Jack Nicholson's Dating History Is Packed With Gorgeous Celebrity Women

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"I've had everything a man could ask for," Jack Nicholson told Daily Mail in 2011. "But I don't know if anyone could say I'm successful with affairs of the heart." Indeed, "The Shining" star has never been short of female company. It would almost be easier to list the famous women he hasn't dated since rising to fame in the 1960s. But, filled with adulterous romances, on-off relationships, and one-night stands, his dating history leaves a lot to be desired.

Of course, some of the many women in Nicholson's life proved to be more significant than others. So, who was the lucky lady who got to exchange vows with the playboy? Which fellow Academy Award winner was he tied to for a good 17 years? And which 17-year-old did he take out to dinner when he was technically old enough to be her grandfather? Here's a look at 12 famous faces who've been wooed by the Hollywood icon.

The first female celebrity that the oft-tragic Jack Nicholson got involved with ended up marrying him. In 1962, the Hollywood star walked down the aisle with "The Terror" co-star Sandra Knight, with the pair going on to have a daughter named Jennifer.

The pair first met when they were working as messengers for MGM Studios. "He and his friends were a little older, and they were always laughing and having fun, so I thought they were really cool," Knight told Closer Weekly." But sparks only flew five years later, when the couple attended the same Martin Landau acting class. Unfortunately, the marriage didn't last long; the pair divorced in 1968.

In another interview with the same magazine, Knight had nothing but positive things to say about their time as husband and wife. "The real Jack is a loving, caring, giving person," she said. "We had a very beautiful, sweet marriage." While Knight walked down the aisle with John Stephenson in the 1980s, her ex-husband has never had the urge to get hitched a second time. "Marriage was a hot stove," "Nicholson: A Biography" writer Marc Eliot added. "He touched it, got burned and never did it again."

Sandra Knight might have been the first co-star Jack Nicholson entered into a relationship with, but she certainly wasn't the last. In 1970, the womanizer had a fling with "Five Easy Pieces" castmate Susan Anspach. Once again, he soon heard the pitter-patter of tiny feet, although it appears as though he did his best to ignore it.

Indeed, Nicholson refuted he was the dad of Caleb Goddard for several decades: Mark Goddard, who married Anspach that same year, became the boy's legal father. "That is the torture of it," Anspach later remarked in 1996 (via Los Angeles Times) about the situation. "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.'"

However, speaking to Rolling Stone in 1998, the Hollywood favorite seemed to publicly acknowledge for the first time that there was a connection. "Caleb and I have been getting along beautifully now," Nicholson claimed. "Having said that, based on the legality — the extremely unpleasant litigious nature of most of my relationships there — I'm not really at liberty to say what I think about it." The actor was no doubt referring to his various court battles with Anspach, including the dispute over a $600,000 sum he believed was a loan and she believed was a gift.

"We were two maniacs," model and actor Mimi Machu once said (via Radar Online) about her relationship with the oft-shady Jack Nicholson, which started around the early 1970s. "I'm interested in sex," Nicholson concurred. "I'm preoccupied with sex. I love it."

The pair were more than happy to mix business with pleasure. Machu played the girl that every member of The Monkees kisses in "Head," the subversive musical film that Nicholson wrote. She also shared the screen with her lover in biker movie "Hells Angels on Wheels," "Drive, He Said," (Nicholson's first time in the director's chair), and counterculture classic "Psych-Out."

According to reports, Machu — whose real name was Mireille Machu, though she was often credited as I.J. Jefferson — became increasingly jealous of the latter's leading lady Susan Strasberg. In fact, she made a point of watching the actor intently when she had to get intimate with Nicholson for a scantily clad love scene.

Jack Nicholson appeared to break the "bro code" in 1971 when he began stepping out with Michelle Phillips, the Mamas and the Papas vocalist who had been married the year previously — albeit only for eight days — to his good pal Dennis Hopper.

The pair first met during Phillips' attempt to cross over from music to acting when she auditioned for his directorial effort, "Drive, He Said." "I think he would've given me the part, but I turned it down because the girl was having sex on the kitchen table, and I found that very offensive," she explained to Smashing Interviews in 2021. "I didn't see that there was any reason to put that scene in there, and I told Jack that."

Although Nicholson disagreed with Phillips over this creative decision, he was still obviously charmed by her. "The next thing I knew, he was inviting me out to dinner," the latter recalled. "So we had a very, very nice relationship for about two years." In a chat with Vanity Fair, the singer explained that her ex's trust issues — he'd only just discovered that his late sister was actually his biological mother, and his late mother was actually his grandmother — was instrumental in their split. "He'd been raised in this loving relationship ... surrounded by women ... Now I think he felt women were liars."

Although Jack Nicholson never married again after his split with Sandra Knight, he did forge a much longer relationship with another Hollywood star. Indeed, he spent 17 years together with Anjelica Huston, but it's fair to say their romance was an on/off thing.

The couple, who worked together on "The Postman Always Rings Twice," "The Crossing Guard," and "Prizzi's Honor," first met at Nicholson's 36th birthday bash in 1973. "I fell in love with him at first sight," Huston later recalled to Violet Grey. "He opened the door of his house, and I thought, 'Now we're talking.' He had the most beautiful smile I've never seen in my life." The pair went on to share many happy times over the years, with Nicholson claiming to Rolling Stone that he'd "never had a greater moment" than seeing his girlfriend pick up Best Supporting Actress at the 1986 Academy Awards.

The womanizer often spoke fondly of Huston in public, too, describing her as "the love of my life" to People (via Yahoo! Entertainment) and insisting that he'd repeatedly asked for her hand in marriage. However, Nicholson's wandering eye eventually proved to be their downfall. After numerous alleged affairs, Huston finally called it a day in 1990, later acknowledging to "Watch What Happens Live" that he "wasn't as obsessed with me as I was with him." Here's a closer look at the truth about their relationship.

One of the many women Jack Nicholson reportedly had an affair with during his lengthy relationship with Anjelica Huston was Winnie Hollman, a model from Denmark, who also added to the confusion over his fatherly history. Indeed, in 1982, Hollman welcomed daughter Honey into the world, insisting that the "One Flew Over the Cuckoo's Nest" star was the father.

This news became wider public knowledge 24 years later thanks to an interview with the National Enquirer. Here, Honey claimed (via Jack Nicholson Online) that, away from the prying eyes of the press, she'd fostered a "regular father/daughter relationship" with Nicholson: "My dad's never been a stranger. When I was a kid, my mom took me to see him and when I got older I went on my own. ... We have similar facial features and my mom says I have the same temper as him. ... I scream and shout a lot," she continued. The plot thickened, however, when news emerged that Honey's biological father wasn't Nicholson, but his longtime friend, Lou Adler, who was already the known father of Winnie's younger son, Sonny.

Best known for being both the wife and the mother of Canadian prime ministers, Margaret Trudeau has never held back about her eventful love life. The activist, who was married to Pierre Trudeau for 13 years and gave birth to Justin Trudeau in 1971, has publicly spoken of celebrity flings with everyone from Lou Rawls to Ryan O'Neal over the years. In her 1982 book, "Consequences," she admitted she was left crushed when Jack Nicholson left her for another woman.

"I wanted him badly," Margaret wrote (via UPI), having revealed that they said farewell to each other with a night of passion. "But I didn't need him." She was also more than happy to discuss the Hollywood star in her 2015 book, "The Time of Your Life," describing him (via Chatelaine) as a "wonderful, funny, truly free man." Margaret, who also had a 15-year marriage with real estate developer Fried Kemper, was particularly taken with Nicholson for his sense of freedom. "He understood that marriage and monogamy were simply not ideally suited to his life as a movie star," she wrote. "How I loved my time with him."

Janice Dickinson sure didn't hold back in her 2002 memoir, "No Lifeguard on Duty." The famously outspoken model dished the dirt on numerous celebrity relationships, including one with Jack Nicholson, which was kickstarted at a swanky New York bash where apparently everyone from Dustin Hoffman to Warren Beatty were also hoping to woo her.

"I left with Jack — much to Warren's chagrin," Dickinson wrote (via Daily Mail) about the night in question. "I'm a sucker for a man who knows how to make me laugh." But the "America's Next Top Model" judge certainly wasn't laughing the next morning, when Nicholson asked her to keep their night of passion a secret. "He was lying there naked, propped up on the pillows, grinning that famous grin," she recalled. "I couldn't believe he could be so full of himself."

Despite wanting to keep things on the down low, Nicholson tried to get in touch with Dickinson again on several occasions. But, at a time when she was looking for something more serious, she gave him a wide berth. "I also felt a little guilty about Anjelica Huston, Jack's long-time girlfriend," she admitted. "I'd met her and liked her, so, I wondered, why I was sleeping with her man?" Here's a look at other dark secrets movie stars of the 1970s tried to hide.

While the majority of Jack Nicholson's celebrity conquests have preferred to keep quite about their dalliances, Karen Mayo-Chandler was more than happy to spill the beans. In fact, during a 1989 interview with Playboy, the actor and model seemed to relish the opportunity to give a little too much information.

Mayo-Chandler, who met Nicholson two years earlier in Aspen, Colorado, recalled how the "As Good As It Gets" star would pursue her around the bed dressed in nothing but orange socks and satin blue underwear. "He's a nonstop sex machine," she claimed (via New York Post). As well as revealing that their post-coitus snack of choice was peanut butter and jelly sandwiches, the Brit also went into further detail about exactly what they got up to in the bedroom. "He's into fun and games ... like spanking, handcuffs, whips, and Polaroid pictures."

In 2002, Mayo-Chandler also disclosed that Nicholson's sex drive had waned since their time together. "He told me a couple of years ago that he couldn't keep it up all night like he used to with me," she told Sunday Mirror. But she also insisted that their relationship was more than physical: "He was the one true love of my life and I really wanted to settle down with him and have his children. It was not to be back then ... But I still love him dearly — and I always will."

In 1989, a 52-year-old Jack Nicholson headed out on what was arguably the most controversial date of his career — the Hollywood star went to dinner with an It girl who, at the time, was only 17 years old! After they met at a supermodel gathering in London, Amanda de Cadenet — the wild child daughter of racing driver Alain de Cadenet — and Nicholson continued their night out at a London eatery, the pictures from which inevitably made the pages of the tabloids. 

The pair appear to have circled each other's orbits several times throughout the mid-90s, too. In 1993, it was reported that the Oscar winner had brushed de Cadenet's leg while appearing on morning TV show "The Big Breakfast," and during a joint chat with Interview magazine, de Cadenet's pal, Courtney Love, insinuated that the pair had reunited following Nicholson's split from Rebecca Broussard. Despite their significant age gap, de Cadenet has insisted that the former hellraiser wasn't the dirty old man many purported, but instead that he'd only ever been the perfect gentleman.

In 1989, Jack Nicholson embarked on an affair with Rebecca Broussard, an actor who'd just made her screen debut in action classic "Die Hard." According to reports, it was when the latter became pregnant with their daughter Lorraine that the former's long-term on/off girlfriend Anjelica Huston finally decided to hit the off switch for good.

Nicholson and Broussard ended up staying together for five years, welcoming another future actor, "Smile 2" star Ray Nicholson, into the world before Broussard ended things in 1994. Their split appeared to hit the Academy Award winner hard. In an interview with Vanity Fair, he admitted, "You're left. You're abandoned. And you're not going to be over it for another year — whatever the f*** you do ... If it takes that long, I'm willing. I don't think I got the time, but I'm willing to do the time. I'm going to give my need the time."

Nicholson, who acknowledged that he was still very much in love with Broussard, also hinted at why they separated, adding, "I trusted her too much. I'd trust again too much tomorrow night because I like her. She's great." Speaking to the same magazine, his ex confirmed there was another man in her life, but contrary to reports, he wasn't the cause of their split.

After allegedly, and apparently reluctantly, becoming a sixth-time father thanks to a dalliance with waitress Jennine Gourin, Jack Nicholson gave the tabloids further ammunition when he began dating a woman 33 years his junior. Indeed, the press had a field day when it emerged that the playboy was in a relationship with Lara Flynn Boyle, a fellow actor best known for her performance as Donna Hayward in "Twin Peaks."

Despite the significant age gap, the pair ended up dating on and off for seven years before calling it a day in 2006. It's not known exactly what caused the split, but in a piece for Vanity Fair, Nicholson's daughter, Lorraine Broussard, theorized that the glare of the media spotlight may have played a part." Lara's relationship with my father was a point of no return in which she went from being a woman on the verge of stardom — a person validated for her work — to a mere celebrity," Broussard wrote. "The public became so infatuated with Lara that, like the Eucharist, they swallowed her whole." In 2024, Boyle — who married Donald Ray Thomas shortly after the split — told People that she and Nicholson were still on good terms, describing their period together as "seven years of great times, it's seven years of wonderful." Here's a look at why Jack Nicholson disappeared from Hollywood.