23. Michael Douglas & Diandra Luker: $45 Million

Long before his high-profile marriage to Oscar-holder actress Catherine Zeta-Jones, Academy Award-winning actor Michael Douglas was married to the daughter of an Austrian diplomat, Diandra Luker. The two met while Douglas was visiting Luker’s school, Georgetown University, to promote a film he was producing, none other than One Flew Over the Cuckoo’s Nest.

Luker, who was only 19 years old at the time, didn’t have a clue who Douglas was. However, it only took two short weeks for her to fall in love with the actor and accept his marriage proposal. The couple’s 1977 union unfortunately ended in separation in 1995. Luker filed for divorce and received a $45 million settlement, half of the actor’s net worth — plus a cut of his earnings from his Wall Street films.

22. Phil Collins & Orianne Cevey: $47 Million

English musician Phil Collins, responsible for such legendary tunes as “In The Air Tonight,” is no stranger to pricey divorces. Dating back to 2008, his third and last divorce, from Swiss native Orianne Cevey, marked the greatest settlement ever reached in a British celebrity divorce at the time: $47 million.

Collins first met Cevey in 1994 while he was on tour and she was working as a translator. They were married for six years and had two children together before parting ways. Cevey earned a sizable cash payout from their divorce. Against all odds, the couple announced that they had reunited once again in 2016.

21. Paul McCartney & Heather Mills: $48.6 Million

Beatles icon Paul McCartney first met his second wife Heather Mills at the Pride of Britain Awards in 1999. Their relationship was riddled with drama from the start; Mills had been engaged to filmmaker Chris Terrill, but soon broke it off to be with the “Hey Jude” singer.

The couple’s marriage lasted six years before their explosive divorce was finalized in 2008. As part of the divorce settlement, Mills was awarded $48.6 million, which was only a fifth of the amount that she had originally requested. In addition to the money, the former model also received properties in New York and the UK.

20. James Cameron & Linda Hamilton: $50 Million

Between 1997 and 1999, famed Terminator creator James Cameron was married to the actress who played the franchise’s star character Sarah Connor, Linda Hamilton. The two first met on set and moved in together after filming Terminator 2: Judgment Day. But as Hamilton revealed in an interview with People, it didn’t take long for the pair to realize they were “terribly mismatched.”

The two both admitted later on that the woman Cameron had actually fallen in love with was Hamilton’s on-screen counterpart Sarah Connor, not the actress herself. After an affair-fraught marriage, they filed for divorce. Hamilton was awarded $50 million as a settlement. Luckily, it seems there’s no bad blood between the two, as the actress ended up returning to the franchise in 2019 to film Terminator: Dark Fate.

19. Kevin Costner & Cindy Silva: $80 Million

Field of Dreams and The Bodyguard icon Kevin Costner met his first wife Cindy Silva while the two were studying at California State University at Fullerton in 1975. Costner revealed to People in 1989 that he was blown away by her intelligence and beauty, and the two ended up marrying in 1978.

Over the course of their sixteen-year marriage, the couple had three children together and even worked alongside one another. But rumors of Costner’s alleged infidelity started circulating shortly after they filmed Dances With Wolves together. It wasn’t long before the couple announced their divorce in 1994. Silva walked away from the proceedings with $80 million.

NEXT: We had no idea these celebrities were able to walk away with this much through divorce settlements.

18. Madonna & Guy Ritchie: $92 Million

After nearly eight years of marriage, the “Queen of Pop” ended her relationship with British director Guy Ritchie in 2008. Madonna told Newsweek that their split was due to an extinguished spark in their relationship, whereas Ritchie told Details that their marriage felt like he had “stepped into a soap opera.”

Whatever the reason behind their split, Ritchie was said to have walked away with a settlement ranging anywhere from $76 million to $92 million. The exact amount remains unconfirmed, though according to Reuters, part of the sum included the pair’s country house in western England, along with the pub they co-owned.

17. Steven Spielberg & Amy Irving: $100 Million

When Steven Spielberg first met Amy Irving in 1976, they were both on their way to becoming Hollywood stars. Irving had just received exposure thanks to her role in the horror film Carrie, and Spielberg had just finished directing the massively successful blockbuster movie Jaws.

Their relationship was on-again, off-again for many years until they finally married in 1984. Some four years later, the pair filed for divorce and Irving was awarded half of her husband’s fortune: $100 million. The divorce settlement was reached after a judge discredited their prenuptial agreement, which had been written on a cocktail napkin. Moral of the story? Napkin prenups don’t count!

16. Tiger Woods & Elin Nordegren: $110 Million

Golf legend Tiger Woods was no stranger to making headlines for crushing it in his sport, but in 2009 he made headlines for a different reason. He was at the center of a highly-publicized infidelity scandal, in which he was accused of cheating on his Swedish-born wife Elin Nordegren with at least 120 different women.

Woods had been married to the former nanny for six years at the time of the scandal and the pair shared two children together. It didn’t take long for Nordegren to file for divorce, and when she did, she received $110 million of her ex-husband’s money.

15. Harrison Ford & Melissa Mathison: $118 Million

E.T. screenwriter Melissa Mathison and Star Wars actor Harrison Ford first met in 1979 while on the set of Apocalypse Now. They started seeing each other shortly thereafter, and got married in 1983, in what was Ford’s second marriage and Mathison’s first.

The pair spent a total of 18 years by each other’s side and had two children together before calling it quits on their relationship in 2001. With millions of dollars at stake and no prenup in place, their marriage was officially dissolved in 2004. Mathison reportedly walked away with a staggering $118 million. As part of the settlement, she was also entitled to royalties from the films Ford had worked on during their marriage.

14. Garth Brooks & Sandy Mahl: $125 Million

Garth Brooks, one of country music’s biggest names, met his first wife Sandy Mahl while working as a bouncer at a local Oklahoma bar in his final year of college. Mahl had gotten into an argument with another girl in the women’s restroom when Brooks was called to break up the fight.

Brooks ended up driving Mahl home later that night and the rest is history, so they say. The two said “I do” in 1986 and had three daughters together. Unfortunately, the pressure from Brooks’ exploding career proved to be too much for the couple., and they filed for divorce in 2001. Mahl was awarded $125 million in the settlement.

NEXT: This well-known Hollywood name blew all of her billion-dollar divorce settlement.

13. Neil Diamond & Marcia Murphey: $150 Million

Rock and Roll Hall of Famer Neil Diamond met television producer Marcia Murphey while he was married to his first wife Jaye Posner. Never mind that the “Sweet Caroline” singer was legally bound to another at the time he met Murphy; the chemistry between the two was described by onlookers as being so strong that it was nearly palpable.

The couple ended up marrying and were together for a total of 25 years before their relationship went south and they filed for divorce. According to Forbes, Murphy received half of Diamond’s $300 million estate. Diamond later told the Daily Mail that her settlement was enough to live on for the rest of her life, and that she was “worth every penny.”

12. Michael Jordan & Juanita Vanoy: $168 Million

Nearing the end of the 1980s, basketball legend Michael Jordan was right on the cusp of international fame when he met former model Juanita Vanoy. The pair ended up walking down the aisle in 1989 and started having kids not long after.

17 years of marriage and three children later, Jordan and Vanoy’s marriage started to suffer as a result of the NBA star’s growing fame. They announced their split in 2002, but then tried reconciling shortly after before filing for divorce once more in 2006. The split was said to be “mutual and amicable,” and Vanoy walked away with $168 million in her pocket.

11. Arnold Schwarzenegger & Maria Shriver: $250 Million

Like everyone who says “I do,” Arnold Schwarzenegger and Maria Shriver thought their marriage would last for eternity. Unfortunately, however, the union between this Kennedy family member and the Terminator himself didn’t last. Shriver decided to file for divorce in 2011 following 25 years of marriage together.

Shriver pulled the plug on their relationship two months after the Schwarzenegger made headlines for fathering a child with the couple’s housekeeper of many years, Mildred Baena.Because there was no prenup agreement in place, Shriver was awarded $250 million, along with custody of the couple’s kids. The pair have been separated ever since then, but they never finished the paperwork, so they’re still legally married.

10. Angelina Jolie & Brad Pitt: $400 Million

Brangelina fans all over the world were left completely shocked when news of the pair’s divorce came out in September of 2016. After two years of marriage, Jolie filed for divorce from her Hollywood icon husband and cited irreconcilable differences as the reason.

Jolie opened up to Madame Figaro in October of 2019, saying the couple’s split left her feeling “smaller, insignificant,” and unable to recognize herself anymore. As for their divorce settlement — well, that’s still being worked out even though years have passed since. The two are still working out how to split their $400 million empire, which includes five homes and a winery.

9. Robert Johnson & Sheila Crump: $400 Million

In the year 2000, the co-founders of Black Entertainment Television (BET), Robert Johnson and Sheila Crump, made history when they became the first African-American billionaires ever. They were granted this title after landing a jaw-dropping $3 billion deal with the multinational media conglomerate, Viacom.

Three years later, the couple made history once again when Sheila Crump walked away from their divorce settlement with a staggering $400 million. The pair had been married for a total of 33 years before Crump called it quits after learning of her husband’s alleged three-year affair. But fans say it wasn’t all bad news for Crump, whose net worth catapulted to $670 million following the divorce.

NEXT: Can you guess who tops our list at number one of the biggest celebrity divorce settlements ever?

8. Mel Gibson & Robyn Moore: $425 Million

Following Mel Gibson‘s finalized divorce from former dental nurse Robyn Moore in 2011, the Braveheart star was not only single, but also short of a mind-boggling $425 million. The couple first met towards the tail end of the 1970s when they were both residents of the same Adelaide, Australia home.

31 years of marriage and seven children later, Moore filed for divorce and Gibson was forced to hand over half of his $850 million fortune. The star’s immense wealth is the result of heavy investment in real estate, and of course, the loads of commercially successful films he has both directed and starred in.

7. Dmitry Rybolovlev & Elena Rybolovleva: $604 Million

Russian oligarch Dmitry Rybolovlev and his wife of 26 years Elena separated in 2008 in what was a highly-publicized and incredibly bitter divorce battle lasting six years. At the time the divorce was finalized in 2015, Rybolovlev was the 165th richest man in the world. He had a net worth equaling $8.5 billion, which he’d amassed through starting a fertilizer business.

Rybolovlev first met his ex-wife before he made his fortune, but as the money came flowing in, so too did their marital problems. The former cardiologist student filed for divorce from her billionaire husband citing his “serial infidelity.” She was initially awarded $4.5 billion in the settlement before she appealed and ended up with $604 million.

6. Adnan Khashoggi & Soraya Khashoggi: $874 Million

Saudi Arabian billionaire Adnan Khashoggi was only 15 years old when he married United Kingdom native Sandra Daly in 1961. Converting to Islam, Daly changed her name to Soraya Khashoggi, and the couple raised five children together over the course of their marriage.

In 1979, the English ex-pat sued her prolific weapons dealer husband for $2.54 billion, which marked the largest sum ever requested in a divorce settlement to date. The former Mrs. Khashoggi ended up walking away with $874 million. It was a sum that reflected her unfathomable live of privilege, complete with 17 homes around the world, three private jets, and an ungodly amount of jewels.

5. Harold Hamm & Sue Ann Arnall: $974.8 Million

For most people, a $1 billion divorce check would feel far from small. But when Sue Ann Arnall — the ex-wife of Oklahoma oil tycoon Harold Hamm — received a settlement for this amount, she fought back for more money with guns blazing.

Arnall and Hamm were married for 26 years years before they filed for divorce in 2012. The chief executive of Continental Resources wrote a check to his ex-wife for $974.8 million dollars, but Arnall deemed the amount negligible compared to Hamm’s $18 billion fortune. She took the case to the Oklahoma Supreme Court to demand more money, but they ended up ruling in favor of the oil magnate.

4. Bernie Ecclestone & Slavica Radić: $1.2 Billion

The chief executive officer of Formula One racing Bernie Ecclestone met his former wife Slavica Radić while at a promotional event in 1982. Radić was working as a model at the event and quickly captured Ecclestone’s attention, who was 28 years her senior and a foot shorter than her.

The two tied the knot not long after and remained together for 23 years, during which time they had two daughters. Their marriage eventually turned sour, and Radić filed for divorce on the grounds of her husband’s “unreasonable behavior.” She was granted a $1.2 billion payout and topped the Sunday Times‘ list of Richest Divorcees.

3. Rupert Murdoch & Anna Torv: $1.7 Billion

When Australian media mogul Rupert Murdoch called it quits on his 32-year marriage with wife Anna Torv in 1999, he handed over $1.7 billion of his assets, with a staggering $110 million of it in cash. But the money wasn’t the most shocking part of the story.

What’s arguably just as shocking is the fact that Murdoch re-married within 17 days of his divorce being finalized. Torv revealed to Australia Women’s Weekly in 2001 that her ex-husband’s affair with Wendi Deng was an unoriginal plot to end their marriage. While she believed they had a “wonderful, happy marriage,” she said that he obviously had not.

2. Alec Wildenstein & Jocelyn Wildenstein: $3.8 Billion

Jocelyn Wildenstein — commonly referred to as “Catwoman” — went from billionaire to bankrupt in 2018. The Switzerland native reported that she was in millions of dollars of debt, despite winning an estimated $3.8 billion in her 1999 divorce settlement from French-American art dealer and businessman Alec Wildenstein.

The couple had been together for 13 years before Wildenstein pulled the plug on their relationship and gave his socialite ex $2.5 billion, plus an added $100 million every year over the span of 13 years. While an astonishingly large amount, the Catwoman’s funds seem to have disappeared only two decades later.

1. Jeff Bezos & MacKenzie Bezos: $35 Billion

It should come as no surprise that the person who tops our list of giving out the most expensive divorce settlement is also the richest man in the world: Amazon CEO Jeff Bezos. The multi-billionaire announced to the world in January of 2019 that he and his wife were splitting after 25 years of marriage.

As part of the settlement, Business Insider reported that author MacKenzie Bezos granted the Amazon mogul “all of her interests in the Washington Post and Blue Origin,” as well as voting rights in her share of the company. In turn, her ex-husband got 75% of the Amazon stock they co-owned together. This left MacKenzie with almost 20 million shares in Amazon, said to be worth $35 billion. All thanks to that, she now ranks as the third richest woman in the world.

Honorable Mention: Kelsey & Camille Grammer – $30 million

Star of famed sitcoms Cheers and Frasier, Kelsey Grammer, met his dancer/model ex-wife Camille on a blind date in 1996. A year later they were married. After thirteen years, Camille filed for divorce in 2010 citing Grammer’s unfaithfulness as reason for wanting out.

Though the couple share two children together and Camille has kept the last name Grammer, it appears there’s been no reconciliation between these two. Despite going separate ways a decade ago, the couple have given recent interviews alluding to a nasty breakup.

Honorable Mention: Hulk & Linda Hogan – $25 million

Divorces can be expensive, brother! After rumors (and later a video tape) emerged in 2007 reporting Hulk’s infidelities, wife Linda filed for divorce. What followed was a long, arduous settlement that took years to complete and was anything but amicable.

Since the split the former WWE star, who literally used to call everyone ‘brother’, eventually moved on, but not before going through some hard times as a result of the nasty breakup. He is now happily remarried and recently won a high-profile lawsuit against the media company that released the aforementioned tape.

Honorable Mention: Mick Jagger & Jerry Hall – $25 million

Gimme’ shelter….and millions of dollars! After nine years of marriage, Rolling Stones front man and model/actress Jerry Hall called it quits. Apparently, the relationship was troubled from the beginning (the two reportedly were involved with other people when they first met in the mid ’70s).

Both parties did not have any trouble moving on, however. Jagger reportedly was involved in multiple relationships, and most recently has been seeing Melanie Hamrick, a professional ballet dancer. Jerry Hall remarried to high-profile businessman, and fellow member of this list, Rupert Murdoch in 2016.

Honorable Mention: Johnny Carson & Joanna Holland – $20 million

Best known for hosting The Tonight Show With Johnny Carson, the famed television personality shocked guests of the show’s 10th anniversary party by announcing that he and former model, Joanna Holland, had been secretly married. Eleven years later Holland filed for divorce in 1983.

It took two years and an 80-page settlement to annul the marriage. All told, Holland ended up with $20 million in cash and obtained properties from Carson. Reflecting on his three marriages, Carson once joked, “Me giving advice on marriage is like the captain of the Titanic giving lessons on navigation.” Perhaps he was right.

Honorable Mention: Lionel Richie & Diane Alexander – $20 million

Former Commodore and music legend Lionel Richie tied the knot to second wife, Diane, in 1997 after being romantically involved for years. The couple had two children together, a son, Miles Brockman Richie, and Lionel’s youngest, active model, Sophia Richie.

No stranger to the world of fashion, former designer, Diane, made headlines by requesting an astounding $15,000 a month to go towards clothes, shoes, and handbags. All said and done, Lionel said hello to the single life, but not before saying goodbye to 20 million hard-earned dollars.

Honorable Mention: Jeff Gordon and Brooke Sealey – $15 million

Famed Nascar driver turned announcer, Jeff Gordon met Brooke Sealey in 1993 after winning the first two qualifying rounds for the Daytona 500. Sealey, a Winston Cup model, and Gordon at first had to hide their relationship due to an unwritten rule prohibiting drivers from dating the models.

What started in secret ended in headlines, with the couple filing for divorce in 2002. Despite efforts to dispute such a large settlement, stating that he had ‘put his life on the line’ to earn his living, Gordon was ordered by a judge to fork up a lump sum of $15 million.

Honorable Mention: Jennifer Lopez & Cris Judd – $6.6 million

Before moving on to A-list celebs like Marc Anthony and Alex Rodriguez, Jennifer Lopez married actor/choreographer Cris Judd in 2001. The second of Lopez’s four marriages (not counting multiple engagements), this relationship would prove to be the most short lived.

While $6.6 million might not seem like a lot of money compared to some of the other figures on this list, if you consider the duration of marriage, the total equates to over $750,000 a month! Lopez is of course currently engaged to former Yankees superstar Alex Rodriguez, and Judd remarried in 2009, welcoming a baby daughter in 2013.

Honorable Mention: Slash & Perla Ferrar – $6.6 million

Famed Guns N’ Roses guitarist, Slash aka Saul Hudson, and former model/actress wife, Perla Ferrar, called it quits after seventeen years of marriage. It took over four years for the divorce to be finalized after initially being filed in 2014.

All told, Ferrar collected over $6.6 million, two cars, a house in Los Angeles, and primary custody over their two children. Reportedly, the couple did not sign a prenuptial agreement, which entitled Ferrar to half of Slash’s annual income from 2001-2014. Now let that be a lesson to you!

Honorable Mention: Kris Humphries & Kim Kardashian – Unknown

Before marrying hip-hop icon Kanye West, Kim Kardashian was married (albeit briefly) to former NBA player Kris Humphries. The two wed in Montecito, California in a ceremony that was famously televised on E! After just seventy-two days of marriage, the couple filed for divorce citing irreconcilable differences.

While the amount of the couples’ settlement is not available to the public, it is known that Humphries got to keep, and later sold the 20-carat, $2 million dollar engagement ring that he used to propose to Kim. Reflecting on the marriage, Humphries admitted that he was lost, and in a ‘bad place’ during the course of their relationship.

Sources: Worthy, Insider, Wealthy Gorilla