When a couple breaks up, no matter how long they were happy together, or even how long they were miserable together, it is seldom easy or seamless, and there's always a broken heart involved.

When celebrities break up, there’s a lot more than just broken hearts on the line; there are whole estates. Without an iron-clad prenup for the A-listers, things can get a little pricey. The beautiful people spend the better part of their lives acquiring mansions, cars, various collections, and even in some cases, children. Of course, every bit collected before and during a marriage is fair game for what jilted exes believe is owed to them.

Depending on the level of fame and fortune, some of these settlements can set up an ex for life and way beyond. Read on to see what some of the most expensive divorces in celebrity history are.

Angelina Jolie And Brad Pitt

They met on the set of Mr. & Mrs. Smith back in 2005. Two of Hollywood’s most beautiful people, Brad Pitt and Angelina Jolie were starring as a bored married couple who were each leading a double life as assassins, and then they both find out about it. Rumors were immediately swirling that Brad had cheated on his then wife Jennifer Aniston with the then-sexpot, Jolie.

No matter how ridiculous the settlement is, as it stands right now, the Jolie-Pitts were together since 2006, and have been married since 2014.

They have earned over $600 million together with a slew of property, including a Villa and Winery in France, as well as two houses in California and one in New Orleans.

Not to mention custody of all six kids…King Solomon couldn’t split this up amicably. No matter how they hooked up, eventually the words Brangelina and Team Jen became part of the lexicon and the two actors became a globe-trotting pair, adopting three kids and having three of their own. Despite the misgivings about how it started, plenty of people were still shocked when the pair called it quits in 2016.

Madonna And Guy Ritchie

For someone who has always been depicted as a voracious man-eater, you'd think Madonna would have better lawyers. After all, her latest ex-hubby, British film director Guy Ritchie certainly plenty of his own pounds to spend, thanks to directing hits like Snatch, and the Robert Downey Jr. Sherlock Holmes movies.

He was still able to grab a cool $50 to $60 million pounds ($76-92 million dollars) and maintain ownership of the couples’ pub, The Punchbowl.

The couple combined was worth over 500 million, but Madge has been wowing crowds since the early eighties, and Ritchie's first big break in movies didn't come until over a decade later with Lock, Stock, And Two Smoking Barrels. Since Ritchie makes significantly less, somehow that entitles him to more of Madonna’s money for whatever the reason.

The two have shared custody of their two children and Madonna’s oldest, Lourdes from another relationship.

Britney Spears And Kevin Federline

Never before in history had a man with so little, achieve so much. At the time of Kevin Federline’s marriage to Britney Spears, the greaseball’s listed occupation was “pizza delivery boy and dancer.” Not to knock pizza delivery boys, but can you see the pimply-faced kid coming to your door to give you a pie marrying a famous pop star?

Nevertheless, somehow the guy managed to ruin Britney forever since her name will forever be linked to his. To add to the absurdity of all of this, K-Fed had left a pregnant girlfriend to wed Britney at the time.

Federline got $500K for each year they were married, half the worth of their Malibu home, and the real kicker – $25K a month for child support and HE gets the boys four days a week.

So, for all of us losers out there, K-Fed will forever be the measuring stick for how you could overachieve by doing absolutely nothing.

Charlie Sheen And Denise Richards

In hindsight, no one should be shocked that Charlie Sheen had a failed marriage. He loves drinking, drugs, and philandering around – why any woman thought they'd be able to make an honest man out of him is beyond us. Or maybe that was the point; get inside with one of the biggest names in Hollywood for enough time before you carve out a piece of his wallet with a handy divorce lawyer.

Denise gets $52,000 a month for child support, and $60,000 for alimony.

Somehow, Denise Richards was only wife number two for Sheen. The pair married in 2002, and anyone can bet on what eventually ended this marriage. Apparently, he was fascinated with young boy p*rn, finally ending the marriage. This only came to light last year with allegations against Sheen.

Prince Charles And Princess Diana

The wedding of Charles, the Prince of Wales and Lady Diana Spencer was something the entire world bore witness to. Similar to their eldest son, William in this century, the wedding was watched by a global audience of over 1 billion people, and London declared the day a national holiday. Diana would traverse the globe to try and use her title to help people. Charles would eventually cheat on the future queen with Camila Parker Bowles.

Talk about a prenup! Since she was regarded as pretty much the sweetest lady on the planet, combined with the fact that she was mother to the future king, Diana remained in good standings.

Diana remained a member of the royal family and kept her title as the Princess of Wales. She would continue to receive all of the accoutrements of a Princess, until her untimely and tragic death in 1997.

Diana famously commented, “Well, there were three of us in this marriage so it was a bit crowded.”

Johnny Depp And Amber Heard

For over ten years, during his rise from quirky actor to superstar, Johnny Depp seemingly had a fairytale romance with girlfriend, and gorgeous French star, Vanessa Paradis. Together, they had two kids, at least one horse, and a palatial estate and winery in France.

They separated in 2012 and somehow the outlaw actor found his way to marrying Amber Heard in 2015. 23 years his junior, they had a fairly mundane relationship. That is, until the end came, barely 15 months after getting hitched. While she didn’t get nearly as much as every other divorcee on this list, she certainly gave her spouse the biggest headache; or at least the most publicized one.

Heard was only awarded $7 million, which she claimed she would be donating to the ACLU

Heard filed a restraining order, citing abuse, which both his daughter and ex Vanessa both scoffed at. A judge denied Amber’s request for sole possession of the couples’ dog. Friends came to Depp’s defense and stated Amber Heard was trying to blackmail Johnny, which she denied. For whatever reason, she retracted her request for $50K a month in spousal support.

Michael Jordan And Juanita Vanoy

Ask anyone born in the early eighties, basketball fan or not, who the greatest player of all time is and more likely than not, an image of the tongue-wagging, dunking-from-the-free-throw-line number 23, Michael Jordan would instantly be conjured. True he had a phenomenal Bulls team behind him, but he was clearly the reason the team won six titles and dominated the sport. All of that greatness yielded “His Airness” a whole lot of scratch.

By the end of the road, Ms. Vanoy ended up with $168 million dollars, which was the largest celebrity divorce at the time.

Before that however, they lived a pretty decent life. On his way to becoming the best player ever, he married Juanita Vanoy during his second season with the Bulls in 1989. Together, they had three kids but in 2002 the wheels of their marriage began to fall off. They tried to make things work but were back on the divorce track in 2006. Jordan and Juanita finally and officially called it quits, ending the marriage “mutually and amicably.”

Mel Gibson And Robyn Moore

Say what you will about Mel Gibson, but between his professional and personal life, when it’s all said and done, he will have one of the most interesting biographies that an actor could have. An upstate New York native, who was raised in Australia, Gibson made his mark in the Mad Max series, before becoming a Hollywood heartthrob for the ladies, and a hero for the boys in the Lethal Weapon movies. All of this before the mid-nineties, when he seemingly took over the world and starred in all kinds of classics. Shortly after Mad Max took off, Gibson married Robyn Moore in 1980. Way to get a prenup Ms. Moore!

She was entitled to half of all of Mel's earnings. The prenup allowed her to get $425 million dollars, over $140K for every year of their 30 years together.

The divorce was finalized in 2009, after Gibson was spotted with Oksana Grigorieva, and after his racism scandal, Robyn Moore was probably more than glad to be rid of him.

James Cameron And Linda Hamilton

Epic director James Cameron is a workaholic who also doesn’t seem to want to come home to an empty house. The guy has been married five times! Either that, or he just likes dating and then marrying his producers and stars. By the time he started to fall for his Terminator starlet, Linda Hamilton, the Avatar auteur had already been married twice.

Cameron and Hamilton had been dating in 1991, when she was at her most buff and badass, coming off the heels of her performance in Terminator 2, and the pair had dated for six years until marrying in 1997, when Titanic took over the world. Needless to say, one of the stars of that film was pretty face, Susan Amis, (who played Rose’s granddaughter), would soon find herself dating her director.

For his indiscretions, Hamilton terminated the marriage and was awarded $50 million dollars. 

Being wife number three, she should have seen it coming. To be fair, Amis has seemingly found a way to keep Cameron faithful, as the pair have been married since 2000.

Tiger Woods And Elin Nordegren

There was a time when Tiger Woods was the most well-known athlete in the world, and simply known for being the wonder-kid who had taken the golfing world by storm and usurped the culture of the sport. There was a time when Swedish beauty, Elin Nordegren, was just a nanny to one of Tiger’s fellow players on the PGA tour. With several other golfers trying to take their swing at the blond bombshell, it would be Tiger who would end up marrying her in 2004.

After a crazy car accident in 2009, Woods’ infidelity was revealed, and in 2010, the $100-million-dollar divorce was finalized.

From a girl working at a boutique in Sweden, to a nanny for Jesper Parnevik, to a very wealthy woman thanks to her ex-hubby’s philandering ways - don't let anyone tell you it doesn't pay to be beautiful.

Rupert Murdoch And Anna Torv

A media mogul of the highest order, Australian-born Rupert Murdoch is the owner of Newscorp and 21st Century Fox. There's not a whole lot the guy can't handle or influence can't reach. According to ex-wife Anna Torv (no not that actress that starred on Fringe and now Mindhunter, this is her aunt), Murdoch was as ruthless in ending their marriage as he was in business.

The couple stayed together for 32 years, 1967-1999, until the mogul started seeing Wendi Deng, who was 30 at the time. She said, “He was extremely hard, ruthless and determined that he was going to go through with this, no matter what I wanted or what I was trying to do to save the marriage. He had no interest in that whatsoever.”

Tory received over one billion in assets, including $110 million in cold hard cash.

While Torv might have been heartbroken, surely becoming a billionaire helped mend Torv’s feelings and help her move on. The settlement might be the largest in recorded history.

Steven Spielberg And Amy Irving

Thanks to Robyn Moore and Amy Irving, we now know how important it is to sign prenuptial agreements, especially when it comes  to Hollywood marriages. After all, both Moore and Irving wound up walking away with half of their respective exes’ fortunes at the time of their divorces. Although, Irving had to jump through a few more hoops to get what was owed to her thanks to her marriage to Steven Spielberg.

The couple met in 1976 and were off and on until marrying in 1984. She wanted to be known for being an actress and not just Spielberg’s wife, and the trials of trying to make a name for herself independently took a toll on their marriage.

Since their prenup was simply written on a dinner napkin, it was contested in court. Their judge ruled that it counted, and Irving walked away with over $100 million.

Not bad for “just being” Steven Spielberg’s wife.

Kelsey And Camille Grammer 

For over thirty years, Kelsey Grammer has made a name for himself playing the voice of Sideshow Bob on The Simpsons, and of course Dr. Frasier Crane on not one, but two series. Sprinkle in a few other roles, as well as producing duties for a few more, and you have an actor who is pretty well off.

His third wife Camille, was a Playboy model who was trying to break into Hollywood, having parts in Private Parts and Club MTV. The two met in 1996 and married in 1997. By 2009, the bloom had come off the rose and the two began divorce proceedings.

When it came to the end, she ended up getting $60 million for irreconcilable differences.

She cited verbal abuse, while he surmised that she had thought she was marrying Frasier Crane. Grammer remarried flight attendant, Kayte Walsh just two weeks later.

Johnny Carson And Joanna Holland

If you ask comedians who their biggest influence was, nine times out of ten, they'll tell you that the person they looked up to was none other than the king of late night, Johnny Carson. In an era before instantly being able to watch anyone and anything, Johnny was on our TV’s making entire families howl with laughter every night for thirty years. During a celebration for the tenth anniversary of the show in 1972, he announced he had married Joanna Holland earlier that afternoon.

Needless to say, friends and associates were shocked since it was so sudden, but their love did last a few years until their divorce in 1985.

Holland walked away with $35 million in cash and property.

The king of late night reportedly also ripped up their prenup agreement, which is how Holland was able to get so much of Carson’s money and property.

 Kevin Costner And Cindy Silva

Like many of us who fell in love in college, Hollywood heartthrob, Kevin Costner also fell for his. He married Cindy Silva in 1978 after dating for three years. That was before Costner became a star and before he became eye candy for plenty of ladies in the eighties.

One of the easier divorces on this list, it cost the Field Of Dreams star only $80 million dollars.

According to an article in People, when the couple split, Silva was getting tired of the one-two punch of Costner’s sexy leading man roles and her hubby’s wandering eyes. In 1994, after sixteen years together, she got fed up and the couple amicably resolved all of their issues.

Harrison Ford And Melissa Mathison

Harrison Ford and Calista Flockhart  had been together so long that none of us really knew when it started. They dated for several years, before they decided to get married in 2010. Prior to this current marriage however, Ford was with screenwriter, Melissa Mathison.

While you might not know that name, here are several films she wrote up until her death in 2015 - E.T., Twilight Zone: The Movie, and The Indian In The Cupboard. While her husband was adventuring as Han Solo and Indiana Jones, she too was writing some of the most memorable adventures of the eighties and nineties.

Mathison was awarded between $85 and $118 million, plus royalties from several of Ford’s blockbusters, which included two Indy flicks, The Fugitive, and Air Force One.

Their divorce was finalized in 2004, and is still considered one of the biggest in Hollywood history.

Neil Diamond And Marcia Murphey

Thanks to “Sweet Caroline,” being played at every Red Sox home game, Neil Diamond most likely will be getting royalties until his grandkids have grandkids. Of course the Basher has a plethora of other songs in his catalogue that have captivated fans for years. The Solitary Man also has hits like “You Don't Bring Me Flowers,” and “America.”

The Rock and Roll hall of famer also had a few stints of marriage too. Following marrying his high school sweetheart, Diamond married production assistant Marcia Murphy in 1969.

After 25 years of marriage, they filed for divorce, awarding Murphy with $150 million.

Interestingly, Diamond was actually happy to pay it, and he took full responsibility for the end of the marriage.“I assume a lot of responsibility for what went wrong,” Diamond told people. “But I was taken aback by how many friends dropped me."

Garth Brooks And Sandy Mahl

Somehow, Garth Brooks finds himself in the upper echelon of musicians, second only to Elvis and the Beatles as far as sales go. In 1986, before his career took off, he married his college sweetheart, Sandy Mahl. Mahl had gotten Brooks’ attention when the two met in an Oklahoma bar where Brooks was working at the time. After 15 years and three kids together, the pair called it quits in 2001.

The end of their marriage would cost the country crooner $125 million, which is still one of the biggest payouts for a divorce ever.

Mahl would take her money and use it to open up the Wild Heart Ranch in the former couple’s home state of Oklahoma. Brooks would bounce back relatively nicely, marrying fellow country singer Trisha Yearwood in 2005, who herself was worth 40 million at the time.

Paul McCartney And Heather Mills

If you believe in hoaxes and conspiracies, then this marriage should have been annulled long before it actually ended in 2008. After all, the real Paul McCartney has been dead since 1966, if you believe the long-guarded theory.

All kidding aside, after McCartney’s first marriage to Linda Eastman ended with her tragic death to cancer, he began being seen with former supermodel, Heather Mills. Paul didn't practice what he sang however, and love was not all he and Heather needed when the couple divorced shortly after getting together.

Mills was awarded 24.3 million pounds ($38.5 American), plus 35K pounds ($70K American) every year in child support for the couple’s daughter, Beatrice.

Combine that with fees for the nanny and schools, and the one-legged model made off like a one-armed bandit.

Donald And Ivana Trump

Here’s Donald and Ivana’s marriage in a nutshell. In an episode of the Something To Wrestle With podcast, Bruce Prichard recalled a story from Wrestlemania V, which emanated from the Trump Plaza in Atlantic City. It involved Jake the Snake Roberts, who was going to hurl his beloved snake Damian at his opponent, who would duck and the snake would land on Ivana.

Trump laughed, but Ivana wanted her security detail to make boots out of the reptile. At least back then, Trump was in on the joke and not seemingly trolling everyone. When Ivana filed for divorce in 1992, the now-president had the gall to devalue his estate to mitigate what she would be able to get after 15 years of marriage. As much as she would have gotten, we still shouldn’t feel bad for her.

She wound up with $14 million dollars, as well as some of his property.

Ivana got their estate in Greenwich, Connecticut, an apartment at Trump Plaza, and every March full use of the Donald’s Palm Beach mansion. She also dodged a big-time bullet of being the First Lady Of The United States.