Jack Nicholson: The Hollywood Heartbreaker


With his patented sunglasses and sinister smile, Jack Nicholson worked his way to the top of the film industry. As one of the most recognized actors and notorious ladykillers, Jack’s life and career are filled with these juicy details.

Who’s Your Daddy?

That is a question Jack has been receiving his whole life to which he answers, “I don’t know.” The commonly believed theories are either Eddie King or Donald Furcillo. To this day, Jack has no idea who his father is, and he does not care.

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Who’s Your Daddy?

The Love Of His Life

Much has been made of his many relationships and flings. Outside of his romantic loves, Nicholson has fallen in love with art collecting. His collection includes original pieces from many famous painters including Picasso, Rodin, Matisse, Modigliani, Magritte, and Botero. A research company ranked him fifth on a list of Hollywood’s top collectors. His $100 million collection pales in comparison to George Lucas’s $600 million collection or the $2.3 billion in art that David Geffen owns.

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The Love Of His Life

The Laura Flynn Boyle Incident

In 1999, Jack was connected romantically with Lara Flynn Boyle. According to actor David Spade, Jack asked her out right in front of him while they were dating. Boyle got mad at Spade for “not sticking up” for her. Spade responded that he was outranked in the situation. The National Enquirer got hold of a story that claimed Jack and Boyle were in a car crash together. When Boyle climbed out of the car, she shouted, “I have a boyfriend! I can’t be here!”

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The Laura Flynn Boyle Incident

Animator Before Actor 

Before he became Jack, Nicholson took a job as an office worker at MGM’s cartoon studio under William Hanna and Joseph Barbera. Hanna and Barbera are the duo behind Tom and Jerry, The Flintstones, The Jetsons, Top Cat, and Yogi Bear. The legendary animators took notice of the young Nicholson’s drawings and hoped to bring him onto their animation team. They asked him to join, but Jack had his heart set on acting and declined the offer.

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Animator Before Actor

Thanks, Rip Torn

If he has not already, Jack Nicholson should thank Rip Torn for helping him get his break. Before Nicholson joined Easy Rider, Torn was set to play biker and former lawyer George Hanson. At dinner one night, Torn and star/director Dennis Hopper got into a fight. Hopper was so angry that he fired Torn. Nicholson got the call for the job in his place. Relatively unknown at the time, Jack took home $329 a week from his replacement gig.

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Thanks, Rip Torn

A Slap In The Face

In 2004, Jack Nicholson and Kate Moss were rumored to be a thing. They were spotted leaving a restaurant after attending New York Fashion Week. When the press asked him about the encounter, Jack responded, “There are two kinds of women. The ones who want to jump into bed with me and the ones who want to slap my face when I try to sleep with them. I’m hoping Kate doesn’t slap me in the face.”

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A Slap In The Face

Blowing Up The Blockbusters

Jack Nicholson takes himself quite seriously as an actor and makes sure that we do too. One way he does so is by not appearing in blockbuster films. He told The Sun, “I had the most chilling thought that maybe people in their twenties and thirties don’t actually want to be moved anymore. They may want just to see more bombs, more explosions, because that is what they have grown up with. And I’ll never do that type of movie.”

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Blowing Up The Blockbusters

A Tale Of Two Old Friends

When you are as famous as Jack Nicholson, you have too many friends. One of his oldest friends became a star in his own right. Nicholson and Danny DeVito were childhood neighbors growing up in New Jersey. Their families used to own a hair salon together. Picture Jack and Danny running around the streets of New Jersey working on their skills, acting out different scenes and try not to laugh at the possibility.

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A Tale Of Two Old Friends

A Real Life Joker

On screen, Jack Nicholson frequently plays dark characters, but growing up he was anything but. Nicholson attended Manasquan High School in New Jersey. For the 1954 yearbook, Nicholson was voted Class Clown by his classmates. Once he got famous, the probably joked about him attending a class reunion. The joke would turn on them. In 2004, he made a surprise appearance at his 50-year high school reunion. They were delighted to see the pride of the class of 1954.

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A Real Life Joker

Don’t Let The Sunglasses Go Down On Me

Anytime you see Jack Nicholson in public – whether at a Lakers game, film premiere, or grocery shopping – you will never see him without sunglasses. They have become part of his signature look, but are also important for his vision. The glasses have prescription lenses for shortsightedness. He once joked, “With my sunglasses on, I’m Jack Nicholson. Without them, I’m fat and seventy.” Don’t be so hard on yourself, Jack, we still love you.

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Don’t Let The Sunglasses Go Down On Me

Receiving High Praise Early On

He might not have become a star until his 30s, but Nicholson’s dream of making it big started with some kind words from one of Hollywood’s biggest influencers. Jack was working hard to make it in the industry, and after his first screen test, MGM co-founder Louis B. Mayer applauded his effort. He told Jack, “I don’t know what we can use you for, but if we ever do need you, we’ll need you real bad.”

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Receiving High Praise Early On

Turning Roles Away

Not that his career needed more classics than it already has but Nicholson chose not to be a part of some the biggest hits to ever grace the big screen. How would Jack have fit in as Michael Corleone in The Godfather? Could he have established the same hair-raising vibes in Silence of the Lambs as Hannibal Lecter? We have to leave it up to our imagination. He also turned down lead roles in Rain Man, The Exorcist, and The Sting.

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Turning Roles Away

Starting Out Small

It takes time to become a star of Jack’s magnitude. Before he got to Easy Rider, As Good As It Gets and One Flew Over The Cuckoos Nest, Nicholson was floating around stage productions and bit TV parts. His first feature film role did not come until The Cry Baby Killer (1958). Jack played the lead in the Roger Corman film as a teen who takes people hostage. It helped him get a part in Corman’s Little Shop of Horrors two years later.

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Starting Out Small

Golfing With Gold

They say money cannot buy happiness. But can it buy a good round of golf? Nicholson once spent $75,000 on a set of custom made golf clubs. With that price tag you would hope the clubs are made of gold, which they were (24-karat gold), as well as carbon fabric and platinum. Japanese company Honma made the clubs. Celebrities such as Marc Anthony and Danny DeVito also purchased the expensive clubs.

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Golfing With Gold

Returning To The Big Screen

It has been seven years since his last film, but it appears as if Jack Nicholson will be making a comeback in 2017. Paramount Pictures has brought in Jack and Kristen Wiig to star in a remake of the Oscar nominated German film, Toni Erdmann.  His last appearance reunited him with As Good As It Gets director James L. Brooks in 2010’s How Do You Know. Hopefully, we will see Jack back in theaters soon.

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Returning To The Big Screen

Staying In School

When Jack was elected Class Clown in high school, it was not just for his keen sense of humor. He was also a huge trouble maker. In one particular school year, Jack received detention every single day of the year. At least he had plenty of time to do his work after school. In a strange twist for such a poor student, Nicholson now has a theater and a drama award named after him at his alma mater.

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Staying In School

What’s Monogamy?

Has a word or concept ever escaped your brain every time you try to recall it? For Jack, that word is monogamy. He is incapable of remembering the word when it is appropriate to use in context. For a guy incapable of keeping it in his pants, it should not be surprising. Jack is a legendary ladies man and has never been able to hold relationships for long due to his infidelity. Maybe one day the word will sink in.

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What’s Monogamy?

The Three Best Friends

Coming up in the early 1960s, Nicholson became close friends with Bruce Dern and Harry Dean Stanton. They were all struggling actors trying to find work, mostly taking small parts on TV westerns. Andy Griffith Show fans might be able to spot Jack in a few episodes too. He became so close with Stanton that he began writing his friend’s name or initials in almost all of his films. It usually appears as graffiti or a carving on a tree.

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The Three Best Friends

One Shot At Matrimony

As big of a serial dater and philanderer as he is, Jack Nicholson was actually married at one point in his life. Jack married Sandra Knight on June 17, 1962. They had one daughter together, Jennifer. The marriage would not last long though. Nicholson and Knight separated in 1966 and finalized their divorce two years later. Jack has had long term relationships since but has not said “I do” in quite some time. It does not appear to be in the cards for him again.

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One Shot At Matrimony

The Court Side Crazy

Basketball fans are sure to find Jack Nicholson sitting court side at most Los Angeles Lakers home games. He has been a season ticket holder for decades, becoming part of Lakers lore. Jack can be found sitting next to music executive and his friend Lou Adler. Both guys seem to love wearing sunglasses indoors. Rumors spread that Jack has had film production schedules set around Lakers game, but he has stated that it is only a rumor.

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The Court Side Crazy

Monkee-ing Around Hollywood

The year before he received international recognition in Easy Rider, Jack put together a project for the television rock stars, The Monkees. Jack, along with the film’s director Bob Rafelson, wrote the script and produced the film. He made a small uncredited appearance, as did his Easy Rider co-star Dennis Hopper. The film is a collection of musical, trippy vignettes. Many famous names appeared in cameos such as musician Frank Zappa, boxer Sonny Liston, and football player Ray Nitschke.

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Monkee-ing Around Hollywood

Chez Nicholson – Clothing Optional

Rolling Stone journalist Erik Hedegaard had quite an interesting experience when he went to interview at his home. Nicholson was in the middle of three months where he did not leave the house and did not wear clothes ever. Jack would bare all no matter who was in the house, including his daughter. Later, Jack’s biographer claimed that he did so to prepare for an illicit scene in a film. He wanted to get comfortable not having clothes on around people.

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Chez Nicholson – Clothing Optional

Anger Management

When Jack Nicholson starred in Anger Management with Adam Sandler, surprisingly, he was the calm presence. As a young man living in New Jersey, he worked as a cook as he looked for acting jobs. One time, he messed up a pancake order and made them “three inches thick.” The angry customer approached him about it and said, “What the hell is this?” Jack lost his cool. He punched the pancake stack and replied, “Make your own damn pancakes!”

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Anger Management

Easy Access Underground

Living on Mulholland Drive had its perks for Jack. Recently, it was uncovered that a series of tunnels connected the Playboy Mansion to some homes in the surrounding area. Blueprints specifically mentioned the homes of “Mr. J. Nicholson,” “Mr. W. Beatty,” “Mr. K Douglas” and “Mr. J. Caan.” We can reasonably conclude this alludes to Jack, Warren Beatty, Kirk Douglas, and James Caan. They all lived nearby. No one has confirmed or denied their existence, but they reportedly were closed in 1989.

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Easy Access Underground

Cravings He Cannot Contain

Jack has an insatiable desire for being intimate. Anjelica Huston used to call him “The Hot Pole.” He was once quoted as saying “I had a large appetite.” It is the reason that most of his relationships failed. Jack understands that his trouble keeping it in his pants affects his life and he thinks he knows why. He compared it to elements of the universe, that when it becomes ignored or unfulfilled, you start to act irrationally.

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Cravings He Cannot Contain

Bring Real Life Into The Movies

One of Jack’s other breakthrough roles after Easy Rider was Five Easy Pieces. In a famous scene, Jack tries to order toast from a diner waitress. The waitress has no interest in serving him toast without him ordering the meal it comes with, a chicken salad sandwich.  He told her to hold the sandwich “between your knees.” Jack claimed this happened to him at a Los Angeles restaurant called Pupi’s. He told the screenwriter, and it became part of the film.

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Bring Real Life Into The Movies

The Oscar Winning Fifth Choice

After his stupendous performance in One Flew Over the Cuckoo’s Nest as Randle Patrick McMurphy, Nicholson earned his first of three Academy Awards for Best Picture. Amazingly, he was not first, second, third or even fourth choice for the part. Marlon Brando, Gene Hackman, Burt Reynolds, and James Caan all turned the part down, opening the door for Nicholson. It is a good thing they said no because it gave audiences one of the greatest performances in film.

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The Oscar Winning Fifth Choice

Bad Boy Drive

Nicholson lived near or next to plenty of famous faces in Hollywood. His co-star in The Missouri Breaks, Marlon Brando, was a longtime neighbor of his on Mulholland Drive in the Hills. Brando would stop by to raid Jack’s fridge. His trademark was to leave nothing but his underwear behind. When Jack’s friend Warren Beatty moved in a couple of houses down, the strip was nicknamed Bad Boy Drive for their antics and flirtatious ways.

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Bad Boy Drive

A Tribute To Brando

Nicholson loved his time living next to Marlon Brando. When Brando died in 2005, and his house went up for sale, Jack decided to buy the house for himself. He had no intentions of living there, however. Even though he paid $5 million for the 3,040 square foot property, Nicholson demolished it. As a tribute to his pal, he planted frangipani flowers where the house once stood. Brando had nicknamed his home “Frangipani,” so Jack felt it was the only way to lay his friend’s home to rest.

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A Tribute To Brando

The Top Billin’ Villain

When Jack Nicholson received top billing in Batman, it came as a bit of a shock. Tradition generally put the hero at the head of the bill, which would have meant Michael Keaton would be the first actor listed. Instead, Nicholson was listed up to for his performance as the Joker. Jack smartly secured a percentage of merchandising from the film. He made somewhere between $60 to $90 million for his connection to the film.

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The Top Billin’ Villain

The Road Rage Incident

Note to drivers: do not cut Jack Nicholson off when he is on the way to the driving range. One unlucky Mercedes met the wrath of Jack when he did just that. Jack grabbed his two iron and smashed the car’s windshield with it. He settled out of court for $500,000. His golf instructor noted, “you have to have a near-perfect grip, and a killer shoulder turn (to do that damage)… and I taught those to Jack Nicholson.”

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The Road Rage Incident

The Manson Family Connection

The Manson family terrorized California during the late 60s. One of their victims, actress Sharon Tate, was a friend of Jack Nicholson’s. When Charles Manson’s high profile murder trial got underway, Nicholson made sure to see justice for his friend. He attended as many of the proceedings as he could, going almost every day. One of his biographers wrote that he was infatuated by Manson too. “He was fascinated by Manson’s persona and the crazy way he looked.”

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The Manson Family Connection

Inducting The Nature Boy

Beyond his super fandom of the Lakers, Jack’s sports craziness extends beyond basketball. He is a huge WWE nut. For years, he has been petitioning to induct Ric Flair into the WWE Hall of Fame. Jack says that John Cena is his favorite wrestler now. Nicholson also has dreams of his own wrestling organization. He’s said he would start one if he can get Jim Carrey, Tom Cruise, Robert Downey Jr., and Johnny Depp to join the project.

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Inducting The Nature Boy

A Walk In The Streep

While filming the 1987 film Ironweed, Jack found himself entangled with co-star Meryl Streep. The two disappeared into Nicholson’s trailer at one point and rumors began to swirl. He is 13 years older than her, but his biographer Marc Eliot claims they were not discussing the script. One witness claimed, “‘Whatever is going on inside that Winnebago, it’s starting to get out of hand, to the point where it’s embarrassing a lot of people on the set.” Meryl was married, adding to the scandal.

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A Walk In The Streep

Who’s Your Mamma?

Jack Nicholson’s life is filled with family mystery. Not only does he not know his father, but his mother also lied to him through her death. Jack learned through a Time magazine researcher that his sister was actually his mother, that his mother was actually his grandmother, and that his other sister was his aunt. He was born 50 miles from his hometown to keep his birth a secret and to protect the family’s reputation. He was 37 years old when he found out.

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Who’s Your Mamma?

Putting The Breaks On Carly Simon

When Jack Nicholson stayed the night at Carly Simon’s apartment, she woke up to find him conducting business calls in bed the next morning. She claimed he used a different voice almost as if he was trying to impress. He ended their relationship by saying he was falling for another woman whom he was seeing. Simon responded, “I really like seeing you, and I’m glad you told me before I invited you to my wedding in which you were my groom.”

Putting The Breaks On Carly Simon

Womanizer, Womanizer

Jack loves acting and loves art, but he loves nothing like he loves women. The press frequently referred to him as Jack the Jumper or the Great Seducer. Cher once said about Jack, “I think he likes women more than any man I’ve ever known. I mean he really likes them.” The list of famous ladies he has had encounters with includes Lara Flynn Boyle, Melanie Griffith, Veronica Cartwright, Michelle Philips, Rebecca Broussard, and Margaret Trudeau, the mother of the current Canadian Prime Minister.

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Womanizer, Womanizer

Still In Love

After his breakup with longtime girlfriend Rebecca Broussard, Jack opened up about their relationship to Vanity Fair. He felt abandoned by their breakup, but that does not mean he did not still love her. In fact, he told the magazine that not only is he still in love with Rebecca, but with every woman that he has ever loved. It’s an interesting statement from a man known more from bouncing from gal to gal than committing his love to someone.

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Still In Love

Saving Some Romance For The End

Jack has lived many romantic lifetimes compared to the average person. Now 80 years old, Jack has stayed out of the spotlight (outside of the occasional Lakers game) and lives alone in his Mulholland Drive home. He claims that he would still love “one last romance,” but is not confident that he will find it. One source claims that he is “afraid of dying alone in that house.” We hope he finds the right woman for his twilight years.

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Saving Some Romance For The End

His Longest Relationship

For 17 years, Jack Nicholson was able to sustain a relationship. That he made it that long is impressive on its own. Actress Anjelica Huston lived with him for the majority of that time, moving in with him as he filmed Chinatown. They met at a party at his house and she became infatuated with him immediately. Huston won the Academy Award for Best Supporting Actress for Prizzi’s Honor, a film they starred in together (it was directed by her father too).

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His Longest Relationship

The End With Anjelica

Huston claims that she did not really know about his reputation when they first started dating, but she should have picked up on it because he was best friends with Warren Beatty. She was aware of his affairs for years, occasionally finding other girls things in the house. It started to weigh on her but did not come to a tipping point until Rebecca Broussard became pregnant with his child. She broke it off in 1990.

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The End With Anjelica