Charlie Sheen’s Girlfriend Rankings: Who Lasted the Longest? Shocking Details Revealed

Charlie Sheen has gained notoriety in Hollywood for being something of a rebellious figure, often referred to as a troublemaker, a partygoer, and generally someone with a wild streak. Over the course of his impressive career and life, Charlie has dated many women, several of whom are well-known in their own right. His portrayal in Two and a Half Men only served to strengthen this playboy image among fans.

Taking into account that a significant number of Charlie Sheen’s past partners were well-known in the adult film industry, let me present to you an unparalleled compilation of all Charlie Sheen’s girlfriends, arranged strictly based on the duration of their relationships with the actor. Enjoy!

20. Winona Ryder (1986) – Short Fling

It might surprise you to know that Charlie Sheen and Winona Ryder had a brief romance back in 1986. At the time, they were both relatively young, similar in age. Their romantic connection began on the set of the film “Lucas,” where they played love interests. Interestingly enough, their characters in the movie also shared a brief romance, mirroring their real-life relationship during the making of the film.

For the first time, Winona landed a significant acting role. Despite their relationship only lasting as a brief fling with Charlie, there’s speculation that it was he who encouraged Winona to adopt a stage name. Originally, her last name is Horowitz, but if the rumors are accurate, Charlie Sheen suggested she change it, leading to her becoming widely recognized as Winona Ryder in Hollywood.

Even though she’s recognized for numerous ventures, it’s likely that newer audiences recognize her most from her portrayal of Joyce Byers in Stranger Things.

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

Similar to numerous other ladies on this roster, Kacey Jordan was a renowned adult entertainer whom Charlie Sheen had romantic inclinations towards. Notably, their brief, tumultuous relationship occurred following another one of Sheen’s relapses. It has been whispered that Charlie forked out more than $30K to Jordan, solely for the pornstar to spend two days in his company.

36 hours of nonstop partying landed Charlie in the hospital. While this was happening, it’s said that the pair had a brief encounter before Sheen went into a frenzy and destroyed the location. There are rumors about their relationship having ups and downs after that event, but the details remain uncertain.

Later on, Jordan admitted that she ended her pregnancy with Charlie’s child, felt strongly about taking her own life, and struggled severely with drug addiction due to the difficult nature of their relationship and separation.

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

As a movie enthusiast, let me share some trivia: Capri Anderson is actually Christina Walsh, a well-known adult film star who caught the eye of Charlie Sheen after watching her performances. While their brief encounter was labeled as a relationship, many speculate that it may have been more about mutual interests than a deep connection.

In summary, it lasted only briefly in 2010, but long enough for a significant event to unfold. This took place at Hotel Plaza, where an altercation occurred that was severe enough to necessitate police intervention. Charlie, in an unusual state, damaged the room extensively. Capri Anderson sought safety by hiding in the bathroom during this incident.

Initially, they both maintained silence about the incident in public, but following Sheen’s revelation that Anderson attempted to blackmail him for a million dollars, causing his mental breakdown due to drugs and alcohol, leading to threats on her life, she subsequently confided in ABC News, disclosing these details. This is why she sought refuge in a bathroom.

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

This incident occurred quite early on, and the exact duration remains uncertain. During their initial years at high school, Robin Wright and Charlie Sheen were a couple. After parting ways amicably in their teenage years, it’s intriguing to see how they both evolved into distinct personalities, yet managed to achieve significant success in their respective careers.

Additionally, while he was in a relationship with Robin, Charlie also maintained a close friendship with Sean Penn, who eventually married Robin Wright. Interestingly, Wright is now wedded to Clement Giraudet, a high-ranking executive at Yves Saint Laurent, outside of the movie industry.

16. Heidi Fleiss (Late 1980s)

If it weren’t for the high-profile trial in which Charlie Sheen ultimately testified, Heidi Fleiss might have remained unknown. As time went on, it became clear that Heidi and Charlie shared an unusual connection.

Essentially, Fleiss often accompanied Sheen, but they weren’t in a romantic relationship. Charlie Sheen admitted to paying Heidi Fleiss over $50,000 for her services as an escort during a period of about a year or so. The exact duration isn’t clear, and it wasn’t a long-term relationship, which is why including her at number sixteen on this list is appropriate.

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

The duration of Tamara Beckwith’s relationship with Charlie Sheen isn’t clear, but it left an impact, causing quite a stir and a brief romance that people still recall today. This is notable because Tamara is among the few women that Charlie Sheen dated who weren’t actresses or adult film stars.

Beckwith was a well-known British socialite and television personality who shared a fondness for enjoying life to its fullest, much like Sheen. Their lifestyles were quite alike in this respect, but their connection, initially intense, fizzled out quickly, leading them to part ways not long after they became acquainted.

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

Indeed, it’s not an error or typo. I’ve paired these two ladies on the list because they were actually with Charlie at the same point in time. In 2011, he was as uncontrolled as you can get – flush with cash, loaded with alcohol, drugs, and plenty of time to celebrate.

Initially attracted to Bree Olson’s work in the adult entertainment industry, Charlie Sheen decided to invite her to move in with him in Los Angeles. Olson accepted the offer but later found out that Sheen was already residing with another woman there – Natalie Kenly, a graphic designer who shared similar wild nightlife habits with Charlie.

The women consented to move forward with their relationship, and Charlie referred to them as his “Divinities.” Shortly after, feelings of jealousy and bitterness surfaced, causing both women to part ways from Sheen within a month. This unconventional trio persisted for several months in 2011.

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

In the early 90s, Brittany Ashland was a promising young actor, but her acting career took an unexpected turn when she experienced challenging relationships, notably with Charlie Sheen, which largely kept her away from public attention.

In late 1996 through early 1997, Ashland and Sheen had a relationship that lasted over half a year. However, things quickly turned sour and became violent. Ashland, in response, took legal action against Sheen due to a violent incident that occurred at his home in Agoura Hills. Brittany claimed that Sheen, under the influence of drugs and alcohol, physically assaulted her by throwing her onto a marble floor, rendering her unconscious and causing injury.

Later on, it’s said that he attempted to discard her blood-stained garments and warned her ominously that if she revealed anything, he would take her life. Eventually, Charlie admitted to not being guilty and was given a fine, as well as a year of supervised release without prison time.

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

Known professionally as Brett Rossi, Scottine Ross was, unsurprisingly, a renowned actress in adult films who caught Charlie Sheen’s eye and attraction. Before her successful career in the adult film industry, she was a model. Their relationship began in November 2013, after Sheen paid $10K for a date with Rossi.

Initially, Ross resisted the idea but eventually agreed, leading to the development of a relationship that even included an engagement for some time. However, things changed when Sheen (not Ross) decided to end the relationship a month prior to their planned wedding.

Following this incident, Scottine allegedly overdosed in the year 2015 but managed to survive. Subsequently, she began making a series of accusations against Sheen, including claims that he coerced her into having an abortion and intentionally infected her with HIV.

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

It’s worth noting that the name Georgia Jones isn’t a genuine one; it’s an alias, more famously known in the adult entertainment industry. Her real identity is Alison Michelle Thompson, whom Sheen encountered through her professional endeavors. The pair began dating in 2021, and their relationship had its ups and downs for roughly a year before they eventually parted ways.

Remarkably, Georgia was about half Charlie’s age when they began their association. At that time, Charlie was 46 years old, while Georgia had recently turned 23. It seemed promising, as rumors indicated that Georgia even lived with Charlie, but the relationship didn’t last. Isn’t it surprising that a romantic connection with a well-known adult entertainer didn’t endure?

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

There’s not a lot of information available regarding Charlie Sheen’s relationship with Dolly Fox, including its intensity, how they initially connected, or its exact duration. It appears that the pair were together for roughly two years during the 1980s, but it didn’t seem to develop further. This was a period when Sheen was also involved with multiple other women.

I’ve got an interesting tidbit to share! I’ve learned that Dolly and Charlie were once together, thanks to the legendary pop artist Andy Warhol. In his personal diaries, he chronicled their relationship, which has recently been brought to life in a fascinating documentary series on Netflix. It’s not about Charlie Sheen or Denise Richards, but rather the intriguing account penned by Warhol himself.

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

In 1989 and 1990, Charlie Sheen had a peculiar relationship with Kelly Preston. This relationship gained notoriety due to an unusual event – specifically, an incident where Charlie accidentally shot Kelly in her arm. The relationship didn’t last long, but it left a lasting impression because of this extraordinary incident involving Charlie firing a gun at Kelly.

It seems that Sheen had a gun which accidentally discharged, striking Preston in the arm. Fortunately, she was unharmed, and they continued to date briefly thereafter. However, they eventually split up in 1990. Soon after, Preston began dating John Travolta, and the couple remained together for nearly three decades before Kelly succumbed to breast cancer in 2020.

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

It’s uncertain if Charlie Sheen and Stephanie Seymour had a consistent two-year relationship, as it appeared to be a series of ups and downs between two high-spirited individuals. However, it seemed that the relationship held more significance for Sheen.

Although Seymour was engaged in a two-year romance with Axl Rose of Guns ‘N’ Roses, he openly declared his affection for Stephanie, stating they were deeply in love and content in their relationship. They stayed together for some time before Seymour reunited with Rose, and Sheen went on to marry his first wife. I will provide more details about her shortly.

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

Reflecting on my perspective, I would express that Paula Profit was undeniably a significant relationship in Charlie Sheen’s life. Our bond, spanning approximately two years from 1984 to 1986, deepened to a level that transcended the ordinary. The gravity of our connection didn’t stem from impending nuptials or such commitments, but rather, it was Paula who carried the weight of an imminent change – she became pregnant and eventually gave birth to Charlie’s first child (one of the five he has today).

At the age of 19, Paula became pregnant with Sheen’s child, and by the time she gave birth at 20, they had already parted ways. It was shortly after this separation that Charlie began earning his notorious Hollywood Bad Boy image.

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

In 1996, Charlie briefly dated Winona Ryder. Soon after, he encountered Charlotte Lewis. Their relationship with Charlotte was much more substantial; it lasted nearly two years, although both were quite young. Notably, Charlotte was just 19 when their courtship began.

Charlotte, though rapidly rising in Hollywood, remained relatively innocent in the realm of relationships. She expressed that Charlie was consistently kind and considerate as a partner, yet Lewis doubted Charlie’s brother when he cautioned the budding starlet about Charlie’s significant struggles with substance abuse.

Shortly thereafter, Charlotte personally witnessed this situation unfold, and their relationship came to an end because of Sheen’s persistent issues with alcohol.

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

Charlie’s bond with Donna Peele, though lasting less than two years among his other similar relationships, carried a greater weight. This is because Donna was Charlie’s first spouse, although she wasn’t the mother of his kids. Recall the trial I mentioned earlier involving Ms. Fleiss?

Essentially, it was disclosed during the trial that Sheen was engaged to Donna Peele, implying that they were a couple throughout the legal proceedings.

Ultimately, the trial became overwhelming for the couple, as Peele found out about how much money Charlie had spent on Ms. Fleiss and her escort service. Following their divorce, Charlie expressed that if “a bad car breaks down,” then his relationship with Donna was faulty from the start.

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

It appeared that Charlie’s separation from Kelly Preston affected him more deeply than many realized. Shortly afterward, he once more fell into struggles with substance abuse and found solace in Ginger Lynn Allen, a well-known adult film star from the early 1990s. Their relationship endured for quite some time but was marked by significant periods apart when they weren’t together.

For a more conversational rephrase, consider this: Allen stood by Charlie during his five-year battle with drug and alcohol addiction in rehab, yet their relationship eventually fizzled out. At one juncture, Ginger described Charlie as being kind and affectionate when he was sober but uncontrollable when intoxicated.

This completely supported all the past and future assertions by his ex-girlfriends about him having controlling behavior and becoming physically abusive and aggressive when under the influence of alcohol.

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

It’s likely that Brooke Mueller had one of the most beneficial relationships for Charlie Sheen throughout his life. Known for her career in real estate, they started dating in 2006. Intriguingly, it seemed that Hollywood’s notorious Bad Boy found stability, managed to stay clean, and appeared healthier and happier than ever before.

In 2008, the couple got married, and shortly afterwards, Brook delivered lovely twin sons who became Charlie’s fourth and fifth offspring. Unfortunately, their happy family life didn’t last too long because Sheen resumed heavy drinking, which led to a significant transformation in his behavior.

Back in the wintery season of 2009, during the heartwarming holidays of Christmas, I found myself facing an unfortunate incident involving domestic violence that resulted in my arrest. Post this difficult period, I chose to part ways with my partner, filing for divorce. Despite the challenging separation, we’ve managed to maintain a line of communication for the sake of our now-teenage children, who have grown into young adults since then.

2. Julia Stambler (2017-2022) Five Years

Presently, it’s unclear whether the happy pair are still an item due to Mr. Sheen’s absence from public view for a considerable period, however, we do know that Charlie and Julia Stambler began dating in 2017. Despite her being younger than Charlie, she appeared to have a positive impact on him as he seemed to be in better shape compared to a few years prior to their relationship commencement.

It’s surprising to note that Julia, who was previously their twins’ nanny, is now in a relationship with Charlie and Brooke’s son, Charlie. Despite this unexpected development, Mueller approves of their relationship, expressing relief that Charlie is with Stambler rather than some model or actress from the adult entertainment industry. They first made their relationship public during one of Charlie’s daughter’s birthdays when he introduced Julia as his new companion.

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

To round things off, Denise Richards was Charlie Sheen’s longest-lasting relationship. In my humble opinion, she is the most strikingly beautiful woman on this list when compared to Mr. Sheen. However, that’s just a personal perspective. The duo were together for roughly six years, from 2000 to 2006. They first crossed paths on the set of their joint project, titled Good Advice.

In the course of their two-year union, the actress and actor welcomed two lovely daughters, born during this period. Unfortunately, their bond began to fray when Denise was expecting their second child, coinciding with her filing for divorce as well as a protective order against Sheen.

At the divorce proceedings, Denise asserted that Charlie exhibited abusive, aggressive, and unpredictable behavior, particularly when under the influence of alcohol or drugs, which led to her initial desire for a divorce. Despite the acrimonious nature of the divorce, they now maintain a friendly relationship and frequently socialize with their daughters.

2025-06-07 06:49