42 Heartbreaking Facts About Tragic Hollywood Love Stories

Christine Tran

“So it’s true, when all is said and done, grief is the price we pay for love.”―E.A. Bucchianeri, Brushstrokes of a Gadfly

Tragic romance isn’t just for the sad songs and sad movies. It’s also for the sad songwriters and sad filmmakers who make that stuff. Hollywood and the entertainment history are ripe with stories of broken hearts… and other broken body parts. Although many romantic tragedies end in death, the end of conjugal bliss doesn’t necessarily mean the end of life. Sometimes, “tragedy” is just the name we give to the series of conflicts that lead up to the lackluster end. With such grim possibilities, is it any wonder that tragic romance is such tabloid fodder?

From mysterious plane crashes to deadly disease, many random factors can bring a romance to its tragic conclusion. Grab a tissue and get ready for these 42 starstruck facts about tragic Hollywood love stories.

42. 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 died penniless from an apparent drug overdose in 1965 at the age of just 42.

41. He’ll Always Be With Us

After the tragic suicide 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.

40. 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 breast 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 away in Travolta’s arms in 1977, and the actor would not pursue a serious relationship again for 15 years.

39. 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 died one year later at the age of 58, she would have married him again.

38. 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%.

37. Unhappily Ever After

When they met, Prince Charles of Wales was dating Diana Spencer’s sister, but it was Diana whom the heir married in 1981. A third wheel would be a common factor for the rest of their marriage as both Charles and Diana would embark on extramarital affairs. Most notably, Charles rekindled a relationship with Camilla Bowes Parker; the release of their steamy phone calls would be majestically called “Squidgygate.” In the aftermath of the scandal, the royal couple was royally divorced in 1996.

36. Together for Ever

Millions mourned with John F. Kennedy Jr. perished while piloting his plane on July 16, 1999. But he didn’t die alone; the crash also claimed the life of his wife, Carolyn Bessette. The couple went down with Carolyn’s sister, Lauren. They were truly together ‘til the watery end.

35. 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 overdose in a brothel; Kardashian and her family rushed to his hospital bedside. At the time, the divorce papers to were signed, but not filed.

34. The Day The Music Died

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 with his sudden demise. She was pregnant at the time and miscarried soon after.

33. Carry On

Maria Holly (nee Santiago) would blame herself for her husband Buddy Holly’s death 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.

32. Not A Prank Call

On March 31, 1993, Eliza Hutton got the call that 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.

31. Puppet Love

Not all tragedies end in death. Or are even felt by the partners involved…especially when the couple is made of felt. In 2015, Miss Piggy and Kermit the Frog held a press conference to announce they had broken up after 40 years. The separation was amicable, but we’re sure that generations of fans who grew up shipping them on The Muppets—and fully expected them to stay together because…they’re puppets—were heartbroken.

30. 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 his Monteith’s death by overdose in July 2013. Michele had claimed on numerous occasions that Monteith made her feel like “the luckiest girl in the world.”

29. 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 death 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 his death by suicide.

28. 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 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 suicide are still ambiguous.

27. The Mournful Month

September was a busy month for beloved actor John Ritter and his actress 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 start. Ritter passed away from an aneurysm on September 11, 2003—what would have been their daughter Stella’s fifth birthday.

26. It Takes Two

In 2009, Brittany Murphy and her husband Simon Monjack both died suddenly—five months apart from each other. Murphy died from apparent pneumonia, heart conditions, and over-the-counter medication. Monjack reportedly died from coronary arrest. Murphy’s family has insisted on multiple occasions that toxic mold in their home was the culprit. To date, the reasons remain unclear.

25. 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 and died on March 18, 2009. Neeson and Richardson had 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.

24. 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 died just half an hour later, apparently losing the war with the struggles that had torn him and Williams apart.

23. The Only Woman For The Man In Black

In 2003, Johnny Cash, the “Man in Back” of country music died less than four months after the passing 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 the June’s death.

22. Separation Anxiety

Over 200,000 people died 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, Atlee would not be found, so she had to leave the country without any knowledge of her partner’s whereabouts. But she eventually got closure: Atlee’s body was later discovered and confirmed dead.

21. 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 stabbed by in the heart 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.

20. To Follow Him Anywhere

When rock star Jim Morrison died 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 on heroin in a Hollywood apartment. Do broken hearts stop in twos?

19. Sad Song

Because people are unreasonable, Beatles fans hated Yoko Ono even more after the death 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, ”At Least I Had That, One Guy Understood Me”.

18. 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 died. As Wilder said, “The fact is, Gilda didn’t have to die. But I was ignorant. Gilda was ignorant. The doctor was ignorant.” In her memory, Wilder co-founded “Gilda’s Club,” a non-profit organization that supports survivors of cancer and their families.

17. Big Star, Big Mystery

Natalie Wood’s death 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 wine bottle in rage. That evening, Wood went missing and was discovered dead in the water by morning. To this day, the exact circumstances of her death remain a mystery.

16. 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 stabbed to death in her hotel bathroom in 1978. Many fans think Sid was passed out at the time, but the police jailed him immediately for her murder. With no firm evidence, the case was dropped, only for Vicious himself to die three months later from a heroin overdose. 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.

15. Addicted to You

Blake Fielder-Civil was in prison when he was informed that his ex-wife, Amy Winehouse, had died of alcohol overdose. 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 death, although he admits to introducing her to hard drugs and self-harm during the early days of their relationship.

14. 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 died in her sleep from a heart condition. She had left behind her unfinished true crime 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.

13. 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 passed away from 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.

12. 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 suicide 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 suicide again.

11. Not for Long

Christopher Reeve passed away 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.

10. 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. 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, killing everyone on board, including Lombard herself.

9. 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 war’s start. After her tragic death, Gable finally joined the armed forces.

8. 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 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 death, when Gable died, he was interred beside Lombard.

7. You Don’t Give Up on Marilyn Monroe

Film legend Marilyn Monroe eloped with baseball legend Joe DiMaggio in 1954, but the marriage lasted only nine months. DiMaggio was upset his wife did not forgo her bombshell image after marriage. Following a mental breakdown and another divorce on Marilyn’s part, her ex re-entered her life. Just four days before her death from an overdose in 1962, DiMaggio quit his job to ask for Marilyn’s hand in remarriage.

6. Undying Devotion

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.”

5. 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.

4. 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 died just 10 years later.

3. 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 smoking taking a toll on Tracy’s his health, Hepburn stayed by his side until his death. Despite her devotion, Hepburn abstained from attending her life partner’s funeral out of respect for Tracy’s legal widow and children.

2. 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 died. Unfortunately, Harris passed away from ovarian cancer in 1991, aged 43. But the tragedy didn’t end there; Brosnan’s adopted daughter Charlotte would die from the exact same disease that took both her mother and her grandmother.

1. Families That Never Were

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 up soon after.But not long after, in 2001, Syme was killed in a traffic collision and police found depression medication 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.

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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