Costner is still acting and no longer married, if the rumors are true, we can probably guess which one he chose.
As the couple had been married so long and Costner’s career had really taken off, there were a lot of assets to sort through. There was also, of course, the matter of the couple’s three children. When all was said and done, the marriage settlement equaled a whopping $80 million, which is no small feat, even for the Hollywood heartthrob. Apparently, Costner learned from his costly mistake, and when his next divorce came along, he made sure a prenup was firmly in place.
Harrison Ford and Melissa Mathison — $85 Million
Another long-time celebrity couple, Harrison Ford and Melissa Mathison are next on our list. The couple was married for 21 years (practically a lifetime in Hollywood) before finally calling it quits. Ford is, of course, a well-known actor, and Mathison is a screenwriter with plenty of credits to her name as well. The two met in 1976 on the set of Apocalypse Now, but Ford was still married to his first wife at the time. Then, after his starring role in Star Wars rocketed him to fame, he and his first wife ended up divorcing. Ford and his second wife Mathison got together very soon after, and within a year of dating in 1983, they tied the knot.
The couple was together for two decades and had two children together, but as they married with no prenup in place, their divorce got very messy and very costly. As many celebrity divorces do, it took almost two years to sort out all the assets and finalize the legal piece. In the end in 2004, the divorce cost Ford $85 million, launching him into one of the most expensive celebrity divorces in Hollywood.
Madonna and Guy Ritchie — $92-76 Million (Estimated)
Madonna and Guy Ritchie were one of Hollywood’s hottest couples until they weren’t. While their breakup might have been very public, the details of their settlement were far less so. The couple announced their plans to divorce in October of 2008 after eight years of marriage and two children. The two met at a dinner party in 1998 and tied the knot in 2000, the same year their little boy, Rocco, was born. Eight short years later, the once-happy couple decided to part ways.
According to People, there were several contributing factors in the couple’s divorce. Allegedly, Ritchie was not supportive of Madonna’s association with Kabbalah, the Jewish mysticism practice, and her feelings on adoption, which is a shame as the couple adopted a child from Malawi together. The two apparently also had different views on fame and celebrity, and all of these essential issues led to the pair going their separate ways.
Ritchie, a British film director, and Madonna, an international superstar, had an estimated combined wealth ranging in the hundreds of millions with Madonna making up the lion’s share of that amount. Ironically during the divorce, Madonna took on the legal council of Fiona Shackleton, who also had her hands full with the McCartney-Mills divorce. The couple was tight-lipped about what their actual settlement ended up being, but reports indicate it landed somewhere in the $92-$76 million range, making it one of the highest divorce settlements in Hollywood.
Steven Spielberg and Amy Irving — $100 Million
The Steven Spielberg and Amy Irving divorce is one of the most bizarre and costly on the Hollywood hot list. The director and the young actress met in 1976 and hit it off right away. Yet, it turned out the young actress preferred time in the spotlight and didn’t like being in her director husband’s shadow. The couple broke up in 1980 but reunited in 1985, and a wedding soon followed, but not before a prenup was drafted.
Now, here’s where the story takes a bizarre turn. The prenuptial agreement was not drafted by a lawyer on a legal document — it was drafted by Spielberg on a cocktail napkin. Then, three short years later, when the couple decided to divorce, Spielberg attempted to use the “document” as a prenup. Shockingly enough, it did not hold up in court, and the short-lived marriage and prenup debacle ended up costing Spielberg $100 million for his mistake. The story and the settlement amount itself became a legend in Hollywood circles, as the plot twists and turns of this divorce story sound more like something from one of Spielberg’s movies than his private life. Yet, in this case, truth is stranger than fiction, and not only did it land Spielberg a spot in Hollywood folklore, it landed him a spot on our most expensive divorces list.
Michael and Juanita Jordan — $168 Million
Michael Jordan’s basketball career was the stuff of dreams — unfortunately, his personal life, especially his divorce, was more the stuff of nightmares. Michael Jordan and his wife Juanita were married for 16 years and had three children together, although their time together was so tumultuous, it landed them on several “most toxic couples” lists. Yikes.
The two got married in a small Vegas ceremony in 1989 right at the beginning of Jordan’s lucrative career, meaning most of Jordan’s wealth was acquired during the marriage. Interestingly enough, while their final divorce occurred in 2016, it was not the first time the couple had considered parting ways. A divorce was filed in 2002 but revoked after the couple decided to try to reconcile. The final divorce came through in 2016. The split was outwardly amicable with lawyers and publicists claiming the couple were still on good terms. Yet, the final settlement landed at $168 million, making it one of the biggest payouts in Hollywood history. So, what the divorce lacked in drama, it seemed to make up for in monetary compensation. Not exactly a slam dunk for Mr. Jordan.
Mel Gibson and Robin Moore — $425 Million
Mel Gibson and Robin Moore experienced 30 years of marital bliss followed by one of the most dramatic and public divorces in Hollywood. The couple met in the late 1970s when Gibson was still a struggling actor and Moore was working as a dental assistant. The two got married in 1980 and share seven children together.
Moore filed for divorce following Gibson’s very publicized Malibu arrest for suspicion of driving under the influence, which sparked his well-known anti-semitic rant. Moore left Gibson the next day and filed for divorce soon after. Earlier in the month, Gibson was also caught canoodling with Oksana Grigorieva, whom he later had a baby with. So, clearly, a lot of drama for what was once one of Hollywood’s most likely-to-succeed couples.
Let’s be honest, 30 years in a Hollywood marriage is as close to lifelong as many of them ever come. So, not only was it disappointing to see one of Hollywood’s former heroes take a serious nosedive, it was sad to watch a marriage many believed in do the same. Yet, 30 years and a divorce settlement of $425 million later, Mel Gibson and Robin Moore parted ways. Surprisingly enough, however, while his marriage was toast, Gibson’s career did recover with several hit action movies blowing up on streaming.
Rupert Murdoch and Anna Torv — $1.7 Billion
We are now entering the divorce settlement territory that actually makes the McCartney settlement look fairly reasonable. These divorce numbers leave the millions and start hitting the billions with the Murdoch family being a prime example. Rupert Murdoch and his former wife Anna Torv were married for 32 years and share three children. While the long-lasting marriage seemed good, as with many of the Hollywood marriages when they go bad, they go really bad. The newspaper journalist married the media mogul in 1967, but by the ’90s, infidelity rumors plagued the couple. By 1999, it appeared Murdoch had found a new love interest, Wendi Deng, who he married 17 days after his divorce from Torv.
The couple did not have a particularly lengthy divorce process as the entire thing was wrapped up in three months. Torv allegedly was interested in an attempted reconciliation, but Murdoch had already moved on. Torv received an impressive $1.7 billion in the divorce.
Bill and Melinda Gates — $6.3 Billion
Bill and Melinda Gates are household names. Their legendary advances in the technology field are matched only by charitable contributions. Not only is the power couple known for founding Microsoft, but they also founded a successful non-profit: the Bill and Melinda Gates Foundation, which is known for donating over $4.5 billion to various causes. Yet, despite these two seeming like a dream team, behind the scenes, their marriage had turned into a nightmare.
The couple married in 1994 after meeting at Microsoft and dating for seven years. They were together for 27 years, share three children, a large non-profit, and several successful businesses. Yet after what seemed like a long, happy marriage, the two abruptly called it quits. Melinda Gates told Vanity Fair that a big part of the decision to divorce was her husband’s association with the notorious Jeffery Epstein. Melinda states she knew working with Epstein was a mistake from day one, calling him “personified evil.” No argument here. Her husband Bill was also known for having at least one very public affair with rumors of others plaguing the marriage. At the end of the day, Melinda decided to call it quits.
As the two got together in the early Microsft days and were together nearly three decades, there were a lot of assets to sort through. When all was said and done, Melinda walked away with $6.3 billion in stocks. Considering the last Forbes estimate of Bill placed him at a net worth of $130 billion, we’d say he got off pretty easy. Gates began dating again soon after the divorce was finalized.
Jeff and McKenzie Bezos — $36 Billion
Jeff and McKenzie Bezos’ divorce made headlines for more reasons than one. It’s not every day that men worth $136 billion divorce without a prenup. Yet, that is exactly what happened with Jeff Bezos. He and his wife McKenzie decided to call it quits after 25 years and four children. The pair met in 1992 where McKenzie worked as Jeff’s administrative assistant, and within a year, they were married. Eventually, Amazon, Jeff’s company, would skyrocket, making him a billionaire and apparently putting a lot of strain on the marriage.
Finally, after McKenzie caught Jeff sending “sleazy” photos to his mistress, she decided to call it quits. The affair scandal was instantly public, yet despite the media frenzy, the two at least attempted to maintain an air of amiability. As the couple got together pre-Amazon success and had been together nearly three decades, a lot of the assets were acquired during the marriage, making for a messy separation process. Yet, when all was said and done, McKenzie walked away with $36 billion. The settlement made her the richest woman in the world via divorce. An odd accomplishment, but one McKenzie quickly turned to gold as she gave away a reported $1.7 billion to charity. Way to keep it classy, McKenzie! The settlement is, to date, one of the largest in Hollywood history.
It’s becoming rarer these days to see high divorce settlements in Hollywood, the land of the prenups. Yet, when they do happen, they are often just as dramatic as the shows and movies the couples are known for. They serve as shining examples of what happens when seemingly good marriages go so wrong. It also goes to show that while everything might be bigger in Texas, everything is more glamorous in Hollywood, even the divorce settlements.