He has enjoyed many accolades and success in Hollywood due to his incredible acting chops. However, his reputation as a bad boy playboy has proceeded to be more of a talked about subject than the awards for his acting. He has been with some of the most famous women in the tinsel town. We are talking about Lara Flynn Boyle, Kate Moss, Angie Everhart, Janice Dickinson, and and Joni Mitchell. The free spirited man has always been able to keep his romances from getting too serious, if they were getting to be too much, he would cut them off.
What is rather unfortunate, is that after all of these years and women, Jack has sadly found himself alone in his older years. The 80-year-old Hollywood legend is now as single as can be and is finding it hard to find a companion who is interested in him and not his money. His prime is behind him in terms of appearance and he has also grown weary of jumping around from relationship to relationship. On the subject, Nicholson said, “I would love that one last romance but I’m not very realistic about it happening.”
Then | Sandra Knight
We thought it would be most appropriate to begin with the one woman that Jack Nicholson actually married – Sandra Knight. Jack and Sandra were married in 1960 and had one daughter together, Jennifer. Their marriage ended in divorce in 1968. Sandra was an actress and writer. In the 50s and 60s, she was in a long list of low budget films that made her a minor celebrity.
Now | Sandra Knight
After her marriage to Jack, Sandra remained very much under the radar of Hollywood. Now in her late 70s, she remarried and is still married to her second husband, John Stephenson. Sandra is also a painter and has focused her creativity on her many pieces of art over the years. She will always have that title though, the woman who married Jack Nicholson.
Then | Mimi Machu
Jack was with Mimi during the late 60s, among many other women he was seeing at the time after his divorce. Mimi was just another one on the long list of women he was parading around with. Cher, who knew Jack but is not on this list, said, “I think he likes women more than any man I’ve ever known, I mean he really likes them.”
Now | Mimi Machu
Mimi isn’t known these days. She was in films like The Muppet Movie, Being There, Second-Hand Hearts, Lookin’ to Get Out, and Hollywood a Go Go as an editorial editor and assistant. Her acting credits include Hells Angels on Wheels, Psych-Out, Head, Mod Squad, and Drive, He Said. Her last credited role was in 1971. Under the radar it is, Mimi.
Then | Susan Anspach
Depending on who you want to believe, Jack and Susan were not only seeing each other during the time that they were starring together in the film Five Easy Pieces, but Susan also said that Jack is the father of her son Caleb, who was born in 1970. Jack wasn’t convinced. Their relationship was short lived, and Susan was already married so she never pursued paternity.
Now | Susan Anspach
Susan is known for her role in films like Blume in Love, Five Easy Pieces, and Play It Again, Sam. Her latest role was in 2009 in the film Wild About Harry. She has split her time as both a film actress as well as a stage performer. She was in an off-Broadway play, A View from the Bridge, alongside actors Dustin Hoffman, Jon Voight, and Robert Duvall.
Then | Michelle Phillips
Jack and Michelle were an item from 1970 to 1972, off and on. Michelle was an actress and singer, like all the other women he had a thing for. Jack really did have a creative type in mind in the women he dated. Michelle was the co-founder of the epic band The Mamas & the Papas in 1965. She was with her husband, John Phillips, whom she started the band with until 1969, after which time she met Jack.
Now | Michelle Phillips
Michelle is the last surviving original member of The Mamas & the Papas. She went on to pursue acting in addition to her music, going as far as getting a Golden Globe nomination for her role as Billie Frechette in the biopic Dillinger in 1973. Michelle continued to act until 2009, with her last role being in the film Betrayal.
Then | Candice Bergen
Chalk this up to pure rumor but we want to believe it so we are going to list it – Jack and Candice were together for a brief amount of time when they were working together on the film Carnal Knowledge in 1971. The name alone screams intimacy! Candice got her start as a model, seeing as she was such a stunner, and moved into acting in 1966.
Now | Candice Bergen
Candice moved on from Jack and their film together to be in the production that set her off the charts – Murphy Brown. From 1988 until 1998, Candice was the star of the sitcom and was shot to fame. She went on to star in shows like Boston Legal. She also appeared in films like Sweet Home Alabama, Miss Congeniality, Love Letters, The Women, and The Best Man, to name a few.
Then | Joni Mitchell
Seems appropriate that a free spirit like Jack would find his way to the mother of all free folk, Joni Mitchell. The two had a short fling in the early 70s, what a time it was! Fresh off of her stint in Woodstock, Joni was the escape that Jack was looking for in a woman. The singer and songwriter was hitting her all-time high with her 1971 record, Blue.
Now | Joni Mitchell
Joni is one of the most legendary musicians to date. Her music has crossed generations and continues to inspire. She has released 19 studio albums, two live albums and six compilation albums. She just can’t stop creating more music! She has won nine Grammy Awards throughout her career, which we agree is very well-deserved. She has recently battled some health scares, such as her 2015 brain aneurysm.
Then | Bebe Buell
If Bebe looks familiar to you it is because she was also in a relationship with another very famous man – Steven Tyler. Bebe and Jack were rumored to have had a fling in the 70s, around the same time the Bebe was linked to Mick Jagger and Iggy Pop. Bebe herself is a former model, singer and Playboy Playmate of the month for November 1974.
Now | Bebe Buell
Today, Bebe is known for being the mother of another very famous woman, actress Liv Tyler. Along with her musical career, that spans 30 years, Bebe was linked to famous men like Todd Rundgren, Steven Tyler, Coyote Shivers, whom she was married to, as well as Jim Wallerstein. The character of Penny Lane in the film Almost Famous is said to be about Bebe.
Then | Winnie Hollman
During the time that Jack was in a relationship with Anjelica Huston, he was also seeing other women; much to the dismay of Anjelica. One of those women was Winnie Hollman. Winnie was a Danish model who took most people’s breath away. Jack and Winnie were together for a short while but it was enough for Jack to father a child with her, his daughter Honey Hollman, who was born in 1981.
Now | Winnie Hollman
Winnie was a model and actress. She was in films like Cocaine Cowboys, Eyes of Laura Mars, and Miss Skandinavia 1971, where she played herself in the television movie. In Eyes of Laura, in 1978, she played a model. Those were her only film credits. Today, she is under the radar entirely and is not seen, unlike her very famous ex-boyfriend and baby daddy.
Then | Rachel Ward
Who said that Jack was just about the low IQ women? He loved a woman with some brains. Jack had a short-lived relationship with Rachel Ward in 1981. Rachel is an English actress, director, screenwriter and Columnist. Rachel was with Jack a couple of years before she met her one true love, husband Bryan Brown, whom she married in 1983 and has been married to ever since.
Now | Rachel Ward
Rachel has continued to work but every so often changed her ‘major’ so to speak. She started out as a model, appearing in Vogue and Cosmopolitan. She then transitioned into acting, where she was nominated for a Golden Globe for her role in the film Sharky’s Machine. She continued to act in films like Fortress, and Against All Odds. She then continued her transition and made her way into writing.
Then | Veronica Cartwright
Our darling playboy and bad boy, Jack Nicholson, had an affair with Veronica Cartwright back in 1987. Veronica was already married to her third husband at the time, Richard Compton. Veronica is an American actress who reached stardom with her role in The Birds, The Children’s Hour, Invasion of the Body Snatchers, and Alien. In 1987, when she was having her affair with Jack, she was also in the film the Witches of Eastwick.
Now | Veronica Cartwright
Veronica never reached A-list status, but has been working as an actress steadily over the years. Her television and film credits are very long and her most recent projects, where she appeared, was in shows like The Loud House, Criminal Minds, Drop Dead Diva, The Nine, 7th Heaven, and in films like The Odd Way Home, and The Town That Dreaded Sundown.
Then | Karen Mayo-Chandler
In the late 80s, Jack was going out with Karen Mayo-Chandler. The English-born model and actress was known for her appearances in Harper’s Bazaar and Vogue. Karen was also in the December 1989 issue of Playboy magazine. In that issue, she recalled her relationship with Jack. She was also in several films in the 80s and 90s, some of which are Africa Express, Beverly Hills Cop, and down on Us.
Now | Karen Mayo-Chandler
Karen sadly passed away in 2006 from breast cancer. The model and actress was beloved by many and will continue to live on in the pages of the magazines she modeled for and the films she was a part of. She stopped acting long before her death, with her last role being in the 1997 film Dark Planet.
Then | Amber Smith
If you are tall, beautiful and are in the entertainment industry, then most likely you are going to be linked to Jack Nicholson. Jack and Amber Smith were said to have been an item for a brief time in 1993. Amber is an actress and a model. Smith has continued to work in Hollywood, but her roles were minor and remained that way.
Now | Amber Smith
Amber has not acted since 2010. She currently lives in Tampa, Florida and is still remembered for her success in the 90s. For Amber, the 90s were all about her modeling work. She was featured on the cover of magazines like Cosmopolitan, Vogue, Marie Claire, and Elle. In March of 1995, she was in Playboy magazine. She was also the face of brands like Buffalo Jeans, Volkswagen vehicles and walked the runway for Chanel.
Then | Melanie Griffith
Sweet Melanie Griffith was linked to bad boy Jack Nicholson back in the 70s. This was never confirmed by either party or photographed to prove it, but the 70s were a funny time, when everything was possible. The 70s were the beginning of Melanie’s career, with roles in The Drowning Pool, The Garden, Joyride, and One on One. Jack was much more well known and experienced than Melanie was in the acting world.
Now | Melanie Griffith
Today, Melanie is just as famous as Jack, although not as celebrated. She was married to Don Johnson, with whom she has two children, as well as Steven Bauer, and Antonio Banderas, whom she has one more child with. Griffith is a Golden Globe Award-winning actress and an Academy Award nominee. It was her work in Working Girl that earned her the accolades.
Then | Angie Everhart
Angie Everhart is known for being one of the top supermodels of the 90s. Coincidentally, 1993 was also the year that she was rumored to have been seeing none other than Jack Nicholson. He somehow managed to nab these women at the height of their success. Angie was in several Sport Illustrated swimsuit issues throughout the 90s, making her a very well known woman.
Now | Angie Everhart
Angie has been with many famous men. When we say many, we mean it. She was married to actor Ashley Hamilton (son of George Hamilton), engaged to Sylvester Stallone and engaged to none other than actor Joe Pesci! Angie was also in Playboy magazine in 2000, in an effort to jumpstart her career. These days she is focusing on her health as in 2013 she was diagnosed with thyroid cancer.
Then | Amanda de Cadenet
Back in 1995, Jack was seen getting awfully close to photographer and actress Amanda de Cadenet. Much like many of the women on this list, Amanda is much younger than Jack. She moved to Los Angeles in 1995, which is when she met Jack. Amanda was in several films around that time, such as Four Rooms, Fall, and Brokedown Palace.
Now | Amanda de Cadenet
Since her time with Jack and in those films, which were the only ones she was in, Amanda has focused on her photography, which was her true passion. Amanda worked for magazines as a photographer, and took the photos of celebrities such as Sofia Coppola, Olivia Wilde, Drew Barrymore, and Keanu Reeves. Amanda is most recently working as a late night television talk show host.
Then | Cynthia Basinet
Cynthia Basinet and Jack were an item from 1997 through 1999. Cynthia is one of the more obscure of Jack’s girlfriends as she is a singer, rather than an actress, and was only known around the time she was with Jack. The pop singer sang a version of Santa Baby, which she later gifted to Jack, who remained a close friend after they parted way romantically.
Now | Cynthia Basinet
These days, Cynthia is not heard of very much. She devotes her time to her humanitarian work, which is focused mainly on the issue of the 200,000 Sahrawi refugees who are living in the area of the Western Sahara desert. When she went there to visit, she made a statement that read, “As a single mother, I understand only too well what lack of security can do in undermining what the Saharawi believe in and wish for as a society. Their ability to withstand all for 30 years in the pursuit of self-determination is truly a role model for us all, as we enter the new millennium. For they had displayed faith, honor, compassion and resourcefulness in the face of such opposition.”
Then | Paz de la Huerta
Paz de la Huerta is an American model and actress. Much like the other women on this list, they were entranced by Jack’s charm and ease. The two were said to have been seeing each other at the time of The Departed premiere in 2006. Nicholson took Paz to the premiere as his date, sparking even more rumors that the two were an item.
Now | Paz de la Huerta
Paz is known for her role in the films The Cider House Rules, Choke, A Walk to Remember, Enter the Void, and for her outstanding role as Lucy Danzinger in HBO’s hit series Boardwalk Empire. Paz is a devout Scientologist, and was even in their documentary, My Scientology Movie, in 2015. Paz’s has been in several films since 2015 but all five of the films have yet to be completed as they are in the post-production stage.
Then | Kate Moss
As if Kate Moss needs an introduction! Nicholson landed himself one seriously famous babe when he was spotted with Moss back in 2004. The two were seeing partying together and looking mighty cozy. Kate has always had a thing for older men, although she didn’t end up marrying one. Back in the early 2000s, her career was waning, explaining the Nicholson connection.
Now | Kate Moss
Kate was at the height of her career in the 90s, when her very thin frame brought with it the rise of heroin chic. Her substance abuse came into the light at that time and was criticized by many. In 2005, several brands and labels dropped Moss as a representative due to her substance issues. In 2011 she married Jamie Hince, whom she divorced in 2016.
Then | Lara Flynn Boyle
Lara Flynn Boyle was one of Jack’s more famous girlfriends. The two were in a relationship from 1999 to 2001, which is considered a very long period of time for Jack (who was known for his very short flings after the 80s). The two attended premieres and Hollywood events together, prompting everyone to think that perhaps Lara was the one to tame Jack. We were all wrong.
Now | Lara Flynn Boyle
Lara is most well known for her role as Assistant District Attorney Helen Gamble on the show The Practice. She was on the show from 1997 until 2003, which is curiously when she was also with Jack. Over the years, Lara has undergone several procedures to keep herself looking youthful, sadly they only made her look more strange than anything else.
Then | Anjelica Huston
Out of all of the women on this list, Jack was with Anjelica the longest. The two were not married but they were in an on and off relationship from 1973 until 1990. The two met through her father, John Huston, who was a director. The relationship ended when Jack got Rebecca Broussard pregnant and she could no longer ignore the many infidelities on Jack’s end.
Now | Anjelica Huston
Anjelica is a legend in Hollywood today. She doesn’t act as much as she used to, but her role as Morticia Addams made her an icon. Anjelica’s most recent roles are mainly voice roles. She leant her voice to animated films like Tinker Bell, Thirst Street, and Arctic Justice: Thunder Squad. Anjelica is also a published author, having written three books in 2013 and 2014.
Then | Janice Dickinson
Everyone has heard of Janice, ‘the first supermodel’ or as she introduces herself. Janice was very open about her fling with Jack, which occurred in 1980. Both Jack and Janice were full on party animals during the 80s, doing whatever they pleased, which worked for them as they were both into the same things. Of her time with Jack she recalled, “Jack was okay between the sheets, but he upset me a little the next morning. ‘I want you to do me a favor,’ he said as I was dressing to go to a photo shoot. ‘Don’t tell anyone you’ve just had sex with a star.'”
Now | Janice Dickinson
Janice continued her modeling career as well as made her reality television debut in 2003. She was a judge on the show America’s Next Top Model. She has always had a big mouth and says exactly what is on her mind. She was also on the show Botched, where she had her infamous breast augmentation fixed on television. Janice is known for her affinity for plastic surgery.
Then | Meryl Streep
This one is a pure rumor but it is so juicy that we have to put it in here! According to a source, Jack and Meryl were seeing each other while they were filming the movie Ironweed in 1987. The problem with this rumor is that Meryl was already well into her marriage with current husband Don Gummer, not to mention a mother of two by then!
Now | Meryl Streep
Meryl is also a woman on this list that needs no further introduction, but we’ll give you one anyway. Meryl is the most decorated actress in Hollywood. She has won three Academy Awards, two BAFTA Awards, and EIGHT Golden Globe Awards. Her list of nominations is way too long to list. Her most well-known roles were in the films The Devil Wears Prada, The Deer Hunter, The Bridges of Madison County, and Angels in America, to name a small few.