Show Me The Money! Hollywood’s Top 20 Largest Divorce Settlements

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Apr. 21 2019, Updated 12:10 a.m. ET

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Marriages generally start in a great place—loving looks and gentle touches in public, and crazy hot sex in the bedroom. But the honeymoon doesn't last and at least half of all marriages end in divorce, often with one party parting with a lot of money.

MORE: Love Wins! 20 Celebrity Couples Who Survived Cheating & Sex Scandals

There are some insane amounts of cash exchanging hands when the rich and famous go bust. Just ask the likes of Paul McCartney, Phil Collins, Harrison Ford, and Michael Douglas. So just what are Hollywood's top divorce settlements?

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 MORE: Pay Up! Inside Brad Pitt's New Girlfriend Neri Oxman's Expensive Divorce

Check out who in Hollywood reached some of the biggest divorce settlements in history—including one that culminated in the billions!

1. Rupert and Anna Murdoch

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Settlement: Reportedly $1.7 billion

Rupert and Anna Murdoch had been together for 32 years when they divorced in 1999. It's reported that Anna took $110 million in cash, while the rest were in assets. Just over two weeks after the divorce, Rupert married Wendi Deng—they divorced in 2013—but that settlement was only purported to be in the hundreds of millions. So rather paltry in comparison.

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2. Steve and Elaine Wynn

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Settlement: Reportedly $741 million in stock

Steve Wynn, the hotel magnate, is living proof that if you don't learn from history, you're doomed to repeat it. He first married Elaine in 1963 but they divorced in 1986. Five years later, they remarried and it lasted until 2010 where things couldn't have gotten more bitter. According to Forbes, Elaine is now worth $2.5 billion while Steve is worth $3.5 billion.

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3. Mel and Robyn Gibson

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Settlement: Reportedly $425 million

Mel and Robyn Gibson spent 31 years together and produced seven children—until 2009 when she found out he was producing children with another production company (Oksana Grigorieva).

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4. Robert and Sheila Johnson

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Settlement: Reportedly $400 million

Robert Johnson was married to Sheila for more than 33 years and in that time, both of them co-founded BET which later sold to Viacom for $3 billion. Sheila has since become the second wealthiest black woman in the U.S. but not because of the settlement. She’s part-owner of several sports teams including the Washington Capitals (NHL), the Washington Wizards (NBA) and the Washington Mystics (WNBA).

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5. Michael and Juanita Jordan

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Settlement: Reportedly $168 million

Michael Jordan was with his wife Juanita for 17 years and had three kids—but it looked like it was all about to crash down in 2002 when she filed for divorce. Fortunately, they reunited but by 2006 finally realized there was nothing to salvage and it ended for good. Michael has since remarried.

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6. Neil Diamond and Marcia Murphey

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Settlement: Reportedly $150 million

Neil Diamond and Marcia Murphey were married for 25 years when it finally went south. Diamond's estate, valued at $300 million, was allegedly split in half with Ms. Murphey taking $150 million. Diamond now says the settlement isn't true but remains mum on what it was, saying only that Murphey "got enough to live on for the rest of her life."

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7. Garth Brooks and Sandy Mahl

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Settlement: Reportedly $125 million

Garth Brooks and Sandy Mahl split in 2001—to the tune of $125 million dollars, a price guaranteed to inspire hundreds of country songs. They'd been together since college and got married in 1986. They had three daughters. Brooks later married Trisha Yearwood in 2006 who he originally met in 1987.

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8. Tiger Woods and Elin Nordegren

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Settlement: Reportedly $110 million

Elin Nordegren watched as Tiger Woods crashed his Escalade into a tree back in 2009 then watched as he crashed his bank account into hers to the tune of an estimated $110 million dollars. In 2018, Nordegren listed her mansion for almost $50 million in order to "downsize."

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9. Greg Norman and Laura Andrassy

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Settlement: Reportedly $103 million

Greg Norman's 25-year marriage to Laura Andrassy scored her around $103 million dollars. The world's former number one golfer watched her score a hole in one—but has since gone on to marry again—twice. His next marriage, if he ever tees one up, will be number…fore.

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10. Steven Spielberg and Amy Irving

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Settlement: Reportedly $100 million

Steven Spielberg and Amy Irving's prenup was a novel affair in that it was written on the back of a napkin. But four years or so later, it wasn't novel enough for a judge who deemed it useless and gave Irving $100 million dollars. No word on what had been written on the napkin.

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11. Harrison Ford and Melissa Mathison

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Settlement: Reportedly between $85 million-$118 million

Harrison Ford met his screenwriter ex-wife Melissa Mathison (she wrote E.T.) on the set of Apocalypse Now in 1979. Because there was no prenup, it took almost three years to reach a settlement—hence the sketchy numbers. By all accounts, they remained on good terms until she passed away in 2015.

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12. Madonna and Guy Ritchie

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Settlement: Reportedly between $76 million-$92 million

Reports are sketchy about how much the actual 2008 divorce settlement between Madonna and Guy Ritchie was, as Madonna's publicist told the AP it was "between" $76 million and $92 million. They had one kid together and adopted another but the marriage ended when Madonna realized the romance had left the relationship.

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13. Kevin Costner and Cindy Silva

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Settlement: Reportedly $80 million

After sixteen years of marriage, Kevin Costner and Cindy Silva called it quits to the tune of $80 million dollars. Their relationship began in 1975 and lasted until 1994, bearing three children too. Costner has since remarried and had three additional kids.

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14. Kenny Rogers and Marianne Rogers

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Settlement: Reportedly $60 million

"Lady," sang Kenny Rogers, omitting the part about "you cost me $60 million." Kenny Rogers divorced from wife number four Marianne but maintains she deserves every penny. Awww. Classy.

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15. James Cameron and Linda Hamilton

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Settlement: Reportedly $50 million

James Cameron and his actress wife Linda Hamilton parted ways in 1999, costing Cameron $50 million. He'd already made Titanic by then so it could have sunk him. But Avatar was all his.

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16. Paul McCartney and Heather Mills

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Settlement: Reportedly $48 million

Heather Mills took Paul McCartney for an arm and a leg when their marriage ended after just four years to the tune of nearly 50 million dollars. Even McCartney had a little trouble flashing his trademark "thumbs up" sign after this one.

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17. Phil Collins and Orianne Cevey

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Settlement: Reportedly $47 million

The story of Genesis—from Phil Collins' point of view—cost him $47 million when he divorced Orianne Cevey in 2008. The three—Phil, Orianne, and the money—reunited in 2016.

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18. Michael Douglas and Diandra Douglas

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Settlement: Reportedly $45 million

In 2000, Michael Douglas split with wife Diandra—who then took home around $45 million (along with, presumably, the home). Michael's since moved on to Catherine Zeta-Jones.

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19. Kelsey Grammer and Camille Grammer

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Settlement: Reportedly $30 million

Kelsey Grammer married one-time MTV dancer Camille—who then danced all the way to the bank with a divorce payment of around $60 million. After 13 years together it was an ugly divorce but then, most are.

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20. Donald Trump and Ivana Trump

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Settlement: Reportedly $25 million

Donald Trump's often had to pay out lots of high-figure settlements—and one of them was to his first wife Ivana. At a paltry $25 million, however, it would seem that in this one case at least, Trump exercised the Art of the Deal.

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