For much of his life, Jack Nicholson had no idea about a dark family secret. When a reporter dug up the truth, the actor was in for the shock of a lifetime.
1. He’s The Man With The Most
Jack Nicholson has had so many outrageous roles in movies that it's hard for fans to pick the best. Is it the murderous hotel caretaker in The Shining, the misplaced patient in One Flew Over the Cuckoo’s Nest, or a detective after the truth in Chinatown? Fans adore him, and so do the members of the Academy.
In fact, Nicholson went on to become the male actor with the most Oscar nominations ever. Of course, none of this compares to the success he’s enjoyed in the bedroom.
2. They Made A Bizarre Family Decision
Born on April 22, 1937, in Neptune City, New Jersey, Jack Nicholson posed a major problem for his family. His mother was a showgirl named June Francis Nicholson. June was just 17 years old at the time—and so the family made a drastic decision.
They decided that June’s parents would raise their grandchild as if he were their son and tell little Jack that his mother was his sister. Great plan, except Nicholson’s eventual fame would make it impossible to keep this a secret.
3. He Was A Clown
The first hint that Nicholson would be an actor was when his school voted him “Class Clown”. The not-so-funny part of being the class clown was that Nicholson spent nearly every afternoon in detention. But don’t worry about Nicholson. He had a childhood friend named Danny Devito who was just as funny as he was.
Little did Nicholson know, these boyhood chums would soon meet up again in Hollywood.
4. He Got A Big Break
While still a teenager, Nicholson went to Hollywood and, after working for a short time with animators Hanna and Barbera, he joined the Players Ring Theater to learn how to act. He quickly started getting small parts in soap operas and on the stage. In 1958, his big break fell in his lap. He was going to be the lead actor in a movie.
But things didn’t turn out as planned.
5. He Almost Quit
Nicholson’s first big screen attempt was The Cry Baby Killer, and he wasn’t quite ready for the experience. The film failed to make any money, and it almost crushed Nicholson’s career. You see, he was so overwhelmed by the experience that he took a break from Hollywood to go “find himself”.
But instead of finding himself, Nicholson found something better.
6. He Had A Mentor
Even though Nicholson hadn’t done much with his first film, the producer—Roger Corman—became Nicholson’s mentor. For the next ten years, the actor pretty much only made films with Corman. In films like The Little Shop of Horrors and The Terror, Nicholson honed his skills, laying down the groundwork for a massive career.
However, when his big break didn’t materialize, Nicholson took a major swerve.
Georges Biard, CC BY-SA 3.0, Wikimedia Commons
7. He Tried Writing
Maybe frustrated by his inability to become a film star, Nicholson turned to writing. In 1967, he wrote a script called The Trip and he turned to Corman to direct. This film documents a man’s trip on a psychedelic substance. Apparently, Nicholson took some himself before writing the script—all in the name of authenticity.
The Trip was popular among the counterculture, and Nicholson was ready to continue in that vein. But there was one major obstacle to overcome.
8. They Didn’t Need Him
A film called Easy Rider would prove to be a perfect vehicle for Nicholson's career—but he almost missed out on the part. This counterculture film already had a full cast, but luck was on his side. Two cast members—Dennis Hopper and Rip Torn—had an argument, and Torn walked away from the film.
Nicholson got the offer instead, and it changed his life forever.
Kevork Djansezian, Getty Images
9. His Career Turned Around
Even though Nicholson wasn’t one of the two main actors in Easy Rider, his performance wowed critics and audiences. Nominations started rolling in, even one from the Academy for Best Supporting Actor. On Oscar day he didn’t take home the statue, but it was a huge turning point in his career.
Nicholson was now hobnobbing with celebrities, and it was about to get dangerous.
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10. He Got Scared
Nicholson became friends with Roman Polanski, who would later direct him in Chinatown. In 1969, members of the Manson family stormed the Polanski house and mercilessly took the life of Sharon Tate, Polanski’s wife. Nicholson supported the director while he grieved, but he also took the macabre event personally.
For the next while, any time Nicholson went to bed, he'd have a hammer hidden beneath his pillow. But there was something even stranger that Nicholson did while at home.
Larry Bessel, CC BY 4.0, Wikimedia Commons
11. He Didn’t Wear Anything
Nicholson had a fear of appearing with no clothes on in a movie. To combat this he committed to walking around in his birthday suit for three whole months. It didn’t matter who stopped by, even his own daughter got to see him undressed. Nicholson would eventually bare all for the camera—but before that, he would make an even more memorable scene.
12. He Made A Scene
In 1970, Nicholson made Five Easy Pieces with Karen Black. Both got Oscar nominations, but only Black won. What Nicholson got instead was a career-defining scene where he squabbles with a waitress about getting exactly what he wanted to eat. Years later, Shirley MacLaine said that watching him in that scene made her want to work with him.
There was no shortage of women who wanted a piece of Nicholson, but some of them landed him in the messiest situations possible.
Columbia, Five Easy Pieces (1970)
13. He Got Her In Trouble
Back in 1962, Nicholson had married Sandra Knight, his co-star in the horror film The Terror. The two had a child together and then separated in 1966. This would end up being Nicholson’s only attempt at marriage, but certainly not his only child. While making Five Easy Pieces, Nicholson had a relationship with co-star Susan Anspach.
When Anspach became pregnant, things spiraled out of control.
Unknown Artist, Wikimedia Commons
14. He Denied It
Anspach was sure that Nicholson was the father of her child, but she married someone else anyway. While pregnant with what she claimed was Nicholson’s child, she walked down the aisle with Mark Goddard—Lost In Space’s Don West. Goddard valiantly adopted Nicholson’s son Caleb as his own.
Nicholson simply walked away from the situation and into another even trickier one.
15. He Broke The Bro Code
In 1970, Nicholson’s Easy Rider co-star—and best bud—Dennis Hopper married the Mama & the Papas singer, Michelle Phillips. This union only lasted a little over a week, and Nicholson saw no problem with elbowing his way in and dating Phillips himself. You’d think that Nicholson was breaking some kind of “bro code” with this behavior, but easy-going Hopper didn’t seem to mind.
What was strange was Phillips' very different opinions of these two close friends.
16. He Was The Perfect Boyfriend
After being married to Dennis Hopper for eight days, Phillips only referred to the Blue Velvet star as “the name that shall never pass my lips”. Nicholson, on the other hand, seemed to be the perfect boyfriend. He encouraged her to pursue acting, and she said it was the best advice ever. Nicholson and Phillips lasted just a year, and after that, he was on the prowl all over again.
This time he’d meet his match.
Borsari, Peter, Wikimedia Commons
17. He Played Games
Nicholson met Anjelica Huston when she came as someone’s guest to a party at his own house. She ended up staying the night, and the games quickly began. Nicholson made a date with Huston and then canceled. When Huston by chance saw him that night with another woman, she was ready to go ballistic.
18. He Got Caught
Huston had caught Nicholson with another woman on the night they were supposed to go out—and she was ready for a showdown. What happened was completely the opposite. It turned out that Nicholson was with his ex Michelle Phillps, and Huston and she became good friends. Huston forgave Nicholson, and they began falling for one another in earnest.
But as we'll later learn, this might have been his most toxic relationship of all.
Kremlin.ru, CC BY 3.0, Wikimedia Commons
19. He Turned Down A Classic
In 1973, the producers of a film that had “classic” written all over were looking for two men to star together. This was The Sting and Nicholson received an offer to star opposite Paul Newman. Nicholson thought the film would be a success but turned it down to do the more compelling The Last Detail.
When Oscar time came around, something very strange happened.
Warner Bros., The Shining (1980)
20. It Was A Battle
The role that Nicholson had turned down in The Sting went to heartthrob Robert Redford, and it’s hard to imagine anyone else—let alone Nicholson—playing the part. At that year’s Oscars, both Nicholson and Redford received nominations. It was a battle for who had made the right decision, and in the end, they both lost to another Jack: Jack Lemmon.
With all this Oscar attention, Nicholson was becoming famous, and reporters had started digging into his personal life.
21. His Life Was A Lie
Remember, Nicholson lived most of his life thinking that his mother was his sister and his grandparents were his parents. But this secret was no match for Time magazine researchers. In preparing for an article about Nicholson, they did some digging and unearthed the truth. The researchers heartlessly called him and told him about his bizarre family background.
This news could have sent Nicholson to the loony bin, but he went there for a film instead.
22. They Didn’t Want Him
In the early 1970s, a popular book was about to get a cinematic treatment. The book was One Flew Over the Cuckoo's Nest and what everyone wanted to know was who would play the important lead role. The director wanted Deliverence’s Burt Reynolds, but the producers insisted on Nicholson, and he got the part.
The author of the book, Ken Kesey, was not happy with the casting of Nicholson. It was going to be a bumpy ride.
United Artists, One Flew Over the Cuckoo's Nest (1975)
23. He Went Behind His Back
Nicholson and director Milos Forman disagreed on how the story in One Flew Over The Cuckoo’s Nest should play out, and for a few weeks, the actor did the unthinkable. He began running his own rehearsals behind Forman’s back. In exchange for his bad behavior, Nicholson took home an Academy Award.
Next for Nicholson was a chance to work with his long-time hero.
Los Angeles Times, CC BY 4.0, Wikimedia Commons
24. He Met His Idol
One person that Nicholson had always idolized was Marlon Brando and, in 1976, a dream came true for him. He was going to act opposite his hero in The Missouri Breaks. Things weren’t exactly as Nicholson had anticipated, though, as he soon became frustrated with Brando’s constant need to use cue cards to remember his lines.
But this was just the beginning of Nicholson’s problems with Brando.
Urpo Rouhiainen, CC BY 4.0, Wikimedia Commons
25. They Didn’t Get Along
As it turned out, Nicholson’s acting debut with Brando would be a disaster. The two didn’t get along at all, and in their few scenes together, the director chose to shoot them separately. Not only that, but the movie—which audiences had high expectations for because of the stars’ recent Oscar wins—was also a bit of a dud.
The sad thing was what Nicholson had given up to work alongside Brando. It was nothing less than a classic film with one of Hollywood’s leading directors.
United Artists, One Flew Over the Cuckoo's Nest (1975)
26. He Needed To Be The Center Of Attention
The film Nicholson could have made instead of The Missouri Breaks was one with acclaimed director Steven Spielberg. He was casting his Close Encounters of the Third Kind and he offered Nicholson the lead role. It wasn’t that Nicholson thought it would be a bad film—he just didn’t want all the special effects to upstage him.
That same year, there’d be a notorious close encounter at Nicholson’s own house.
United Artists, The Missouri Breaks (1976)
27. It Happened At His House
Remember, Nicholson was friends with director Roman Polanski. Well, Polanksi used Nicholson’s house for an infamous photoshoot with a 13-year-old girl named Samantha Jane Gailey. The photoshoot allegedly took a dark turn, as Polanski took advantage of the young girl. Apparently, Nicholson had no idea what was going on at his house.
Los Angeles Times, CC BY 4.0, Wikimedia Commons
28. He Looked Crazy
In 1980, Nicholson made a film that would define his career. This was The Shining—and it was fraught with controversy. The first problem was that the author of the book—Stephen King—did not want Nicholson for the part. He wanted someone who looked normal to slowly descend into madness. King’s opinion was quickly dismissed, and Nicholson got the role.
But it wasn’t smooth sailing from there.
29. He Played Hooky
While filming The Shining in the UK, the Wimbledon tennis tournament was on, and Nicholson really wanted to attend. To make this happen, Nicholson called in sick. The problem was that because of his fame, the cameras caught him in the stands watching the tournament. When director Stanely Kubrick saw Nicholson at Wimbledon, he went ballistic.
As always, Nicholson survived and even went on to get into even stickier situations.
Warner Bros., The Shining (1980)
30. It Was Complicated
In 1981, Nicholson was making the very steamy The Postman Always Rings Twice with Jessica Lange. To complicate things, Nicholson’s on-again-off-again girlfriend, Huston, was also in the film in a supporting role. You can imagine it was a tense set, as Nicholson and Lange were heating up the set with some very hot scenes. To make matters worse, Nicholson said he had a crush on Lange.
It looked like Lange didn’t reciprocate Nicholson’s interest, but don’t worry, someone else was waiting on the sidelines.
Lorimar Film Entertainment, The Postman Always Rings Twice (1981)
31. He Was Wanted
While there seem to be a lot of stories of directors and authors not wanting Nicholson in their films, the case was quite different when it came to 1989’s Batman. As it turned out, the creator of Batman, Bob Kane, gave his own recommendation for the actor to play the Joker. It was, of course, Nicholson.
In Batman, Nicholson wreaked havoc on the streets of Gotham City. As it turned out, Nicholson himself could cause a little chaos on the streets.
32. He Paid The Price For His Road Rage
In 1994, Nicholson suffered a bit of road rage. He was so angry that he went at a man’s Mercedes-Benz with a golf club and smashed the window and roof. Officers charged him, but Nicholson got out of any serious trouble when he sincerely apologized, allegedly giving the driver a check for $500,000.
This payment got him out of trouble, but more problems with the law came two years later.
United Artists, One Flew Over the Cuckoo's Nest (1975)
33. He Didn’t Want To Pay
In 1996, Catherine Sheehan brought a lawsuit against Nicholson alleging that he offered to pay her $1,000 for a night in bed. Instead of paying her, she said he roughed her up. Nicholson later paid her a settlement of $40,000, but then Sheehan came looking for more. A judge dismissed the case.
Nicholson’s reputation with women had taken a beating, and it was time for him to do something nice.
Lorimar Film Entertainment, The Postman Always Rings Twice (1981)
34. He Finally Said Yes
For almost 30 years, Nicholson had been denying that he and his former girlfriend, Susan Anspach, shared a child. Well, in 1998, Nicholson was feeling very paternal and decided to come clean. He proudly announced that he was Caleb Goddard’s biological father. The two apparently had a warm relationship.
But don’t feel too warm and fuzzy about Nicholson, he was about to show how heartless he could be.
Columbia, Five Easy Pieces (1970)
35. He Tried To Take Her Away
Back in 1994, Nicholson and Broussard had ended their relationship, and for a few years, Nicholson was on the dating scene. When he was out on the town one night, he ran into Twin Peaks actor Lara Flynn Boyle. Nicholson didn’t see any problem with asking her out, even though she was standing right next to her boyfriend David Spade.
It’s likely that funnyman Spade was shaking in his boots. He was about to do battle with one of Hollywood’s most notorious womanizers.
36. He Turned Her Off
Nicholson did manage to lure Boyle away from Spade, and the two had a five-year relationship. It must have been an ordeal for Boyle because, at the end of it, she swore she was through with dating actors. In Nicholson’s favor, she did say, “I left with a bang when it came to actors". It may have been Nicholson’s wandering eye that soured Boyle on actors.
After all, he has quite the list of romantic accomplishments.
Columbia, Five Easy Pieces (1970)
37. He Had A String Of Affairs
As it turned out, Nicholson had relationships with quite a variety of women. The list includes supermodel Kate Moss, Canadian folk singer Joni Mitchell, and heiress Christina Onassis. Pamela Anderson once reported seeing Nicholson getting intimate with two women at Hugh Hefner's mansion. The real question is how many women there were in total.
This ballpark figure is quite the shocker.
38. He Allegedly Slept With Thousands
Some say that Nicholson has slept with over 2,000 women. When asked about this outrageous number, Nicholson simply said that he didn’t keep count. However, out of all the women he ever slept with, his most brutal betrayal had to be the one he dealt his long-time love, Anjelica Huston.
Columbia, Five Easy Pieces (1970)
39. He Got Another Woman Pregnant
Infamously, Nicholson was still in a relationship with Anjelica Huston in 1989 when a woman he was having a secret affair with got pregnant. The woman was waitress Rebecca Broussard. But the way in which he broke the news to Huston was absolutely tactless.
Columbia, Five Easy Pieces (1970)
40. He Broke Her Heart
Nicholson had his chef prepare a gorgeous dinner for both him and Huston. But over dessert, he dropped the bombshell, saying, "I have something to tell. Someone is gonna have a baby". The sour cherry on top of this news was that the actor still expected their relationship to continue as it had been.
Huston was already furious, but what happened next kicked her anger up another notch.
41. He Was Black And Blue
Huston was already furious at Nicholson for impregnating another woman when a news story broke. The article described how Nicholson had recently been cavorting with a young woman and playfully hitting her with a ping-pong paddle. That afternoon, an irate Huston arrived at Nicholson’s office and landed more than a few punches. Nicholson later said that he had bruises all over his body.
It was now up to Nicholson to smooth things over.
TriStar, As Good as It Gets (1997)
42. He Sent A Beautiful Gift
Huston later said that she thanked Nicholson for letting her hit him. Nicholson certainly could have stopped the furious Huston, but he chose not to, and it made her feel good. Later, Nicholson got even more forgiveness when he had a gift delivered to Huston. It was a bracelet that Frank Sinatra had once given to Ava Gardner.
It made Huston feel better, but the relationship was more or less over.
Featureflash Photo Agency, Shutterstock
43. He Moved On
In the wake of his messy relationship with Huston, Nicholson started things up with the woman who was carrying his baby. This made sense, and Nicholson and Broussard ended up having two kids together in total. Lorraine and Ray both took “Nicholson” as their surname, and both ended up being actors. Nicholson seemed content to play the perfect husband and dad.
But before you judge him too harshly, here’s one fact that makes Nicholson look very, very good.
44. He Was A Supporter Of Women
The truth is, every time Nicholson has won a Best Actor Oscar, his female co-star has also taken home a trophy. This was true for Helen Hunt in As Good As It Gets, Shirley MacLaine in Terms of Endearment, and Louise Fletcher in One Flew Over The Cuckoo’s Nest. This may indicate that he is a very supportive co-worker on set.
Nicholson also threw his support behind some pretty questionable figures.
TriStar, As Good as It Gets (1997)
45. He Visited A Dictator
The communist country of Cuba is mostly off-limits to Americans, but this didn’t stop Nicholson. In 1998, he visited the island nation and even met up with its then-dictator, Fidel Castro. Nicholson called Castro, who many say had deprived his citizens of some basic human rights, "a genius".
Back in America, Nicholson was about to lose one of his basic rights. His right to privacy.
46. He Got Fooled
Nicholson lived next door to Marlon Brando, and their houses were so close they shared the same driveway. One day, Brando told Nicholson that he had sold his house to Rocky star Sylvester Stallone. This news floored Nicholson, as he assumed Stallone’s over-the-top lifestyle would ruin his privacy.
Nicholson breathed a huge sigh of relief when he found out Brando was playing an April Fool’s Day joke on him. As it turned out, Nicholson may have had the last laugh.
TriStar, As Good as It Gets (1997)
47. He Had A Weird Way To Grieve
The section of Mulholland Drive that Nicholson lived on had the nickname “Bad Boy Drive” because of the womanizing reputations of Jack Nicholson, Marlon Brando, and Warren Beatty too. When his buddy and neighbor Brando passed away, Nicholson did something that some people would call heartless. He bought Brando’s house and tore it down.
But the truth behind this purchase was a shocker.
United Artists, One Flew Over the Cuckoo's Nest (1975)
48. His Heart Was In the Right Place
As it turned out, Nicholson’s purchase of Brando’s house was a true act of charity: He planned to give it to Brando’s grieving family. Strangely, the family didn’t want it, as it was in a horrible state. Nicholson didn’t have many choices, so he razed it and put in a garden. It looked like Bad Boy Drive was becoming a thing of the past.
And Nicholson’s career was going in a similar direction.
TriStar, As Good as It Gets (1997)
49. He Went Low
The final picture on Nicholson's very impressive list of movies is How Do You Know, with Reese Witherspoon and Paul Rudd. This movie was a failure both commercially and financially. Worse still, it seemed to end the careers of both Nicholson and his long-time collaborator: writer, director, and producer James L Brooks.
Nicholson had entered the final act of his life, and things did not look good.
Columbia, How Do You Know (2010)
50. He’s Losing It
These days, Nicholson rejects any offers to act and seems content to do what he wants. This includes eating what he wants, living the way he wants, and some days just sitting under a tree and reading a book. While this life may sound idyllic to some, those close to Nicholson say that he’s staying home for a tragic reason.
Like so many of his characters, Nicholson is reportedly slowly losing his mind. Nicholson still has his legacy to look back on—but based on some of the roles he missed out on, it could have been even more impressive.
Featureflash Photo Agency, Shutterstock
51. He Could Have Replaced Him
Throughout his career, Nicholson was often up for the same roles as Harrison Ford. As it turned out, Nicholson had been in the running to play Han Solo in the original Star Wars movie, and the leads in Raiders of the Lost Ark, Blade Runner, The Mosquito Coast, and Witness. It makes you wonder. If Nicholson had snagged these roles, would we even know who Ford was?
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