March 23, 2023 | Christine Tran

Scandalous Facts About Hollywood's Worst Divorces

Love hurts. It’s a cliché. And here’s another cliché: celebrity divorce. But just like songs about how "love hurts," the public can’t seem to quit stories about the rich and famous couples who just couldn’t work things out. Celebrities, like "normal" people, can discover that—gasp!—their once-happy marriages have crumbled around them. From tabloid battles to broken vows and big court payouts, please indulge in these 65 scandalous facts about celebrity divorces.

1. Squeezing Him Out

In the middle of her split from Charlie Sheen, Denise Richards reportedly made a bizarre demand to her divorce lawyer. Allegedly, she insisted that she get some of Charlie Sheen’s sperm as part of their divorce settlement, though Richards has since said that it was Sheen himself who faked the message. Honestly, either story is crazy enough for me.


2. Keeping Up with the Roads Not Taken

Kris Jenner has stated her only regret in life was divorcing her first husband, Robert Kardashian, in 1991. In her memoir, Jenner admitted to an affair with their friend Todd Waterman while she was still married. Shouldn't the affair have been the greater regret? Either way, Robert Kardashian passed on in 2003.

Celebrity Divorce FactsGetty Images

3. Two Strikes, You’re Out

Few Hollywood "love stories" match the drama of the union between Elizabeth Taylor and Richard Burton. Married to other people when they hooked up while filming Cleopatra, the couple themselves would marry and divorce each other twice. They first got hitched in 1964, but divorced in 1974 after Burton had an affair with a young co-star.

However, the two realized they were still in love after a meeting about their financial affairs, and married again 1975… before they divorced for the second (and last) time in 1976 due to Burton’s wandering eye (again).

Old Hollywood Scandals FactsGetty Images

4. Not My Baby, Baby

Sheri Shepherd, the former co-host of The View, split from her husband just a few months before they were set to welcome a child via surrogate mother. Shepherd renounced maternity of the child and accused Sally of an utterly devious plan: that he'd never intended to stay married to her, and was welcoming the child so he could seek child support from her. 

If that's true, that's got to be one of the most underhanded plans there is, but regardless, the nasty battle ended with a settlement in which Shepherd pays $4,100/month in child support for Sally and his son. 

Celebrity Divorce FactsWikimedia Commons

5. Married to the Job (and Eventually Someone Else)

James Cameron’s 1997 film Titanic might have sunk another romance—his own. His fourth wife, Linda Hamilton, once said: "The Titanic was the mistress he left me for". The Terminator star described every year she was married to the director as "terrible on every level," as Cameron was consumed by work with his cinematic leviathan.

In 1999, she walked away with a $50 million settlement (one of the biggest in Hollywood history at the time) and Cameron quickly married his actual, human mistress—Titanic actress Suzy Amis. 

Celebrity Divorce FactsGetty Images

6. California, Here She Comes

In 2016, Deadpool star Morena Baccarin finalized her divorce from American film producer and director Austin Chick, citing "irreconcilable differences". Then, just one month after their separation, Baccarin declared her plans to marry her Gotham co-star, Ben McKenzie. Chick claimed that he came home one day to get his things and found the former The OC star there, playing with Chick and Baccarin's kids. He claimed that McKenzie was obviously fresh from a shower.

Baccarin and McKenzie married in 2017 and have one daughter together.

Celebrity Divorce FactsGetty Images

7. Get In, Get Out, Stay Safe

When Katie Holmes divorced Tom Cruise after five years of marriage, she had reason to fear for her life. The Church of Scientology, of which Cruise is a devoted member, is known for treating defectors with harassment, intimidation, and threats of bodily harm. Holmes immediately went into hiding when the news of their split broke.

She was eventually granted full physical custody of their daughter, Suri, and the matter was resolved in 11 days. 

Leah Remini FactsGetty Images

8. Spousal Scuffles

Alec Baldwin and Kim Basinger divorced in 2002, but the custody battle for their daughter Ireland ensued for years after. It culminated in an infamous voicemail where Baldwin called Ireland—who was 11 years old at the time—a "rude, thoughtless pig". By 2008, this divorce had left hundreds of court documents, 91 court proceedings, and approximately $3 million in judicial costs.

More than a decade later, in 2016, Basinger evaluated things between her and her ex as "cool now". Thank goodness for that.

Power Couples factsGetty Images

9. When Life Leaves Your Marriage, Make Music

Marvin Gaye was not in great financial shape at the time of his divorce from Anna Gordy, so his lawyer negotiated a compromise in which half the royalties from Gaye’s next album would go to Gordy. A great album and title were born: Here, My Dear (1978).

Marvin Gaye FactsGetty Images

10. Royal Bounty

Princess Diana’s marriage to Prince Charles was extremely strained, and the media began reporting about both of their infidelities. Queen Elizabeth wrote each of them a letter with one chilling demand. The Queen urged Diana and Charles to get a divorce. By August of 1996, her will was done. The young couple went their separate ways after a notoriously stressful marriage.

History's Worst BreakupsGetty Images

11. A Step Down

When Charles and Diana were divorced, Diana was stripped of her "royal highness" status. This meant she had to curtsy to those who had it, including her own children.

Princess Diana FactsFlickr

12. Strong Words

The 2006 divorce between David Hasselhoff and Barbara Bach was famously ugly. However, the Baywatch star slo-motion walked away with at least two important properties: his right to his nickname, "the Hoff," and its related catchphrase, "Don’t Hassle the Hoff". What a deal.

The Spongebob Squarepants MovieGetty Images

13. Blink and You’ll Miss It

It seems like yesterday that Kim Kardashian and Kris Humphries spent $10 million on a four-hour E! television special to get married. With that kind of investment, you’d think it would last more than ten weeks. It didn’t, of course.

Kim Kardashian FactsGetty Images

14. Unlucky in Love and Everything Else

Drew Barrymore and comedian Tom Green were married for five whole months in 2001. It couldn't have been a great time for either; in that timespan, he managed to get diagnosed with testicular cancer—but the nightmare didn't stop there. Barrymore also had her home destroyed in a fire. Bad omens, maybe?

celebrity divorces factsGetty Images

15. Quite the Social Life

Long before the Kardashians became famous for being famous, that honor went to Zsa Zsa Gabor. While she was a noted actress in her prime, Gabor’s more lasting fame came from her scandalous socialite activities in the most elite circles of Old Hollywood. During her life, Gabor was married to nine different men, and seven of these marriages ended in divorce, while another was annulled.

But hey, maybe Zsa Zsa was just an utterly hopeless romantic?

Hilton Family Facts Wikipedia

16. Keeping It Symmetrical

One of Gabor’s many husbands was Oscar-winning British actor and singer-songwriter George Sanders. Like many of Gabor's relationships, their love was incredibly passionate but also incredibly volatile: they married on April 2nd, 1949 and divorced exactly five years later to the day, on April 2nd, 1954. Really, it'd be poetic if it wasn't so sad.

Zsa Zsa Gabor factsGetty Images

17. Sisters Share

Maybe Sanders never quite got over Zsa Zsa, because in 1970 he married her older sister Magda after a whirlwind romance. Unfortunately, this union was just as ill-fated as his other foray into the Gabor family: they divorced after a mere 32 days, and the split even quickly drove Sanders into an alcoholic bender.

Hilton Family FactsFlickr,kate gabrielle

18. $uperstar $eparations

Madonna and director Guy Ritchie’s eight-year marriage came to an end in 2008. The Material Girl paid Ritchie a $92 million settlement—one of the biggest divorce payouts in Hollywood history. Also, Madonna’s lawyers accused Ritchie of being verbally abusive, calling her a "granny," while Ritchie’s lawyers accused Madonna of being emotionally controlling, rarely allowing her husband to eat meat or host friends at home.

Maybe it's not a tragedy the two split.

Madonna FactsGetty Images

19. Pattern Recognition

When Brad Pitt starred with Marion Cotillard in the WWII drama Allied in 2016, rumors began to spread that Pitt was having an affair with his co-star. Of course, as many would remember, the same rumor had plagued Pitt when he was married to Jennifer Aniston and working alongside Angelina Jolie on Mr. & Mrs. Smith. The rumors reached a fever pitch when Angelina Jolie filed for divorce on September 16, 2019but the truth was much darker. 

Power Couples factsWikipedia

20. Up in the Air

The story—much of which was speculated on—is as follows. It's alleged that Pitt was inebriated on a private flight with his family, and that he was having an argument with Jolie when his adopted son Maddox, 15 years old at the time, stepped in to defend his mother. It's said that Pitt struck the boy. Five days later, Jolie filed for divorce—but that's not all. 

Angelina Jolie factsGetty Images

21. So Much for a Happy Ending

The Los Angeles Department of Child and Family Services and the FBI were called in to investigate the matter. Pitt was ultimately cleared, but a long custody battle ensuedwith a heartbreaking ending. While Pitt and Jolie agreed to joint custody of their six children, Pitt and Maddox remain estranged.

Angelina Jolie with her children visit the Louvre in Paris.Getty Images

22. Payback?

Hollywood darlings Meg Ryan and Dennis Quaid were married for ten years—until Ryan started up an affair with her Proof of Life co-star, Russell Crowe, that is. She’s since claimed that Quaid committed his own fair share of adultery throughout their marriage, but it’s an accusation he denies.

Meg Ryan and Dennis Quaid split after nine years of marriageGetty Images

23. C’mon and Slam, and Welcome to the... Alimony

The first time Michael Jordan and his wife Juanita Vanoy filed for divorce in 2002, they decided to reconcile. The second time, in 2006, they did not, and it cost him: the NBA legend paid Vanoy a hefty settlement of $168 million. I wonder how many Jordans it took to pay that off?

LeBron James FactsFlickr

24. Jon & Kate Plus 8 Minus Jon

Remember Jon & Kate Plus 8? At the height of the show’s popularity, Jon and Kate Gosselin—the parents and stars of the TLC reality show—had a very real, very public split in 2009. Despite the network's best efforts to keep them together, Jon attempted to quit the show on "moral grounds" and accused the show of siding with Kate.

In 2016, he told Entertainment Tonight that he hasn’t seen all of his eight kids together in three years.

Celebrity Divorce FactsGetty Images

25. Newlyweds No More

2005 was a big career year for Jessica Simpson, but it also came with immense heartbreak. In December, she and Nick Lachey officially divorced. Fans were shocked, but according to Lachey, their reality TV show Newlyweds had driven a rift between them. As he said, "Jessica and I began playing these parts even when we were by ourselves".

But there were even more scandalous reasons behind the split.

shutterstock_187219751 Jessica Simpson, Nick LacheyShutterstock

26. The Meddler

Lachey was reportedly "blindsided" by the divorce, and an unhappy Simpson dropped the news on him in the car after they were out for dinner. To make matters worse, Lachey partly blamed Jessica’s father Joe for the split. As Lachey later said, "Was he an influence in our marriage? Absolutely". And the bitterness didn’t end there…

Jessica Simpson FactsFlickr,Eva Rinaldi

27. For Love and Money

Jessica Simpson later confessed her biggest regret about her marriage to Lachey: the massive payout she had to give him. According to rumors, Joe Simpson discouraged Jessica from signing a prenup with Lachey when they married since the boy band alum was worth a lot more than her at the time. This came back to bite her in a big way.

By the time they split in 2005, Simpson was a much bigger star than Lachey, and she reportedly had to pay him a whopping $12 million to finalize their divorce. Ouch. She later called him her "biggest money mistake".

Rich Kid Syndrome FactsShutterstock

28. Let’s Play Pretend

Irish actor Colin Farrell allegedly hitched himself to British singer-songwriter Amelia Warner in Tahiti back in 2001—and then split up the same year. According to Farrell, the marriage was never official and "just a thing [they] did on a holiday". Farrell has a tattoo of Warner’s name around his ring finger. That could be hard to explain in future relationships.

Colin Farrell Speaks at Adobe EMEA SummitGetty Images

29. The Era of the Lavender Marriage

Rock Hudson was the subject of frequent rumors about his sexuality, and when he married Phyllis Gates, many thought it was to dispell those rumors. However, despite the fact that Gates insisted she was in love with Hudson and didn’t marry him to cover up his sexuality, the couple was doomed to a heartbreaking end.

Rock Hudson factsGetty Images

30. We Call That Blackmail

Three years after tying the knot, Gates divorced Hudson in 1958, giving "mental cruelty" as her reason. Hudson, for his part, let her go quietly without making a fuss. Maybe that was because she now had some cruel leverage on him.

Janet Leigh factsShutterstock

31. The Confession Tapes

According to The Hollywood Reporter, just as their marriage was dissolving, Hudson's wife Phyllis Gates hired a private detective to record her confronting her husband about his sexuality. The tape’s contents would have ruined Hudson. On the recording, Gates asks Hudson about his bedroom habits with boys, and accuses him of picking men up off the street.

Though Hudson denies picking anyone up, he answers her honestly about sleeping with men, saying he "lasts longer" with boys because "Boys don’t fit". It’s an incredibly frank conversation for a couple in the 1950s.

Rock Hudson factsFlickr, Insomnia Cured Here

32. She Terminated Him

After Arnold Schwarzenegger, the Governator himself, admitted to fathering a child with their housekeeper, his now ex-wife Maria Shriver walked away from the marriage with a big bad $250 million settlement. I'm guessing she didn't leave saying "I'll be back".

Movie Industry factsGetty Images

33. Every End is A Beginning

Married for 50 years, Hollywood legends Paul Newman and Joanne Woodward served as a model for the celebrity marriage, but few people remember how their romance began with adultery. They initially met in 1953 and reconnected on another film set in 1957. At that point, Newman had been married to Jackie Witte since 1949—and they even had three kids!

Nevertheless, Newman and Woodward began an affair, with him claiming to be drawn to her "modern and independent" nature. Eventually, Newman came clean and begged Witte for a divorce. Witte initially begged to stay together for the kids, but she relented and granted Newman the split after finding out that Woodward was pregnant.

Not the classiest move there, Paul.

Paul Newman factsGetty Images

34. This Gold Goose Cuts Herself Loose

Sonny and Cher rose to fame as a musical duo, but things fell apart when their careers floundered. Cher filed for divorce in 1974, citing "involuntary servitude". According to her, Sonny had withheld money from her and treated her "more like a golden goose than a wife".

Cher FactsGetty Images

35. Wandering Eyes Settle Down

Acting legend Humphrey Bogart’s marriage to Mayo Methot was absolutely fraught with drama; the tabloids had even dubbed them "the Battling Bogarts" (Methot once stabbed Bogart in the shoulder, but Warner Brothers suppressed the scandal). But when Methot caught word of her husband’s on-set affair with a woman young enough to be their daughter—the 19-year-old Lauren Bacall—she came to the set of The Big Sleep to keep an eye on them.

Not liking what she saw, Methot apparently sent Bogart packing (although some say he initiated the divorce). Soon after, Bogart wed Bacall, and the pair remained together until his passing in 1957.

Old Hollywood Stars facts

36. Let’s Go Shopping

Khloe Kardashian’s prenuptial agreement with Lamar Odom reportedly entitles the reality star to $500,000 for every year they were married. She also gets $25,000/month in support, a new car at the end of each lease cycle, $5,000 for shopping, $1,000 for beauty care, and courtside seats at Lakers games. Not too shabby. 

Kim Kardashian FactsGetty Images

37. Charitable Statement

After only 15 months of marriage, 30-year-old actress Amber Heard divorced the 53-year-old Johnny Depp, citing verbal and physical torment. The two reached a settlement wherein Heard would receive a one-time $7 million payment—which she promptly donated to the Children’s Hospital of Los Angeles and the American Civil Liberties Union.

Someone acting like a good person in a divorce? This is unheard of!

The Rum Diary - European Premiere.Getty Images

38. Under Par Matrimony

One day in 2010, an utterly bizarre saga began to unfold on sports networks, cable news channels, and gossip sites. First, there were reports that golf legend Tiger Woods had crashed his SUV into a tree. Then, it was alleged that he'd been fleeing his furious wife, Elin Nordegren. It took a while longer for the whole story to come out.

It was reported that his soon-to-be-ex-wife, Elin Nordegren, had gone through his phone and called the woman he was sleeping with. Waking Woods up to confront him, she reportedly began hitting him with her fists before chasing him into his car and out onto the streets with a golf club! After the dust settled, Elin walked away with a reported $100 million for ex-husband’s indiscretions.

Sports Scandal FactsGetty Images

39. Trail by Contract

Terrence Howard, best known for his TV show Empire, had been married to Michelle Ghent for only 13 months when she filed for divorce. According to Ghent, Howard expressed possessive behavior; some texts were permitted as evidence, one from Howard declaring, "I will never allow a restraining order or anything to keep me from my wife".

In turn, Howard accused Ghent of blackmailing him to get spousal support. A judge overturned their divorce settlement in 2015, claiming that Howard had signed it under duress. Ya, blackmail will do that to ya.

Celebrity Divorce FactsGetty Images

40. First Marriage Worst Marriage

Gloria Swanson was one of the biggest stars of Old Hollywood. She became pregnant shortly after marrying her first husband Wallace Beery. It should’ve been a happy time for the young couple, but there was one problem—Beery didn’t want to have children with his wife. Swanson later revealed that Beery went to chilling lengths to avoid having a family.

She said that he made her drink a mystery liquid that ended up terminating the pregnancy. Thankfully, the couple would separate and divorce by 1918.

Gloria Swanson factsWikipedia

41. Golden Couple

Gloria Swanson’s next marriage was to man-about-town Herbert K. Somborn. Not only was he president of a film company, he was also the owner of Hollywood hotspot and landmark the Brown Derby restaurant. For Swanson, who was still an up-and-coming star on the verge of fame at that point, it was a match made in heaven—but it wouldn’t be for long.

Gloria Swanson factsWikimedia Commons

42. Trial of the Century

The six-year marriage between Swanson and Somborn produced a daughter, Gloria Swanson Somborn—but it also produced an utterly scandalous divorce case that rocked Hollywood to its core.

Gloria Swanson factsGetty Images

43. Lucky 13

During their divorce proceedings, Somborn accused Swanson of adultery—but that wasn’t the worst part. Somborn claimed that not only had Swanson cheated on him, but she had also done so with 13 different men, many of them famous. They included her frequent collaborator Cecil B. DeMille, the "Latin Lover" Rudolph Valentino, and director and producer Marshall Neilan.

Gloria Swanson factsBeyond the Rocks (1922), Paramount Pictures Glor

44. Til Countersuit Do Us Part

The marriage of musical icon Liza Minnelli to David Gest didn’t just end in divorce—it ended in multiple lawsuits! Gest sued Minnelli for $10 million, claiming she drunkenly went after him, at one point resulting in a five-day hospital stay and nerve damage. Minnelli countersued and accused Gest of stealing $2 million from her.

In the end, they dropped the suits and settled the divorce in 2007. Is that considered a happy ending? I can't tell.

Liza Minnelli FactsGetty Images

45. Musical Disharmony 

After the tragic passing of his second wife Linda, Paul McCartney was heartbroken. Sadly, his next relationship would be an utter nightmare. Macca married Heather Mills in 2002 without a prenup. As a result, the former Beatle had to pay his wife $48.6 million in their eventual (extremely acrimonious) divorce. The singer later called the marriage one of his worst decisions ever.

Strangest Coincidences FactsMax Pixel

46. RIP Two Marriages and a News Site

In 2012, the news website Gawker published less than a minute of a tape involving Hulk Hogan engaging in some very inappropriate stuff with his best friend’s wife. At the time, he was still married to his own wife of 25 years, Linda Hogan. Linda filed for divorce soon after, and in turn, Hulk Hogan sued the website for $31 million, effectively sending it into bankruptcy.

Something about the fact that Hogan got $31 million out of sleeping with his best friend's wife, while married himself, just doesn't sit right with me.

80s Kid factsWikipedia

47. His Filmography, Her Bank Account

Mel Gibson and his wife Robyn Moore Gibson were married for almost three decades and had seven kids together. As Mel's mental health destabilized, evidenced by his drunken anti-Semitic rants, Robyn filed for divorce in 2007 (can't blame ya there, Robyn). As part of their settlement, Robyn received more than $425 million.

On top of that sweet plum, she also gets half of the residuals on all the projects that he worked on during their marriage.

Mel Gibson factsShutterstock

48. No Happy Endings

Robin Williams met his wife, Marsha Garces, when she worked as a nanny for the actor’s children in 1989. Although they were married for 19 years, Williams relapsed into drinking, and they divorced "amicably" in 2010. This, sadly, was a sign of things to come—Williams never managed to get sober and he took his own life on August 11, 2014.

Mrs. Doubtfire FactsWikimedia Commons

49. Waiting Periods Are Out

It came as a shock to all when Project Runway host Heidi Klum and singer Seal split up in 2012. Klum accused Seal of having anger issues, and Seal accused Klum of conducting an affair with her bodyguard, Martin Kristen. Although Klum insisted they didn’t start dating until the couple had separated, this fact was probably cold comfort to Seal.

Celebrity Divorces FactsGetty Images

50. First Comes Love, Then Comes Marriage, Then Comes…

Debbie Reynolds and Eddie Fisher were a Hollywood golden couple. They had two children together: daughter Carrie was born in 1956, and son Todd in 1958. At first, things couldn't be happier, and many people in Hollywood and beyond saw them as the perfect American couple. Sadly, these people were all wrong—their union was doomed to an utterly heartbreaking end.

Debbie Reynolds factsGetty Images

51. With Friends Like These

Many readers know where this one’s going. When Reynolds and Fisher were together, they were close friends with Elizabeth Taylor and her husband Mike Todd. When Todd perished in a plane crash in 1958, Taylor was utterly grief-stricken, and Fisher was all too happy to lend her a shoulder to cry on. Soon enough, the pair began an affair that would leave Reynolds devastated. The tabloids, predictably, went wild.

Debbie Reynolds factsWikimedia Commons

52. Four Degrees of Separation

Debbie Reynolds recalled the exact moment, decades ago, when she figured out that her husband, Eddie Fisher, was having an affair with Reynolds' best friend, Elizabeth Taylor. Reynolds called Fisher’s room, and when he wasn’t there, she tried calling Taylor’s. When Fisher answered, she heard Taylor’s voice in the back, and asked her soon-to-be-ex-husband, "Would you just roll over and put Elizabeth on the phone?"

Debbie Reynolds factsFlickr, Dan Perry

53. Done Dirty

The affair had dire consequences. Not only did the couple divorce in 1959, but Eddie Fisher's long-running variety show was canceled because of his ruined image. For her part, the public labeled Elizabeth Taylor as a "homewrecker". The illicit pair would go on to marry in 1959, but Taylor later said that she only married Fisher because of her overwhelming grief.

Debbie Reynolds factsGetty Images

54. Safety Papers

When Britney Spears married dancer Kevin Federline, she initially didn’t want a prenup. Don't panic though! Spears’s family was money-conscious and pressured her into drawing one up (thank God). It came in handy: when the couple broke up in 2006, Federline reportedly walked away with only $1 million.

Justin Timberlake factsGetty Images

55. Broken Hearts & Banks

When musician Phil Collins split with Jill Tavelman in 1996, he paid £17 million in divorce settlements, a whopping sum at the time—but the worst was yet to come. When he divorced Orianne Cevey in 2008, he had to shell out even more, £25 million to be exactI wonder how Tavelman felt about that? It became the largest settlement in a British celebrity divorce.

As of date, the actor has no intention to marry again, but he has recently rekindled his romance with CeveyWe’re sure his bank account is shuddering in anticipation.

Disney Movies FactsWikipedia

56. Surprise, We’re Over

After marrying Frank Sinatra and putting her career on hold in 1966, actress Mia Farrow spent two long years playing housewife while he continued to work. Bored of her bland, domestic lifestyle, she agreed to play the role of Rosemary Woodhouse in Roman Polanski’s Rosemary’s Baby. As the movie's filming schedule ran over time, Farrow received a heartbreaking letter.

Sinatra had served her with divorce papers.

Seinfeld FactsGetty Images

57. Endless, Problematic Love

Divorce was only a punctuation mark in the long and complicated story of Marilyn Monroe and Joe DiMaggio’s relationship. The star couple had only been married for nine months when Monroe announced that she was divorcing DiMaggio on the grounds of "mental cruelty" and his possessive behavior. DiMaggio didn’t take it well.

Famous Last Words FactsWikimedia Commons

58. Just Remember, You Belong to Me

He would show up to her house at random to see if she was with new men, and he enlisted his friend, none other than the also recently divorced Frank Sinatra, to have Monroe’s phone bugged (the "possessive" part is ringing true). Even when his harassment abated, DiMaggio never got over Monroe—when she overdosed in 1962, he took charge of the funeral plans and sent flowers to her grave twice a week, every week, until he himself passed on in 1999.

DiMaggio’s last words were reportedly, "I’ll finally get to see Marilyn". Like sure, that's romantic, but does that make up for the other stuff? 

Joe DiMaggio and his Bride Marilyn Monroe.Getty Images

59. The Jerk Took Her to the Cleaners

After glamorous old Hollywood star Rita Hayworth left her cruel first husband Edward Judson, he came up with a disturbing plan for revenge. He demanded her whole assets, before he would grant her wish for a divorce.

Rita Hayworth Facts Wikimedia Commons

60. Racing Against the Clock, and Each Other

Although Tom Cruise and Nicole Kidman called their divorce as an "amicable separation," their settlement was less than friendly. Cruise listed their separation date as December 2000—just shy of their tenth anniversary—while Kidman contended she was informed of their divorce two months later, in February 2001. This little difference meant a big deal.

Nicole Kidman factsGetty Images

61. What a Difference a Day Makes

Why did the ten-year mark matter when it came to the divorce between Kidman and Cruise? Under California law, a marriage is considered "long-term" at ten years, at which point Cruise would have to support his ex until she remarried (but seriously, how much "support" could Kidman possibly need?). Cruise reportedly caved to Nicole’s demands after she threatened to use DNA samples to prove she had suffered a miscarriage just weeks after Cruise announced their separation.

Yeah, doesn't sound that amicable to mebut it didn't end there. 

Nicole Kidman factsGetty Images

62. I Always Feel Like Somebody's Watching Me

There was speculation that Scientology was to blame for the divorce, but very little was known about the split’s awful details until former Scientologists revealed that Cruise and the Church of Scientology actually had Kidman’s phone tapped during their marriage. Cruise and Kidman’s two children also reportedly refuse to speak to their mother since the divorce, and have called her a "suppressive person".

Nicole Kidman factsDays of Thunder, Paramount Pictures

63. Young Love

Few people know that silent film star Jean Harlow was married before she ever became famous. When she was still a freshman at her prep school, she met and fell head over heels in love with Chuck McGrew, a handsome 19-year-old from a wealthy family. The two lovebirds simply couldn’t wait: they married in 1927 after a scant year of dating.

Despite all her efforts to keep her relationship together, McGrew and Harlow divorced in 1929. Still in her teenage years, Harlow now had one failed marriage under her belt.

Jean Harlow

64. Church Isn't for Everyone

In 2003, the 19-year-old Wilde got married to Tao Ruspoli, a filmmaker and Italian prince (we’re not joking about that, either). Interestingly, because they were eloping, Wilde and Ruspoli got married in an abandoned school bus with almost no witnesses. Their marriage lasted until 2011, when they got divorced.

Olivia Wilde factsGetty Images

65. Run Away With Me

Classic Hollywood star Lana Turner was a hopeless romantic, and threw herself into passionate—and reckless—trysts. When she was still a teenager, she ran away to Las Vegas and eloped with the dashing bandleader Artie Shaw after just one date. Though Shaw was almost a decade older than the ingénue, Turner said she was "stirred by his eloquence".

Lana Turner factsWikimedia Commons

66. Bitter Split

Sadly, the hasty marriage dissolved as quickly as it came in a mere four months, but it left Turner with permanent emotional scars. Shaw himself admitted he was a "very difficult man," but Turner’s confessions about the union were even darker. According to her, he mistreated her "like an untutored blonde savage, and took no pains to conceal his opinion".

Worst Ways They’ve Been Dumped FactsShutterstock

67. Fool Me Twice

Bizarrely—and tragically—Turner’s second marriage was a mirror image of her first. She eloped to Las Vegas with Steve Crane after just a week of dating, but then divorced him after just four months. It turned out that Crane was, well, already married, and Turner split the moment she found out his previous divorce hadn’t been finalized.

Robert Redford factsShutterstock

68. Over Before It Began

Elisabeth Moss has been married once in her life, tying the knot with Saturday Night Live alum Fred Armisen after only a year of dating. They met on the set of SNL in 2008 when Moss’s Mad Men co-star Jon Hamm was hosting the sketch show. Moss accompanied Hamm and even joined in a sketch. The relationship between Moss and Armisen raised a few eyebrows due to their 16-year age gap.

After only eight months of marriage, they were divorced.

Elisabeth Moss Facts Getty Images

69. Cons of Marrying a Comedian

Moss did not mince words when discussing her split from Armisen, hinting that he may not be as fun as he appears on SNL. In one interview, Moss revealed that she found the marriage "extremely traumatic". In an interview with Howard Stern, Moss said of her ex: "One of the greatest things I heard someone say about him is, 'He's so great at doing impersonations. But the greatest impersonation he does is that of a normal person.’" 

Outrageous Reasons for Divorce factsShutterstock

70. You Thought That Was Short

Among Nicolas Cage's relationships, his brief marriage to Elvis Presley's daughter Lisa Marie is probably the one that most people remember. But believe it or not, Cage’s marriage to Presley wasn’t even his shortest! In 2019, not long after his divorce from his longtime wife Alice Kim, Cage married Erika Koike in Las Vegas.

After just four days together, he filed for an annulment, and the split was finalized soon after.

Nicolas Cage factsGetty Images

71. Sing It Loud

After Zooey Deschanel divorced musician Ben Gibbard, she was heartbroken—but it was about to get so much worse. Following their breakup, Gibbard fuelled speculation that his album Kintsugi was about the divorcee. He wouldn’t say exactly which songs were about Deschanel, but people were quick to point out one hostile lyric.

In the lead single, Gibbard asks, "How could something so fair be so cruel?"

Celebrity Couples FactsShutterstock

72. The Quarter-Day Marriage

Italian actor Rudolph Valentino (nicknamed "the Latin Lover") was one of the most popular and sought-after stars in silent era-Hollywood, and many fans were heartbroken when he married American actress Jean Acker. But as soon as the ceremony was over, it all began to fall apart. She immediately regretted the decision and proceeded to lock Valentina out of their honeymoon suite.

After 20 minutes of knocking on the door, he simply gave up and went home. In the divorce proceedings, Acker would claim they never consummated the union. I guess they wouldn't have had time!

Rudolph Valentino FactsWikimedia Commons

73. Not-So-Smooth Sailing

Valentino's second marriage was somehow even rockier than the first. His second bride Natascha Rambova was not popular with a number of Valentino’s friends and the marriage disintegrated to the point where Rambova was eventually banned from his film sets. That bad blood didn’t end when he passed on. In his will, Valentino left Rambova an utterly cruel tribute.

He bequeathed her one single dollar bill. Ouch.

Mel Gibson factsPixabay

74. Relationship Baggage

Renee Zellweger has the typical actor relationship history, from dating co-stars to breaking off engagements and even a quick marriage. She married country music singer Kenny Chesney, but after only four months of marriage she filed for an annulment, and the reason why made the tabloids go wild. 

Celebrity Couples FactsShutterstock

75. The Rumor Mill

When Zellweger filed for an annulment from her union with Chesney, under "grounds for divorce," she had written "fraud". The media immediately began speculating about their relationship. Specifically, they speculated that Kenny was gay, which Renee found sad to hear. She later revealed that this was only a judicial term that helped along the annulment, and it wasn’t at all reflective of Chesney’s character or of their brief relationship together.

When the annulment happened, Zellweger and Chesney released a statement saying they split because of the "miscommunication of the objective of their marriage".

Renee Zellweger factsShutterstock

Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36

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