Devastating Facts About Hollywood's Most Tragic Love Stories

June 4, 2024 | Scott Mazza

Devastating Facts About Hollywood's Most Tragic Love Stories

No one knows heartbreak like Hollywood. There's a reason that Los Angeles is known as the City of Broken Dreams, and it's not just because of failed auditions. With the highs and lows that accompany fame and fortune, it's no wonder that Hollywood stars are so prone to heartbreak, tragedy, and loss. From mysterious plane crashes to bitter divorces to lives spent mourning, these stories prove that being rich and famous doesn't spare you from the devastation that comes from lost love. Grab a tissue and get ready for these 42 devastating facts about Hollywood's most tragic love stories.

1. Finished at the Bottom

Dorothy Dandridge was one of Hollywood’s first black sex symbols and the first black actress to be nominated for Best Actress at the Oscars. Unfortunately, her love life was much less illustrious; in 1959, she married a club owner named Jack Denison. He turned out to be abusive, including financially abusive, as he mismanaged her finances into bankruptcy.

He then had the audacity to divorce Dandridge in 1963. This story doesn’t have a happy ending: unable to get more acting roles, Dandridge went to the grave penniless from an apparent drug OD in 1965 at the age of just 42.

Hollywood's Most Tragic Love Stories

2. He’ll Always Be With Us

After the tragic loss of Kurt Cobain in 1994, his wife Courtney Love kept part of his ashes in a teddy bear. The rest of Cobain’s remains were scattered to other places, including the Namgyal Buddhist Monastery in New York, where they were blessed and mixed into the clay to make memorials.

Musicians Who Died Too Young QuizFlickr

3. Til the End

John Travolta was in the middle of filming Saturday Night Fever when he got horrible news: his partner Diana Hyland had only a few days to live. The couple had been together for a year, but Hyland had been diagnosed with cancer just three months into their relationship. Not one to abandon her, Travolta immediately moved in and looked after Hyland’s son as his own.

She passed on in Travolta’s arms in 1977, and the actor would not pursue a serious relationship again for 15 years.

Tragic Hollywood Love Stories FactsGetty Images

4. Third Would Have Been the Charm

The chaotic romance of Richard Burton and Elizabeth Taylor could fill a list of its own. The couple had married and divorced each other twice. At one point, Burton married someone else out of pure spite against Taylor’s alcoholism. But despite it all, Taylor would say that had Burton not passed on one year later at the age of 58, she would have married him again.

Richard Burton FactsGetty Images

5. Made the Top Two

At the end of her life, Elizabeth Taylor would rank Richard Burton among her favorite husbands. Seeing as she had eight husbands and married Burton twice, he would be proud to make the top 25%.

History’s Greatest Mistresses quizGetty Images

6. Hard to Shake Off

Lamar Odom and Khloe Kardashian divorced in 2013. But the separation did not stop Kardashian from looking out for him. In 2015, Odom was found unconscious from an apparent OD in a bawdy house; Kardashian and her family rushed to his hospital bedside. At the time, the divorce papers were signed, but not filed.

The Kardashians factsShutterstock

7. Buddy’s Best Buddy

Buddy Holly had been married for just six months when his plane fatally crashed on February 3, 1959. He had proposed to his wife, Maria Elena Santiago, on their first date. Even though she had known him for just a few hours, she took a night to say yes. In their short time together, Maria had devoted her life to supporting his band and was devastated by his sudden demise.

Tragically, her nightmare was just beginning: She was pregnant at the time and miscarried soon after.


Buddy Holly FactsWikipedia

8. Carry On

Maria Holly (nee Santiago) would blame herself for her husband Buddy Holly’s demise via plane crash. She claimed Buddy would never have gotten on the aircraft if she had been at his side on tour. Although she would remarry and have three children, Maria would dedicate the next 50 years of her life to keeping Buddy alive in the public memory.

Buddy Holly FactsGetty Images

9. Not A Prank Call

On March 31, 1993, Eliza Hutton got a call that made her blood run cold. Her fiancé, actor Brandon Lee, had been shot on the set of The Crow. She thought it was a joke; the two were set to be married in literally two weeks. Unfortunately, this was no tasteless prank call. Hutton managed to make it to his side, only for Lee to die from his injuries two hours later.

Brandon Lee FactsWikipedia

10. Not Very Gleeful

Just as their characters on Glee were falling in love, actors Lea Michele and Cory Monteith began a long-term romance in real life. The two were together from 2012 until Monteith fatally overdosed in July 2013. Michele had claimed on numerous occasions that Monteith made her feel like “the luckiest girl in the world".

Cory Monteith, Lea Mkichele arrives at the Kathy Hutchins, Shutterstock

11. Body & Soul

The world was shocked when Robin Williams took his own life in 2014. At the time, the comedian had been married to artist Susan Schneider since 2011. Schneider might not have found the passing so sudden; it came to light that Williams had been suffering from Lewy body dementia that earlier been misdiagnosed for Parkinson’s disease.

Schneider claims this condition deteriorated William’s motor skills and played a factor in him taking his own life.

Robin Williams factsShutterstock

12. A Rolling Stone Gathers No Closure

In 2001, rock legend Mick Jagger met his match in fashion designer L’Wren Scott. They apparently had everything in common. That made it more shocking when Scott took her own life in 2014. She had texted her assistant to come over to her condo at a specific time. At said time, the assistant discovered Scott hanging by her scarf in the doorway.

The circumstances of her demise are still ambiguous.

L'Wren Scott FactsGetty Images

13. The Mournful Month

September was always a busy month for beloved actor John Ritter and his actress wife Amy Yasbeck. It was the month of John’s, Amy’s, and their daughter’s birthday, not to mention their wedding anniversary. What should have been a month of celebration began with the worst possible thing that could happen to the loving family.

Ritter passed on from an aneurysm on September 11, 2003—what would have been their daughter Stella's fifth birthday.

Tragic Love Stories FactsShutterstock

14. Crash Course in Grief

Natasha Richardson thought she was perfectly fine after what she called “a tumble in the snow” while on vacation in Quebec. The actress has fallen from a beginner's ski slope, and assured her husband, Liam Neeson, over the phone that she felt fine. Her reassurances turned out to be premature. Later, she began to exhibit signs of a severe head injury. Richardson drew her last breath on March 18, 2009.

Neeson and Richardson had made a pact that if either of them were to enter a vegetative state, the other would pull the plug. A man of his word, Neeson fulfilled her wishes.

Liam Neeson factsGetty Images

15. The Day the Music Died

In 2003, Johnny Cash, the “Man in Back” of country music passed on less than four months after the loss of his beloved second wife, June Carter. They had been married since 1968, but they had met when they were both married to other people 12 years before that. It took a dozen years of personal struggles and Cash’s addiction problems for them to finally tie the knot, and that knot stayed tied until June’s passing.

Johnny CashGetty Images

16. Separation Anxiety

Over 200,000 people perished in the 2004 Indian Ocean Tsunami. One of these people was Simon Atlee, the boyfriend of Sports Illustrated model Petra Nemcova. The couple was on vacation in Thailand when the wave struck, shattering Nemcova’s pelvis so that she couldn’t swim. She managed to survive by holding onto a tree for eight hours.

While Nemcova was rescued, she was faced with heartbreaking news. Atlee could not be found, and so she eventually had to leave the country without any knowledge of her partner’s whereabouts. Nemcova eventually got closure: Atlee’s body was later discovered and confirmed deceased.

Tragic Hollywood Love Stories FactsGetty Images

17. Wild Love

Steve Irwin and his wife Terri married just eight months after they met. Since 1992, they had shared two children and a lucrative conservation career together—until Irwin was stuck in the heart by a short-tail stingray in September 2006. We don’t doubt Terri’s own heartbreak, but she has carried on with their conservation activism in memory of Steve.

Steve Irwin QuizGetty Images

18. To Follow Him Anywhere

When rock star Jim Morrison passed on in this bathtub in 1971 at the age of 27, his girlfriend, Pamela Courson, went into deep denial.  She refused to acknowledge his body, spiraled into drug use, and would still refer to herself as “us” as if Morrison were still alive and well. Just three years later, when Courson herself turned 27, she fatally overdosed in a Hollywood apartment.

Do broken hearts stop in twos?

Jim MorrisonGetty Images

19. Sad Song

Because people are unreasonable, fans of the Beatles came to hate Yoko Ono even more after the passing of John Lennon in 1980. The artist’s life crumbled in other ways too: she was disowned by her family and lost custody of her daughter. But in her own words, Ono took comfort in her survival and as she said of her former partner, ''At Least I Had That, One Guy Understood Me.''

Yoko OnoGetty Images

20. Foundation of Love

Gene Wilder’s beloved third wife, Gilda Radner, suffered a myriad of symptoms related to her ovarian cancer in 1986. Doctors, however, couldn’t properly diagnose her until 1989, the year she passed on. As Wilder said, “The fact is, Gilda didn’t have to die. But I was ignorant. Gilda was ignorant. The doctor was ignorant". But from his anger came a heartbreaking tribute to his lost love. 

In her memory, Wilder co-founded “Gilda’s Club,” a non-profit organization that supports survivors of cancer and their families.

Charlie And The Chocolate Factory factsWikimedia Commons

21. Big Star, Big Mystery

Natalie Wood’s demise in 1981 was officially ruled an “accidental drowning,” but many have their own tragic theories. That night, Wood and her husband, the fellow actor Robert Wagner, were on a boat with Christopher Walken. Wagner was reportedly intimidated by Walken and Wood’s relationship, which made Wagner smash a booze bottle in rage.

That evening, Wood went missing and was discovered lifeless in the water by morning. To this day, the exact circumstances of her passing remain a mystery.

Robert Wagner FactsGetty Images

22. That’s Not Very Punk Rock

Sex Pistols bassist Sid Vicious and his girlfriend, Nancy Spungen, were the most controversial couple in the 70s punk rock scene. The legend of their relationship is so infamous that it’s hard to believe Spungen was only 20 when she was found fatally stabbed in her hotel bathroom in 1978. Many fans think Sid was passed out at the time, but the authorities jailed him immediately for her murder.

With no firm evidence, the case was dropped, only for Vicious himself to die three months later from an OD. With no one else present to tell this vicious tale, it looks this case will remain as cold as the attitudes of the duo themselves.

Punk Music FactsGetty Images

23. Addicted to You

Blake Fielder-Civil was in prison when he was informed that his ex-wife, Amy Winehouse, had perished of alcohol intoxicatio. He has stated that at that moment “I couldn’t stop crying and then I had to go back in my cell. I just sat down and read the letters she’d written to me over and over". These days, Fielder-Civil has to deny to fans and the press that he had any direct role in Winehouse’s demise, although he admits to introducing her to hard substances and self-harm during the early days of their relationship.

Amy Winehouse factsGetty Images

24. When True Love Solves True Crime

In 2016, comedian Patton Oswalt lost his wife, true crime writer Michelle McNamara. They had been married for 11 years and had a daughter, Alice. McNamara passed on in her sleep from a heart condition. She had left behind her unfinished book, I’ll Be Gone in the Dark: One Woman’s Obsessive Search for the Golden State Killer.

With Oswalt’s help, her book was completed, and McNamara’s investigative work would play a big role in apprehending a suspect for the decades-old serial killings.

John Mulaney FactsGetty Images

25. Letters of Love

Natasha McElhone is best remembered for her role in sci-fi classics about star-crossed lovers, like The Truman Show and Solaris. Unfortunately, her off-screen love life has also been tragic. In 2008, her husband Dr. Hirigoyen Kelly succumbed to heart failure when McElhone was pregnant with their third child. It was also one day after their 10th anniversary.

To this day, the actress continues to write letters to her partner; these letters formed the basis of her book, After You: Letters of Love, and Loss to Husband and Father.

Tragic Hollywood Love Stories FactsGetty Images

26. A True Life Partner

After a horsing accident, actor Christopher Reeve became paralyzed from the neck down. The Superman star would go on to be a prolific activist, thanks to the support of his wife, Dana Charles Reeve. In 1992, Reeve had briefly considered ending himself in the early stages of his post-accident life. It was Dana’s reassurance that brought him out of the bleak period, and Reeve never brought up self-harm again.

Christopher Reeve FactsShutterstock

27. Not for Long

Christopher Reeve passed on in 2004 from health complications related to his paralysis. While his wife Dana continued with the couple’s disability activism, she did not outlive her husband long. She would succumb to cancer just two years later in 2006.

Tragic Hollywood Love Stories FactsGetty Images

28. You Don’t Give Up on Marilyn Monroe

Film legend Marilyn Monroe eloped with baseball legend Joe DiMaggio in 1954. For his part, DiMaggio was upset his wife did not forgo her sultry image after marriage, and it caused a rift between the pair. Their union lasted only nine months. Following a mental breakdown and another divorce on Marilyn’s part, her ex re-entered her life.

Just four days before her passing in 1962, DiMaggio quit his job to ask for Marilyn’s hand in remarriage.

Marilyn Monroe FactsWikimedia Commons

29. Undying Devotion

After her passing, DiMaggio sent flowers thrice a week to Marilyn Monroe’s grave. He outlived her by 36 years but never married again, and his last words were apparently, “I’ll finally get to see Marilyn".

Marilyn Monroe FactsGetty Images

30. Prince Harming

While Joe DiMaggio’s undying devotion to Marilyn Monroe looks like the stuff of Hollywood romance, it shouldn’t eclipse how their union also echoed the Hollywood violent thriller. When they divorced, DiMaggio had Monroe’s phones tapped and would show up to her house at random intervals, just to see if she was with other men. Not cool.

Joe DiMaggio and his Bride Marilyn Monroe.Getty Images

31. Her Knight in Noir Armor

It wasn’t just age difference that got between Lauren Bacall and Humphrey Bogart—nor was it really the fact he was already married. It was an unprofessional love triangle between him, her, and the director of their film To Have and Have Not, Howard Hawks. Despite being married as well, Hawks also fell in love with Bacall and threatened to end her career if she didn’t cut things off with Humphrey. His efforts just drove the 19-year-old Bacall into the arms of Humphrey. The film was finished under the salvation of executive Jack Warner. Bogart and Bacall went on to marry, but he passed on just 10 years later.

Mayo Methot factsGetty Images

32. Faith Before Romance

Spencer Tracy and Katharine Hepburn kept their long-time love under wraps; he was a devout Catholic and would not officially divorce his wife. With years of alcoholism and smokes taking a toll on Tracy’s health, Hepburn stayed by his side until his passing. Despite her devotion, Hepburn abstained from attending her life partner’s funeral out of respect for Tracy’s lawful widow and children.

Katharine Hepburn FactsWikipedia

33. Adopting Tragedy

Long before he became Bond, Pierce Brosnan found offscreen love with a former Bond girl, actress Cassandra Harris. Married in 1980, he even adopted Harris’s children as his own after their own father passed on. Unfortunately, Harris succumbed to ovarian cancer in 1991, aged 43. But the tragedy didn’t end there; Brosnan’s adopted daughter Charlotte would perish from the exact same disease that took both her mother and her grandmother.

Tragic Hollywood Love Stories FactsGetty Images

34. Families That Never Were

Few fans know, but Keanu Reeves’s personal life is riddled with tragedy. In December 1999, his girlfriend Jennifer Syme gave birth to a stillborn child. The grief contributed to their split soon after. Then, in 2001, Syme lost her life in a traffic collision. She'd been inebriated at the time, and on top of that, the authorities found both medication and illicit substances in her car.

Reeves was still scheduled to shoot back-to-back Matrix sequels that spring, but had to take “much needed peace time” to deal with this close-timed series of unfortunate events.

Charlie Sheen factsWikimedia Commons

35. The Showman

After a brief marriage to English actor Michael Wilding, actress Elizabeth Taylor married film and theater producer Mike Todd. Todd loved spectacles: for Elizabeth’s birthday, he rented Madison Square Garden, invited 18,000 party guests, and arranged to have the whole thing broadcast on CBS. But their union was doomed to a heartbreaking end: Todd lost his life in a plane crash in 1958; it was Taylor’s only marriage not to end in divorce.

Debbie Reynolds factsWikimedia Commons

36. Sisters Before Misters?

The Taylor relationship that caused the biggest scandal, however, occurred after Todd's demise, when she found comfort in the arms of his old friend, Eddie Fisher. The problem? Fisher was married at the time… to Taylor’s good friend Debbie Reynolds. The fallout was naturally painful, though the two women managed to reconcile. 

As for Fisher and Taylor, their relationship lasted five years, so I guess it had been all worth it?

Eddie Fisher factsGetty Images

37. In Solemn Memory

In 2015, Jim Carrey’s former girlfriend, Cathriona White, was found lifeless from a prescription drug OD. It was ruled that she took her own life. Carrey was devastated and performed pallbearer duties at the funeral. In 2016, White’s husband and mother both filed wrongful demise lawsuits against Carrey that he has characterized as a “cash grab".

The lawsuits claim that Carrey gave White both illicit prescription meds and venereal diseases. White’s lawyer actual statement: “Instead of giving Ms. White flowers and chocolates, Carrey should have given her his [STI] test results… THAT is what she deserved on Valentine’s Day".

Jim Carrey FactsLiar Liar (1997), Imagine Entertainment

38. Dangerous Liaisons

One of Pfeiffer’s earliest roles was playing the innocent and ill-treated Madame Marie de Tourvel in Dangerous Liaisons. She played opposite John Malkovich, who had the infamous role of the unprincipled Valmont. As might be expected on the set of a film about scandal, it was soon reported that the married Malkovich had begun an affair with Pfeiffer.

The affair did not last, but neither did Malkovich’s marriage.

Michelle Pfeiffer factsDangerous Liaisons (1988), Warner Bros.

39. Church Schism

Scientology was blamed for Nicole Kidman's divorce from Tom Cruise, 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.

Nicole Kidman FactsShutterstock

40. The Decline and Fall

When Mary Pickford wed Douglas Fairbanks, they were two of the biggest stars in Hollywood. They often hosted lavish parties at “Pickfair,” their home, but few saw the dark side of their glamorous life together. The massive amount of attention they received strained the marriage. At the end of the silent era, both their careers floundered, creating further tension—and then, in the early 30s, a scandal erupted that would finally tear them apart. Fairbanks began an affair with Sylvia, Lady Ashley, a wealthy socialite. When his cheating became public, the Hollywood golden couple separated.

Power Couples factsFlickr, kate gabrielle

41. The Brangelina of Their Day

As beloved as Frank Sinatra was during his time (inspiring the phrase Sinatramania before anyone had even heard of the Beatles), things took a turn when he infamously divorced his wife, Nancy, so he could marry renowned actress and femme fatale Ava Gardner, with whom he’d been having an affair. The press soundly criticized Sinatra’s actions, tarnishing his once-reasonably wholesome reputation permanently. 

Gardner and Sinatra also had a turbulent marriage, even though Gardner was responsible for saving his career by getting him the part in From Here to Eternity. They divorced after six years together.

Ava Gardner FactsWikimedia Commons

42. Romance is Different in Hollywood

Anyone who has seen Casablanca or Murder on the Orient Express (the first one) will know just how talented Ingrid Bergman was. In her own lifetime, she was hailed as a legendary actress, until she became better known for a scandal which shocked a society that was hooked on Bergman’s wholesome cinematic persona. The news came out that she had begun an affair with director Roberto Rossellini when both were married at the time. 

They ended up divorcing their spouses to become an item, partly because Bergman had become pregnant with Rossellini’s child. The pair would have three children together before divorcing in the 1950s. Despite the damage to her reputation, Bergman’s career endured, and she won another Academy Award later in her career.

Ingrid Bergman FactsGetty Images

43. Talk About a Young Offender

1958 bore witness to one of the biggest scandals ever to rock Old Hollywood. Johnny Stompanato, known mafioso and infamous boyfriend of renowned actress Lana Turner, was found fatally stabbed in Turner’s home. Turner’s daughter, 14-year-old Cheryl Crane, confessed to stabbing Stompanato after he had hurt her mother in the midst of a vicious argument. The murder was ruled to have been justified, proving once again that being in the Mafia doesn’t pay off in a court of law.

Lana Turner factsWikimedia Commons

44. It Could Have Been Much Worse

As shocking as it was that Cheryl Crane had slain Johnny Stompanato, a few rumors persisted that things had gone down differently than was claimed by those involved. The most common of which was that Lana Turner had actually been the one to stab her boyfriend, and her daughter only took the fall because the court would look more favorably on murder if it was a minor who did it. 

A more twisted rumor claimed that Turner hadn’t actually been threatened by Stompanato; she’d actually caught him in bed with her daughter! In her rage, she’d stabbed Stompanato and forced Crane to take the fall. Frankly, we’re doubtful that this version is true, and we really hope that it isn’t.

Lana Turner factsWikimedia Commons

45. Unlucky in Love

Rudolph Valentino impulsively married his first wife, actress Jean Acker, in 1919, two months after they met. Acker had only seemed to be interested in women at the time, and had reportedly been involved in a love triangle with actresses Grace Darmond and Alla Nazimova. Whether or not she was ever actually romantically interested in Valentino is unclear, but her decision to marry him was one she regretted almost immediately.

She locked Valentino out of their hotel room on their wedding night, the couple separated soon after, and Acker moved back in with girlfriend Grace Darmond soon after. They finalized their divorce in 1922, but ironically became good friends afterward.

Devastating Facts About Hollywood’s Most Tragic Love StoriesPicryl

46. Not-So-Smooth Sailing

Valentino's second marriage was even rockier than the first. Rambova and Valentino lived in separate apartments in New York City while they waited out the year required of them by the courts, and they legally remarried on March 14, 1923. Rambova was not popular with a number of Valentino’s friends—June Mathis among them, whom he fell out with.

The marriage disintegrated to the point where Rambova was contractually banned from his sets towards its end, and they divorced in 1925. It was a bitter end, too—Valentino left Rambova one single dollar in his will. Ouch.

Rudolph Valentino factsWikimedia Commons

47. The Woman in Black

For decades after Valentino’s passing, a veiled woman in black has arrived at his tomb on the anniversary of his demise to place a single rose on his grave. The identity of the woman was a mystery at first, until it was revealed that the whole thing was—you guessed it—a publicity stunt, this time cooked up by press agent Russel Birdwell in 1928.

When this got out, several copycats vied to be the new “Woman in Black” and the tradition continued. Film historian Karie Bible is the most recent to have taken up the mantle.

Rudolph Valentino factsGetty Images

48. Playing it Up

The supposed true love of Greta Garbo’s life was silent film actor John Gilbert, with whom she starred in several films. MGM even changed the title of one of their films to Love so that they could advertise John Gilbert and Greta Garbo “in” Love and play up their real-life chemistry.

John GilbertGetty Images

49. Jilted Lover

As much as Garbo and Gilbert were supposedly in love, marriage just wasn’t in the cards for the pair. He proposed several times, finally getting her to agree to a double wedding with King Vidor and actress Eleanor Boardman. On the day of the wedding, however, she stood him up at the altar, leaving him disappointed and understandably angry.

Greta Garbo FactsFlickr

50. Stop the Wedding!

In 1929, Gilbert proposed yet again to Garbo, but she still wouldn’t accept, and he got engaged to Ina Claire instead. The day before they were to be married, Garbo supposedly called Gilbert’s best man and begged him to stop the wedding. His reply was that only she could do that, but Garbo didn’t want to create a scandal, and let it go on.

John GilbertWikipedia

51. The Battling Bogarts

Before marrying Lauren Bacall and becoming one-half of one of the most high-profile Hollywood couples of the era, Humphrey Bogart was married to actress Mayo Methot. And it was not a smooth relationship. They both drank heavily and fought regularly, eventually earning the moniker “The Battling Bogarts” in the press.

Methot became known as “Sluggy” due to her combative nature, and Bogart would later name his yacht Sluggy in her honor.

Mayo Methot factsGetty Images

52. Bogart, Bacall, and Methot

Bogart fell in love with Bacall on the set of To Have and Have Not, and they began an affair. At 3 AM one morning, Bogart called Bacall, saying “I miss you, Baby,” before Methot, who had caught wind of the affair, tore the receiver from his hand and screamed at a terrified Bacall down the line: “Listen, you Jewish b**ch, who’s going to wash his socks?”

Greta Garbo FactsGetty Images

53. Is That All There Is?

Despite the unseemly way they had started their relationship, Lauren Bacall and Humphrey Bogart had a strong marriage. They had two children together, but sadly, their union was doomed to a heartbreaking end. Bogart was by any measure a heavy drinker and smoker, and he was diagnosed with esophageal cancer in early 1956.

After 12 years of marriage, Bogart passed on in 1957. Bacall remained tight-lipped about her late love, saying “being a widow is not a profession".

Rat PackFlickr

54. A Different Kind of Pre-Nup

When Nicolas Cage first met Patricia Arquette, he proposed to her and Arquette playfully made a list of acts Cage would need to check off before she would accept his proposal. When Cage actually started fulfilling each ridiculous request, Arquette started to freak out and hide from him. But no one can hide from Cage for long and she would eventually be pulled into his gravity, and they married in 2001.

It didn't last long—the pair lived together for only nine months after the wedding, but continued to publicly act as a couple until their divorce in 2000. He went on to have another whirlwind marriage with another woman from an even more famous family: Lisa Marie Presley, daughter of Elvis!

Nicolas Cage factsGetty Images

55. Things Are Getting Ugly

Kim Basinger and Alec Baldwin were the picture-perfect Hollywood power couple of the 1990s—both of them certainly looked the part! The pair met on the set of 1990’s The Marrying Man and married in 1995. The pair co-starred in The Getaway, co-hosted an episode of Saturday Night Live together and even guest-starred as a couple in an episode of The Simpsons.

However, things turned ugly after their very public split in 2000—Baldwin even wrote a tell-all book that dished about their divorce and subsequent custody battle over their daughter!

Devastating Facts About Hollywood’s Most Tragic Love StoriesWikimedia Commons, Georges Biard

56. Desilu

By 1960, Ball and Desi Arnaz were famous as a couple both on and off the screen. However, the portrayal of the relationship onscreen was an illusion. Just a day after filming the final episode of I Love Lucy (which was also the day after Arnaz’s birthday), Ball filed for divorce, declaring that her marriage had devolved into “a nightmare".

Desi Arnaz FactsWikimedia Commons

57. So Fresh and So Clean

They may not have made it as a power couple, but Joan Crawford's brief encounter with megastar Kirk Douglas can still join the pantheon of disturbing Hollywood stories. Crawford's obsessive cleanliness reared its pristine head even in her bedroom affairs. In his memoirs, Kirk Douglas recalled a particularly disturbing and bizarre romantic encounter when the two stars once went back to Crawford's house.

In the middle of the act, Douglas reports, Crawford leaned in and murmured into his ear—but it was far from sweet nothings. "You're so clean," she said. "It's wonderful that you shaved your armpits when you made Champion". As Douglas put it, her passionate outburst was "a real conversation stopper".

Kirk Douglas factsWikimedia Commons

58. From Storm to Storm

After Ali MacGraw divorced her second husband in the aftermath of the scandalous affair between her and Steve McQueen, MacGraw promptly married the screen actor in 1973. During her marriage to McQueen, she didn’t act in any films. Aside from any other issues they had, MacGraw suffered a miscarriage during their time together.

Steve McQueen FactsGetty Images

59. Love Never Dies

Although Steve McQueen and Ali McGraw divorced in 1978 after just a few years of marriage, McQueen's friends revealed after his passing that he carried a torch for McGraw, and that she was the love of his life.

Ali MacGraw FactsGetty Images

60. His Heart Was Set on Her

Fred Astaire married his first wife, the 25-year-old divorcee and socialite Phyllis Potter, in 1933—but she didn’t just fall into his arms. He pursued her for two years over the objections of his mother and sister. They ended up having two children and staying together for 21 years, until her demise from lung cancer in 1954. How tragic!

Old Hollywood Stars factsGetty Images

61. Welles Fell for Her

Famed actor, writer-director, and producer, Orson Welles caught a glimpse of a famous pin-up picture of Rita Hayworth in Life magazine. He fell for the ravishing redhead immediately. They married in 1943, but, within a year, their love affair ended for a tragic reason. Welles realized that Hayworth wasn’t the ‘Love Goddess’ she portrayed in films.

Instead, she was an insecure, emotionally-scarred woman who would never heal from her awful past.

Arthur Miller factsGetty Images

62. A Shocking Case of Cold Feet

Rita Hayworth always said that Orson Welles was her greatest love. Right before her 1949 wedding to Prince Aly Khan, Hayworth cried out to Welles, begging him to see her. Welles arrived at her hotel to a startling sight. He found Hayworth’s room lit with candles and his ex-wife in a sensual negligee. She pleaded with him to remarry her and Welles had to calm her down, sadly convincing her that it would never work.

Welles apparently remained haunted by the tragedy of Hayworth’s life, for as long as he lived.

Shawshank Redemption FactsWikipedia

63. Four Year Itch

Hayworth married Khan in 1949 and gave birth to their daughter, Princess Yasmin Aga Khan, in December of that year. The marriage barely lasted until 1953. Although Khan professed to be deeply in love, his actions did not match his words. He was never faithful and may have had an affair with Hayworth's rival Joan Fontaine.

On top of this, Hayworth's temper tantrums—caused by their unstable home life and the residue of Haywood's childhood trauma—were epic. Hayworth married two more times in her life, but never successfully, or for long.

Rita Hayworth FactsGetty Images

64. Drinking Her Problems Away

Both Orson Welles, and daughter Yasmin Aga Khan, commented publicly on Hayworth’s misuse of drinking. They felt utterly helpless as they watched Hayworth slowly destroy herself. Sadly, things would only get worse. In 1974, tragedy struck. Hayworth’s two brothers passed on within a week of each other. Her inconsolable sadness fueled more devastating drinking.

Rita Hayworth FactsGetty Images

65. On-Again/Off-Again

The American aviator/filmmaker Howard Hughes loved very little outside of money, movies, airplanes, and women—but boy did he love women! He met actress Ginger Rogers in 1932 while dancing at the Coconut Grove club (with another woman). Their relationship was on-again/off-again for years, with the pair getting engaged in 1940, and Hughes promising to build her a mansion on Los Angeles's Cahuenga Peak.


66. Jekyll and Hyde

The love affair between Hughes and Rogers soured pretty quickly once his true colors started to show. He started ordering her to be available to him at all times, and she was certain that he had tapped her phones and was following her in order to keep tabs on her. He even tried to regulate how much time she was allowed to spend talking to her mother. Needless to say, warning bells were going off.

Jane Russell factsFlickr, SDASM Archives

67. No More!

Rogers finally broke it off with Hughes when she went to visit him in the hospital after a car crash and he tried to blame the accident on her! He said it was her fault since he'd only driven into traffic because she made him angry by refusing to go to the dentist with him! Enough was enough. Rogers told him that she knew he’d been cheating, gave him back his jewelry (including the engagement ring) and ended things right there.

It was the last time she ever saw him, and the first time, according to Noah Dietrich, anyone had seen him cry. He had that coming!

Ginger Rogers factsGetty Images

68. Family Life

Hollywood songstress Lena Horne was unlucky in love. At the height of her stardom when she was barely out of her 20s, Horne married the handsome Louis Jordan Jones in 1937. For a brief time, it seemed like a fairy tail ending: The couple had two children, daughter Gail and son Edwin. Sadly, it was actually doomed to an utterly heartbreaking end. 

The pressures of stardom became too much for the young lovers, and they separated just four years after the wedding.

Lena Horne FactsGetty Images

69. Second Chance at Love

In the 1940s, it seemed like Horne was willing to give love another shot, and she married prestigious MGM music director Lennie Hayton in 1947 during a lavish ceremony in Paris, France. Their relationship was wracked with scandal: Hayton was a white man, and interracial marriages were still frowned upon—but they were hiding an even darker secret. 

Lena Horne FactsWikipedia

70. A Political Union

In an interview with Ebony magazine, Horne once revealed that her marriage to Hayton was mostly loveless, and that she had only married him to help improve her career prospects and to cross the Hollywood color line.

Lena Horne FactsFlickr

71. First Love

Just off her success with The Wizard of Oz, a teenaged Judy Garland fell madly in love with handsome bandleader Artie Shaw. It was her first real adult romance—but it ended in tragedy. Shaw ended up running away with Garland’s fellow MGM leading lady Lana Turner, an actress who was thought to have more sensual appeal than the girlish Garland.

She was utterly devastated—but the worst was yet to come.


72. Then Comes Marriage…

After a disastrous first marriage, Judy Garland began seeing musician David Rose. He presented the young actress with a diamond engagement ring on her 18th birthday in 1938. There was just one problem: Rose was a married man. Appalled that Garland was involved with the husband of Martha Raye, a popular singer, the studio successfully drove Rose and Garland apart.

Judy GarlandWikipedia

73. Endless Heartbreak

However, after a brief break, Garland and James Rose were finally wed in 1941. Garland was just 19 years old, and Rose was just the first of her five husbands. As we've seen, four of these marriages would end in divorce. Garland's last marriage would end with her tragic, untimely demise.

Judy GarlandGetty Images

74. Curtains

Garland married her fifth husband, nightclub manager Mickey Deans, on March 15, 1969. Sadly, this marriage was also only to last a few months.  On a summer day in 1969, Garland’s new husband walked into his bathroom to find a ghastly sight: Judy unresponsive on the cold floor. He was scared that she’d harmed herself, but the truth was much darker.

Judy Garland FactsGetty Images

75. Friends With No Benefits

Bad romance runs in the family. Judy Garland's daughter Liza Minnelli’s first marriage to Peter Allen ended when he came out as gay in 1974. According to her, she was the last to know: "I married Peter, and he didn't tell me he was gay. Everyone knew but me. And I found out ... well, let me put it this way: I'll never surprise anybody coming home as long as I live. I call first!" Nevertheless, the two stayed close friends until Allen’s 1992 passing.

Liza Minnelli FactsGetty Images

76. Love Square

While still in the closet, Minnelli’s first husband Peter Allen embarked on a secret affair with Minnelli’s own stepfather, Mark Herron. He was still married to Judy Garland at the time, which must have made an awkward event of both family dinners and red carpets.

Liza Minnelli FactsGetty Images

77. In Love With the Wrong Team

Minnelli’s father, Vincente, had rumored relationships with other men. It’s said her mother, Judy Garland, tried to take her own life upon finding her husband in bed with a male lover. Biographers have made this unfortunate connection between mother and daughter’s love lives.

Judy Garland FactsGetty Images

78. First Lady Audrey?

Audrey Hepburn actually dated John F. Kennedy while he was still a Senator! She was devastated when she heard the news of his murder and was the one who told the cast of My Fair Lady, which she was filming at the time. Before leaving the set to cry, she asked all those around to pray for him.

Audrey Hepburn FactsFlickr


79. Affairs of the Heart

Audrey Hepburn also had a love affair with William Holden during and after the filming of Sabrina. Though he was married, the pair found their way to each other. Despite Hepburn’s desire for children, Holden secretly had a vasectomy. When he told her what he had done, she was utterly heartbroken.

Audrey Hepburn FactsWikimedia Commons

80. Art and Reality Blended

On the set of The Razor’s Edge, action star Tyrone Power fell head over heels with Gene Tierney, the woman who portrayed his love interest in the film. Power made no secret of his interest in her, which fuelled rumors that the two were a romantic couple. This wasn’t the case, however, as Tierney was preoccupied with a failing marriage and an affair with a pre-political John F. Kennedy.

Power didn’t get the message until he bought her a scarf with “Love” embroidered into it and Tierney directly asked him to back off.

Gene Tierney FactsFlickr,Film Star Vintage

81. Heartbreak After Heartbreak

After a string of broken relationships and marriages, Tyrone Power vowed to never marry again. That is, until he met Deborah Ann Minardos in 1957. They were married on May 7, 1958, and she became pregnant soon after with the son Power had always wanted—but tragically, their union had a devastating end. Power passed on two months before their son, Tyrone Power Jr., was born.

Lana Turner factsGetty Images

82. Passionate Affair

During the late 1960s, actress Faye Dunaway entered into a relationship with acclaimed Italian thespian Marcello Mastroianni (best known for his work with Federico Fellini). The two of them met when they worked on the film A Place for Lovers (fitting title) and would be romantically involved for two years.

Faye Dunaway FactsGetty Images

83. Bitter Ending

Faye Dunaway’s relationship with Marcello Mastroianni would end in heartbreak for both of them. Mastroianni wouldn’t divorce his wife or leave his children to be with Dunaway, who wanted to marry him and start a family together. Dunaway finally gave up and left him, but later admitted in 1995 that she never quite got over her feelings for him. 

Mastroianni would feel similarly; in a 1987 interview, the aging actor claimed that Dunaway was the love of his life and that he would always regret losing her.

Faye Dunaway FactsGetty Images

84. Easy to Replace

In 1967, French actress Brigitte Bardot and her then-boyfriend Serge Gainsbourg wrote and recorded the notoriously steamy love song, “Je t’aime… moi non plus". Bardot was married to a powerful man at the time, who refused to let the single be released. Bardot begged Gainsbourg not to let the song out to the public; he consented. The next year, Gainsbourg re-recorded the song with his new girlfriend, Jane Birkin. This version was an international success.

Devastating Facts About Hollywood’s Most Tragic Love StoriesPicryl

85. Stay in Touch?

According to Bardot, her first marriage to director Roger Vadim broke down as a result of Vadim’s affairs with men. For her part, Bardot embarked on an affair with her And God Created Woman co-star, Jean-Louis Trintignant. She and Vadim officially divorced in 1957 after less than five years of marriage.

Brigitte Bardot FactsGetty Images

86. Quickie Wedding

As a young actress, Jane Fonda had an extremely troubled love life. She was married no less than three times, with each union ending in divorce. Her first husband was famed director Roger Vadim, the same director who was married to Brigitte Bardot. Although it lasted almost a decade on paper, she married her second husband, activist Tom Hayden, just three days after finalizing her first divorce. Talk about messy.

Jane Fonda factsGetty Images

87. Wedding Bells

On January 20, 1968, actress Sharon Tate married director Roman Polanski, just days before her 25th birthday. Soon after, friends began to note the director's controlling behavior when it came to Tate.

Sharon Tate FactsFlickr

88. Wedded Bliss

Although Tate hoped marrying Polanski would help settle them down as a couple, they hid some bedroom secrets: it was far from a faithful marriage. Polanski had an unapologetically wandering eye, and called Tate's discomfort with his infidelity "Sharon's big hang-up". For her part, Tate was said to have confided in friends bitterly, "We have a good arrangement. Roman lies to me and I pretend to believe him".

Sharon Tate FactsFlickr

89. Love House

In 1969, Polanski and a very pregnant Tate moved into 10050 Cielo Drive. It was a mansion fit for Hollywood's best and brightest: nestled deep in Benedict Canyon, the house used to belong to the couple's friends Terry Melcher and actress Candice Bergen. Tate was reportedly over the moon about the move, and referred to the home as her "love house".

Infamously, it was the house she would die in.

Charles Manson FactsInside Charles Manson

90. Five Lives, Cut Too Short

Tate’s life took a sad, cruel twist when the Manson Family burst into her home, slaying her along with Abigail Folger, Voytek Frykowski, Steve Parent, and her dear friend Jay Sebring. The infamous offense took place on the night of August 9, 1969 in Tate's Cielo Drive home while she was entertaining friends. It was a tragedy that shook the nation—not to mention Polanski, who was abroad at the time.

Sharon Tate FactsFlickr

91. Head Case

During the conflict, film star Bette Davis tragically lost her second husband, Arthur Farnsworth, but he did not die in battle. However, his passing was due to violent reasons: he passed out in a Hollywood street and perished two days later. When the autopsy came back, it revealed that he succumbed to a skull fracture incurred two weeks before.

Davis testified she didn’t know what could possibly have caused the fatal injury. Farnsworth’s demise was labeled an accident.

Bette Davis factsWikipedia

92. It Takes Two

On December 20, 2009, actress Brittany Murphy passed on at the tragically young age of 32. While the cause of her demise was originally listed as natural causes, a subsequent report blamed her passing on “a combination of pneumonia, anemia, and prescription and over-the-counter [meds]". Five months after Murphy’s passing, her husband, Simon Monjack, perished in the same bedroom that Murphy had been in.

Brittany Murphy FactsGetty Images

93. In the Flower of Her Youth

In a disturbing coincidence, the cause of Monjack's demise was also listed as pneumonia and anemia. One reason for the abrupt deaths of Murphy and her husband has been brought forward by Murphy’s mother, Sharon. Sharon maintains that her daughter and son-in-law passed on due to a presence of deadly mold in their house. By contrast, Murphy’s father, Angelo Bertolotti, had toxicology tests done on Murphy’s hair.

The results convinced him that she and her husband were poisoned. Bertolotti has yet to make an accusation on who that poisoner might have been, and it’s worth pointing out that Murphy’s mother, Sharon, and Bertolotti hotly dispute each other’s claims.

Brittany Murphy FactsGetty Images

94. An Untimely Investment

In 1939, MGM studios paid Clark Gable tons of money to finally divorce his wife and marry his mistress Carole Lombard. Gable had been worried that doing a high-profile movie like Gone with the Wind would draw attention to his infidelity, so the studios just paid him to split the difference.

Clark Gable FactsWikimedia Commons

95. Rumors

By all accounts, the marriage was happy until Gable was rumored to be “entertaining” another woman on a film in 1942. Lombard took an early flight home. Unfortunately, this plane crashed into Potosi Mountain, ending the lives of everyone on board, including Lombard herself.

Carole Lombard factsFlickr, Dennis Amith

96. You Win, Honey

Throughout their whirlwind romance, Carole Lombard was a huge supporter of US efforts in WWII. She had asked her husband Clarke Gable to enlist in the effort several times since the conflict's start. After her tragic passing, Gable finally joined the armed forces.

king kong factsGetty Images

97. From Hero to Hysterics

It’s said they had to restrain Clark Gable from scaling the mountain where Carole Lombard had crashed, for he had wanted to rescue her himself. When Lombard’s body was finally discovered, Gable's reaction was utterly devastating. He reportedly sobbed, “Oh, God! I don't want to go back to an empty house,” and then proceeded to reside at their Encino home for the rest of his life.

Despite the fact that he married again twice after her passing, when Gable met his own end he was interred beside Lombard.

Grayscale portrait photo of the actor Clark GableMovie studio, Wikimedia Commons

98. No Change to Restart

Heath Ledger and Michelle Williams had broken up in 2006 as a result of Ledger’s unstable behavior and partying. Just two years later, in January 2008, he was found unconscious in his hotel room. Ledger perished just half an hour later, apparently losing the battle with the struggles that had torn him and Williams apart.

Power Couples factsGetty Images

99. Consummate Professional

When Heath Ledger tragically passed on, Williams was busy filming the movie Mammoth in Sweden. The rest of filming, according to Williams, was “horrible,” and she admitted that she couldn’t even “remember most of it".

Michelle Williams FactsShutterstock

100. America's Sweetheart

In the late '80s and early '90s, Julia Roberts had a reputation as something of a runaway bride (perhaps leading to her casting in a film of the same name in the late '90s). She became engaged to Dylan McDermott after they appeared in Steel Magnolias together, but broke it off when she met Kiefer Sutherland while making Flatliners. Sutherland was already married at the time with a child, but he soon announced his engagement to Roberts.

Julia Roberts FactsShutterstock

101. Runaway Bride

A huge wedding was planned between Roberts and Sutherland, but three days before, Roberts called it off and ran away to Ireland with Sutherland's good friend Jason Patric. Recently, Sutherland revealed he holds no grudges about the whole debacle, saying that Roberts was smart to get out while she did.

Julia Roberts FactsGetty Images

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22

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