Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)

Charlie Sheen is quite an infamous guy in Hollywood, known as a bad boy, a party animal, and an overall wild gun. Throughout his illustrious life and career, Charlie had dated numerous women, many of which were quite famous themselves. His role in Two and a Half Men solidified his playboy status among the fans even more.

Especially considering that many of his former girlfriends were adult movie stars. Without further ado, here’s the ultimate list of all Charlie Sheen’s girlfriends, ranked solely based on the longevity of their relationship with the actor. Have fun!

20. Winona Ryder (1986) – Short Fling

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: IMDb

Believe it or not, Charlie Sheen and Winona Ryder shared a short fling back in 1986. Winona was still a kid, much like Charlie. They worked on a romantic comedy called Lucas together, which was where the two briefly hooked up, just like their movie characters.

It was Winona’s first-ever bigger role. And although things between her and Charlie never went further from a short-term fling, it is rumored that it was Charlie who convinced Winona to take a stage name. Her real surname is Horowitz, but if the rumors are true, Sheen told her to change it. It proved to be a good move, as Winona Ryder became a household name in Hollywood.

Although she’s well-known for many projects, newer generations probably know her best for her role in Stranger Things, where she plays Joyce Byers.

19. Kacey Jordan (2011) – 2 Days Or More

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Inside Edition

Like many other women from this list, Kacey Jordan was a successful adult movie star that Charlie Sheen had a thing for. And, it seems that their short, explosive relationship came right after Sheen went off the rails yet again. It has been rumored that Charlie paid over $30K to Jordan just for the pornstar to spend two days with him.

It resulted in Charlie partying hard for 36 hours straight, which led to him being hospitalized. During that time, the “couple” reportedly hooked up before Sheen went crazy and started smashing the place. There’s talk about the two having an on-again, off-again relationship after that, but that’s unconfirmed.

Jordan later claimed that she had to abort Charlie’s kid, wanted to commit suicide, and suffered from bad substance abuse as a result of their short relationship and breakup.

18. Capri Anderson (2010) – Short-term Relationship

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Daily Mail UK

Capri Anderson is a stage name for Christina Walsh, a high-profile pornstar that, you guessed it, Mr. Sheen liked very much after watching her movies. Now, their short stint together was portrayed as a relationship, but many think they just… you know, done their business.

Anyways, it went on for a short while in 2010, but quite enough for a very high-profile incident to happen. They were at Hotel Plaza when security had to call the police because Charlie went crazy and started trashing the room completely. Capri Anderson hid in the bathroom for a while.

Both kept quiet in public about the incident, but after Sheen spoke out and said that he went crazy because Anderson tried to blackmail him for a million dollars, she opened up to ABC News and told them he went crazy due to drugs and alcohol, and just had a total meltdown, threatening to kill her, which is why she hid in the bathroom.

17. Robin Wright (Early 1980s) – Length Unknown

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Vanity Fair

This one happened particularly early, and nobody is even sure how long it lasted exactly. Robin Wright and Charlie Sheen were together while they were still in high school, during their first couple of years there. They separated on solid terms, but it’s interesting how both grew into such different personas, yet successful nonetheless.

What is more, during the time when he was dating Robin, Charlie was great friends with Sean Penn – who later became Robin Wright’s husband. Now, Wright is married to a guy outside of the movie industry: Clement Giraudet, an executive at Yves Saint Laurent.

16. Heidi Fleiss (Late 1980s)

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: NY Daily News

Heidi Fleiss wouldn’t even be a thing had it not been for the infamous trial where Charlie Sheen eventually testified (more on that a bit later). As it turns out, Heidi and Charlie had quite a unique relationship.

You see, Fleiss was Sheen’s frequent escort lady. While they weren’t in a romantic relationship, Charlie testified to paying Heidi well over $50K in escort services over the course of a year or so. It’s unsure how long it lasted exactly, and it wasn’t really a relationship, so a mention at number sixteen is more than enough for Ms. Fleiss on this list.

15. Tamara Beckwith (1990s) – Brief Short-term Relationship

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Female First

It’s not sure how long the relationship between Tamara Beckwith and Charlie Sheen lasted, but it was enough to cause some drama, fire, and a fling many remember. Why? Well, because Tamara is one of only a few women Charlie Sheen dated that weren’t either actresses or pornstars.

Beckwith was a British socialite and a TV personality that, like Sheen, had a thing for partying, living life to the fullest, etc. They were quite similar in that regard, and their relationship burned bright but burned out fast, and they went their separate ways shortly after hooking up.

14. Natalie Kenly & Bree Olson (2011) – Several Months

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: NZ Herald

Nope, it’s not a typo, nor a mistake. I’ve put the two women here together on the list because, well, they were literally together with Charlie at the same time. 2011 hit and Sheen was as unhinged as ever – he had tons of money, tons of booze, drugs, and a whole lot of time to party.

Bree Olson was a pornstar he grew to like, so Charlie invited her to come to live with him in LA. Olson agreed but realized that Sheen was already living with another woman there – Natalie Kenly, a graphic designer with similar partying affinities as Charlie.

The women agreed to proceed with the relationship, and Charlie called them his “Goddesses.” Soon after, jealousy and resentment started kicking in, and both women left Sheen in a span of a month. The throuple lasted at least for several months in 2011.

13. Brittany Ashland (Late 1996 – June 1997) – 7-9 Months

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)

Brittany Ashland was an actor on the rise in the early 90s. However, she quickly stopped with her acting career and kept out of the headlines most of the time, mostly thanks to her not-so-pretty relationship experience with Charlie Sheen.

The two dated for a bit more than half a year in late 1996 – early 1997, but it turned bad and violent not long into the relationship. Ashland spoke up and sued Sheen for a violent outburst that happened in his home at Agoura Hills. Brittany said Sheen, high on drugs and booze, threw her onto a marble floor, knocking her out cold and causing bleeding.

He then allegedly tried to get rid of her bloody clothes and threatened that if she ever spoke up, he’d kill her. In the end, Charlie pleaded no contest and paid a fine while receiving only one year of probation.

12. Scottine Ross (November 2013 – October 2014) – 11 Months

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)

Scottine Ross, better known by her stage name, Brett Rossi, was – you guessed it again – an adult movie superstar that Charlie Sheen wanted and got. Ross was a model before realizing the money is better in the porn industry. The two started dating in November 2013, after Sheen paid Scottine $10K for a date.

Ross didn’t want to go but gave in, and from that, a relationship evolved, and they were even engaged for a while. That was before Sheen – not Ross – called it off a month before the wedding. 

After that, Scottine overdosed in 2015 but survived, and then started alleging many things about Sheen, like forcing her to abort and giving her HIV deliberately, etc.

11. Georgia Jones (2012-2013) – One Year

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Daily Mail UK

Believe it or not, Georgia Jones is not a real name, and of course, it belongs to a pornstar. Her real name is Alison Michelle Thompson, and Sheen found her via her work. The two started dating in 2021, and their brief relationship was on and off for about a year before they finally separated.

Interestingly, Charlie was exactly twice Georgia’s age when they hooked up. He was 46, and Jones had just turned 23. It almost became serious, as reports suggested Jones even moved in with Charlie, but it never went the distance. Can you imagine a relationship with a pornstar didn’t work out?

10. Dolly Fox (1985-1987) – Around Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: 1stDibs

Not much is really known about Charlie Sheen’s relationship with Dolly Fox, how serious it was, how they met, nor how long it actually lasted, as we know he had flings with other women at the same time. The couple was together, as it seems, for about two years in the mid-80s, but it never went anywhere.

The reason why we know they were together was because of the famous New York pop-cultural icon and artist Andy Warhol. He wrote about the relationship between Dolly and Charlie in his diaries, about which a documentary series was recently made by Netflix. About the diaries, not the Sheen-Fox relationship.

9. Kelly Preston (1989-1990) – Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: NBC News

Charlie Sheen was with Kelly Preston in 1989 and 1990, and it was as weird of a relationship as they come – notably, because of one particular incident. The couple wasn’t together for long, but their relationship was highlighted due to Charlie – quite literally – shooting Kelly in the arm.

Apparently, Sheen was carrying a gun, and it went off, ricocheted, and got Preston in the arm. She was okay, though, and they actually dated a bit more after that but then broke up in 1990. Not long after that, Preston started dating John Travolta, and the two ended up being married for almost thirty years before Kelly lost her battle with breast cancer in 2020.

8. Stephanie Seymour (1992-1994) – Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: The List

Not, it’s unclear if Charlie Sheen and Stephanie Seymour were actually together for two whole years. It was more of an on-again, off-again relationship between two party animals – although it was, it seems, something more for Sheen. 

Despite Seymour being in the midst of a two-year-long relationship with the Guns ‘N’ Roses singer, Axl Rose, Charlie publicly expressed his love for Stephanie, claiming they are in love, in a happy relationship. They were together for a while after that, before Seymour returned to Rose, and Sheen met his first wife. More on her a bit later.

7. Paula Profit (1984-1986) – Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source

One might say that Paula Profit (Paula Speert is the first important relationship in Charlie Sheen’s life. They were sort of together for about two years, from 1984 to 1986, and it became quite serious at one point. Not because they were getting married or something, but because Paula got pregnant, later giving birth to Charlie’s first child (out of five he has today).

Sheen was just 19 when Paula got pregnant and 20 when she gave birth, and they separated not long after that. That’s when Charlie started gaining that Hollywood Bad Boy reputation.

6. Charlotte Lewis (1986-1988) – Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Ron Gaella, Ltd./Getty Images

In 1996, Charlie had that short fling with Winona Ryder, and not long after that, he met Charlotte Lewis. It was much more serious with Charlotte, as their relationship lasted for almost two years, despite both of them being quite young at the time. Especially Lewis, who was only 19 when they started dating.

Charlotte was an upcoming Hollywood star but was still quite naive when it came to relationships. She said that Charlie was always caring and thoughtful as a lover, but Lewis didn’t believe his brother when he warned the young actress that Charlie had serious substance-abuse issues. 

Not long after that, Charlotte saw it herself, and the relationship ended due to Sheen’s constant alcohol abuse.

5. Donna Peele (Early 1995 – Late 1996) – Almost Two Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)

Charlie’s relationship with Donna Peele might’ve been a bit shorter than two years, but it was much more significant than the other two-year relationships he had that are on this list. You see, Donna was Charlie’s first wife – but not the mother of his children. Remember the trial I mentioned earlier regarding Ms. Fleiss?

Well, Sheen actually made his relationship with Donna Peele known on the stand, where he announced their engagement – meaning they were already together during the trial.

However, the trial was eventually too much for the couple to bear, as Peele discovered how much money Charlie spent on Ms. Fleiss and her escort service. After the divorce, Charlie stated that if “You buy a bad car, it breaks down,” referring to his marriage with Donna as being broken since it started.

4. Ginger Lynn Allen (1990-1995) – Around Five Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Daily Mail UK

It seemed that the breakup with Kelly Preston hurt Charlie more than people thought. Not long after that, he went off the rails again with substance abuse and sought comfort in Ginger Lynn Allen, one of the most famous adult movie stars from the early 1990s. Their relationship was quite long but had big breaks between stints where they were together.

Allen was there with Charlie as he went through rehab from drugs and alcohol, but the relationship ended after being on and off for about five years. At one point, Ginger said that Charlie was sweet and loving when sober but completely out of control when drunk. 

That only solidified all the claims from former (and latter) girlfriends claiming he had control issues and violent, aggressive tendencies when intoxicated.

3. Brooke Mueller (May 2006 – May 2011) – Five Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: USA Today

The relationship between Brooke Mueller and Charlie Sheen was probably the healthiest relationship Sheen had been in his entire life. Mueller was a real estate agent, and she started dating Charlie in 2006. The well-known Hollywood Bad Boy appeared to have gotten his sh*t together, finally got clean, and looked as healthy and as happy as ever.

The couple married in 2008, and not long after, Brook gave birth to beautiful twin boys, which were Charlie’s fourth and fifth children. However, things went south not long after their birth, as Sheen started drinking again, causing his behavior to change dramatically. 

It eventually led to an arrest on Christmas of 2009 due to domestic violence, after which Mueller filed for divorce. Despite the ugly divorce, the two are on speaking terms for their kids, who are now 13 years old already.

2. Julia Stambler (2017- ) Five Years (And Probably Counting)

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Entertainment Tonight

Now, we don’t know if the happy couple is still together because Mr. Sheen has kept out of the public eye for quite some time now, but we know that Charlie and Julia Stambler began dating in 2017. She is quite a lot younger than Charlie but seemed to be a good influence on him, as he looked much better than a few years before they started dating.

The weird thing is that Julia was actually the nanny of Charlie and Brooke’s twin boys. Still, Mueller is fine with their relationship, saying she’s happier that Charlie is with Stambler than some “bimbo” or a “pornstar.” The couple made their relationship known on one of Charlie’s daughter’s birthdays when the actor introduced Julia as his new girlfriend.

1. Denise Richards (2000-2006) – Six Years

Charlie Sheen’s Girlfriends Ranked (Based on Relationship Length)
Source: Page Six

Last but not least, Denise Richards was Charlie Sheen’s longest relationship. She’s also the most disproportionately gorgeous woman on this list, compared to Mr. sheen, if you ask me, but that’s just my opinion. The couple was together for about six years, from 2000 to 2006. They met on the set of a project they’ve done together called Good Advice.

During their time together, the actress and the actor got married and had two kids in a two-year span – both being beautiful baby girls. However, their relationship started breaking while Denise was still pregnant with their second child, which is also when she filed for divorce – and a restraining order against Sheen.

During the divorce hearing, Denise claimed Charlie was abusive, aggressive, and erratic, especially when drunk or high on drugs, which is why she wanted the divorce in the first place. The divorce was quite ugly, but today, the two are quite good friends and hang out often with their girls.

  • Luka loves psychological thrillers, horrors, and mysteries. However, high fantasy and fiction are his primary interest, especially Tolkien's Middle-earth universe, Harry Potter, Game of Thrones, and Marvel universe. Amateur filmmaker, screenwriter, cinematography, and trivia enthusiast.