Apart from the perceived happily ever after ending of a classic rom-com, those celebrity hookups we see in the gossip columns infrequently work out. Not that every single one of them is doomed, but more often than not after a few years, the Brangelina's and Bennifer's of this world fall apart.

While there are several lessons from these failed relationships, not coming up with a portmanteau isn't one of them. Divorce being expensive is one, and the reason, therefore, can be the same, no matter what the actual reason. Sometimes, you realize you don't want to split, as one of these celebrity encounters proved.

Robin Wright and Sean Penn - $61 Million

Even today, it's not clear whether Sean Penn and Robin Wright are actually split. Okay, that is a bit of an overstatement, but they threatened to do it so many times that no one believed them when they actually did. It all started after Penn divorced Madonna in 1989.

Wright moved in with Penn, and they had two children. But in 1995, they split, only to reconcile and get married in 1996. Then in 2007, they both filed but reconciled again. Then Penn filed in 2009, only to withdraw. In 2010, Wright filed, and the marriage was over in July that year... allegedly.

 

Madonna and Guy Richie - $75 Million

We're not sure what Guy Ritchie thought he was getting himself into when he married Madonna, but he clearly wasn't ready for it. It's not the fact that they were one of the most talked-about celebrity couples at the time. Or that everything was a little over the top, as their wedding was in a Scottish Castle.

What got to Ritchie was that Madonna started feeling that her status meant she had to be a hero. Over time it just got too much, and the spark fizzled out of the relationship. They divorced with irreconcilable differences, and Ritchie got a tidy settlement of $75 million.

Tiger Woods and Elin Nordegren - $100 Million

The year 2010 was not a good year for Tiger Woods. It was the year before that his troubles started, though, after allegations of infidelity were leveled against him. But it was in 2010 that, after admitting to the allegations, his sponsors dropped him, and his wife, Elin Nordegren, filed for divorce.

She also filed for custody of their two children and was awarded a healthy settlement of $100 million. Nordegren has since moved on and had another child with retired NFL player Jordan Cameron, while Woods is dating Erica Herman, who worked at one of his restaurants. Woods has been recovering from another car accident he experienced in 2021.

Michael Jordan and Juanita - $168 Million

These days Michael Jordan has a model named Yvette Prieto on his arm. But when he was blazing a trail and making his legend in the NBA, it was his long-time wife Juanita Vanoy that stood by his side. They even married in 1989, the same year Jordan made his NBA debut.

They share three children, but in 2002 both filed for divorce. They didn't follow through, eventually reconciling, but in the end, they went through with it, which was confirmed in 2006. It's alleged that Vanoy walked away with a massive $168 million settlement. This is regarded as one of the largest settlements in sports history.

Mel Gibson and Robyn Moore - $425 Million

Between Mad Max, Detective Martin Riggs, and William Wallace, Mel Gibson comes across as a pretty tough guy. But he's actually just a big softy and was brought to tears when he was caught DUI in 2006, fearful that his wife Robyn would leave him. She did exactly that not long after the incident.

Gibson and Robyn Moore met in the '70s after he finished filming Mad Max. He wasn't a big star yet, but by the time they married in 1980, he was. They have seven children together. They finalized their divorce in 2011, and Gibson paid Moore $425 million. Gibson will star in a 2021 film called Panama.

Mick Jagger and Jerry Hall - $40 Million

Like the rolling stone Mick Jagger named his band after, the British singer has gathered absolutely no moss. But he has also lost a few million dollars over the years due to breakups and divorces. One of those is with the former model Jerry Hall.

She wasn't a former model when they started dating in 1977. They never officially tied the knot; they did have an unofficial wedding, which was nullified in court when they split after 22 years. Jagger was ordered to pay a settlement of $40 million. At least Hall's new man, billionaire Rupert Murdoch, can't say she's just in it for the money.

 

Princess Diana and Prince Charles - $32 Million

One of the most high-profile marriages the British royal family has ever had, Prince Charles and Princess Diana tied the knot in fine fashion in 1981. The wedding was watched by an audience of 750 million people worldwide, which is one of the highest viewership for a royal wedding.

It's a pity that didn't translate into a long marriage for them, although they were together for over a decade. But between both of their infidelities and an order from the queen to divorce, their marriage came apart. They finalized in 1996. In 1997, Diana died in a car crash. Prince Charles is now married to Camilla Parker Bowles.

Angelina Jolie & Brad Pitt - Still Finalizing

When it comes to newsworthy couples, Brad Pitt and Angelina Jolie are top of the list. They met on set while working on Mr & Mrs. Smith while Pitt was still married to Jennifer Aniston. But they grew close on set, and after Pitt and Aniston's split was finalized, that they announced their relationship.

They had three children, adopted three more, and eventually married in a chateau in France in 2014. But the marriage lasted just two years, and they announced their separation. They still haven't resolved their divorce; with ownership of the chateau they got married in remaining a particularly hot topic. They've both been declared single, though.

Alec Wildenstein and Jocelyn Wildenstein - $2.5 Billion

Alec Wildenstein wasn't content with just being a billionaire. Oh no, he also delved in art and racehorses. But while he had many interests, he spent most of his life married to one woman. That woman was New York socialite Jocelyn Wildenstein.

They married in 1978 and had a daughter and a son together. Their divorce gained notoriety in the late '90s as reports revealed their extravagant lifestyle and Jocelyn's penchant for plastic surgery. She eventually secured a $2.5 billion settlement and a $100 million annuity payable for 13 years. Alec passed away in February 2008.

Jeff and MacKenzie Bezos - $35.6 Billion

Before the billions of dollars and the biggest online retailer on the planet, Jeff Bezos and Mackenzie Scott were an item. They got married in 1992 and together moved to Seattle to start Amazon. Scott was also instrumental in the development of Amazon into the powerhouse it is today.

But behind the scenes, things weren't going well for them. In fact, by the time they announced their intention to split, they had already been separated for a few years. She settled for a portion of company stocks that amounted to $35.6 billion. Bezos has been dating TV personality Lauren Sánchez since the divorce was announced.

Kris and Bruce Jenner - Amicable Split

If you can remember far enough, then you'll know that Kris and Caitlyn Jenner were not in a gay relationship. Instead, you'll remember that Kris Jenner was once Bruce Jenner, who was once the greatest athlete in the world after winning decathlon gold at the 1976 Olympics.

He and Kris got married in 1991 and have two daughters, the models and entrepreneurs, Kylie and Kendall Jenner. But Bruce was battling his transgender nature, and Kris filed for divorce. This was eventually finalized in March 2015, and in April that year, Jenner went public about being transgender. Their settlement was amicable, with neither seeking spousal support and each keeping their money.

Heidi Klum and Seal - No Spousal Support

Seal and Heidi Klum had a very romantic marriage considering their wedding anniversary ritual. Every year they would find a secluded spot and renew their wedding vows. They started dating after Klum broke up with Formula One team manager Flavio Briatore. Seal even adopted Briatore's, Leni Klum, with the model proclaiming that seal is the child's father.

But despite the romance and the heroism, they eventually separated in 2012. There was no reason given, and two years later, they were officially divorced. There was nothing even remotely ugly about it, and even now, they don't have anything bad to say about one another.

Bill and Melinda Gates - Estimated $65.25 Billion

Bill Gates is famous for being the founder of the computer software company Microsoft. His software, Windows, is responsible for making computers a household item and turning them into multimedia devices. But behind a lot of that success was Melinda Gates, who worked in marketing for the company.

She did work on popular programs such as publisher, Encarta, and Office. The couple married in 1994, and she eventually retired to take care of her family full time. Together they co-founded the world's largest charity organization, the Bill & Melinda Gates Foundation. Their divorce was finalized in 2021, with Melinda citing Bill's involvement with Jeffrey Epstein, a convicted s*x offender.

Jana Kramer and Mike Caussin - $3,200 Child Support

Anniversaries are meant to be happy occasions, a celebration of another year together, or working somewhere or alive. They're not meant for things like breakups and divorces. This is probably why Jana Kramer opted to file before her sixth anniversary with Mike Caussin.

The country singer and One Tree Hill star married the former NFL player in 2015, shortly before announcing that they were expecting their first child. They dealt with several issues, including Caussin's s*x addiction and other issues. But eventually, they called it quits in 2021. It was finalized in May 2021.

Billy Ray Cyrus and Tish Cyrus - Undisclosed Settlement

After Trish Cyrus filed for a divorce from her ex-husband Billy Ray Cyrus in early April of 2022, the internet went into a frenzy as fans were anxious to confirm the settlement details. That is understandable given Trish has an accumulated net worth of about $20 million; however, that figure is both hers and Ray's fortunes combined.

While settlement terms between the couple remain unconfirmed, one could say that Ray might have a lot to lose. He has built a fortune wealth throughout his music career with hit music records and tours on the road. One of such tours was the September 2022 show in Gethsemane, United States.

Jennifer Lopez and Alex Rodriguez - No Settlement

Jennifer Lopez and Alex Rodriguez looked so happy together. The multi-talented Lopez and the baseball legend started dating in 2017 and went so strong that they eventually decided to get engaged in 2019. But that's as far as it went for them.

In April 2021, they announced their split after four years together. There were allegations of infidelity on A-Rod's part, and J-Lo wasn't impressed by this. Despite his, they're still amicable and continue to work together on business endeavors. Since the pair split, there have been rumors that Lopez and her old flame Ben Affleck are dating again. The relationship is being dubbed Bennifer 2.0.

Mary-Kate Olsen and Olivier Sarkozy - Unconfirmed

Despite their 17 year age gap, Mary-Kate Olsen and Olivier Sarkozy gave a relationship a go. Olivier, a French banker, and brother of the former president of France, Nicolas Sarkozy, is the older of the two and married Olsen in 2015 after she was initially cited with an engagement ring in 2014.

The marriage was actually going strong for five years; then news broke that Olsen was filing for divorce. The 2020 lockdown halted proceedings, and she tried to get an emergency order to proceed but was denied. It was eventually finalized in January 2021.

Elliot Page and Emma Portner - Unconfirmed

Elliot Page has been breaking boundaries in recent years. Born Ellen Page, he is noted for his role as Vanya Hargreeves in The Umbrella Academy. He also recently became the first transgender man to feature on the cover of Time Magazine after coming out as trans in December 2020.

Before he came out, he met dancer Emma Portner, who he saw while browsing Instagram. They got married in 2018, but the marriage only lasted two years, and in 2020, they separated. The divorce was finalized in 2021. Elliot is currently doing work on ARK: The Animated Series.

Johnny Depp and Amber Heard - $7 Million

Johnny Depp and Amber Heard have had one of the most volatile divorces in Hollywood history. They started dating in 2012 after meeting on the set of The Rum Diary in 2009. They dated for six years, and in 2015 tied the knot, but the marriage barely lasted a year before Heard applied for the split.

The application came with a restraining order, accusing Depp of physical and mental abuse. Depp shot back, saying she was looking for a quick paycheck. He eventually gave it to her, paying $7 million. He unsuccessfully sued her for $50 million for defamation. Heard is currently filming for 2022's Aquaman and the Lost Kingdom.

Jennifer Aniston and Justin Theroux - Unconfirmed

Justin Theroux must have thought he hit the jackpot when he started dating Jennifer Aniston. As she is affectionately known, America's sweetheart is one of Hollywood's most revered females and almost every man's dream girl. But the world was also skeptical about their relationship.

Even Ellen DeGeneres quizzed her about her intentions to marry Theroux. But marry they did, and the bomb they also did. Apparently, Aniston's social lifestyle wasn't what did it for Theroux, while rumors of Theroux's roaming eye were said to be upsetting Aniston. In the end, they cut their losses and their ties, separating in 2017. Aniston has a role in the upcoming film Hail Mary.

Miley Cyrus and Liam Hemsworth - No Spousal Support

The relationship between Miley Cyrus and Liam Hemsworth was like a long-distance journey. They met on the set of a film called The Last Song and started dating, although it was on-and-off for the most part. Cyrus didn't rest on her laurels when they broke up and dated the likes of Patrick Schwarzenegger and Stella Maxwell.

She and Hemsworth got more serious in 2016 and got to a point where they lived together in a Malibu house. Sadly the house burned down in the Malibu fires, which initially prompted a marriage, although a year later, they divorced. Cyrus is rumored to be dating English singer Yungblud.

Danica Patrick with Aaron Rodgers – Never Married

In July 2020, Us Weekly made it public that Danica Patrick is no longer with Aaron Rodgers after the two dated for two years. Before their split, the former NASCAR superstar encouraged the NFL athlete to mend his strained familial relationships, specifically with his brother Jordan Rodgers.

Since then, they've both moved on, with Patrick now dating the Freshly meal delivery service co-founder, Carter Comstock. Meanwhile, Rodgers found love in "Big Little Lies" actress Shailene Woodley amidst the pandemic, and both of them confirmed in early 2021 that they were engaged.

Jerry Hall and Rupert Murdoch - Ended their marriage by email

The couple tied the knot in March 2016 in a romantic ceremony in London that drew a hundred guests, including the couple's ten children. Jerry Hall is "heartbroken" after media mogul Rupert Murdoch told her that their marriage had ended via email.

The 66-year-old model received an e-mail message from the 91-year-old chairman and CEO of News Corp, telling her that their six-year union had ended and that from now on he would only communicate with her through his lawyers, the media outlet added.

Channing Tatum and Jenna Dewan - Still Working Out Settlement

Channing Tatum and Jenna Dewan met while doing something they both loved doing. This was on the set of the dance-themed film Step Up in 2006. They started dating immediately after meeting and married in 2009, having their first child in 2013. Everything was perfect.

Then out of nowhere, they announced that they were splitting. This came in April 2018, and Dewan eventually filed for divorce, citing irreconcilable differences. Both of them moved on, and while Tatum has been in an on-again-off-again relationship with singer Jessie J. Dewan is engaged to actor Steve Kazee. Tatum has a role in an upcoming film called Dog.

Drew Barrymore and Will Kopelman - Undisclosed settlement

Drew Barrymore is someone who we hoped would live happily ever after, especially since she has been candid about not growing up with a family and how this has shaped her life. She has been honest about her split from ex-husband Will Kopelman in 2016.

In 2017, Barrymore opened up to Ellen DeGeneres, describing her divorce as her worst nightmare because it meant she didn't have a family again. The ghost pain had reared. Fortunately, in 2021, she has gotten back on her feet and hosts the successful "The Drew Barrymore Show."

Evan Rachel Wood and Jamie Bell - Undisclosed settlement

Of all romantic rollercoasters, Evan Rachel Wood and Jamie Bell have ridden their ups and downs. They met while at the Sundance Film Festival, quickly hit it off, then dated for a year and broke up. Wood moved on to the arms of Marilyn Manson, but seven months after their engagement, Wood called it off. Let's breathe.

Wood then reunited with Bell and got married in 2012. Yes! Finally! Alas, they are on a rollercoaster and got divorced in 2014. In a 2015 interview, Wood said that Bell was the lover of her life. In February 2021, on Instagram, Wood named Manson as her alleged abuser.

Katie Holmes and Tom Cruise - $400k Annual Child Support

Katie Holmes and Tom Cruise had one of the strangest marriages and divorces in Hollywood. They were absolutely lovestruck and giddy with one another, at least until their daughter Suri was born. Alarm bells were raised in Holmes when Cruise wanted the child to participate in Scientology at an early age.

Holmes didn't like that and decided a split was the best option. She did this in 2012 and also took her daughter and ran, fearing retribution from the church and that Cruise would abduct Suri. Cruise hasn't had much contact with the child since Holmes is seen as a suppressive person by the church, so he can't have contact with her.

Demi Moore and Ashton Kutcher - Unconfirmed

In a world where a celebrity relationship isn't proper if it doesn't have a portmanteau, Demi Moore and Ashton Kutcher went against the grain. Besides their 15 year age gap, the couple had no name mashup. But yet, they were still a proper Hollywood couple.

At least for ten years or so. They started dating in 2003 and eventually tied the knot in 2005. But by 2011, they separated, and by 2013 divorced. Moore admits to being a little overbearing, although says the act that pushed her over the edge was Kutcher cheating on her. Kutcher is currently married to Mila Kunis; his That '70s Show co-star.

Ben Stiller and Christine Taylor - $200 Million Divorce Cancelled

In a change of tune from the rest of these stories, here is a story about a divorce that neither person actually wanted. Ben Stiller and Christine Taylor met on a show called Heat Vision and Jack. Their relationship was the only good thing to come from that show, and together they starred in a few movies.

But despite working well together and having two children, they ended up separating after 17 years of marriage. Neither one really looked like they wanted a split, and they got along well, co-parenting their children and also never confirmed their massive $200 million split. In 2021 it was reported that they got back together. 

Miranda Kerr and Orlando Bloom - Unconfirmed

Orlando Bloom and Miranda Kerr's relationship reads like a round trip that starts and ends with them being single. They had a whirlwind six-year relationship that saw them dating in 2007, married by 2010, and having their first child in 2011. By 2013 it was over, but they weren't bitter about it.

In fact, they handled it pretty well, always focused on the well-being of their child. They've been co-parenting the child really week, and according to Kerr, they have a great understanding. Bloom is currently engaged to pop singer Katy Perry and has a role in an upcoming film, Needle In A Timestack.

Khloé Kardashian and Lamar Odom - No Spousal Support

A relationship so talked about it even got its own show... Okay, part of that was Khloé Kardashian's popularity in Keeping Up With The Kardashians. But still, it was talked about a lot, and Lamar's substance abuse and extramarital affairs meant it was being talked about for all the wrong reasons.

They married in 2009, but Kardashian filed for divorce in 2013. But just as it was being finalized, Lamar had a drug overdose. This delayed the proceedings since he was in a coma. But he recovered, and it was finalized, and Khloé started a show called Revenge Body, which is currently in its fourth season.

Michael Douglas and Diandra Luker - $45 Million

Featured in the 2022 TV special "The 28th Annual Screen Actors Guild Awards," the American actor/producer Michael Douglas has been happily married to fellow actress Catherine Zeta-Jones since 2000. But tying the knot with the woman of his dreams may have cost Douglas a reported fortune of $45 million.

Douglas and his first wife, Diandra Luker, only finalized their divorce in 2000. After being together since 1977, the former couple's separation was a lengthy and presumably painful one. In the end, Luker got away not only with $45 million but also with a massive Santa Barbara estate.

Kaley Cuoco and Ryan Sweeting - $330K

Kaley Cuoco will surely never be without suitors. This was clear by the characters she played in shows like 8 Simple Rules and Big Bang Theory. She played the object of affection of several characters in these shows and even dated a few of them, including Johnny Galecki, her on-screen love interest in Big Bang.

She married tennis player Ryan Sweeting in 2013, dashing many a man's dreams. But those dreams were re-ignited 21 months later when they got divorced in 2016. Cuoco says that Sweeting changed after they married, and this was a deal-breaker for her. She is set to star in a 2022 film, The Man from Toronto.

Kelly Clarkson and Brandon Blackstock - $908K

The American singer-songwriter Kelly Clarkson and the American talent manager Brandon Blackstock have been involved in a lengthy divorce process since 2020. In March 2022, outlets such as Us magazine reported that the process was finally over and announced some of the details of the settlement deal.

Reportedly, Clarkson agreed to provide her ex-husband with a 5.12% share of their massive former Montana property, which results in a payout of $908K. Other sources (namely, CNN) have also reported that Clarkson will pay a monthly child support fee of $45K to Blackstock as part of the deal (they have two children together).

Blake Shelton and Miranda Lambert - They Split up The Dogs And The Property

Country Music is filled with power couples, but in the mid-'00s, few of them were bigger than Blake Shelton and Miranda Lambert—they were a force. They met after singing a duet in 2005 at a Country Music Television live event. They eventually married in 2011.

But their success led to overloaded schedules, and when Shelton started working on The Voice, the distance took a toll on their marriage. Eventually, both sides reported infidelity, and Shelton started getting cozy with fellow The Voice coach Gwen Stefani. They divorced in 2015, with Shelton and Stafani becoming an item and Lambert marrying NYPD officer Brendan McLoughlin.

Phil Collins and Orianne Cevey - $34 Million

As the rock star that he is, Phil Collins has had his fair share of female partners. But the one that seemed to stick the most was Swiss national Orianne Cevey. The couple first met when she worked as his translator during a tour, and they got married in 2009.

They lived together in Switzerland but split up in 2006. Divorce didn't stop them from being together either, and despite forking out $34 million on a settlement, Collins reunited with Cevey, and they lived in Miami. It all came tumbling down again when she secretly married another man while living with Collins. He sold the Miami house in 2021.

Paul McCartney and Heather Mills - $48.7 Million

In essence, Paul McCartney would have been a one-woman man. He was married to photographer Linda Eastman for 29 years and would have been married even longer had she not passed away unexpectedly. He tried to let it be and even attended therapy to handle her death.

He then married former model Heather Mills in 2002, and they had a daughter named Beatrice Milly McCartney. But the constant media scrutiny became too much for Mills, and she opted out of the marriage. The divorce was finalized in 2008, and Mills got a tidy settlement that amounts to $34K for every day she was married to him.

Katy Perry and Russell Brand - No Spousal Support

Katy Perry is such an open book that she openly cries in front of the camera while dealing with the demise of her marriage to Russel Brand. It was alleged that she even contemplated suicide after realizing that her marriage was down the drain.

There are many theories for their split. It's said that their work schedule kept them apart for too long and that Russel was upset about Perry not finding time for activism. He also wanted children, which perry wasn't ready for. They eventually divorced in 2012. Perry had her first child in January 2020. In 2021 she released a new song called Electric.

Mariah Carey and Nick Cannon - $5K Per Month In a Trust

Despite having his own aspiring music career at the time, Nick Cannon starred as an actor in the music video for Mariah Carey's Bye Bye. They turned heads with the video and started dating soon after shooting the video. They met in 2005 at the Teen Choice Awards.

They married in 2008 too, and also had a set of twins named Monroe and Morrocan. They eventually divorced in 2016, with rumors that Cannon was unfaithful. He cites the fact that they never grew as a couple for his reason. In 2021 Carey sang on a song called Somewhat Loved by production duo Jimmy Jam and Terry Lewis.

Zoë Kravitz and Karl Glusman - Unconfirmed

Zoë Kravitz, the famous daughter of Lenny Kravitz and Lisa Bonet, made waves in films like The Divergent Series, X-Men First Class, and Mad Max: Fury Road, among a host of other films. But she also lived out one of the shorter Hollywood nuptials of modern times.

She married actor Karl Glusman at a cozy ceremony at her father's Paris home in June 2019. They were always open about their relationships and mentioned that they were having issues. It wasn't really shocking when they announce their divorce in January 2021. She is set to star as Selina Kyle/Catwoman in the upcoming 2022 film The Batman.

Dr. Dre and Nicole Young - $2 Million

Hip Hop icon Dr. Dre and his band of brothers from the NWA had a reputation for telling hard-hitting stories through music. They were also pretty popular with the ladies, which is why Dre himself has fathered four children from four different women.

But when he met Nicole Young, that changed, marrying her in 1996. While his previous partners had reported that he was abusive towards them, Nicole reported any of this. She did eventually file for divorce, though, in 2020, due to irreconcilable differences. He still covered her immediate finances with a $2 million payment. He is currently recovering from a brain aneurism he suffered in 2021.

Usher and Grace Miguel - Unconfirmed

The album Confessions by Usher makes him look like a serial cheater. But none of those songs were about him and instead reflected the personal life of producer Jermaine Dupri. Yet infidelity was still the reason for the demise of his relationship with TLC's Chilli Thomas around the time of that album.

It was also part of the demise of his marriage to Grace Harry, his manager. The marriage only last three years. Between her wanting kids and rumors of Usher spreading STIs everywhere, they split up in 2018. In 2021 Usher is set to release its ninth studio album, called Confessions 2.

Rupert Murdoch and Anna Mann - $1.2 Billion

Rupert Murdoch is the rock star of the media mogul world. The guy has been married four times and, sandwiched between his first wife Patricia Booker and third wife Wendi Deng, was Scottish journalist Anna Mann. They were married from 1967 to 1999, making her his longest-standing spouse.

As such received the largest settlement of any of his ex-spouses, scoring $1.2 billion in money and assets. They also have three children, although they were grown-ups at the time of the divorce. Murdoch is currently married to former model Jerry Hall since 2016. The couple isn't renowned for making public appearances.

Sandra Bullock and Jesse James - No Spousal Support

Sandra Bullock would never have met motorcycle builder Jesse James if her godson never wanted to meet him. She used her Hollywood muscle to set up a meeting as a Christmas gift for him, and the next thing we know, she and the Monster Garage man were dating.

But five years into the marriage, and in the middle of them going through adoption proceedings, rumors surface of James having affairs with several women. James tried to fix things, even going to therapy, but the damage was done, and divorce proceedings were followed. Bullock will produce and star in the upcoming film The Lost City Of D.

Brad Pitt and Jennifer Aniston - No Spousal Support

Before the sharp rise and fall of Brangelina, Brad Pitt was in another high-profile relationship. This was with America's other sweetheart (Julia Roberts is the original), Jennifer Aniston. While there was no portmanteau for this one, it still filled many gossip column pages.

And just like every one of their moves was followed when things were going well between them, so every move was followed when they split. Suspicion regarding Pitt and Angelina Jolie's relations started, and apparently, Aniston's unwillingness to have children was also an issue. They were divorced by October 2005. Aniston was last featured in the 2021 episode of the TV series The Morning Show.

Ryan Phillippe and Reese Witherspoon - No Spousal Support

Cruel Intentions was a film that put both Reese Witherspoon and Ryan Phillippe on the map. This was helped by their on-screen chemistry, which gave the film's storyline an added edge. That chemistry was so good that they eventually tried their hand at a relationship and married in 1999.

But that chemistry didn't work off-screen, and eventually, they separated in 2006. By 2007 they were officially divorced. They have two children together, one of whom is Ava Phillipe, their daughter. Witherspoon is set to star in 2022 Legally Blonde 3. Phillippe, meanwhile, last starred in a film called Lady of the Manor.