A Guide To Charlie Sheen’s Girlfriends
Whatever your thoughts are about Charlie Sheen, there is no denying his playboy reputation. Rising to fame in the 80s, the son of Martin Sheen has led a very public, and at times controversial life. Films such as Wall Street, Young Guns, and Major Leauge turned him into one of Hollywood’s leading men and an in-demand actor. But his penchant for the party life soon found the actor in trouble. Substance abuse problems impacted his career and Sheen hit rock bottom during the 90s. But one thing remained consistent: the frequency of Charlie Sheen’s girlfriends.
No matter how bad life was going, New York born Sheen always managed to have a beautiful woman on his arm. He has been married three times, has a fondness for ladies of the night, and has talked about being a sex addict in the past. His harem of lovers only grew when he had a comeback with the hit series Two and a Half Men. At one point he was involved in a consensual relationship with two women at the same time. Even after the announcement that he was HIV positive and that interview where he mentions having tiger blood and winning at life, Sheen has had the women flocking after him.
While certainly a good-looking fella, Sheen must have some sort of it factor. Or maybe it’s the money? Whatever the case, Sheen is a charming gent with a long history of bedding attractive women. To highlight the party animal’s long list of lovers, here is a guide to Charlie Sheen’s girlfriends over the years.
1. Scottine Ross
You will quickly discover Charlie Sheen has a type. Not in regards to looks or personality, but their job. He is a big fan of adult film actresses. Scottine Ross, stage name Brett Rossi, is a model turned pornographic star who dated Sheen for almost a year from November 2013 to October 2014. Sheen met Ross after watching her videos and deciding he had to date her. After pursuing her to no avail, he offered Ross $10,000 for a date. Ross relented and went on a date with Sheen. It must have gone well as the two fell in love, got engaged, and planned to marry, but Sheen called things off a month before the nuptials were to take place.
Four weeks later Ross suffered from a drug overdose. In 2015, shortly after Sheen’s HIV diagnosis became public, Ross accused Sheen of forcing her to have an abortion, assaulting her, and exposing her to HIV. This wasn’t the first or last time Sheen would be accused of bad behavior in a relationship, something that has followed him throughout his career.
2. Denise Richards
Charlie Sheen met his second ex wife Denise Richards on the set of Good Advice in 2000. They had a tumultuous relationship that produced two daughters, Sam J. Sheen (born March 9, 2004) and Lola Rose Sheen (born June 1, 2005). Despite the two seemingly being in love, Sheen’s substance abuse problems raised their ugly head. Denise Richards filed for divorce while pregnant with their second child and got a restraining order against Sheen. She accused him of a number of other serious issues during the divorce hearing, with the two finally cutting ties in 2006.
While they went through a messy divorce, the two are now on good terms and often spend time together with their kids.
3. Capri Anderson
Born Christina Walsh, Capri Anderson is a porn star well known for her dalliance with Charlie Sheen. While it is unclear if they were dating or just ‘seeing each other’ as the kids call it, the two were involved in a highly publicized incident in 2010. The police were called to the Hotel Plaza after Sheen went ballistic and started smashing up his room. They found Anderson hiding in the bathroom. The adult film star remained quiet about what went on until Sheen called her out for trying to blackmail him for $1 million. This set Anderson off. She conducted an interview with ABC News declaring Sheen was off his head and threatening to kill her during his meltdown.
4. Robin Wright
These two famous faces dated briefly as teenagers in the early 80s. There isn’t a lot known about their time together, except it occurred during their first few years of high school. Interestingly Sheen was friends with Sean Penn during that time, who would go on to marry Robin Wright in the 90s. Wright is an award-winning actress who is now married to Clément Giraudet, a Saint Laurent executive.
5. Brittany Ashland
Brittany Ashland and Charlie Sheen dated in the 90s but things turned sour when she accused Sheen of violent behavior. Ashland said Sheen threw her on the marble floor of his Agoura Hills home, knocking her out. He then tried to dispose of her bloody clothes and warned Ashland not to say anything or he would kill her. Sheen pleaded no contest and got off with one-year probation. Ashland has kept out of the headlines since then, occasionally popping up to warn others about Sheen’s violent past.
6. Kelly Preston
These two love birds had a very short romance in 1990 that saw them briefly engaged. The most bizarre story to come out of their relationship was the time Charlie Sheen shot Kelly Preston. Somehow a loaded gun Sheen owned that was in his pants accidentally discharged and hit Preston in the arm. Thankfully she was fine, but the incident must have set off alarm bells. A few months later the two called it quits and Preston was soon going out with John Travolta, who she would go on to marry.
7. Ginger Lynn Allen
After things went south with Kelly Preston, Charlie Sheen turned his attention to Ginger Lynn Allen. One of the biggest stars of the adult entertainment world in the 80s, Allen stuck with Sheen while he attended drug rehabilitation. In an interview with People she described Sheen as great fun when sober, but a nightmare when drunk. “When Charlie’s sober, he’s sweet, kind, loving, generous,” says Allen, who stayed with him off and on for five years. “When he’s drinking and using, he’s out of control.”
8. Brooke Mueller
Brooke Mueller is Charlie Sheen’s third wife. The real estate agent and playboy tied the know in 2008. A year later Mueller gave birth to twin boys, her first and Sheen’s fourth and fifth children. Sheen finally appeared to have his shit together and was thriving in a loving relationship until his erratic behavior once again destroyed another of his marriages.
On Christmas day, 2009, Sheen was arrested for domestic violence. He managed to wrangle his way out of jail time, instead, once again committing to a stay in rehab. Though it was believed the two wanted to try and save their marriage, it was not to be. Sheen filed for divorce and the marriage was declared over in 2011. While it didn’t end well, with Mueller getting stuck into Sheen via the tabloids, the two are now amicable for the sake of their children.
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9. Stephanie Seymour
Glamour model Stephanie Seymour was in the midst of her two-year relationship with Guns N’ Roses frontman Axel Rose when she and Charlie Sheen hooked up. The two had a brief affair, with Sheen apparently declaring his love for Seymour. Even with that being the case, the two didn’t see each other for long. Seymour went back to her boyfriend Rose and Sheen carried on his love for adult entertainers.
10. Donna Peele
Despite being a heartthrob and getting around town in the 80s, it wasn’t until over a decade later that Charlie Sheen finally tried to settle down. In 1995 he married his first wife Donna Peele. Their marriage came crashing down after Sheen was named in the Heidi Fleiss trial. Sheen was forced to testify about his participation in Fleiss’ prostitute ring, where he claimed to have spent around $50,000 on escorts. Peele filed for divorce and the marriage was over a year later in 1996.
11. Bree Olson and Natalie Kenly
Putting these two together might seem like cheating, but considering Charlie Sheen dated them at the same time it makes sense. In 2011 Sheen was living every man’s fantasy. Not only was he super-rich and getting off his face every night, but he was also dating two women at the same time. Having watched pornographic star Bree Olson’s movies, Sheen invited her to LA to stay with him. When she arrived she soon discovered that Sheen already had a live-in girlfriend, graphic designer Natalie Kenly. Somehow the two 24-year-olds were ok with the throuple arrangement and lived together for a couple of months. The ‘Goddesses,’ as Sheen named them, soon began arguing as jealously reared its head. Olson left after a few months and Kenly soon followed, leaving Sheen back at square one.
12. Tamara Beckwith
Tamara Beckwith is one of the rare women to date Charlie Sheen who wasn’t a porn star or famous actress. The English socialite and television personality was everywhere in the 90s. A mainstay of the UK party scene, Beckwith and Sheen dated for a short period in the 90s. It makes sense the two would be attracted to each other: they both love partying and themselves more than anything else.
13. Winona Ryder
Not even Winona Ryder could escape the charms of Charlie Sheen. Before she hit the big time, Ryder starred with actor Sheen in the romantic comedy Lucas. This was Ryder’s first role and she and Sheen allegedly hooked up during filming before the relationship quickly fizzled out.
14. Kacey Jordan
It’s never a good idea to start dating Charlie Sheen after a bender. Pornstar Kacey Jordan met the hellraiser during one of his infamous drug and booze adventures. On this particular occasion, Sheen had to be taken to hospital after 36 hours of non-stop partying. Kacey and Sheen began an on-again, off-again relationship that ended with Jordan trying to commit suicide in a Chicago hotel. She would later go on to say Sheen may have been the father of her aborted child and that he had some serious substance abuse issues. No kidding!
15. Charlotte Lewis
Not long after his encounter with Winnona Ryder, Charlie Sheen’s next conquest was British actress Charlotte Lewis. Unlike Ryder, this relationship lasted for two years. Lewis was only 19 at the time the two got together. She had quickly become touted as the next big thing after her performance in Roman Polanski’s Pirates. While things began well, Sheen’s love of the nightlife soon caused problems and the two parted ways.
16. Julia Stambler
Charlie Sheen’s most recent girlfriend is Julia Stambler, who was the nanny for his twin boys with ex wife Brooke Mueller. The two met when Stambler was just 26 and Sheen was 51, with their 25 year age gap slightly concerning. Despite this, the two have managed to keep things very low-key, with Sheen seemingly very happy. It is not known if Julia Stambler and Charlie Sheen are still dating now as Sheen has been keeping out of the headlines.
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