He has dated some incredibly famous women, while the majority of his love life he has been surrounded by adult film actresses. He certainly has a type. Charlie has been married three times in his life and has five children. His wives are the ones we know most of all – Donna Peele, Denise Richards, and Brooke Mueller. He has a soft spot for beautiful women who are known as free-spirited.
We decided it would be interesting to list the women Charlie has been linked to, as well as where they are today. Some were easy to find, especially the famous ones, while others were practically impossible to find since they have gone underground after their Sheen relationship. Charlie has been in the press in recent years for everything except his acting. In 2015, Charlie announced to the world that he was HIV positive. This little bit of information rocked the world and every woman he had been with. He was diagnosed in 2011 and kept the diagnosis quiet for several years.
Charlie always had a soft spot for women. He was never very good with monogamy and somehow always got into trouble with his lady friends. He has been arrested for alleged abuse but nothing really stuck, but the public image of him has been tarnished for good. The women on this list were all proven to be with Charlie, most of whom were linked to him around the same time! His father, Martin Sheen, sure wouldn’t be proud to know his son was such a party boy. It is slightly sad that we remember him for his escapades and not his career, but he did that to himself.
Then | Robin Wright
Hard to imagine but Sean Penn’s ex-wife, Robin Wright, also known to us as Buttercup, dated Charlie Sheen from 1981 to 1982. It was the time that both Wright and Sheen were breaking into the acting game and were on the same level. Their relationship was a private one, so much so that they were not seen out in public very much, let alone photographed.
Now | Robin Wright
Robin’s career has stood the test of time. She has recently been on the show House of Cards, winning a Golden Globe for her role on the show. She was married to Sean Penn from 1996 to 2010 and has two children with him. Robin’s other famous roles were in the film Forrest Gump, Nine Lives, Everest, and Wonder Woman.
Then | Heidi Fleiss
Heidi Fleiss was a Hollywood madam who supplied the rich and famous with companionship for the night thanks to her ring of good-looking women. Fleiss herself was said to have dated Charlie in 1988. The relationship was casual. When Fleiss was arrested for tax evasion and pandering in 1995, Sheen even testified against her and admitted to spending over $50,000 on the women she supplied.
Now | Heidi Fleiss
After her time in the spotlight for her adult business, as well as spending some time in prison, Fleiss decided that she wanted to live far away from Hollywood. She has since been living in Pahrump, Nevada. She has had some issues with substance abuse and has seen the inside of a rehabilitation facility, but has since gotten on the wagon once more and is seeing better days.
Then | Wynona Ryder
After starring in the film Lucas together in 1986, Winona and Charlie were an item for a bit. This was before Winona hit her big break in the film Heathers. Once Winona hit it big, her and Charlie ended their relationship amicably. It seems as though it is a right of passage in Hollywood, to date a slightly more famous actor until you yourself get noticed.
Now | Wynona Ryder
Winona not only hit it big but was a household name in Hollywood. Her roles in Beetlejuice, Girl, Interrupted, Mermaids, Dracula and Edward Scissorhands made her known worldwide. She did have some off years in the early 2000s but has since made a terrific comeback with the Netflix original series Stranger Things, where she plays the mother of the main protagonist.
Then | Charlotte Lewis
Charlotte Lewis was an English actress who dated Charlie from 1986 to 1988. The couple met while working together on the film Pirates, a Roman Polanski film. Charlotte was only 19 years old when she met Charlie, who completely overwhelmed her. On Sheen, she said, Charlie “was like a child when he made love, sweet and sensitive and very anxious to please. But after a while he began arriving home late. His brother had told me Charlie was an alcoholic, but I didn’t believe it.”
Now | Charlotte Lewis
After her time with Sheen, Lewis went on to appear in Playboy magazine and other lesser known films. Her most recent time in the press was in 2010 when she accused Roman Polanski of assaulting her when she was on the set of Pirates! She hired famed attorney Gloria Allred to represent her. It was later found out that the two were in a short relationship together and that he never assaulted her.
Then | Scottine Ross
Scottine was Charlie’s latest love interest. She is a former adult actress who nabbed herself some Sheen. She and Sheen were engaged from February 2014 until they broke off their engagement in 2015. Ross sued Sheen for $5 million and won as she accused him of being violent towards her, exposed her to the HIV he was hiding for years, and had made her terminate her pregnancy.
Now | Scottine Ross
Scottine is also known as Brett Rossi. She is a model and adult actress. Since her time with Sheen, Rossi has not been in any films or modeling. It seems as though she has diverted all of her energy towards fighting Sheen and getting the most out of her relationship with him. She went so far as to changing her name to Scottine Sheen prior to even marrying.
Then | Cathy St. George
Cathy St. George was Playmate of the Month in August of 1982. Cathy was linked with Sheen from 1988 to 1989. While her time with Sheen was short, they did attend Hollywood events together, as we can see in the following photo. Cathy always had an interest in adult photography and films, which inspired her later career. Her Playboy shoot is still one of the most talked-about centerfolds.
Now | Cathy St. George
After her time with Sheen and on Playboy, Cathy continued to act. She has been in films like Beverly Hills Brats, The Tonight Show with Jay Leno, Who’s Watching Who?, The Eden Formula, Grave Danger, The Wishing Box, The Death Hours, and The Devil’s Show. All of her acting jobs were in lesser known films and shows but she has maintained her presence in Hollywood nonetheless.
Then | Dominique Simone
What can we say, Charlie Sheen had a thing for adult models and actresses. Dominique Simone was one of the many women that came and went from Charlie’s life. Simone and Sheen were dating for a brief time in the early 90s, when Simone was at the height of her career. She was in her early 20s when she was with Sheen.
Now | Dominique Simone
Today, Simone is still in the adult film industry but is far from the top. She was just 17 years old when she earned a scholarship to the Fashion Institute of Design and Merchandising but didn’t end up going down that path as a year later she found herself modeling for adult magazines such as Hustler. She then went on to appear in over 200 adult films in the 90s.
Then | Ginger Lynn
Another woman, another adult film starlet. Ginger Lynn was in an off and on relationship with Charlie Sheen from 1990 to 1996. He was in and out of other relationships but seemed to go back to Ginger. They ended things in 1996 as she said that Charlie drank too much. At the time that the two were together, Ginger was at the prime of her adult film career.
Now | Ginger Lynn
Today, Ginger has 330 adult films under her belt, as well as two films where she was the director. She is not known to everyone like other adult film stars. She has been in films throughout her career but has also experienced several lows, including being in federal prison for falsifying a tax return. She has one son, whom she says she is a single mother of.
Then | Heather Hunter
Heather Hunter and Charlie Sheen were together, if you can call it that, in 1994. Much like Sheen’s other women, she was also in the adult film industry. Her own start in the adult film industry was a fluke. Hunter always wanted to be a rapper and writer, which she would eventually become, but not before she supported herself by stripping and performing.
Now | Heather Hunter
Today, Heather is a painter, author and rap artist, who is still known as an adult film actress as well. About her music, Heather said, “What people may not expect is how serious I am about this. I really want people to take me seriously. Being retired from the adult industry nearly thirteen years ago, I think I’ve done enough in the mainstream business and I want to be accepted as an equal, as an artist. I’m going for my respect whether they give it to me or not.”
Then | Summer Altice
Charlie knew when to date them! Summer was hitting her Playboy primetime with the title of Playmate of the Month in August of 2000 when she was dating Sheen. The two were linked from 1999 to 2000. Summer is known as a model and actress. She was even named after Summer Bartholomew, Miss USA in 1975. The tall and leggy brunette is known for her supreme measurements.
Now | Summer Altice
Altice is much more than Charlie Sheen’s ex-girlfriend, especially since she is one of many. She used to play volleyball at San Diego State University where she studied. She has been in productions like Shanghai Kiss, You, Me and Dupree, Wedding Crashers, The Scorpion King, One Tree Hill, and Extraction. Altice is also a DJ when no one is looking and loves being in the club.
Then | Tamara Beckwith
Tamara dated Charlie Sheen for a very brief amount of time. She knew better. The English socialite is the daughter of Peter Beckwith, a property developer. She tried to go to college but ended up getting pregnant before graduating. The father of her first child, daughter Anouska Poppy Pearl, is William Gerhauser, son of the Finance Director of Playboy bill Gerhauser.
Now | Tamara Beckwith
Tamara has been on many reality television shows to make sure she keeps up appearances and stays relevant. She has been on shows like Celebrities Under Pressure, The Big Breakfast, I’m Famous and Frightened, Dancing on Ice, and has also presented shows on VH1 and MTV. When she isn’t on reality shows, she is a designer of jewelry for QVC as well as a contributing Editor for Hello Magazine.
Then | Tabitha Stevens
This is becoming quite unoriginal, Charlie! Sheen went out with yet another adult film star in the early 90s, Tabitha Stevens. Stevens was known for her adult performances in films and was even inducted into the AVN Hall of Fame in 2007. She is known for her high profile marriages, three of them to be exact. She was married to Kenny Gallo, the infamous ex-mafioso.
Now | Tabitha Stevens
Stevens is known for her plastic surgery as much as she is known for her adult performances. She has said to have had six breast augmentations, Botox treatments, two cheek implants, three nose jobs, one chin implant, lip injections, and one chin implant. We wonder if there is anything in her body that is real. She has been in 330 adult films, eight of them as the director.
Then | Tracy Richman
Tracy isn’t well known and has been fairly under the radar most of her life. The socialite was with Charlie in the late 80s and early 90s. It seems Charlie was a busy man at the time since all of the women it seems were with him at that time. While he had a thing for adult film actresses, he made the occasional exception for the beautiful socialite.
Now | Tracy Richman
Tracy has been very quiet. She released a memoir, titled Enter with Caution. She is an activist and mother and keeps busy with those two jobs. Her activism work is linked to her political stance as well as awareness for health and economic issues. Tracy also devotes much of her time to her daughter, Chloe, with John Morrissey.
Then | Brittany Ashland
Brittany Ashland dated Charlie Sheen in the late 90s. Their relationship was short-lived but a very passionate one, that ended with a domestic abuse charge in 1997. Charlie was accused of a misdemeanor battery charge, which he plead no contest to, after he was said to have grabbed Brittany by the hair and slammed her head into the floor. The photos of Ashland after the event were shown in court, split lip and all. Charlie was sentenced to two years of probation and a one-year suspended prison term, which he never served.
Now | Brittany Ashland
Other than being Charlie’s ex-girlfriend and on the receiving end of his violence, Ashland was also an actress. We don’t hear of her these days as she has gone under the radar, but her acting roles in the early 90s in, what else, the adult film industry. Her credits include, Wild Hearts, Memories, Ghost Writer, Behind the Blinds, Two for the Price of One, and Girls and Guns.
Then | Donna Peele
Donna Peele was Charlie Sheen’s first wife. When they were married, from 1995 to 1996, Donna would accompany Charlie to various Hollywood events. Their relationship didn’t last very long as in 1996, Heidi Fleiss, the famous madam we talked about, was arrested, and with her arrest, the many names of her clients was revealed, Charlie among them. Peele filed for divorce as soon as the news broke.
Now | Donna Peele
We kid you not, there is no trace of Donna after she ended her marriage to Charlie. It is as if she disappeared into thin air, which we have a feeling that it was entirely intended to turn out that way. The model must have decided that she had had enough of the spotlight and celebrity and wanted a quiet normal life elsewhere.
Then | Bree Olson and Natalie Kenly
We are not entering the time when Charlie began acting very strange. In 2011, Charlie dated BOTH Olson and Kenly. He called the duo his ‘goddesses’. Bree is, what else, a former adult film actress, and Natalie is a graphic designer and model. The two were in a relationship with Charlie for a few months in 2011, at which time the two were living with Charlie.
Now | Bree Olson and Natalie Kenly
Today, both of the girls are furious at Charlie’s HIV announcement and have said that he never told them about the diagnosis and that they did engage in unprotected relations. Over time, however, Natalie defended Charlie, stating, “He’s a good man and I feel very fortunate to have spent the time with him that I did, and I’m so sad to hear of his health troubles,” she says. “I hope he’s okay.”
Then | Capri Anderson
Whether they were an item or not, Capri was with Charlie in a hotel room when he started trashing the place to bits, with Capri in the bathroom trying to get away from him. Capri is also an adult film star. She was with Charlie in 2010 when the scandal broke. Charlie damaged the Plaza Hotel room to the sum of $7,000.
Now | Capri Anderson
What brought her unknown name to the public was Charlie Sheen himself, who said that Capri tried to extort him for $1 million and sued her for it. Capri then followed up the allegations with an interview with ABC News where she said that Charlie was heavily intoxicated and had threatened to end her life. Clearly these two weren’t a good match.
Then | Brooke Mueller
Brooke was Charlie Sheen’s third wife. The couple was married from 2008 through 2011 and welcomed two children into the world together – twins, Bob and Max. It was Sheen who filed for divorce from Mueller but it was Mueller who bashed Sheen over alleged violence and substance abuse. The situation at home got so bad that the children were taken from both of them as they were thought to be unfit to parent.
Now | Brooke Mueller
Brooke, other than being Charlie’s third wife, is an actress and real estate investor. Her acting has been in B-rated films, she makes her living off of her real estate business. She has been known as savvy when it comes to flipping homes in California. Brooke has been in rehab several times for substance abuse issues. There was a time when custody of her sons went to her brother, but in 2014 custody was returned to her.
Then | Denise Richards
Denise was married to Charlie from 2002 to 2006. The couple met on the set of Good Advice back in 2000 and were co-stars once again on the show Spin City in 2001. They were married and had two daughters together – Sam and Lola. The marriage didn’t last due to Charlie’s substance abuse and outbursts. Denise filed for divorce in 2005, which was finalized in 2006.
Now | Denise Richards
Denise is well-known even without her marriage to Sheen. She made her mark on Hollywood with her roles in Wild Things, Melrose Place, Friends, Spin City, Two and a Half Men, and Twisted. Her most recent projects include films like American Violence, Altitude and television shows like Jane the Virgin. Denise has been amazing throughout Charlie’s divorce from Brooke, even going as far as caring for his twin sons with Brooke when the two were not thought to be capable.
Then | Kelly Preston
Kelly and Charlie dated from 1987 to 1990. They were even engaged for a while, until Charlie, who was a firearm collector at the time, accidentally shot Kelly in the arm. Needless to say, Kelly didn’t take getting shot by her fiancé in good spirit and ended their engagement. We will always have the memory of the adorable duo walking the red carpet together, though.
Now | Kelly Preston
Kelly went on to marry none other than John Travolta. The two have been married since 1991 and are still going strong. Kelly has also continued to act, starring in films like Sky High, Death Sentence, Old Dogs, The Last Song, Casino Jack, and most recently she played the role of Victoria Gotti in The Life and Death of John Gotti. Preston has three children with Travolta and is often seen on the red carpet with him.
Then | Kacey Jordan
Charlie Sheen is known as a party animal. Therefore, it is no surprise to us when we heard that he was rushed to a hospital after a 36 hour rager which included, amongst other things, a suitcase full of illegal white powder. Sheen and Jordan apparently met that very night and had a whole lot of fun. The two saw each other on and off over the course of the year.
Now | Kacey Jordan
Jordan has not been doing so well since she got tied up with Charlie Sheen. She tried to commit suicide in a hotel room in Chicago a few months after the event and even claimed that the famous actor got her pregnant. She also has gone on record as saying that Sheen has horrible substance abuse problems (despite going in and out of rehab). Kacey Jordan is an adult film actress and has continued to appear in adult entertainment films.
Then | Stephanie Seymour
Stephanie Seymour is a former supermodel who was known for making her rounds with the hottest stars of the early 1990s. In fact, she was in a very serious relationship with Guns N’ Roses frontman Axl Rose when she was wooed by Charlie Sheen. Sheen was able to steal Seymour away from Rose, and the two ended up dating for a brief period of time. Axl Rose was undoubtedly heartbroken and actually filed a few lawsuits against her.
Now | Stephanie Seymour
Bikini supermodel Stephanie Seymour ended up marrying a multi-billionaire named Peter Brant. The couple have 3 children together and Seymour has another son from a previous marriage. She lives with her billionaire husband in a mansion in Greenwich, Connecticut (where all the rest of the Wall street billionaires live) and seems to be doing alright for herself. Except for the fact that she was arrested for a DUI in 2016, she seems to be doing just fine.
Then | Georgia Jones
Another adult film star, Georgia Jones was first spotted with Charlie Sheen at a new years eve party in Cabo San Lucas, Mexico back in 2012. The two were seen smooching at the party, and Charlie Sheen even invited Georgia to move in with him… while another adult film star was still living with him. However, Sheen said that he felt that he had finally found love and that he wanted to make this one last.
Now | Georgia Jones
Sadly, as with the vast majority of his relationships, this one was not meant to be. The two ended up parting ways (despite Sheen taking Jones to see Slash perform in Ireland). Jones refuses to speak to the famous womanizing actor, saying the two have not spoken in several years. When Sheen’s HIV scandal broke, TMZ went to Jones and asked if she was infected. She was thankfully not affected by the virus.
Then | Lindsay Lohan
Charlie Sheen and Lindsay Lohan do in fact seem perfect for each other. The two are both wild party animals and love getting into trouble. However, while there is no concrete evidence that the two ever had a relationship, rumors have been flying around that they may have done something. Sheen even admitted that she has slept over at his house before, but that she “out-drank him” and “tucked him into bed,” whatever that means.
Now | Lindsay Lohan
Charlie Sheen and Lindsay Lohan are still extremely close, with Sheen being described as Lohan’s “guardian angel.” While he may not be the best role model in the world, Sheen does seem to have taken a liking to the troubled Mean Girls star, even helping Lohan pay a tax bill by giving her $100,000. We guess if hanging out with Charlie Sheen gets you six digits in tax help, it’s worth it to have him as your go to.
Then | Mia Isabella
Mia Isabella is another adult film star who has had relations with Charlie Sheen. Perhaps most interestingly, Isabella was not always a woman, having transitioned into her current gender several years ago. Isabella did at one point have a tryst with Charlie Sheen (or perhaps several), but the two never really had what one could call a relationship. Mia has won a plethora of adult film awards, awards which probably put her on Sheen’s radar.
Now | Mia Isabella
Charlie Sheen is not the only celebrity to have had relations with the transgender Mia Isabella. It turns out that rapper Tyga also had relations with the adult film actress over the course of several years. However, now that Mia Isabella is tied up in the Charlie Sheen HIV scandal, Tyga and his (now ex) girlfriend Kylie Jenner have been freaking out over the fact that Tyga may have HIV. Tyga got tested and the results came back negative.
Then | Amanda Bruce
Amanda Bruce is a nurse who met Charlie Sheen and immediately fell in love. The two dated consistently for approximately eight months before they decided to call it quits (probably because Sheen was also seeing some adult film actresses on the side at the same time). However, the nurse said that she was truly in love with the actor, and she does not seem to regret having dated Sheen.
Now | Amanda Bruce
The two did end up breaking up, but Amanda Bruce has still been going on the talk show circuit to talk about her time with Sheen. Following the news that Charlie Sheen had HIV, Bruce said in an interview that she did have unprotected intercourse with the actor. She said that the two had been dating for some time when she became romantically involved with him without using a condom, knowing full well that he was infected.
Then | Stacy Fuson
Stacey Fuson is a former Playboy Playmate who was on the cover of the October 1997 issue. She has also acted in normal roles in non-adult films such as Shallow Hal and American Pie. However, long before she was starring in the top bro comedies of the early 2000s, Fuson was a party animal, just like Charlie Sheen. In fact, it was at a party back in 1999 when the two met each other and ended up hooking up.
Now | Stacy Fuson
Back in 2011, the Comedy Central television station hosted a roast of Charlie Sheen, whereby some of his best friends and the funniest comedians in the United States made fun of him to his face (all in good fun though). One of the people who was present at the roast (perhaps in order to make a point as to how many partners Sheen has had) was in fact Stacy Fuson. No word on if they rekindled their relationship afterwards.
Then | Tara Phillips
Yet another adult film star who dated Charlie Sheen (what is he doing that he just happens to be around these girls all of the time?) Tara Phillips and Charlie dated for a few months back in 1997. Perhaps Phillips fell in love with actor for his role in All Dogs Go To Heaven 2 which had just been released a few months before the two started dating.
Now | Tara Phillips
In the end however, Tara Phillips and Charlie Sheen ended up breaking off their relationship. And believe it or not, it was Tara who decided that she did not want to stay with the actor any longer. She says that his hard partying ways coupled with his substance abuse issues were factors in her decision to break off relations with the actor. It was also around this time that Sheen’s life got a little, well, crazy.
Then | Shauna O’Brien
Adult film star and B-movie actress Shauna O’Brien and Charlie Sheen dated back in the early 1990s. Sheen and O’Brien seemed to have good chemistry, and O’Brien also at one point dated Poison frontman Bret Michaels. She introduced Michaels and Sheen to each other, and the two guys quickly became best friends. In fact, Michaels says that he introduced Sheen to the rockstar lifestyle and taught him how to trash hotel rooms.
Now | Shauna O’Brien
Charlie Sheen and Shauna O’Brien ended up breaking up after only a few months together and they went their separate ways. It does not seem as though dating Charlie Sheen did any favors for O’Brien’s film career as she only starred in adult films and B-movies from that point on. However, O’Brien was interviewed in a PBS Frontline documentary about the adult film industry several years later.
Then | Chloe Jones
Chloe Jones was an adult film actress who was popular in the 1990s, and with whom famous playboy actor Charlie Sheen had a relationship in 1996. The couple saw each other for some time during that year before they called it quits and split up from one another. According to Charlie Sheen, that is the last time he ever saw Jones. However, there may be more than meets the eye.
Now | Chloe Jones
Chloe Jones was found dead in 2005 very shortly after she gave an interview in which she said that Sheen paid her $15,000 for an “adult sleepover.” Sheen was married to Denise Richards at that time, and after the interview came out, Richards divorced Sheen. However, just a few months later, Jones was found dead in her bed at her home in Houston. When Richards asked Sheen if he had anything to do with the death, Sheen had “no comment.”