Jumping Jack Nicholson is Still Looking for Love

What’s your favorite Jack Nicholson screen moment? Browbeating the waitress in Five Easy Pieces? Leering as the Joker in Batman? Or how about ccaring you out of your seat in The Shining? Nicholson’s devilish grin and dancing eyebrows have captivated audiences for 50 years.

Jack Nicholson, Angelica Houston / Lara Flynn Boyle, Jack Nicholson / Jack Nicholson, Meryl Streep / Jack Nicholson.
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But for all the entertainment the three-time Oscar winning actor has provided on screen for all these years, his most dynamic performances may have been in the bedroom. The 84-year-old actor is rumored to have had slept with more than 2,000 women (“I never counted,” he said once).

The Ladies Love Jack

Nicholson is one of the few Hollywood Don Juan’s who has not been targeted by the “Me Too” movement. Could that be because, unlike other actors and entertainment business executives, Nicholson’s advances were not unwelcome?

A dated portrait of Jack Nicholson.
Photo by Michael Tighe/Donaldson Collection/Getty Images

“The thing about Jack is that he likes women more than any man I’ve ever known,” Nicholson’s The Witches of Eastwick co-star Cher told The Sydney Morning Herald. Kim Basinger described him as “the most highly sexed individual I have ever met.”

Women Have Dominated Nicholson’s life

Jack grew up in a house of women and never really knew his biological father. In 1974, Time Magazine informed Jack that the woman he thought was his mother was actually his grandmother, who decided to raise him as her own when his 17-year-old mother, June, got pregnant.

A portrait of Jack Nicholson in his teens.
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He grew up thinking she and his aunt were his sisters. This was not such an unusual situation in the days before birth control pills and legal abortions. (Actor/singer Bobby Darin also learned late in his short life that his sister was really his mother, as did Eric Clapton).

The Truth Made No Difference

By the time Nicholson learned the truth about his birth mother, both women were dead. At the time, he said learning the truth made no difference to him because by then he was already “psychologically formed.” But his lover at the time, Michelle Phillips, believed that learning the truth ended their relationship.

A dated picture of Michelle Phillips and Jack Nicholson sitting in a restaurant.
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Nicholson’s pal Warren Beatty was probably his greatest competitor as a lover. But Beatty suddenly settled down in 1992, marrying actress Annette Bening and fathering four children. Nicholson’s persistent philandering, on the other hand, earned him the nickname Jumping Jack.

A One-Time Wedding

Jack met his only wife, Sandra Knight, on the MGM lot when she was only 14. “I worked for a summer as a messenger girl, and he was a messenger boy,” Knight recalled in a June 2010 interview with Alan Mercer.

A movie still of Sandra Knight.
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“He and his friends were a little older, and they were always laughing and having fun, so I thought they were really cool. Then, I met Jack five years later at Martin Landau’s acting class. We rehearsed a scene from Tennessee Williams’ play Summer and Smoke, and the fire began.”

Bargained with God to Break Vows

In 1963, Knight and Nicholson were reunited in Roger Corman’s historical horror flick, The Terror. Her character was a shape-shifting demon looking to ensnare Boris Karloff. Instead, she captured Nicholson’s heart and quickly led him on his only trip to the altar.

A movie still of Nicholson and Knight in The Terror.
Source: YouTube

“I got married on a Friday because on Wednesday Sandra said she wanted to,” Nicholson recalled in Patrick McGilligan’s biography, Jack’s Life. Nicholson started praying during the 1962 ceremony. “[I] was looking upward and saying, ‘Now remember, I’m very young and this doesn’t mean I’m not never going to touch another woman.'”

Knight Has No Regrets

The marriage lasted until 1968 – the year before Easy Rider catapulted Nicholson into stardom. The couple had one daughter together, Jennifer, who is the mother of up-and-coming indie film star Duke Nicholson, who played a creepy carny in Jordan Peele’s film Us.

A photo of Knight attending an event / Jack Nicholson smiles at the press.
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Like most of the women who have been involved with Nicholson, Knight does not seem to have any regrets. “The real Jack is a loving, caring, giving person,” she told Closer Magazine in June 2016. “We had a very beautiful, sweet marriage.”

Streamy Offscreen Scenes with Susan Anspach

Easy Rider earned Nicholson his first Oscar nomination, but his blazing performance in Five Easy Pieces put him firmly in the Hollywood firmament. His sizzling sex scenes with co-star Susan Anspach continued off-screen. Anspach, who died in 2018, is probably the one woman with very few fond memories Nicholson.

A movie still of Susan Anspach and Jack Nicholson.
Source: YouTube

Anspach claimed that her son, Caleb Goddard, born in 1970, was conceived on the Five Easy Pieces set. Nicholson has never publicly acknowledged Goddard as his son, although Anspach told People magazine he told her, “I accept him totally.”

Caleb was legally adopted by actor Mark Goddard (Lost in Space), who Anspach married in 1970.

Anspach Sues Nicholson Over Loan

The situation between Anspach and Nicholson hit a new low in 1996 when she sued the actor for attempting to recoup $600,000 he had loaned her. Nicholson, who had a signed a legal note in hand, demanded the return of the money.

A photo of Susan Anspach speaking during an interview.
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Anspach contended she never would have borrowed it had she believed she would have to repay it and she needed the funds for Caleb’s education. Nicholson told the Los Angeles Times that Anspach kept insisting that Caleb was his son, but never provided any proof.

Karen Black’s Unrequited Love

The Five Easy Pieces set must have been a hotbed of passion as Karen Black, who played Nicholson’s pregnant girlfriend in the film, later revealed she had an unrequited crush on her co-star.

A still of Jack Nicholson and Karen Black in a scene from the film.
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“He was very beautiful. He just looked right at you … I liked him a lot … He really sort of wanted to date me but I didn’t think of him that way because I was going with Peter Kastner,” Black told Nicholson’s biographer Robert Crane.

Crying in the Lobby at Premier

“Then I went to do Easy Rider, but didn’t see him because we didn’t have any scenes together … At the premiere, I saw him out in the lobby afterward and I started crying … He didn’t understand that but what it was – was that I really loved him a lot.”

A dated portrait of Karen Black attending an event.
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The two never did get together. Black married three times and had a successful career as an actor, mainly in independent movies and theatre, and a songwriter, until her death from cancer in 2013.

Getting Phillips on the Rebound

In 1970, the actor was in Carnal Knowledge. Although the film starred two of the most gorgeous actresses in the business – Candice Bergen and Ann Margaret – Nicholson bypassed them for The Mama’s and The Papa’s singer Michelle Phillips, who had had screen tested and was turned down for Bergen’s role.

A picture of Michelle Phillips and Jack Nicholson in conversation.
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Phillips and Nicholson dated briefly before she moved on to his buddy Dennis Hopper. The pair had a torrid affair before getting married. Eight days later, they divorced, and Phillips returned to Nicholson on the rebound. “He was a lovely guy: charming, sweet, and fun to be with,” Phillips told Vanity Fair.

Are All Women Liars?

Phillips and Nicholson were breakfasting in bed when Nicholson got the call from Time Magazine, informing him that his mom was really his granny. By that point, Nicholson had no way to confront them and deal with the information.

A portrait of Michelle Phillips during an interview.
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Although he publicly brushed it off, claiming he was already psychologically formed and the news did not affect him, Phillips told Vanity Fair that she believes the revelation made Nicholson believe all women were liars, which she thinks signalled the end of their relationship.

The True Love of Jack’s Life

In 1973, 21-year-old Angelica Huston turned up at a party at Nicholson’s Mulholland Drive house. “The front door of a modest two-story ranch-style house opened, and there was that smile,” Huston wrote in her 2014 memoir Watch Me (per Vanity Fair).

A dated image of Nicholson and Houston on the red carpet.
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“‘Good evening, ladies,’ he said, beaming, ‘I’m Jack, and I’m glad you could make it.'” Huston, daughter of legendary filmmaker John Huston and granddaughter of Broadway star Walter Huston, proved to be the love of Nicholson’s life, although they never married or had children together during almost two decades as a couple.

Coping with Jack’s Infidelity

Huston moved in with Nicholson when he was working on Roman Polanski’s 1974 dark thriller Chinatown, which garnered another Oscar nomination for Nicholson. Even looking through the eyes of love, she quickly realized she wasn’t the only female in his life.

A photo of Jack Nicholson and Angelica Houston arriving at an event.
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In her memoir, Huston wrote that Nicholson’s reputation as a “world-class philanderer” was still growing at that stage and that “as prolific as he seems to have been, he was actually quite discreet” when it came to his affairs.

The Last Straw for Huston

“Occasionally, I’d find a piece of female apparel — once a jacket of mine turned up on a girl in the street — or I’d find some hand cream, or a trinket,” she wrote in 2014. “Sometimes I’d take to wearing the jewellery to see if anybody would come up and claim it.”

Angelica Houston poses for the press.
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As long as Nicholson remained discrete, Huston was able to overlook the small things, but things came to a head in 1989 when Nicholson invited her to dinner and casually informed her that another woman was pregnant with his baby.

Punching Jack Out

When Playboy printed an interview with a young woman who claimed to have slept with Nicholson just days later, Huston flew into a rage. “I was going at him like a prizefighter, raining a vast array of direct punches,” she wrote in her memoir.

Angelica Houston reads an excerpt from her memoir on stage.
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Nicholson was devastated by the breakup. “I was annihilated emotionally – that was probably the toughest period of my life. I’m childish and I did make a mistake.” Still, the threat of losing Huston did not stop him from seeing other women.

A Romp with a Bond Girl

Despite Nicholson’s still-lingering relationship with Huston and his blossoming one with Rebecca Broussard, which would eventually produce two children, he still found time for a romp with Bond Girl Jill St. John.

ATL A studio portrait of Jill St. John.

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St. John’s dating resume is about as long as Nicholson’s. Their 1989 affair is just a blip in a scorecard that includes romances with Frank Sinatra, Trini Lopez and Henry Kissinger. Like Nicholson’s pal Warren Beatty, St. John settled down at the end, marrying Robert Wagner in 1990.

Rebecca Broussard Comes on the Scene

Rebecca Broussard entered Jack Nicholson’s life as a friend of his daughter Jennifer. “This was a girl — blonde, sexy, full-lipped, and drowsy-eyed — whom I’d seen working at a dance club in Silver Lake,” Huston revealed in her 2014 memoir.

A picture of Rebecca Broussard and Jack Nicholson in a car.
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Jack had been spending time there after his basketball games. She’d shown up in Aspen the winter before. When Huston went to see Nicholson’s film The Two Jakes (1990), and Broussard popped up again (“she had appeared in a scene, playing his secretary, with a rose between her teeth”), she knew that something was up.

The Kids Change Things

Nicholson went on to have two children with Broussard: actors Ray and Lorraine Nicholson. Both the kids “are crazy about him,” according to their mother, but she and Nicholson began to drift apart when they became parents together.

A photo of Broussard and Nicholson attending an event.
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“After I had my kids, I changed,” Broussard told Vanity Fair in 1994, revealing that she was living with someone more age appropriate. When the magazine reached out to Nicholson for comment, he said that he felt “abandoned” by Broussard.

Jack Moves on To a New Love

“The tough things come to me in such tremendous proportions that they are always cosmically humorous,” he said. “As a literary person, I have to see the humor in it.” Nicholson was apparently devastated when Broussard left him, but he didn’t waste much time getting back in the game.

A dated portrait of Jack Nicholson.
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In the 1994 Vanity Fair article, he admitted he still loved Broussard (“I’m still in love with all the women I ever loved”), but, according to the National Enquirer, he reportedly had a fling with 20-year-old Hollywood waitress Jennine Gourin that same year.

Another Child Jack Denies

According to Gourin, her daughter is the result of that fling. Nicholson has always denied that Tessa Gourin is his child, though biographer Dennis McDougal isn’t convinced. “Tessa looks uncannily like Jack Nicholson today, and there is plenty of documented proof that he is her father,” he wrote.

A picture of Tessa Gourin.
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In 2019, Tessa perfectly recreated Nicholson’s arched eyebrows and maniacal Joker grin from Batman to send a blistering Instagram message to folks who mock her famous family ties, with a caption that read: “I just took a DNA test, turns out I’m 100% that bitch!”

Is It Love or Just Heartburn?

One of the more surprising entries on Nicholson’s hit list is Meryl Streep, who has been happily married to Don Gummer since 1978. Although both deny they ever had an affair, producer Bob Greenhut insists that Jack fell in love with Streep during the shooting of Heartburn.

Jack Nicholson and Meryl Streep pose together during an event.
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Streep and Mandy Patinkin were originally slated to star in the Mike Nichols film. Ironically, Heartburn is the lightly fictionalized account of Nora Ephron’s dysfunctional marriage to journalist Carl Bernstein – which ended when he cheated on her during her pregnancy.

Meryl Kept Turning Him Down

Early outtakes revealed that Patinkin was not comfortable in the role, and Nichols quickly asked Jack to step in. According to Erin Carlson’s biography Queen Meryl, Streep had previously turned down the chance to work with Nicholson in the 1981 remake of The Postman Always Rings Twice.

Meryl poses for the press.
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“Jack kept reminding me that there would be a lot of nude scenes, so I said, ‘Right, but I expect you to be equally sexually explicit,'” Streep says in the book. “He wasn’t so keen on that.” He was keen on sharing the screen with her in Heartburn, however.

Meryl Holds Firm

Greenhut insists that Nicholson pursued Streep. “You know, ‘Let’s go over our lines together later. Maybe we can have dinner.’ I mean, he really had the hots for Meryl. And, of course, she’s married.” According to Greenhut, Streep handled Nicholson’s sexual advances like an absolute pro.

A photo of Meryl Streep.
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Greenhut added: “She had a good way of throwing cold water on Jack whenever he got a little too friendly.” When the pair reunited for Ironweed the following year, however, they reportedly met regularly in Nicholson’s Winnebago, which “seemed to be balanced on four overworked Slinkys” said biographer Marc Eliot. Nicholson and Streep insist their relationship is platonic.

Canadian Nights with Maggie Trudeau

Nicholson was still officially with Huston when he enjoyed a steamy romance with Margaret Trudeau, ex-wife of former Canadian PM Pierre Trudeau and mother of current PM Justin Trudeau. Trudeau was just 19 when she met the much older politician on a family vacation. The age gap would prove to be their undoing.

Maggie Trudeau speaks during an interview.
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Margaret was already well-known in her own right as a New York socialite by the time she and Pierre split in 1977, and by summer the following year, she was hooking up with one of the city’s most famous sons.

All Night Long

In her 1982 book, Consequences (via UPI), Trudeau called Jack Nicholson “the first real rival to Pierre” when it came to the men. “I discovered just how much room there is in the back of a Daimler,” she wrote, adding that they “made love all night.”

A dated portrait of Trudeau.
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Nicholson was still on-and-off with Huston, which put a quick end to the affair. Trudeau was left feeling gullible, but like most of Nicholson’s conquests, she looked back on her carefree days with the actor “fondly.”

Trudeau’s Tribute to Nicholson

“The only man I ever dated who enjoyed freedom as much as I did was Jack Nicholson,” she wrote in her 2015 memoir, The Time of Your Life (via Chatelaine). “He was a wonderful, funny, truly free man.”

A dated portrait of Jack Nicholson.
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“He understood that marriage and monogamy were simply not ideally suited to his life as a movie star. How I loved my time with him,” she wrote with sincere admiration.

Buell Takes on New York Rockers

The majority of the famous men that Bebe Buell seduced were rock stars, but the Virginia native also has a few Hollywood stars in her impressive collection of former beaus, including Jack Nicholson.

A studio portrait of Buell.
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Buell rose to prominence in the early 1970s after moving to New York to pursue a modeling career and wound up in a relationship with rocker Todd Rundgren. She went on to relationships with David Bowie, Iggy Pop, Steven Tyler (father of Buell’s daughter, actress Liv Tyler), and Mick Jagger.

Jagger Warns Buell About Jack

According to Buell, it was Jagger who warned her about Nicholson. “Mick tells me that you’re gonna hurt me,” Buell told the actor, per Edward Douglas’ biography, Jack: The Great Seducer. He reportedly responded: “Well, I might, but you’ll have a damn good time before I do.”

A picture of Buell during an event.
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They slept together for the first time at Jagger’s house, Buell said. Nicholson was apparently so enamored with Buell that he flew her out to Los Angeles for a late-night drive-in Nicholson’s old Volkswagen, his so-called “cover car.” Nicholson told Buell to ditch all those “sleazy” rock star types — and then proceeded to have sex with her.

Climbing Twin Peaks with a Spade

The story of how Jack Nicholson became involved with Twin Peaks star Lara Flynn Boyle is pretty darn hilarious for everyone except the guy who told it, David Spade. The comedian and actor was going out with Boyle in the late ’90s.

A picture of Lara Flynn Boyle and Jack Nicholson attending an event.
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When the young couple got the chance to party with Nicholson, they didn’t hesitate. But Spade really didn’t interest Jack. “Nicholson asked Lara Flynn Boyle out in front of me, while we were all smoking a doob somewhere,” Spade told Details (via Page Six).

Boyle Protested too Much

“She got mad because I didn’t stick up for her. I said, ‘I’ve been in this town long enough to know when I’m outranked. You’re either gonna go out with him or you’re not.'” According to Spade, Boyle protested that she wasn’t interested in Nicholson.

Boyle attends an event.
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“She goes, ‘No way, he’s worse than Trump!'” But that apparently wasn’t true. She allegedly started seeing the much older man on the down-low, but it all came out when Boyle and Nicholson were involved in a road traffic accident, Spade said.

Try Keeping Out of Car Accidents

“[She] crawled out of the sunroof and yelled, ‘I have a boyfriend! I can’t be here!'” She couldn’t keep the story out of the tabloids, however. “That’s how I found out,” Spade said. “She and I didn’t talk too much after that.”

Boyle poses for the press.
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Nicholson and Boyle came out as a couple at the 1999 Emmys, according to the Daily Mail. The two initially broke up in 2000, later reuniting before splitting permanently in 2004, after which Nicholson was linked to English supermodel Kate Moss.

A Rolling Jack Gathers No Moss

Rumors that Nicholson was dating Kate Moss began to swirl in September 2004 when they were spotted leaving a New York restaurant together. The actor stoked the flames, telling The Sun that his goal was to get the British supermodel — 37 years his junior — between the sheets.

A photo of Kate Moss during an event.
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“There are two kinds of women,” Nicholson told Vogue Magazine. “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.”

Moss Didn’t Want a Jumping Jack

Moss didn’t look as though she was about to smack the actor as they left Spice Island in New York and got into a limo. “They really seemed to enjoy themselves,” one onlooker told the tabloid. So, how come they didn’t last?

Kate Moss poses for the press.
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An insider claimed that Moss was indeed willing to settle down with someone, but that someone was never Nicholson. “She feels she’s ready to find Mr. Right,” the source said. “She wants someone who can understand and cope with the goldfish bowl in which she lives.”

Jack’s Final Fling with Paz

In 2006, when he was 69, Nicholson dated actress Paz de la Huerta, who is 47 years his junior. The pair got the rumour mill running when they walked the red carpet together at the premiere of The Departed.

Jack Nicholson and Paz de la Huerta pose for the press.
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When asked about her relationship to the actor in an interview with The New York Times Magazine, de la Huerta revealed that she had met Nicholson at a party at The Roosevelt Hotel when she was 19.

Now They Want to Be Friends

De la Huerta told the interviewer, “He said to me: ‘They don’t make them like you anymore. I haven’t seen a beautiful girl like you since 1965.’ I said, ‘Let’s go make my boyfriend jealous.’”

Paz de la Huerta smiles at the press.
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So, he had her cornered, she said, “and he was flirting with me, and my boyfriend got completely jealous. We’ve stayed friends.” Take it from her, folks. She knows what she’s talking about.

In Love with the Lakers

These days, the 84-year-old retired (he hasn’t made a movie since 2010) actor’s main love is the Los Angeles Lakers, although with COVID still raging and being of a vulnerable age, he is not courtside as often as he once was.

A photo of Jack Nicholson watching the Los Angeles Lakers.
Photo by Allen Berezovsky/Getty Images

He and his son Ray were last spotted at a game in January 2020. Now Nicholson concedes his days of dating are over, and he prefers to stay in and watch a film. “I got tired of arguing with women about going to dinner,” he says. “The food is better at my house.”

Still Looking for Romance

His family would like him to sell the house in the Hollywood Hills, but he is determined to stay put and is still hoping for another romance. “I would love that one last romance,” he told the Sydney Morning Telegraph. “But I’m not very realistic about it happening.

A picture of Jack Nicholson and Ray Nicholson.
Photo by Allen Berezovsky/Getty Images

“What I can’t deny is my yearning. I’m definitely still wild at heart but I’ve struck biogravity. I have had everything a man could ask for but no one could say I’m successful with affairs of the heart.

He Made Mistakes

“I don’t think relationships are fixed things. People are necessarily complex and confused beings. We don’t always do the right thing, say the right thing and behave the way we always want to behave,” he told the Daily Mail.

portrait of Jack Nicholson smiling.
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Sadly, he concluded, “I used to be irresistible to women. I don’t feel that way anymore.”

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