Inside Jack Nicholson's Complicated Love Life

Tinseltown has seen its fair share of ladies men over the decades, though few can match up to three-time Academy Award winner Jack Nicholson when it comes to womanizing. Even by Hollywood standards, the New Jersey native is on another level. When the Independent compiled a list of "the great seducers" of history, Nicholson's name appeared alongside the likes of Lord Byron and Giacomo Casanova. That may seem like hyperbole, but if reports are to be believed, then the actor has more than earned his place in the annals of playboy history — he's said to have slept with over 2,000 women in his time.

This figure has never been verified (when Nicholson was asked to confirm it, he replied, "I don't count," per the Daily Mail), but first-hand accounts from the people who have known him personally over the years indicate that the number is indeed very high. "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 said (via The Sydney Morning Herald), while Kim Basinger, who was obsessed over by Nicholson's Joker in Tim Burton's Batman, described him as "the most highly sexed individual I have ever met."

According to Nicholson, women came to know him as "Jack the Jumper," which made it harder for him to gain their trust. He's had a couple of long-term relationships, but Nicholson has always been the fling king. Let's take a look back at his complicated love life.

Jack Nicholson learned his craft from veteran Hollywood acting coach Jeff Corey, who set him on the path to stardom when he introduced him to B-movie producer Roger Corman. The actor worked with Corman on numerous low budget flicks before making his mainstream breakthrough, including 1963's The Terror. He met his first and only wife, actress Sandra Knight, on the set of the grindhouse horror flick. A whirlwind romance ensued, and they tied the knot soon after. "I got married on a Friday because on Wednesday Sandra said she wanted to," Nicholson said, according to Patrick McGilligan's biography, Jack's Life. Unfortunately, reality set in during the ceremony.

Nicholson was brought up Catholic, and when he realized he'd rushed into the marriage, he started talking to god. "[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 told Closer magazine that they "had a very beautiful, sweet marriage" for a time, though it clearly wasn't meant to last. They divorced in 1968, but not before welcoming a child, Jennifer Nicholson. Their daughter worked sporadically in Hollywood, but it's her kid that's got people talking. Up-and-coming actor Duke Nicholson prefers to chat sports rather than films when he sees his grandfather, but he's a big fan of his work. "The Shining is one of the greatest horror films of all time," Duke told The Hollywood Reporter.

Sandra Knight ended her marriage to Jack Nicholson when it became clear he was going to "become a big star and have lots of temptations," she told Closer (via The Sydney Morning Herald), adding, "I couldn't go along for the ride." Her prediction came true soon after their divorce. Nicholson shot to prominence with his performance in counterculture classic Easy Rider, released in 1969. The following year, he starred alongside Susan Anspach in Five Easy Pieces. The two engage in a steamy affair in the film and, according to Anspach (who died in 2018), they got physical off-screen, too.

The actress claimed that they conceived her son, Caleb Goddard, during the making of the critically acclaimed drama. The two became involved in a nasty legal battle when Nicholson attempted to recover loans he had made to Anspach over a period of several years, loans that she said went towards the cost of keeping their son. According to Anspach, the A-lister has acknowledged that he's the father in private ("I accept him totally," she claims he told her, per People), but has never done so publicly. "That is the torture of it," Anspach told the Los Angeles Times. "Jack would say, 'I didn't have a father and I'm a superstar. It didn't hurt me.' And I would say, 'But you didn't have to see your father on every corner. You are ever-present, ubiquitous. You are too famous to do this. It's unkind.'"

Jack Nicholson followed up Five Easy Pieces with 1971's Carnal Knowledge, a comedy-drama about the sexual conquests of college roomies Jonathan and Sandy, played by Nicholson and Art Garfunkel. The part of Susan (the girl the two boys end up fighting over) was played by Candice Bergen, but she wasn't the only actress considered. Michelle Phillips of the Mamas and the Papas took part in a screen test, and while she didn't get the part, she did get the leading man. Nicholson and Phillips began dating, though it wouldn't last very long. After losing out on the Carnal Knowledge role, Phillips signed on to appear in Dennis Hopper's The Last Movie instead, and she would end up falling for the bad boy actor-director.

To call Hopper's marriage to Phillips short-lived would be an understatement — their tumultuous union lasted just eight days. Single once more, she decided to give things another shot with Nicholson. "He was a lovely guy: charming, sweet, and fun to be with," Phillips told Vanity Fair. The California native told the magazine that things started going downhill after "Jack had a life-changing experience," which is putting it mildly. They were eating breakfast in bed one morning when an investigative journalist called and informed Nicholson that the woman he thought was his mother all his life was actually his sister. "Jack was incredulous," Phillips recalled. "He'd been raised [...] surrounded by women.... Now I think he felt women were liars."

Jack Nicholson and Anjelica Huston were never married and they didn't have any children, but, in many ways, she's always been the love of his life. It was 1973 when the 21-year-old daughter of filmmaker John Huston moved from New York to Los Angeles and received an invite to a gathering at Nicholson's Mulholland Drive party pad. "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). "'Good evening, ladies,' he said, beaming, and added in a slow drawl, 'I'm Jack, and I'm glad you could make it.'" She ended up staying the night.

Nicholson called her to arrange a second date a few days later, but he had to cancel because he had a "previous obligation," Huston recalled him saying. She went out with friends instead, though as fate would have it, they ended up at the same restaurant as Nicholson and his so-called previous obligation. "Jack was sitting in a booth with a beautiful young woman whom I immediately recognized — I had seen photographs of them together in magazines — as his ex-girlfriend Michelle Phillips," Huston wrote. "I lifted my glass airily and said, 'I'm downstairs, and I just thought I'd come up to say hi.' He introduced Michelle, not missing a beat. She was charming." According to Huston, she and Phillips would actually become friends in the weeks that followed.

Anjelica Huston moved in with Jack Nicholson when he was working on 1974's Chinatown, another critical hit for the in-demand actor. She was thrilled about the idea, but she quickly came to the realization that she wasn't the only female in his life. In her memoir, the former model and actress said 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. "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's Watch Me (per Vanity Fair). "Sometimes I'd take to wearing the jewelry to see if anybody would come up and claim it, but that never happened."

They would continue to appear on red carpets together for the best part of two decades, despite Nicholson's wandering eye. Huston was able to overlook the small things, but when Nicholson invited her to dinner one night in 1989 and informed her that another woman was pregnant with his baby, it was the beginning of the end. 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."

The way Janice Dickinson tells it, she had her pick of Hollywood's most desirable men when she was at the height of her power in the 1980s. In her autobiography, No Lifeguard On Duty, the former fashion model claims that Warren Beatty, Dustin Hoffman, Robin Williams, and Jack Nicholson were all vying for her affection at one glitzy New York party she attended. "I left with Jack — much to Warren's chagrin," Dickinson said (via the Daily Mail). "I'm a sucker for a man who knows how to make me laugh." They retired to Nicholson's hotel suite and spent a fun night together, but she saw a different side to the actor the following morning.

According to Dickinson, the Hollywood bad boy asked her for a "favor" as she was getting ready to leave: keep the fact that she "just had sex with a star" to herself. "He wasn't kidding, either," she added. "He was lying there naked, propped up on the pillows, grinning that famous grin. I couldn't believe he could be so full of himself." The Brooklynite said that Nicholson tried calling her a few times after their one night together, but she ghosted him. "He was fun, sure, but I wanted a proper relationship," Dickinson wrote in her 2002 tell-all. "I also felt a little guilty about Anjelica Huston, Jack's long-time girlfriend. I'd met her and liked her, so, I wondered, why I was sleeping with her man?"

Homeland star Mandy Patinkin was supposed to appear opposite Meryl Streep in 1986 rom-com Heartburn, but director Mike Nichols came to the quick conclusion that the co-stars had no chemistry and replaced his leading man with his good friend, Jack Nicholson. According to Erin Carlson's biography Queen Meryl, Streep had previously turned down the chance to work with Nicholson in 1981's The Postman Always Rings Twice. "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 is quoted as saying. "He wasn't so keen on that." He was keen on sharing the screen with her in Heartburn, however.

"He starts falling in love with Meryl," producer Bob Greenhut recalled. "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. He added: "She had a good way of throwing cold water on Jack whenever he got a little too friendly." When the pair reunited for Depression-era drama Ironweed the following year, however, they reportedly met regularly in Nicholson's Winnebago, which "seemed to be balanced on four overworked Slinkys" during the shoot, according to biographer Marc Eliot (via the Daily Mail). Nicholson and Streep both denied that any affair ever took place.

Another model that found herself under Jack Nicholson's spell for a time, Marie Helvin, claims that she had to rebuff the A-lister's advances for years. The Tokyo-born beauty was married to famous fashion and portrait photographer David Bailey when Nicholson — one of Bailey's "best friends" at the time, according to Helvin — made his first pass at her. "Jack would raise the stakes a little when Bailey was away, taking me out for dinner," she revealed in an article published by London's Evening Standard. "He was an incorrigible flirt, and I found his attention flattering." She admitted that she "fantasized" about having an affair with the actor, and Nicholson would reportedly tell anyone who would listen how much he was into Helvin, but she was loyal to Bailey. Plus, she knew that Nicholson was still hung up on his longtime lover. "Jack was desperately trying to get back with Anjelica Huston," Helvin said.

Later, when Helvin's marriage to Bailey was history, Nicholson got his shot. The pair hooked up when the actor landed in London to film scenes as the Joker in Tim Burton's Batman, but the sexual tension that once existed between them was no longer present. "Our flirtation felt flat," Helvin wrote. "We went back to my [apartment] together with a sense of heavy-heartedness. The spark had gone — we had simply waited too long. When he finally left, I didn't care if I never heard from him again."

Margaret Trudeau — ex-wife of former Canadian prime minister Pierre Trudeau and mother of current Canadian prime minister Justin Trudeau — has been with several famous and influential men over the years. She was just 19 when she met the much older politician on a family vacation to Tahiti, and the age gap between them would prove to be their undoing. 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.

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." Of course, Nicholson was still on-and-off with Anjelica Huston, and that's why the affair ended. Trudeau was left feeling gullible, but she came to look back on her carefree days with the actor fondly. "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. 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."

The term Hollywood royalty is sometimes overused, but it definitely applies to Melanie Griffith, daughter of The Birds star Tippi Hedren and mother to Fifty Shades of Grey's Dakota Johnson. She was 18 when she married actor Don Johnson, her mother's co-star in The Harrad Experiment. The doomed union lasted just six months. Unshackled from her older husband, Griffith was free to become the perennial wild child she's now remembered as. One of the places she frequented was Helena's, a Los Angeles club that catered to Tinseltown's hard-partying elite in an age before smartphones made public debauchery impossible. "It was so much fun because that was the thing: to dance, hang out at Helena's and do drugs," Griffith told The Hollywood Reporter.

Jack Nicholson was an investor in Helena's and a regular customer alongside his pals Harry Dean Stanton and Marlon Brando. "Oh, he was there every Friday," founder and host Helena Kallianiotes said of Nicholson. Griffith didn't confirm where she hooked up with Nicholson, but the smart money is on Helena's. When the Body Double star sat down for an interview with Porter magazine in 2017, she revealed that she snagged Nicholson, Warren Beatty, and Ryan O'Neal during her man-eating years. "I did have a little thing with those three back in the day," she said (via Vanity Fair). "Yeah, they were awesome. I am friends with all of them, pretty much. I'm sure there's a couple I've forgotten about."

Anjelica Huston's father, John Huston, was visited by Jack Nicholson shortly before he died in 1987. Nicholson swore to the Oscar-winning filmmaker "on his deathbed that he would take care of his beloved daughter," London's Evening Standard reported, adding, "Even before the funeral, however, he was entertaining a young British starlet called Karen Mayo-Chandler." According to Marc Eliot's book, Nicholson, the actor entered into "an intensely sexual affair" with Mayo-Chandler, who would dish the dirt on their wild romps when she posed for Playboy a few years later. 

The model and actress (who died of breast cancer in 2006) referred to Nicholson as "that horny little devil" and "Spanking Jack" in an accompanying tell-all interview, revealing that he refueled himself with peanut butter and jelly sandwiches between sessions in the bedroom. "He had this image of being like Bogart, a loveable rogue, a naughty little boy," Mayo-Chandler told the famous men's mag, and he apparently lived up to that image. She called Nicholson "A guaranteed non-stop sex machine into fun and games, like spankings, handcuffs, whips and Polaroid pictures." 

Nicholson was apparently blindsided by Mayo-Chandler's Playboy interview. There was no doubt that he was going to see it, being a friend of Hugh Hefner and a regular guest at the Playboy Mansion. In 2015, Playboy staff reportedly stumbled across blueprints that pointed to the existence of a tunnel leading from the Playboy Mansion to Nicholson's nearby home (via Vanity Fair).

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. 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 tangle with the likes of David Bowie, Iggy Pop, Steven Tyler (father of Buell's daughter, actress Liv Tyler), and Mick Jagger. 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" (via Rocks Off).

They slept together for the first time at Jagger's house, Buell said. Nicholson was apparently enamored with the country girl afterward, so much so that he flew her out to Los Angeles where they went 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. "My butt was going 50 miles an hour," Nicholson reportedly told her after the deed was done. Bebe described the experience in her 2001 memoir, Rebel Heart. "I was having my first very cool sex-against-the-car-with-Jack Nicholson lesson," she wrote (via Kirkus).

The woman that Jack Nicholson impregnated while still with Anjelica Huston was a young actress named Rebecca Broussard. "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 (per Vanity Fair). "Jack had been spending time there after his basketball games. She'd shown up in Aspen the winter before, as his daughter Jennifer's friend." 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.

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. "After I had my kids, I changed," Broussard told Vanity Fair in 1994, revealing that she had shacked up with a man 25 years younger than her A-list baby daddy (according to Nicholson, by biographer Marc Eliot, Nicholson was likely having his own affair with French starlet Julie Delpy at the time). When the magazine reached out to Nicholson for comment, he said that he felt "abandoned" by Broussard. "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."

Jack Nicholson was apparently devastated when Rebecca Broussard left him, but he didn't waste much time getting back in the game. He told Vanity Fair that he still loved Broussard in 1994 ("I'm still in love with all the women I ever loved," he said), but, according to the National Enquirer, he reportedly had a fling with 20-year-old Hollywood waitress Jennine Gourin that same year. 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 told the outlet.

Nicholson was also seen with school dropout-turned-TV presenter Amanda de Cadenet (pictured), who "was just 17 when she was taken out to dinner by a 52-year-old Jack Nicholson one night in 1989," Express reported. According to de Cadenet, she met Nicholson when she was out with some supermodels in London one evening. "Jack and I ended up going out later that night," she said. Judging by a giggly conversation between de Cadenet and friend Courtney Love (via Interviews With Amanda), she hooked up with Nicholson again after his split from Broussard. "Amanda took me up to Jack Nicholson's, and her nipple popped out, and I covered it up," Love said during their 1995 Interview magazine chat. "Jack said, 'Why did you do that?'" De Cadenet went on to defend Nicholson from accusations of lechery, calling him "a sweet gentleman."

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, and when the young couple got the chance to party with Nicholson, they didn't hesitate. Unfortunately for Spade, the A-lister wasn't interested in him. "Nicholson asked Lara Flynn Boyle out in front of me, while we were all smoking a doob somewhere," Spade told Details (via Page Six). "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.'"

The way Spade tells it, Boyle made out she wasn't interested in Nicholson ("She goes, 'No way, he's worse than [Donald] 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. "[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." Nicholson and Boyle came out as a couple at the 1999 Emmys, per the Daily Mail.

Rumors that Jack 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 himself when he told The Sun that his goal was to get the British supermodel — a whopping 37 years his junior — between the sheets. "There are two kinds of women," Nicholson is quoted as saying (via Vogue). "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 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? An insider with knowledge of the situation claimed that Moss was indeed willing to settle down with someone, but that someone was never Jack 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 — so that means meeting someone who's wealthy and famous." Moss would later walk down the aisle with Jamie Hince, one half of the British indie rock duo The Kills, but it didn't last. They separated in 2015 and finalized their divorce the following year.

Jack Nicholson has a history of hitting on actresses at the Oscars, and it doesn't always go to plan. He apologized to Nicole Kidman after he tried to chat her up in front of Keith Urban back in 2006 ("I didn't know she was engaged — or that she was standing with her fiance," Nicholson said, per the Daily Mail), and he was at it again almost a decade later when Jennifer Lawrence was named Best Actress by the Academy. As Lawrence spoke to ABC about her triumph, Nicholson appeared in the background of the shot and, after spotting her, decided to crash the interview.

The then 76-year-old told Lawrence that she "did such a beautiful job" with Silver Linings Playbook, the film that put her there. Lawrence played ball — she joked with the Hollywood icon that he was "being really rude" by interrupting her, which made his permanent grin widen even further. "I'll be waiting," Nicholson told her before disappearing into the throng. When Lawrence was asked about Nicholson at the premiere of her film The Hunger Games: Catching Fire later that year, she told Extra TV: "Oh, are we dating? Are we an item? I'm not going to say what he did or didn't do. He could have or could not have sent me flowers and a bottle of Cristal."

He's been quiet in recent years, but he "would love that one last romance," Closer quotes him as saying.