Ah, Hollywood. It's the land of glitz and glamor, but also of, uh, not so nice things. From fiery affairs and messy divorces to horrific tragedies and family-ruining feuds, there's no business like show business when it comes to jaw-dropping celebrity scandals. We've compiled the least known and most surprising bits of Hollywood lore. Sit down and buckle up, y'all.
1. Michael Caine's Family Secret
Michael Caine is the ultimate cool Cockney lad, but it turns out that his life isn't a wry comedy. It's a dang soap opera. In 1989, the actor was devastated by the passing of his mother Ellen Frances Marie, only for his grief to transform into a profound sense of betrayal. Caine discovered that his mother had been lying to everyone in the family—even her husband and children.
It turned out that Caine had an older half-brother named David. He had been born with severe epilepsy and confined to a hospital for his entire life. The only hints to David's existence were the occasions when Caine’s mother visited her secret son in the hospital.
2. Halle Berry's Bad Romance
In 1991, Halle Berry was physically abused by a boyfriend to the point of losing 80% of hearing in her left ear. Berry has not disclosed the identity of her abuser—but she has stated that he is an established name in Hollywood and that the incident occurred while she was filming The Last Boy Scout. Commentators have identified the actor Wesley Snipes and the singer Christopher Williams as dating Berry around this time. Make of that what you will.
3. Drew Barrymore's Tragic Life
Drew Barrymore is such a ray of sunshine that most people have forgotten her tenure as one of Hollywood's OG bad girls. After becoming a child star in ET, Barrymore struggled with alcoholism and illicit substances, and eventually tried to end her own life when she was just 13 years old (Drew, no!). Thankfully, she was found in time and taken to a hospital to recover. Afterwards, Barrymore's mother took her daughter in. Just joking, she sent Drew to a mental institution, where she stayed for a year and a half.
Barrymore says no one told her she was going to be institutionalized, which is incredibly scary and upsetting. But on the other hand, Drew admits that if her mother had told her it was coming, she probably just would have run away. The ends justify the means? Either way, once Drew was released, she emancipated herself from her mom, legally becoming an adult at the age of just 14. Despite all this, Barrymore thinks fondly of her mom, even though the two don’t speak that often.
4. Oprah's Sad Childhood
Before she was a household name, Oprah fell out of the tragedy tree and hit every branch on the way down. Born to a single teen mom, Oprah grew up so poor that she wore dresses made of potato sacks. Then, at just 14 years old, Winfrey became pregnant, only to give birth to a premature boy who passed shortly after birth. Somehow, that's not even the worst part of Oprah's awful childhood. On a 1986 episode of her show, she revealed that she had been molested by her cousin, uncle, and a family friend, starting when she was nine years old.
Despite all this, Oprah has fought to protect children, using her show and her immense fame to launch projects like Oprah’s Child Predator Watch List.
5. Angelina Jolie's Bad Girl Past
Ah, no one did "emo theater kid" quite like Angelina Jolie. Before she became a philanthropic beauty, Jolie made headlines for making out with her OWN BROTHER on the red carpet and "romantically" combining arts 'n crafts with blood. Exhibit A: In 1996, Jolie eloped with her Hackers co-star Jonny Lee Miller. The bride wore black leather pants and a white shirt...on which Jolie had written Jonny’s name in her own blood. Exhibit B: Back when Angelina and Jolie and Billy Bob Thornton were together, they sliced their fingers open, "smeared a little blood on these lockets,"and wore them as necklaces. Romance!
6. Billy Bob's Betrayal
Speaking of Billy Bob's questionable relationships, not enough people know that he and Laura Dern were engaged back in the 1990s. However, the romance ended when Dern had to leave town to film a new movie. While she was away, Billy Bob met, fell in love with, and then married Angelina Jolie. Oh, from whom did Laura Dern learn about all this? I'm glad you asked. She had to hear it from her friends because Billy Bob ghosted her. Bro dumped his fiancé and fully married another chick without even letting Dern know. That's ice cold, even for Hollywood.
7. Keanu Reeves's Heartache
Keanu Reeves is the internet's favorite boyfriend, which leads me to believe that deep down, we don't want a bad boy. We want a sad boy. Here's the heartbreaking back-story: Keanu was set to welcome his first daughter into the world in 1999 with then-girlfriend Jennifer Syme, only for tragedy to strike. The baby was stillborn at eight months old.
Keanu and Jennifer named her Ava Archer Syme-Reeves and buried her in January 2000. This heartbreaking loss proved to be too much for the couple to handle and they separated a few weeks later, but remained friends. Two years later, Reeves had to bury another loved one when Jennifer passed in a car accident after losing control of her vehicle and getting thrown from the driver's seat.
8. Nicole Kidman's Dramatic Divorce
Fans blamed Scientology for Nicole Kidman's divorce from Tom Cruise, but very little was known about the split. That is, until former Scientologists revealed the awful details about the couple’s final days. They’ve alleged that, among other things, Cruise actually had Kidman’s phone tapped without her knowledge or her consent. Oh, and no biggie, Kidman was also pregnant when Cruise announced that he had filed for divorce. Soon after their split went public, she suffered a miscarriage. Yikes.
9. Woody Harrelson's Dark Roots
Welp, there's only one way to say this: Woody Harrelson's dad was an honest-to-god hit man. He actually made history for assassinating a federal judge.
10. Matthew Broderick's Fatal Drive
Actor Matthew Broderick took the lives of a mother and daughter while on vacation in Ireland with Ferris Bueller’s Day Off co-star Jennifer Grey. Their rented BMW crossed the center line, colliding head-on with an on-coming vehicle. He was convicted of "careless driving" and had to pay a $175 fine. Ferris doesn’t sound like such a righteous dude now, does he?
11. Mark Wahlberg's Bad Boy Past
Actor Mark Wahlberg had a bit of rough youth, and um that's putting it lightly. Wahlberg was a small-time drug dealer and spent time locked up for viciously attacking two Vietnamese men. He hit one with a stick and punched the other, causing the victim to go blind in one eye. He was originally charged with attempted murder, but was able to plead to a lesser charge of contempt. Wahlberg was sentenced to two years in prison but served only 45 days.
12. The Wild Life Of Robert Downey Jr.
Before Robert Downey Jr. got clean and became Iron Man, his various dependence issues got him into a ton of trouble in the 1990s and early 2000s. For example! He broke into a neighbor's house, was locked up by authorities more than once, and sped down a road while firing a pistol into the sky. After seeming to get clean in rehab, Downey relapsed over the Thanksgiving weekend by hosting a wild party at a hotel in Palm Springs.
By the time the authorities arrived, they found Downey carrying illicit substances and in the company of several dancers. Worst all, one was dressed as DC's Wonder Woman. Don't tell the MCU fanboys. I don't know how they'd ever recover.
13. Renee Zellweger's Weird Wedding
In 2005, after a whirlwind marriage, Zellweger filed for an annulment from country star Kenny Chesney. It was an instant scandal: under "grounds for divorce," she had written one iconic word: "Fraud". She later revealed that this was only a judicial term that helped along the annulment, and didn't reflect Chesney’s character or the nature of their brief relationship.
But of course, that didn't stop gossip magazines from loudly wondering if Chesney was gay (for the record, he insists he is not). Either way, when the annulment happened, Zellweger and Chesney released a statement saying they split because of the "miscommunication of the objective of their marriage". Well then...
14. Heath Ledger's Dark End
When authorities investigated the circumstances surrounding Heath Ledger’s tragic and untimely end, a strange name kept coming up in connection with their case: Mary-Kate Olsen. They soon discovered that Mary-Kate had a close but almost off-the-radar friendship with Heath Ledger just before his passing. In fact, she was the first person notified when his housekeeper found his body. Officers brought her in for questioning, but Mary-Kate’s lawyer told them she would talk only if she was given immunity—so there are still some things we may never know about that fateful day.
BRB gotta go watch the "I love you, baby" serenade scene in 10 Things I Hate About You to make myself feel less depressed.
15. Dane Cook's Troubled Years
Back in the mid 2000s, Dane Cook was everyone's favorite comedian, with one of his shows selling out Madison Square Gardens. Then Cook seemed to disappear just as quickly as he'd shot to the top. The truth is that Cook's life went off the rails for a few years. His mother sadly passed in 2006, then Cook lost his father just one year later. In 2010, Cook had to deal with another kind of family unrest when he found out that his former manager Darryl had stolen millions of dollars from him. Oh, and Darryl wasn't just Dane's old manager. He was his half brother too. Ouch.
16. Pierce Brosnan's Pain
Long before he became James Bond, Pierce Brosnan found offscreen love with a former Bond girl, actress Cassandra Harris. Married in 1980, Brosnan even adopted Harris’s children as his own after their own biological 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 die from the exact same disease that took both her mother and her grandmother.
17. 50 Cent's Horrible Roots
Everyone knows 50 Cent got shot nine times in his youth, but strap in because it turns out that's just the beginning when it comes to his unbelievably awful childhood. First, his father left the family, leaving 50 to be raised by his single mother, Sabrina. Then Sabrina passed in a fire when 50 was just eight years old. With both his parents out of the picture, 50 was raised by his grandparents instead.
By the time he was 12, 50 Cent started dealing dope. At 19, he spent time behind bars for possession. Then, at 25, an assailant infamously shot him nine times. 50's voice gained a slight slur because of a wound to his cheek. Shortly after, his deal with Columbia Records fell apart and his would-be debut album got shelved. The assailant, meanwhile, succumbed to an attack just a few weeks later. Make of that what you will.
18. Celine Dion's Scandalous Relationship
High school sweethearts are cute...but meeting your future husband when you're literally 12 and he's 38? Um, I have some questions about that. And yet, that's how Celine Dion met René Angélil, her longtime music manager and husband. In the early years of Dion's career, Angélil literally re-mortgaged his house to finance Dion's first album. At the time, she was 13 years old.
In Dion's memoir, she says that the couple only became romantic when she was 20. Despite their initial meet-creepy, they stayed together until René's passing in 2016.
19. Jim Carrey's Breakdown
Jim Carrey is a weird dude. Known for completely becoming Andy Kaufman in Man on the Moon, his immersion made "method acting" look like child's play. Carrey made people call him Andy and constantly took things too far during filming. This got on the cast and crew’s nerves, and at one point he got so caught up in the role that he spit in Jerry Lawler’s face, who then went after Carrey and tried to choke him.
Carrey became so fixated on the role of Kaufman that he claims "Jim Carrey" didn’t exist during the filming of the movie and instead he was possessed by the spirit of Kaufman. It’s also worth noting that Carrey said he had a psychotic breakdown while filming Man on the Moon, which might contribute to the whole possession theory. Aaaand now he hates vaccines too. Is no childhood icon sacred?
20. Paris Hilton's Past Trauma
In her 2020 documentary, This Is Paris, the reality star Paris Hilton finally shared her real story. After years playing up her ditziness on TV, Hilton revealed that it was a persona and that she'd been through much more than anyone knew. During her teenage years, Hilton was a bit of a rebel, which eventually led her parents to send her to Utah's Provo Canyon School, where Hilton alleges that she was horribly abused by staff and teachers.
Hilton says that she still has visceral nightmares and often struggles to sleep because of her dark memories. While at the school, she says that teachers would force the students to take mystery medications and if Hilton refused, she'd be sent to solitary confinement for up to 20 hours. Sometimes, the staff didn't even let her wear clothing as part of the punishment.
21. Orlando Bloom's Secret Identity
Until he was 13 years old, Orlando Bloom was under the impression that his stepdad, anti-apartheid lawyer and activist Harry Bloom, was his biological father. Bloom entered puberty by finding out that the person he thought was a family friend, Colin Stone, was his real dad. Family reunions just got a lot more awkward in the Bloom house.
Elizabethtown (2005), Paramount Pictures
22. Hollywood Hit And Runs
What is it about Hollywood actors hitting innocent people while driving? We've already talked about Matthew Broderick but Ferris Bueller is far from the only person to take a day off from driving carefully. In 2006, the singer Brandy Norwood got into a car accident that ended up taking the life of a woman named Awatef Aboudihaj. Back in 2001, Rebecca Gayheart pleaded no contest to vehicular manslaughter after her driving tragically took the life of a nine-year-old boy named Jorge Cruz Jr. Caitlyn Jenner's part of this depressing club, too. While driving, she was part of a fatal collision that took the life of a woman named Kim Howe.
23. Jim Carrey's Loss
In 2015, Jim Carrey’s former girlfriend, Cathriona White, was found deceased of a prescription drug OD. The courts determined that she had taken her own life. Carrey was devastated and performed pallbearer duties at the funeral. In 2016, White’s husband and mother both filed wrongful death lawsuits against Carrey that he has characterized as a "cash grab".
The lawsuits claim that Carrey opted out of the usual boyfriend gifts like flowers and chocolates and instead gave her unauthorized prescription meds and STIs. White’s lawyer released this iconic 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". Call the burn unit. Man down.
24. Jennifer Hudson's Heartbreak
Sadly, Cats is not the worst thing that has happened to Jennifer Hudson. Not by a long shot. On October 24, 2008, Hudson received the worst news anyone could ever hear. Her mother and brother had tragically been shot and both had passed. Though her little seven-year-old nephew Jordan was missing, in time, the authorities found his body and revealed that sadly, he had perished too. The person who caused all this heartbreak turned out to be William Balfour, the angry ex-boyfriend of Hudson's sister Julia.
25. Mark Ruffalo's Terrible Loss
True story: Mark Ruffalo filmed a movie in the town where my ex's mom worked at a hippie dippy organic food store. He went in and tried to get the student discount because, and I quote, he was a "student of life". She didn't give him the discount.
Just before this devastating failure, Mark Ruffalo went through the other fight of his life. He was diagnosed with a brain tumor that caused partial facial paralysis. Luckily, doctors removed the mass, but not before it left its mark on Ruffalo, causing the actor to go deaf in his left ear. Though that's enough excitement for a lifetime, Ruffalo was in for more hard times in 2008. On December 1st, Mark Ruffalo’s brother Scott was shot in the head. Despite attempts to save his life, Scott passed a week later. The case remains unsolved as of 2020.
26. Jessica Simpson's Hidden Trauma
If you haven't read Jessica Simpson's recent memoir, Open Book, get on it. That book is a WILD ride from start to finish, including Christian jazzercize classes called "Jump For Jesus," the DL on Simpson's messy on-again-off-again relationship with John Mayer, and one absolutely chilling revelation. When she was just six years old, Simpson says that the daughter of a family friend assaulted her while they were sleeping in the same bed.
As she later recalled of the mistreatment, "It would start with tickling my back and then go into things that were extremely uncomfortable". Ashamed of what she thought it said about her, Simpson repressed the memories for years and refused to confront them for even longer. This repression helped drive her addictions to booze and diet pills. She only started dealing with the trauma after going to therapy.
27. Nicki Minaj's Terrifying Childhood
Nicki Minaj's childhood makes the cutthroat world of hip hop music look like ice cream and teddy bears. When the rapper was young, she watched her parents' abusive relationship play out on a daily basis. Minaj recalls seeing her father pull her mother out of the car and drag her down the street for two full blocks. On one especially horrific day, her father set the house on fire...while Nicki's mother was still inside the building. Thankfully, she escaped without injuries, which is probably a significant part of why Nicki and her father are on good terms these days.
28. Kelsey Grammer's Tragic History
Kelsey Grammer played a therapist on Frasier but Jesus H. Christ, did you know that he could use a lifetime supply of therapy in real life too? This poor man has already dealt with more tragedy, pain, and suffering than most people will ever see. When Grammer was 13, his father's life was taken in front of their house. When he was 20, a mass murderer ended his sister's life. And then, when he was 25, Grammer lost his two half-brothers in a freak scuba diving accident.
Unfortunately, Grammer's mid-30s saw him undergo even more tragedy. For one, um, eventful year, he was married an exotic dancer named Leigh-Anne Csuhany. Grammer claims that Csuhany was abusive towards him in every way imaginable—physically, mentally, verbally—and that she fired a pistol at him, threatened to kill herself, and purposely miscarried their child.
As a result of these tragedies, Grammer turned to booze and illicit substances to try and mask the pain, which inevitably got him in trouble with the law on numerous occasions. He was locked up for driving while inebriated and put in cuffs twice for possession. After serving 30-days in lockup, he had his probation extended after testing positive for the drug again. Nowadays Grammer says he has overcome these issues and made peace. All I can say is: My condolences to Kelsey Grammer.
29. Katie Holmes's Controversial New Fling
When it comes to love, Katie Holmes has been through the ringer. After her whirlwind romance with Tom Cruise went sour, she filed for an incredibly acrimonious divorce. Then, Holmes secretly dated Jamie Foxx for about five years, with some saying that she couldn't date anyone publicly as part of her, ahem, unusual divorce agreement.
Now, Holmes has a new man in her life: the restauranteur Emilio Vitolo. There's just a few problems with this dude: 1) He was engaged to another woman, the designer Rachel Emmons, when he met Holmes, and 2) He apparently only broke things off with Emmons when pictures of him and Holmes came out online. Katie, girl, walk away.
30. Britney Spears's Creepy Conservatorship
Controlling your child star is basically a prerequisite for stage moms and dads, but Britney Spears's family takes that idea to a whooole 'nother level. After shaving her head and divorcing Kevin Federline (tabloid nickname: "K-Fed"; post weight gain, nickname: "Well Fed" #NeverForget), Spears had a scheduled visit with one of her sons. But when it was time to return the boy to Federline’s home, Spears allegedly locked herself in a room with her child. From there, things went from bad to worse. The authorities had to intervene and eventually hospitalized Spears on a "5150"—essentially committing the pop star to a psych ward.
To make matters worse, Spears was also put under a "conservatorship" which meant that her father completely controlled her money and her career to this day. Over a decade after her time in the hospital, Spears is still not allowed to make her own choices. As though that's not dramatic enough, it’s alleged that when Spears broke her father's rules, he forced her into a psychiatric facility against her will. Though Spears was released soon after and made a video assuring fans that she was alright, people still have a lot of questions about the whole thing. To this day, her relationship with her father remains as complicated as ever. In 2020, Spears tried to get out from under her father's thumb by filing new court documents, but to no avail. It would take another year before Britney was finally free from the cage of conservatorship.
TL;DR: You'll never listen to "Overprotected" the same way.
31. Shania Twain's Twisted Childhood
Shania Twain’s childhood was anything but idyllic. Her step-father, Jerry, was an alcoholic, abusive man, and the family struggled to make ends meet. Twain was deeply affected by Jerry’s treatment of her mom. She has nightmarish memories of violent nights where she would hear her parents screaming and try to stop Jerry from hitting her mother.
Sadly, Jerry wasn't just harmful to Shania Twain's mother. Though Twain had previously revealed that Jerry harmed her physically and psychologically, in a 2018 interview, she admitted that he was intimately mistreating her too. Oh, and to make matters worse, when Twain was 22, her parents passed in a car crash, leaving Twain to take care of her sisters all by herself. Man! I feel like a woman crying.
32. Will And Jada's Strange Marriage
For years, Will Smith and Jada Pinkett-Smith have been hounded by rumors that they were in an open marriage. Well, it turns out that those rumors were kind of true. After the singer August Alsina claimed that he'd had a long-standing affair with Jada in the 2010s, Pinkett-Smith firmly denied it, only to change her story and admit that they'd been "entangled" during Will and Jada's separation. But that's not the end of the saga. Not by a long shot.
First, Alsina was a whopping 20 years younger than Pinkett-Smith and, as he and Jada have both said, they got together when he was "sick". That's...a lot of blurred lines. Then, during Jada and Will's Red Table Talk episode where they discussed their separation, Jada FORCEFULLY implied that Will had seen other women during their separation.
The internet's favorite guess as to who Will romanced? Margot Robbie. She and Smith appeared in two movies around the time of the separation and, in a now-legendary game of Jimmy Fallon's "Loaded Questions," Robbie coyly revealed that the answer to one question was Will Smith, but refused to say what the question specifically asked. Hmm....
PS: Will and Jada ended their Red Table Talk ep by bumping fists and saying "Bad Marriage For Life". I know it's a rife on "Bad Boys For Life" but my dudes, that does not make your marriage sound so good.
Bad Boys for Life (2020), Columbia Pictures
33. Marlon Brando's Tragic Family
Marlon Brando's most famous role will always be Don Corleone in The Godfather. But here's a not fun fact: Brando seemed drawn to horrible family dynamics both on screen and off. On May 16, 1990, Brando's son Christian went to visit his half-sister Cheyenne (Brando's daughter with another woman) and Cheyenne's partner Dag Drollet.
Unfortunately, the family reunion could not have gone worse. Christian claims that Cheyenne told him Dag was mistreating her, leading Christian to confront Dag. During the altercation, Christian's pistol went off accidentally and hit Dag, who quickly passed on. For any other family, this would be where the story ended...but not the Brandos.
During Christian's lengthy trial, Cheyenne, who was pregnant, tried to take her own life not once, but twice. Over the years, Cheyenne's demons kept pursuing her until the courts eventually took her son away. In the end, Cheyenne took her own life by hanging. Christian, meanwhile, served five years for involuntary manslaughter and now wonders if Cheyenne was even telling him the truth when she said Dag was hurting her.
34. John Mayer's TMI
Of all John Mayer's many ill-fated romances, his on-again-off-again relationship with pop star Jessica Simpson has gone down in infamy. They dated in the 2000s, but Simpson recently revealed Mayer's straight-up mean behavior in her recent memoir. According to Simpson, Mayer constantly broke up with her then took her back, purposely putting her through repeated heartbreaks because it helped him write better songs. Oh, but it gets worse!
In 2010, Mayer gave a now-infamous interview with Playboy where he claimed that Simpson was "[sensual] napalm". Unsurprisingly, this led Simpson to cut off all contact with Mayer immediately. And yet, Mayer's "napalm" comment wasn't even the most offensive thing he said. He also made disturbing comments about interracial dating, referring to his privates as "David Duke" and joking that he was going to "start dating separately" from his member. How gallant of you, John.
35. Johnny Depp And Amber Heard: The Messiest Match
Johnny Depp proposed to Heard on Christmas Eve 2013, but soon after the couple married, Heard was already filing for divorce. On May 25, 2016, Heard split from Depp and fled a temporary restraining order at the same time, alleging that Depp had been verbally and physically abusive. Depp immediately struck back at his ex, alleging that she was defaming him to get his fortune.
A court battle ensued, with the pair eventually reaching an agreement where Depp paid Heard a $7 million settlement—which she immediately donated to charity. They released a joint statement, saying that their relationship was volatile, but that "there was never any intent of physical or emotional harm"—but actions speak louder than words, and Depp's actions suggested that he was still pretty ticked. He altered a tattoo that read "Slim" (his nickname for Heard) to read "Scum" and then "Scam". Well then.
36. The Ultimate He-Said She-Said
In 2018, Depp dropped a shocker in a new lawsuit. He submitted evidence that he claims proves Heard was hurting him, not the other way around. For her part, Heard submitted photos showing bruises that she claims she sustained from Depp, while Depp leaked audio of a conversation where Heard seems to admit to hitting him. Not content with this level of "hot mess" the sparring exes soon reached dizzying new heights of tabloid fodder.
While Heard was filming London Fields, Depp got jealous of her relationship with co-star Billy Bob Thornton. Depp, naturally, responded by cutting his finger and writing on the mirror in blood, "Starring Billy Bob and Easy Amber". However, Depp's version of the story was just as messed up. He claims that he lost the tip of his finger when Heard flung two booze bottles at him during a fight. Because of the cut, Depp caught MRSA a total of three times and even had to be hospitalized.
37. David Letterman's Sordid Affair
In September 2009, David Letterman revealed that he was being blackmailed. An unknown person threatened to reveal that Letterman had affairs with several female employees unless he paid $2 million. Letterman explained that he immediately contacted the authorities and cooperated in a sting operation where he gave the blackmailer a phoney check.
The man went into custody after attempting to deposit the check. In the end, he was revealed to be Robert Halderman, a producer of the CBS show 48 Hours.
38. Letterman's Sad Stalker
Yes, David Letterman's life is so insane that he gets two entries on this list. Back in the early 80s and 90s, Letterman had a stalker by the name of Margaret Mary Ray. Ray was schizophrenic and would frequently trespass on Letterman’s property, once stealing Dave’s Porsche from his driveway. Ray served 34 months in lockup and psychiatric hospitals for stalking Letterman. When Ray was released in the mid-1990s, her attentions shifted away from Letterman to astronaut Story Musgrave.
Tragically, in 1998 Ray took her own life by kneeling on the tracks in front of an oncoming train. Both Letterman and Musgrave expressed their sympathy after her passing.
Late Show with David Letterman, CBS
39. Brittany Murphy's Mysterious Demise
Just before Christmas 2009, Brittany Murphy was found lifeless in her LA home. At first, officers explained her demise as a misuse of prescription medications, along with a combination of pneumonia and anemia (Brittany, girl, why didn't you go to a doctor??). But then the mystery—and man oh man, the tragedy—suddenly deepened. Five months after her passing, Murphy’s husband Simon Monjack passed on in the very same bedroom, with the same eerie symptoms. Record scratch—wait, what?
This creepy coincidence led Murphy’s remaining family to a disturbing conclusion. Murphy's mother now believes that her daughter and son-in-law succumbed to poisonous mold in their house. Meanwhile, Murphy’s father had toxicology tests done on Murphy’s hair and became convinced that she and her husband were poisoned. But somehow, when it comes to Brittany Murphy, things only get weirder. Buckle up.
40. Conspiracy Rising
In 2004, a former Department of Homeland Security officer Julia Davis reported an influx of "suspicious" people entering the US. Believing there could be a terror attack (and frustrated that her bosses weren't doing anything about it), Davis turned whistleblower and brought in the FBI. At this point, Davis claims that DHS lashed out at her. This is where Brittany Murphy comes in and things officially go off the rails.
Davis claims that she was close friends with Murphy, and that Murphy even testified on her behalf. She says that, as a result, the DHS put Murphy and Monjack on a watch list and even targeted Monjack, who was British, for deportation. In Davis's 2012 documentary, she clams that Monjack and Murphy thought they were under surveillance and that the government had bugged their phones. Lo and behold, a few days after Monjack made his suspicions public, Murphy passed on.
If you think this sounds like a wacko conspiracy theory, you're not alone. Murphy’s mother Sharon has refuted all of Davis’s claims about her daughter, saying that "Brittany never cooperated with Julia Davis, never signed any statement in support of her, never met with her and barely knew she existed".
41. Kelly Preston's Dark Relationship
Long before she married John Travolta, Kelly Preston (RIP) was engaged to Charlie Sheen—until one night, when he made a classic boyfriend mistake and accidentally shot Preston in the arm. Seriously. As the story goes, she was accidentally shot and shortly after, they broke off their engagement (FAIR, KELLY). For decades, there’s been wild speculation about that night.
Sheen has finally addressed the rumors. He claims that while he was downstairs making coffee, she picked up a pair of his pants and as his revolver fell out of the pocket, it went off. The shrapnel clipped Preston's arm, and Sheen helped her call 9-1-1. Of course, that's all according to Sheen—we wish we could hear Preston's side of the story.
42. Owen Wilson's Sad Day
File this one under more sad comedians. In 2007, Luke Wilson found his brother Owen covered in blood and disoriented. He called 9-1-1 and was able to get Owen help in time to save his life. It was later confirmed that this was an attempt on his life; Owen had taken a bunch of pills and slit his wrist. He didn’t say much on the subject, only releasing this statement: "I respectfully ask that the media allow me to receive care and heal in private during this difficult time". To this day Wilson likes to keep silent about his private life, often refusing to answer personal questions.
43. Faye Dunaway's On-Set Fury
While filming Chinatown, it's rumored that Faye Dunaway lived out every actress's dream and threw a cup of her own urine in an overbearing director's face. In this case, said director was Roman Polanski. Apparently, he forbade Dunaway from taking any bathroom breaks. Thus, to rectify multiple tensions at once, Dunaway relieved herself in a cup and promptly flung the contents at Polanski’s mug. Can you blame her?
Getty Images
44. Matt Damon's Brutal Break-Up
Matt Damon is known as a Hollywood good guy, but let this be a lesson that literally nothing in this world is sacred. Damon dated his Good Will Hunting co-star Minnie Driver for a year, only for their relationship to implode in spectacular fashion. While Damon was on the Oprah Winfrey show, Damon denied having a girlfriend which was, apparently, the first that Driver heard of their break-up. What happened to the chivalry of sending a text?
Getty Images
45. James Lipton's Shady Gig
Before James Lipton hosted Inside the Actor’s Studio, he spent a year in Paris working as—and I'm trying to put this sensitively—an agent for escorts, shall we say. Despite his risky business, Lipton is fairly open about his past. He insists that the French treat their women well and referred to this job as one of those "rites of passage, no question about it. It was a great year of [his] life".
46. Julia Roberts's Real-Life Runaway Bride Moment
When Julia Roberts and Kiefer Sutherland met on a movie set, they began a whirlwind romance. There was just one problem: Sutherland was already married. Even so, young love barrels forward. Sutherland hastily divorced his first wife and proposed to Roberts; the couple then planned a massive wedding. Then, just three days before the ceremony, Roberts dramatically called it all off.
Sutherland was heartbroken, but it was about to get much worse. Roberts ran away to Ireland with another man, who just so happened to be Jason Patric, an actor and, awkwardly, Sutherland's good friend. Recently, Sutherland revealed he holds no grudges about the whole debacle, saying that Roberts was smart to get out while she did.
9. Hollywood's "Adult" Connection
Impress your friends with this surprising lil tidbit: Many of Hollywood’s biggest stars got their start in the racy film industry. Sylvester Stallone, Marilyn Monroe, Kevin Costner, and Cameron Diaz dared to bare all before their "legitimate" film careers took off. Even Jackie Chan starred in a 1970s XXX film called All In The Family. True to form, Chan did all his own stunts.
48. Kevin Hart's Dark Side
What is it about beloved comedians having secret dark sides? In 2017, Kevin Hart was accused of having an extramarital affair while his second wife Enniko was pregnant. To make matters worse, someone was trying to blackmail money off Hart, claiming they had video evidence of the affair. And on top of that, it was discovered that the person trying to blackmail Hart was his friend (!), actor Jonathan Todd Jackson, AKA Action Jackson.
The LA district attorney's office ended up giving Jackson two extortion charges. In September 2018, Jackson pled not guilty. Hart would later publicly apologize for his moral transgression, and he and Enniko have seemed to put his affair in the past. Wowza, that kid is gonna see some weird stuff when he googles his parents.
49. Jack Nicholson's Dramatic Past
Anjelica Huston had scores of Hollywood affairs, but her relationship with Jack Nicholson was by far her most heartbreaking and her most dramatic. She was the love of the lothario’s life for 17 years—until the day Nicholson committed the ultimate betrayal. He had Huston over for dinner one night and informed her "Someone is having a baby". Except by "someone," he meant him, with another woman. Ouch.
And as if that wasn't enough scandal for Jack's personal life, strap in for this one: When Nicholson was 37, Time Magazine revealed that the woman he thought was his mother was actually his grandma. It turned out that Nicholson's "sister" June had actually given birth to him when she was just 17, and her parents stepped in to raise June and her baby son Jack like they were siblings. June literally took this secret to the grave. She passed on four years before Time revealed her true identity.
50. Charlize Theron's Harrowing Childhood
Remember how Charlize Theron won an Oscar for playing a woman who kills men? Yeah...turns out she has some lived experience with that sensitive subject. When Theron was only 16 years old, her alcoholic father flew into a terrifying rage and threatened to destroy both Charlize and her mother. As her father waved a pistol around and tried to hit the women, Charlize's mother managed to grab her own weapon and shoot her husband. So TL; DR: Charlize Theron saw her mom kill her dad in self defence.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16
