There’s truly nothing that compares to a Hollywood love story. But the stakes of those relationships are so high because of busy schedules, relentless media attention that can put immense pressure on even the most enchanting celebrity relationships. While some couples' relationships end in a long-term marital bliss, others don't necessarily have a happy ending.
From crazy horrific claims to drawn-out legal battles, some of Hollywood's A-listers have gone through astonishing messy divorces.
Prepare yourself for an emotional rollercoaster filled with intense love, shocking betrayals, and dramatic confrontations as we explore the most scandalous and headline-grabbing celebrity breakups in history.
1. Christie Brinkley and Peter Cook
Back in 2008, Supermodel Christie Brinkley and architect Peter Cook got a divorce which became New York's nastiest legal battles. Peter admitted that he was cheating on Brinkley with an 18-year-old assistant in 2007. As per Today's report, he allegedly paid $300,000 to keep quiet.
Shocking details were revealed when the media covered the court proceedings and all this was while the duo were figuring out things. They settled with Brinkley keeping 18 disputed properties in the Hamptons properties and giving Cook $2.1 million, according to The New York Times. She also secured sole custody of their two children.
2. Jimmie Allen and Alexis Gale
Jimmie Allen, country music star and his wife who was a registered nurse, Alexis Gale who announced their separation in April 2023 surprising the fans and sparking widespread speculation, especially because the news came just days before welcoming their third child together.
According to reports, a web of tension and alleged infidelity that plagued their relationship. Despite all the chaos, the duo took the decision to co-parent their children amicably. While the split was heartbreaking, both Allen and Gale have focused on maintaining a stable environment for their kids amid the media frenzy.
3. Kim Kardashian and Kris Humphries
Reality TV Star, Kim Kardashian and NBA player, Kris Humphries had one of the most publicized splits in celebrity history. Duo filed for divorce in 2011, 72 after their lavish televised wedding.
The whirlwind romance quickly fizzed out amid allegations of manipulation and media exploitation. Kris said that the marriage was a publicity stunt and Kardashian cited irreconcilable differences.
Until 2013, the legal battles went on till 2013 making headlines for two years. Once the divorce was finalized with no spousal support exchanged, wrapping up one of Hollywood's shortest yet most dramatic unions.
4. Linda and Hulk Hogan
Back in 2007, wrestling legend Hulk Hogan and his wife, Linda faced a stormy split after 24 years of marriage. The divorce was a huge scandal including Linda's allegations that Hulk was unfaithful, and her subsequent relationship with a 19-year-old man.
Apart from that, there were financial disputes as Linda sought a huge portion of Hulk's assets. The divorce was finally finalized in 2009 when Linda received over 70% of their liquid assets, including a $3 million property settlement, as per reports.
The drama was out in the media and on their reality TV show Hogan Knows Best.
5. Mia Farrow and Frank Sinatra
Back in 1968, Frank Sintara and Mia Farrow's divorce surprised the entire Hollywood. Two years back in 1966 with Sinatra who was 50 and Farrow was 21 which caused media madness.
Their age gap and different lifestyles led to constant scrutiny but the breaking point came when Farrow refused to abandon filming Rosemary's Baby to join Sinatra on his film set.
Despite the turbulent end, their relationship supposedly remained amicable.
6. Tom Brady and Bridget Moynihan
Actress Bridget Moynihan and NFL superstar Tom Brady began their relationship in 2004 who were at the peak of their careers. Fans were surprised when they announced their break in 2006, and the scandal only intensified when Moynahan announced that she was pregnant with Brady’s child shortly after their split.
Brady started dating supermodel Gisele Bundchen already by then and that became a very publicized love triangle.
Despite their split in December 2006, they’ve since mastered the art of peaceful co-parenting and they seem to be on good terms.
7. Brad Pitt and Angelina Jolie
Angelina Jolie and Brad Pitt met each on the sets of Mr and Mrs Smith back in 2004 which was a highly publicized romance. At the time, Brad was married to Jennifer Aniston and it lead to speculation about his affair with Angelina. After Jennifer and Brad got a divorce in 2005, 'Brangelina' was known as a Hollywood power couple. However, after a decade and 6 children later things went sour.
Things changed when Angelina filed for a divorce in 2016 and their split became a messy custody battle that went on for long. Apart from that there were allegations of child abuse which were later cleared out. But the rise and downfall of Brangelina was one of the most talked-about breakups in Hollywood history.
8. Princess Diana and Prince Charles
A marriage that was the epitome of fairy tale romance was of Prince Charles and Princess Diana but behind their public facade, their relationship was turbulent and the cracks in their relationship were seen from the beginning with reports of infidelity happening on both their ends.
During a popular 1995 interview, Diana said, 'Well, there were 3 of us in this marriage, so it was a bit crowded.' The duo separated in 1992 and got a divorce in 1996. However, Diana died in a tragic car accident in 1997.
Despite them parting ways, Diana and Charles' relationship is still a topic of discussion of fascination for the public and media, to this day.
9. Taylor and Russell Armstrong
There was always a stormy turbulence with tragedy in Taylor and Russell's relationship. The cast members of 'The Real Housewives of Beverly Hills' and their marital problems were out in front of the cameras. Their problems with finances, allegations of abuse were all open for the public to watch.
Unfortunately in August 2011, Russell was found dead after he committed suicide. His death shed light on the pressures and challenges faced by reality TV stars and the toll it can take on their mental health.
Since then, Taylor has been advocating about awareness regarding domestic violence and mental health.
10. Julia Roberts and Kiefer Sutherland
The cyclonic romance between America's sweetheart Julia Roberts and actor Kiefer Sutherland hit a dramatic end a few days before their wedding date in 1991. After being engaged for a year, there were rumors about infidelity on Kiefer's part.
Julia Roberts called off the wedding before they could reach the altar and went to Ireland with Sutherland's close friend, actor Jason Patric. Their sudden split was publicized with endless speculation and no concrete answers about what really happened. Both stars eventually moved on, and now Roberts has been married to Daniel Moder for over two decades while Sutherland is dating model Cindy Vela.
11. Cher and Sonny Bono
The quintessential couple Sonny and Cher captured hearts with their music and TV show but their marriage wasn't so pleasant. The duo got married in 1964 and became famous with hits like "I got you babe." During the 1970s, their relationship fell apart because of personal differences and professional tension.
The couple filed for a divorce in 1974 which shocked fans which put an halt to the most favorite entertaining partnerships. They maintained an amicable relationship to co-parent their child Chaz Bono, and a professional relationship for a time, continuing to co-host The Sonny & Cher Comedy Hour.
12. Lamar Sally and Sherri Shepherd
Television personality Sherri Shepherd's split from screenwriter Lamar Sally was rife with drama and legal battles. Married in 2011, their union crumbled by 2014, leading to a contentious divorce. The most scandalous element was their surrogacy arrangement, as Shepherd and Shelly had a baby carried by a surrogate, but split up just months into the pregnancy.
Shepherd initially tried to distance herself from financial and parental responsibilities for their newborn son, but the court ultimately ruled against her, requiring Shepherd to uphold her obligations. The messy, public battle over their child and finances turned their breakup into a significant media spectacle.
13. Tom Cruise and Katie Holmes
Tom Cruise and Katie Holmes were affectionately called 'TomKat'. When Katie filed for a divorce 6 years after their marriage in 2012, the split was smooth, swift and kept in secrecy which even caught Tom off-guard.
There were apparently rumors that the reason for divorce was Katie's desire to protect their daughter, Suri from Tom's ties to Scientology. The divorce was finalized in just 11 days, with Holmes securing primary custody of Suri. Neither Cruise nor Holmes have married since.
14. David Gest and Liza Minelli
In the early 2000s, the renowned producer and reality television personality David Gest was introduced to the iconic Hollywood star Liza Minnelli by the one and only, Michael Jackson. Although their pairing seemed questionable to many, they were undeniably captivated by each other.
The couple tied the knot in 2002, with Jackson serving as the best man. However, just 16 months later, their marriage had unraveled. Their relationship quickly became fraught with turmoil, marred by accusations of financial exploitation, abuse, and threats. The ensuing legal disputes were settled out of the public eye. After their separation, Liza Minnelli did not enter into another marriage, and David Gest remained single until his death in 2016.
15. Sandra Bullock and Jesse James
One of the most beloved women in Hollywood, Sandra Bullock had experienced a catastrophic crisis when her 5 year married life with entrepreneur and TV personality Jesse James fell apart in 2010. She also won an Oscar for The Blind side and shortly after discovered about Jesse's infidelities when women came forward with allegations of an affair with James.
Their separation was pretty public with Sandra filing for divorce amidst the scandal. Despite the heartache, Bullock focused on her newly adopted son, Louis, and came out stronger, personally and professionally.
16. Madonna and Sean Penn
Actor Sean Penn and pop icon Madonna's marriage was a tumultuous one. In 1985, their vulnerable marriage was scarred by allegations of domestic violence and heated confrontations that were in the media for the world to look at.
However, in 1986 the couple filed for a divorce stating irreconcilable differences. In spite of their fiery romance and contentious split, both Madonna and Penn have spoken fondly of each other in interviews over the years, acknowledging the intense, though troubled, love they once shared.
17. Jennifer Garner and Ben Affleck
In 2003, on the set of Daredevil Jennifer Garner and Ben Affleck became very close friends which turned into a fairytale romance. The couple had 3 beautiful children and created beautiful memories together while spending good time in the spotlight during their decade long marriage. Eventually, they called it quits in 2015.
There were rumors about Ben having an affair but through the proceedings the couple wee civil and were spotted together on family outings, so they made a strong commitment to prioritize co-parenting over all the drama between them.
18. Megan McKenna and Pete Wicks
British reality television personalities Pete Wicks and Megan McKenna were known for their tumultuous and dramatic relationship, which was prominently featured on the show ‘The Only Way Is Essex.’ Their romance began in 2015 and quickly attracted attention due to their frequent and intense arguments, which became a regular feature of the series.
By 2017, their on-again, off-again relationship reached a breaking point, leading to a final separation after accusations of infidelity against Pete came up. Their breakup captivated fans and kept them eagerly following tabloid reports for the latest developments. Despite the highly publicized fallout, both Wicks and McKenna appear to have moved forward in their lives, with recent indications suggesting that they may now have a more amicable relationship.
19. Khloe Kardashian and Lamar Odom
Khloe Kardashian and Lamar Odom's relationship had turbulence from the beginning. The couple got married in 2009 after their cyclonic romance which was fan favorites on 'Keeping Up with the Kardashians.' Their marriage was in trouble because of Lamar's struggle with addiction and infidelity.
In 2013, Khloe filed for a divorce which got finalized after 3 years. The split was particularly sad when Lamar suffered a near-fatal overdose in 2015 while Khloe supported him throughout his recovery despite their separation.
These days, both Khloe and Lamar are single. Odom has three adult kids, while Kardashian has two young children.
20. Mariah Carey and James Packer
Australian billionaire James Packer and Pop Diva Mariah Carey were dating since 2015 and in January 2016, the couple made headlines when James proposed with a 35-carat diamond ring.
Things went sour quickly among the duo by October when they called off their engagement amid rumors of intense arguments.
After they broke up, Carey was in the headlines because she kept her $10 million engagement ring, which she has since parted ways with.
Looking back on the relationship, Packer admitted that "It was a mistake for her and a mistake for me," as Vanity Fair reported.
21. Kate Gosselin and Jon
Jon and Kate Gosselin's marriage was thrust into the limelight through their reality television show, ‘Jon & Kate Plus 8.’ Initially, the series offered a seemingly cheerful and engaging glimpse into their family life. However, as time progressed, the show began to expose the unraveling of their marriage, revealing a backdrop of allegations including infidelity, financial mismanagement, and deep-seated personal conflicts.
In 2009, after a decade of marriage, Jon and Kate announced their separation, which led to a highly contentious and public divorce. Their split was marked by intense legal disputes over custody and ongoing public confrontations. Even after the end of their marriage, both Jon and Kate have continued to lead their lives in the public eye, frequently clashing with one another and maintaining a strained relationship years after their separation.
22. Charlie Sheen and Denise Richards
Denise Richards and Charlie Sheen first crossed paths in the year 2000, and their relationship quickly progressed, culminating in marriage in 2002. However, by 2005, their marriage had deteriorated significantly, leading Richards to file for divorce while she was pregnant with their second child. The situation rapidly escalated into a contentious and bitter dispute, as Richards made serious allegations against Sheen, including accusations of substance abuse, threats of violence, and infidelity.
Following their separation, the couple engaged in a protracted and acrimonious battle over the custody of their daughters, a dispute that lasted for several years. Ultimately, Richards was awarded primary custody of their children. Despite the highly charged and turbulent nature of their past relationship, Richards has occasionally expressed a commitment to maintaining a civil relationship with Sheen, emphasizing the importance of doing so for the well-being of their daughters.
23. Kelsey Grammer and Camille Meyer
Kelsey and Camille Grammer's marriage, which began in 1997, lasted nearly 14 years before coming to a dramatic and public end in 2011. Their separation was prominently featured on the reality television series *The Real Housewives of Beverly Hills*, where viewers saw Camille grappling with the emotional fallout from Kelsey's sudden decision to leave her for a younger woman. Kelsey had reportedly been unfaithful, eventually marrying Kayte Walsh, who was the woman he had been involved with during their marriage.
The divorce proceedings laid bare significant financial and emotional conflicts between the couple. Camille was awarded a substantial settlement as part of the divorce settlement. In a particularly sensational twist, Kelsey Grammer remarried only two weeks after the divorce was finalized, further fueling the drama surrounding one of Hollywood's most high-profile breakups.
24. Elin Nordegren and Tiger Woods
Tiger Woods is a popular golf champion, and Elin Nordegren, a Swedish model, saw their marriage implode dramatically in 2010 after Woods' numerous infidelities came to light. The couple, who had tied the knot in 2004, initially appeared to have a perfect relationship. However, their seemingly idyllic marriage fell apart when Nordegren uncovered evidence of Woods' multiple affairs, sparking a major public scandal.
In 2010, the couple finalized their divorce, with Nordegren receiving a substantial settlement of $100 million, as reported by Forbes. This high-profile split significantly impacted Woods' public persona and professional life, while Nordegren chose to step away from the media spotlight to concentrate on raising their two children. Since 2019, Nordegren has been in a relationship with former NFL player Jordan Cameron, whereas Tiger Woods remains single.
25. Kevin Costner and Christine Baumgartner
Kevin Costner's second marriage, which began in 2004 with handbag designer Christine Baumgartner, initially appeared to be thriving. However, their relationship encountered serious difficulties in 2023, when Baumgartner filed for divorce, citing irreconcilable differences as the reason for their separation.
The news of their split quickly made headlines due to the contentious nature of the divorce proceedings. During this process, they reached an agreement to share joint custody of their three teenage children. However, Baumgartner's request for a substantial $248,000 per month in child support, as reported by The Los Angeles Times, added a surprising twist to the situation. Despite the public scrutiny and the initial shock surrounding their breakup, both Costner and Baumgartner have since emphasized their commitment to co-parenting in a cooperative manner, aiming to provide stability and a sense of normalcy for their children amidst the upheaval.
26. Alec Baldwin and Kim Basinger
Kim Basinger and Alec Baldwin were Hollywood's golden couple after they fell in love while filming 'The Marrying Man.' They were sure that their love was everlasting and they did not sign a prenup.
Sadly, their relationship led to a public break up which was nasty while their daughter, Ireland, was caught in the middle of a bitter custody battle.
However, Kim recently opened up that she and Alec are 'cool now' so the once-angry exes must have figured out how to co-parent in peace.
27. Johnny Depp and Amber Heard
Among other broken Hollywood marriages, there are some which are more bitter and public break-ups than Johnny Depp and Amber Heard's. Johnny and Amber's relationship was volatile and their divorce was finalized in 2017 after just 15 months of marriage.
The couple sued each other later in a notorious trial that set social media on fire with leaked images, explosive allegations and incriminating court testimonies. Ultimately, they reached a $7 million settlement, which Heard donated to two charities, as per BBC news report.
28. Pamela Anderson and Tommy Lee
Pamela and Tommy's relationship was a rollercoaster ride which ended dramatically as it began. They got married on 19 Feb 1995 and 4 days after hanging out, their tumultuous romance constantly made headlines for their infamous wild antics.
In 1997, Tommy was under arrest for alleged spousal abuse, and Anderson filed for divorce, requesting custody of their two sons, Brandon and Dylan. After Tommy was released from jail, the pair were on-again and off-again for years—they just couldn’t stay away from each other. Their relationship was so juicy that it inspired a documentary.
29. Jennifer Lopez and Ben Affleck
Jennifer Lopez and Ben Affleck were affectionately called 'Bennifer' were the epitome of the early 2000s celebrity power couples. They got engaged in 2002 and their love story was published from the beginning so when they called it quits before their wedding in 2004, they broke hearts around the world.
Both went on to have other high-profile marriages and relationships, and shockingly, Bennifer reunited in 2021, rekindling their romance and eventually marrying in 2022.
They also had a documentary made together where everyone learnt about their different attitudes to privacy, and there have since been rumors about another split, but with this couple, who really knows?
