DEMI MOORE & BRUCE WILLIS – SETTLEMENT: REPORTED $90 MILLION
In the ‘90s, Demi Moore and Bruce Willis were among Hollywood’s hottest pairings. But by the ‘00s, their marriage had run its course, and the couple decided to part ways. Their divorce proved to be an expensive one, with the Die Hard actor reportedly paying Moore $90 million.
The exes remained on good terms over the years as they co-parent their three daughters. They even quarantined alone with their children in 2020 after Willis’ current wife, Emma Heming, was unable to make it to the family’s Sun Valley, Idaho home before travel restrictions took effect.
STEVEN SPIELBERG & AMY IRVING – SETTLEMENT: REPORTED $100 MILLION
Director Steven Spielberg and actress Amy Irving pulled the plug on their union in 1989 after four years of marriage. According to Insider, the Carrie actress reportedly walked away with $100 million. But things could have easily turned out another way.
Apparently, the judge that presided over their case didn’t recognize their prenup. That’s because the agreement was only scrawled on, of all things, a napkin. Both went on to marry other people following their split. Spielberg, who is preparing for the release of his film West Side Story in 2021, is moving on with actress Kate Capshaw.
BEN STILLER & CHRISTINE TAYLOR – ONGOING: $200 MILLION AT STAKE
Zoolander actor Ben Stiller has been together with his wife Christine Taylor since 2000. That’s probably why the couple hasn’t quite made their separation final yet after announcing their split in 2017. In fact, they’ve even been spotted together at the Emmys two years later.
If the pair do end up finalizing their breakup for good, Stiller’s $200 million fortune will be at stake. It is not yet known if the couple signed a prenup. If they didn’t, Taylor might be entitled to half of that wealth. Things are still up in the air as the Meet The Fockers star is busy with his work with the United Nations.
MADONNA & GUY RITCHIE – SETTLEMENT: REPORTED $92 MILLION
During the happier times of their marriage, Madonna and her ex-husband Guy Ritchie were a power couple in the entertainment world. She’s the Queen of Pop, and he a hotshot English director. Unfortunately, their romance fizzled out in 2008 and led to a high-profile divorce. When their split was settled, the Sherlock Holmes director reportedly walked away with as much as $92 million.
That figure includes the couple’s country estate in Ashcombe, England, which alone costs $30 million. Today, Madonna and Ritchie have moved on, with both of them being in relationships. The Material Girl singer is dating dancer Ahlamalik Williams while Ritchie is married to Jacqui Ainsley.
ANGELINA JOLIE & BRAD PITT – ONGOING: $420 MILLION AT STAKE
Once among Hollywood’s most enduring couples, Angelina Jolie and Brad Pitt shocked the world when they announced their separation in 2016. The famous Brangelina was no more and worse; they spent the next years battling it out over child custody and the splitting of their properties.
As of 2021, their separation is not yet finalized. Together, they have a combined fortune of $420 million, which might be at stake as they settle matters. Last we heard, the Maleficent star was trying to sell their chateau in France, with Pitt allegedly blocking her attempts to unload the winery.
ELIN NORDEGREN & TIGER WOODS – SETTLEMENT: REPORTED $110 MILLION
Another controversial split that rocked the public around the same time is that of golf pro Tiger Woods’ and his ex-wife Elin Nordegren. Their breakup was marred with cheating accusations and setbacks in his sports career. There’s also the $110 million he reportedly had to pay out to settle the dissolution of his marriage to the mother of his two kids.
Aside from that sum, Norderdegren also received their home in Windermere, Florida, as well as $20K in payments for their children. Today, she is dating another sportsman in NFL star Jordan Cameron. Meanwhile, Woods made a successful golf comeback but is currently recovering after surviving a crash in February 2021.
MEL GIBSON & ROBYN MOORE – SETTLEMENT: REPORTED $425 MILLION
The year 2011 was extra tough for Braveheart actor Mel Gibson. Not only did he lose his better half in his divorce, but he also lost half of his fortune. And so, after 31 years of marriage, his ex-wife Robyn Moore reportedly walked away with $425 million.
That sum includes the fruits of Gibson’s work as an actor and director, not to mention the properties he’s acquired over the years. All’s well that ends well, though, as he has since moved on to date his current girlfriend, Rosalind Ross. Gibson is also busy working on multiple projects, including a feature called Stu, which would be directed by Ross.
HULK HOGAN & LINDA HOGAN – SETTLEMENT: AT LEAST $10.4 MILLION
Hulk and Linda Hogan were reality TV royalty in the ‘00s thanks to the success of their show Hogan Knows Best. Trouble came to paradise in 2007, though, when Linda chose to end their marriage after his alleged affair with his daughter’s friend came to light.
In the end, the couple arrived at an agreement that saw Linda receive at least $10.44 million from properties and joint financial assets. She also got a 40% ownership stake over the former WWE wrestler’s various companies. As of 2021, Hulk is still hard at work and owns a store called Hogan’s Beach Shop.
JUSTIN THEROUX & JENNIFER ANISTON – SETTLEMENT: UNKNOWN
Speaking of amicable celebrity breakups, let’s talk about Justin Theroux and Jennifer Aniston’s union. Although only married for two years, the pair remain good friends to this day. In fact, The Leftovers actor continues to talk fondly about his ex , saying that he cherishes her friendship.
That said, it’s safe to assume that the former couple didn’t have trouble dividing their marital possessions either, given their rather peaceful breakup. It is not known how much was involved in their separation. Both continue to be extremely wealthy as of 2021, though, with Aniston having the larger net worth of $300 million.
GARTH BROOKS & SANDY MAHL – SETTLEMENT: REPORTED $125 MILLION
Country artist Garth Brooks was married to his first wife, Sandy Mahl, for much of the biggest years of his music career. So, it comes as no surprise that she was able to walk away with a huge settlement when they called it quits when their separation was finalized in 2001.
Multiple sources put that amount at $125 million, which is among the largest payouts ever in terms of celebrity breakups. Moving forward, Mahl remained single and focused on raising their three daughters. The Dance singer, on the other hand, remarried and found continued success in music. As of July 2021, Brooks is back on his previously postponed stadium tour.
TED DANSON & CASEY COATES – SETTLEMENT: REPORTED $30 MILLION
The Good Place star Ted Danson had his fair share of relationships before he found love again with his current wife, actress Mary Steenburgen. He notably had a much-talked-about separation from his second wife Casey Coates in the ‘90s. Their marriage hit a rough patch after childbirth led to serious health complications for Coates.
With rumors of Danson’s secret relationship with then his co-star Whoopi Goldberg swirling, Coates separated from the Cheers actor. She got a reported $30 million sum in the end. Fast forward to 2021, Danson is celebrating the 26th anniversary of his marriage to Steenburgen.
WISSAM AL MANA & JANET JACKSON – SETTLEMENT: REPORTED AROUND $200 MILLION
It seemed like a fairy tale romance while it lasted. But pop superstar Janet Jackson and Qatari billionaire Wissam Al Mana’s marriage came to an end in 2017. The sad news came just months after the birth of their first child together.
According to sources, their divorce is being settled in London, with the All For You singer seeking full custody of their son Eissa. As of 2021, their split has not been finalized, yet it seems, but a $200 million sum is reportedly up for grabs. Jackson is currently living in the United Kingdom.
KEVIN COSTNER & CINDY SILVA – SETTLEMENT: REPORTED $80 MILLION
From college sweethearts to man and wife, Kevin Costner and Cindy Silva’s love story was truly an inspirational one. Even good things come to an end, though, as the pair decided to go their separate ways in the ‘90s after three kids and 16 years of wedded bliss.
Since they were married during The Bodyguard star’s peak years in Hollywood, Silva got a hefty sum upon their split. Forbes reports that she went home with $80 million, which was a huge chunk of his wealth at the time. Today, Costner, who last starred in Zack Snyder’s Justice League in 2021, is happily married to his second wife, Christine Baumgartner.
JOHNNY DEPP & AMBER HEARD – SETTLEMENT: REPORTED $7 MILLION
Going from an amicable split to an acrimonious one, let’s talk about Johnny Depp and Amber Heard’s infamous row. The pair pulled the plug on their marriage in 2017, with the Aquaman actress receiving a reported $7 million sum. She later pledged to donate it to the Children’s Hospital Los Angeles and the American Civil Liberties Union.
Depp contested that promise, though, in 2021 as the exes remain at odds with each other over years-long accusations of abuse from both parties. The Pirates Of The Caribbean actor notably lost a libel case against The Sun in 2020 over claims that he was an abusive husband to Heard.
NEIL DIAMOND & MARCIA MURPHEY – SETTLEMENT: REPORTED $150 MILLION 
While many Hollywood splits are filled with scandal, Neil Diamond and Marcia Murphey’s was among the more amicable ones. Some would even describe it as generous, with the latter receiving a $150 million settlement, half of the fortune the Sweet Caroline singer built over the 25 years they were married.
It’s not hard to see why the two parted ways on good terms. They shared a lot of happy times and saw their sons grow up together. In the end, Murphey even said that she was “worth every penny.” Diamond later remarried and continued to build his wealth through music. He released a record of his performances with the London Symphony in 2020.
MICHAEL JORDAN & JUANITA VANOY – SETTLEMENT: REPORTED $168 MILLION
NBA superstar Michael Jordan and Juanita Vanoy ended their 17-year marriage in 2006 after years of trying to salvage it. What resulted is one of the most expensive splits in sports history. When the matter was settled, Vanoy reportedly got a sum of $168 million.
The good news is that the exes parted amicably and maintained contact over the years for their children. Jordan, whose finances bounced back quite fast and is now a billionaire, married his second wife, Yvette Prieto, in 2013. As of 2021, the former Chicago Bulls player has a net worth of $1.6 billion.
MICK JAGGER & JERRY HALL – SETTLEMENT: RUMORED $41 MILLION
British rocker Mick Jagger and American stunner Jerry Hall took their split to a different level when they opted for an annulment in 1999. The Rolling Stones singer’s legal representation claimed that his Bali, Indonesia nuptials with Hall was invalid. This was corroborated by the High Court of Justice.
Still, The Independent reports that Hall possibly got $41 million from her ex during the proceedings. She went on to marry media magnate Rupert Murdoch in 2016. Meanwhile, Jagger never remarried but embarked on other long-term relationships over the years. As of 2021, he’s with dancer Melanie Hamrick.
MARIAH CAREY & JAMES PACKER – SETTLEMENT: REPORTED $5 – 10 MILLION
Now, songstress Mariah Carey and Australian billionaire James Packer’s split is a bit different. See, they never made it down the aisle because of a contentious split after he popped the question. According to a People report, the We Belong Together singer asked for $50 million to settle their breakup.
In the end, though, sources say that she was only granted between $5 to $10 million. That includes the flashy engagement ring she received from Packer in 2016. He continued to speak highly of Carey, who launched a new business called Mariah’s Cookies in 2020, following their split describing her as a woman of substance.
PHIL COLLINS & ORIANNE CEVEY – SETTLEMENT: REPORTED $46.6 MILLION
Phil Collins and his third wife, Orianne Cevey, had a fairytale romance. They met in snowy Switzerland during a tour in the ‘90s and married just a couple of years later. However, their union fell apart in the mid-’00s leading to the start of an expensive and messy split.
The In The Air Tonight singer reportedly paid Cevey around $46.7 million to settle matters. Despite rekindling their romance, the pair came to a head again in 2020 when Cevey allegedly refused to leave Collins’ Miami Beach property, saying she has an ownership stake in it.
PAUL MCCARTNEY & HEATHER MILLS MCCARTNEY – SETTLEMENT: REPORTED $48.7 MILLION
The Beatles member Paul McCartney found love in the arms of Heather Mills following the tragic death of his beloved first wife, Linda. Unfortunately, that romance ended on a sad note, too, when McCartney and Mill’s marriage fell apart rather acrimoniously in 2008.
The English activist reportedly sought $250 million from her ex but was only granted $48.7 million after their divorce mediation. That latter sum amounts to about $34K for each day of her four-year union with the Wings singer. As of 2021, McCartney is married to Nancy Shevell and still making music with the release of his 18th album.
JAMES CAMERON & LINDA HAMILTON – SETTLEMENT: REPORTED $50 MILLION
He was a blockbuster director. She was a silver screen leading lady. But James Cameron and Linda Hamilton’s romance didn’t last forever despite them being well-matched. After a brief marriage, the pair decided to get the divorce papers out in 1999, with The Terminator star leaving with a reported $50 million sum.
It all turned out for the best, though, as they both continued to thrive apart from each other. Cameron, who married Suzy Amis in 2000, is currently gearing to release his much-anticipated Avatar sequels. Meanwhile, Hamilton carried on playing the tough female roles she’s known for. We last saw her in the 2021 TV series Resident Alien.
KENNY ROGERS & MARIANNE GORDON – SETTLEMENT: REPORTED $60 MILLION
Here’s more reason to love the late country star, Kenny Rogers. Upon the settling of his separation from his fourth wife, Marianne Gordon, The Gambler singer didn’t seem to have hard feelings about how things ended. Gordon was granted $60 million, which Rogers said she deserved after standing by him even when money was steep.
He even revealed in an interview that the Hee Haw star got along well with his fifth wife, Wanda Miller. Gordon, whose marriage with the Islands In The Stream singer lasted from 1977 to 1993, also remembered him fondly following his death at 81 in 2020.
CHANNING TATUM & JENNA DEWAN TATUM – SETTLEMENT: UNKNOWN
With their good looks and shared passion for dance, it really seemed like Step Up co-stars and former couple Channing Tatum and Jenna Dewan were a match made in heaven. Unfortunately, their romance fizzled out in 2018 after nine years of marriage and welcoming a daughter together.
But while their breakup was finalized a year later, the exes are reportedly still battling it out in court to settle financial matters. According to a 2021 PageSix report, Dewan is seeking mediation when it comes to her share of the Magic Mike franchise’s income.
BILLY BUSH & SYDNEY DAVIS – SETTLEMENT: UNKNOWN
TV host Billy Bush and his wife Sydney Davis were on the road to celebrate two decades of wedded bliss when they pulled the plug on their marriage. The split was reportedly caused by a resurfaced tape of the Today co-presenter with Donald Trump bragging about groping women.
Bush and Davis finalized their separation in 2019 but did not disclose the specific details, including custody matters, of their settlement. Rehabilitating his image in the years that followed, the Bush political family member landed a job hosting Extra, which he still has as of 2021.
JANE FONDA & RICHARD PERRY – AMICABLE SPLIT: UNKNOWN
Veteran actress Jane Fonda has walked down the aisle quite a few times. So, she definitely knows a thing or two about going through a divorce, too. That said, it’s no surprise that the Grace And Frankie star parted ways without hard feelings from her music producer boyfriend, Richard Perry, in 2017.
The pair began dating in 2009 and even lived together in a four-bedroom home in Beverly Hills. Although they weren’t married, they shared the estate and listed it for almost $13 million before they called it quits. As of 2021, Fonda says that she’s done with relationships.
MARC ANTHONY & SHANNON DE LIMA – SETTLEMENT: ESTIMATED $360K
Latin superstar Marc Anthony has had several high-profile marriages throughout his three-decade career. The last being with Venezuelan model Shannon de Lima, who he married in 2014. They called it quits just two years later, with some saying that their breakup was prompted by an onstage kiss Anthony shared with his ex-wife Jennifer Lopez.
De Lima denied those claims saying she got along well with the Selena actress. In the end, the couple’s separation was finalized in 2017, with de Lima receiving $10,000 a month for three years. That amounts to about $360K in total. Anthony is currently preparing for a tour of the Americas and Spain that would last until 2022.
RUPERT MURDOCH & WENDI DENG – SETTLEMENT: UNKNOWN
From the moment they exchanged vows on a luxury yacht, Rupert Murdoch and Wendi Deng’s married life was one of grandeur. Their separation in 2013 was no different. With billions at stake, the media tuned into the estranged couple’s negotiations.
They settled matters in the same year but didn’t publicize the exact figures involved in the case. Deng did get to continue living in the family’s Fifth Avenue penthouse, though, together with their two daughters. Meanwhile, Murdoch went on to marry Jerry Hall in 2016 and is worth $22.2 billion as of 2021.
CHRIS PRATT & ANNA FARIS – SETTLEMENT: REPORTED $0
Once one of Hollywood’s enduring couples, comedic duo Chris Pratt and Anna Farris called it quits in 2017. Both rich movie stars in their own right, the exes notably waived their right to spousal support and child support. What’s more, they agreed to share custody of their son Jack without much contention.
Compared to other Hollywood splits, theirs was definitely an amicable one. Years later, and it looks like their setup is working just fine. Pratt, who we’ll see next in Thor: Love And Thunder in 2022, is married to Katherine Schwarzenegger. Meanwhile, Farris is dating cinematographer Michael Barrett.
REBA MCENTIRE & NARVEL BLACKSTOCK – SETTLEMENT: REPORTED $47.5 MILLION
Country star Reba McEntire and her music manager ex-husband Narvel Blackstock were another power couple whose union lasted decades. But as with many on our list, they ended up pulling the plug on their marriage and announced their decision to split in 2015.
Things moved fast from there, and the couple settled things just months later. The exes kept the details of their separation under wraps, but some sources say that it involved a $47.5 million settlement. Last we heard, the How Blue singer is still incredibly wealthy and active in the music scene. She most recently performed at Macy’s 2021 Fourth of July celebration.
TOBEY MAGUIRE & JENNIFER MEYER – ONGOING: $75 MILLION AT STAKE
While some celebrity exes move fast, some take their time when splitting up. That’s the case with Spider-Man actor Tobey Maguire and his ex-wife Jennifer Meyer. After announcing their separation in 2016, the pair reportedly filed for divorce in 2020, citing irreconcilable differences.
Fortunately, the exes seem to have parted on good terms with Meyer, even writing a Father’s Day message for Maguire months before making their split official. The proceedings are likely still ongoing as of July 2021, but it’s safe to assume that his $75 million fortune might be at stake.
MIRANDA LAMBERT & BLAKE SHELTON – SETTLEMENT: UNKNOWN
Before Blake Shelton wed his longtime love, Gwen Stefani, in July 2021, The Voice coach was hitched to country singer Miranda Lambert. The exes parted ways in 2015 in a rather cut and dry separation that saw them divide their most precious assets.
The two reportedly had a prenup, which might explain the fast pace they settled their split. Lambert notably walked away with the pets as well as their Nashville home while Shelton kept their Oklahoma ranch. However, there are no exact figures detailing exactly how much cash was involved in the separation.
BILL GATES & MELINDA GATES – ONGOING: $128 BILLION AT STAKE
With their shared passion for charity, it truly seemed like Bill and Melinda Gates’ union was bound to go the distance. That’s why many were shocked when they announced their separation in May 2021 after 27 years together. What’s more, people are curious about how their split would affect the Microsoft co-founder’s $128 billion fortune.
According to Forbes, Melinda can go home with about $65 billion if they end up agreeing on a 50-50 split. The publication also reported that the estranged couple has begun dividing their assets already ,with Bill transferring almost $2.4 billion in securities to Melinda.
DAVID SCHWIMMER & ZOE BUCKMAN – SETTLEMENT: UNKNOWN
David Schwimmer and his former wife Zoe Buckman are proof that exes don’t need to be enemies when all’s done. Married in 2010 and divorced in 2017, the pair remains on friendly terms with each other to this day. So, while they didn’t publicize the details of their split, it’s safe to say that they settled financial and personal matters just fine.
Buckman, who is a professional photographer, has even been spotted hanging out with the Friends star as they co-parent their daughter Cleo. As of 2021, Schwimmer doesn’t appear to be dating anyone new but is busy starring in the British TV series Intelligence.
LOGIC & JESSICA ANDREA – SETTLEMENT: UNKNOWN
Fame can be a difficult thing to navigate for a couple. That seems to be the case with the rapper Logic and his ex-wife Jessica Andrea’s separation. Married in 2015, the pair headed for a split in 2018 following the success of his song 1-800-273-8255.
According to TMZ, Andrea walked away with an unspecified amount of money as well as her Chrysler. Meanwhile, Logic kept their home and wasn’t obliged to pay any spousal support. He went on to marry blogger Brittney Noell in 2019 and welcomed their first child together in 2020.
ARNOLD SCHWARZENEGGER & MARIA SHRIVER – SETTLEMENT: REPORTED $250 MILLION
While Arnold Schwarzenegger’s marriage to Maria Shriver had its highs, it also had lows. Among the latter is the revelation of the Terminator star’s affair in 2011, which then led to the couple’s separation. According to NBC San Diego, the former governor of California ended up paying Shriver $250 million, maybe even as much as $375 million.
However, it’s also worth noting that their split is yet to be finalized as of 2021. Rumors are swirling that they’re in the process of doing so soon, though. For now, Schwarzenegger seems busy with work as he prepares to star in a film called The Legend Of Conan.
EWAN MCGREGOR & EVE MAVRAKIS – SETTLEMENT: UNKNOWN
Ewan McGregor’s split from his wife of over two decades, Eve Mavrakis, caused quite a stir in 2018. That probably has to do with the whispers that he had an affair with his Fargo co-star Mary Elizabeth Winstead. In the end, Mavrakis, who is the mother of four of McGregor’s children, walked away with an unspecified amount.
According to Us Weekly, the exes would split his Star Wars royalties as well as residuals from the projects he worked on prior to their separation. Last we heard, McGregor and Winstead welcomed a son together in June 2021.
NAOMI WATTS & LIEV SCHREIBER – AMICABLE SPLIT: UNKNOWN
Hollywood stars Naomi Watts and Liev Schreiber quite the picture-perfect life together with their two children during their 11 years together. So, it’s no surprise that many fans were saddened to hear about their decision to split up in 2016.
Since the pair was never married, it’s difficult to ascertain whether they had to divide up their fortune following their breakup. What’s clear, though, is that they remain on friendly terms despite everything. Watts, who we’ll see next in the 2021 film Lakewood, moved on to date actor Billy Crudup. Schreiber, meanwhile, is with Taylor Neisen.
CHRISSY METZ & MARTYN EADEN – SETTLEMENT: UNKNOWN
This Is Us breakout star Chrissy Metz had already gone through a lot even before we met her as one of The Big Three. That includes the dissolution of her marriage with her ex-husband Martyn Eden. First meeting on a dating app, they were wed in 2008 and were divorced come 2013.
That said, not much is known about the specific details of their separation. Metz says that she still checks on her ex and is working on being “a better ex-wife.” The one-time Emmy nominee is set to reprise her role in the hit NBC drama’s upcoming new season.
JACK OSBOURNE & LISA STELLY – SETTLEMENT: UNKNOWN
We first met a young Jack Osbourne as he starred in his family’s hit reality TV show The Osbournes in the ‘00s. Seeing him grow up over the years, we’ve also sadly watched him get his heart broken. That happened when he and his ex-wife Lisa Stelly called it quits in 2018.
Fortunately, their breakup seems to have ended without much public drama. An Entertainment Tonight report says that Osbourne paid a sizeable sum for child support and got joint custody of their three children. Last we heard, he celebrated 18 years of sobriety in 2021 and is still co-parenting with Stelly.
RACHEL BILSON & HAYDEN CHRISTENSEN – AMICABLE SPLIT: UNKNOWN
Jumper co-stars Rachel Bilson and Hayden Christensen broke up even before they got the chance to tie the knot. The pair dated for about a decade until 2017, when they announced that they were done for good. They share a daughter, who was born during their long engagement in 2014 and co-parent her together to this day.
Since they were never married, it remains unclear how Bilson and Christensen divided their shared possessions following the split. As of 2021, neither of them have married, although The O.C. actress was rumored to be dating comedian Bill Hader.
JEFF BEZOS & MACKENZIE SCOTT – SETTLEMENT: REPORTED $38 BILLION
With an eye-popping fortune worth over $200 billion, Jeff Bezos is the reigning richest person in the world in 2021. What’s even more impressive is that he managed to grow his wealth by that much even when he forked over $38 billion in Amazon shares to his ex-wife MacKenzie Scott (formerly Bezos) in 2019 during their high-profile separation.
Scott then went on to earmark half of her fortune for donation. Since then, the American novelist has remarried and is now the wife to Seattle educator Dan Jewett. Meanwhile, Bezos moved on to date entertainment reporter Lauren Sánchez.
KATE BECKINSALE & LEN WISEMAN – SETTLEMENT: UNKNOWN
Like many Hollywood pairings, exes Kate Beckinsale and Len Wiseman met on the job. In their case, it was the set of Underworld in 2003. They were married just a year later. Unfortunately, their whirlwind romance didn’t translate to a lifelong love as they went their separate ways in 2015.
The dissolution of their union was finalized in 2019, with Beckinsale reportedly getting to keep all of her post-split earnings. She went on to date a string of comedians as a newly single woman, including Saturday Night Live star Pete Davidson. Catch her next in her upcoming film Jolt in 2021.
HARRISON FORD & MELISSA MATHISON – SETTLEMENT: REPORTED $85 MILLION
Harrison Ford may be happily married to Calista Flockhart today, but he had to part with a serious amount of cash to his second wife, Melissa Mathison, first. According to Forbes, he paid $85 million, a huge chunk of his earnings, to settle his breakup with the late E.T. screenwriter in 2004.
By that time, the pair was married for 21 years and shared two children. The Star Wars actor remarried in 2010 and has pretty much earned back that payout as he remains in demand today. His next giant payday will come around 2022, when his upcoming Indiana Jones project is released.