Charlie Sheen. Crazy as heck, with a history of failed relationships, drug rehabilitation, and the strangest catchphrases, such as “tiger-blood” and “#winning.” He is one of the creepiest and saddest actors that we have seen in a long time. And while he started out as a great actor with tons of potential, now he is just drowning ever deeper into the pit of despair. From his HIV diagnosis to his tumultuous romances and flings around the adult film circuit, to his multiple divorces and lawsuits, is there any hope left for poor Charlie Sheen?
We aren’t sure, but what we do have for you is a list of The 20 Sexiest Women Charlie Sheen Has Been With. While Charlie gets compared to Donald Trump, we are going to take a step back from him and focus on the many women that he has been with. Charlie may be a lost cause now, but back in his heyday, he was quite the stud. He was able to get many girls and he even married some of them. Donna Peele, Denise Richards, Brooke Mueller, and his ex-fiancee Brett Rossi; these are just some of the ladies who have been romantically linked to the wild and crazy actor. You also better believe he's had his fair share of adult stars, with over 10 of them appearing on this list!
So sit back and take a look at Charlie Sheen’s intimate inventory of porn stars, reality TV stars, and B-list models. He sure knows how to pick ‘em, huh? In all seriousness though, these women are attractive and we hope that they recover from their time with Mr. Sheen.
20 Ginger Lynn
She is in her 50s now, but back in the 1980s, Ginger Lynn was a huge adult film actress. She had even been awarded achievements with XRCO and AVN, among others. Between 1990 and 1992, Ginger Lynn was dating Charlie Sheen, who was hopped up on drugs at the time. She even helped him through a drug rehabilitation treatment program, accompanying him it appointments and such. In 2000, Ginger Lynn was diagnosed with cervical cancer, but she received treatment and surgery and is now cancer-free. She hasn’t done too much acting lately, but at least she is in good health.
19 Brooke Mueller
Brooke Mueller was actually married to Charlie Sheen from 2008 to 2010. They even had a set of twins together. But then Charlie Sheen got really weird and there were charges of domestic abuse and serious relationship troubles. The pair split up for good, with Brooke having full custody of the twins (they weren’t even permitted to go to Charlie’s home). Brooke also filed for a restraining order against her ex-hubby. Brooke isn’t perfect, though. She went through an intensive rehabilitation program in 2011 to help her reach sobriety. Now she spends a lot of her time avoiding the media and flipping homes.
18 Summer Altice
This 36-year-old California native was a hot commodity back in the day. In the 1990s, she was a smoldering sexy model and she was signed to the Elite modeling agency. She definitely solidified herself as a modeling sex symbol, appearing in publications such as Max and GQ. In the summer of 2000, she was Playmate of the Month. She actually continues to work today, doing some modeling gigs here and there while also working as a DJ at a nightclub in Los Angeles. Right up Charlie Sheen’s alley, eh? The two were briefly linked, but not anymore. No endless summer for Charlie.
17 Tabitha Stevens
AVN Hall of Famer Tabitha Stevens is yet another adult actress who has been romantically linked to Charlie Sheen. Are you noticing a pattern yet? Anyway, Tabitha was 25 when she jumped into the industry, and she even managed a sex toy shop with Derrick Lane. She married Kenny Gallo, then Donny Osterholt, and then Gary Orona, and she has appeared in countless D-list television programs, such as Dr. 90210 and The Jerry Springer Show. What a gem. Who knows if she looks the same now as she did when they dated though, especially considering she has spent upwards of $20,000 on plastic surgery.
16 Shauna O’Brien
Shauna O’Brien is yet another adult film actress, but she has also appeared in mainstream movies and she also works as a model (x-rated and mainstream). She has also been featured in plenty of music videos for bands such as Poison, Danzig, Motley Crue, and Danger, Danger. Oh and yes, she was also supposedly a cheap one-night stand for Charlie Sheen. Charlie usually ends up meeting these types of ladies during weekend jaunts on the town, I suppose nothing else livens up the party like Shauna! Some of Charlie Sheen’s more erotic romances are from the distant past, back when washed-up actresses were at their prime.
15 Charlotte Lewis
Charlie Sheen switched it up a bit when he went for the stunning Charlotte Lewis, an English cutie from Kensington, London. Her first acting gig was in a Roman Polanski film, Pirates. In 1993, she was featured in Playboy magazine (which seems to be a prerequisite for being a Charlie Sheen love toy). Of course there was the whole Roman Polanski scandal, and Charlotte ended up suing the director for sexual assault. The actress has supposedly been with lots of different dudes, some of them more likeable than others. Hmm, we wonder where Charlie Sheen would fall on that list?
14 Dolly Fox
Apparently Dolly Fox and Charlie Sheen were a romantic couple that went way back. They were dating from 1985 to 1987, back when their fashion sense was on-pointe. And yes, you guessed it! Dolly Fox was a huge adult film star. (Hello, the name says it all. If ‘Dolly Fox’ isn’t an adult star name, then we will eat our hat). Anyway, it really does not surprise us at this point that Charlie Sheen has been linked to yet another such film actress. After all, he is known for frequenting events such as the AVN weekend in Las Vegas. And his ex-wives are a clue, too.
13 Stephanie Seymour
A one-night stand between Charlie Sheen and Stephanie Seymour dates back to 1992. This one was quite messy...Stephanie was in a relationship with Axl Rose, the singer of Guns N’ Roses at the time. Still, she had a little bit of fun with Charlie Sheen and now she is forever embedded in the list of girls who have gotten with this delusional actor. As you would expect, Stephanie was a killer model and she worked for many iconic brands and publications. The California native definitely had a lot of celebrity connections, both in music and fashion. No wonder Charlie wanted her.
12 Heather Hunter
Heather Hunter is pretty interesting, because yes, she does have a history of naughty film work, but she more recently has delved into more artistic endeavors, such as painting. Back in 1994, Heather and Charlie met while having fun at a party. They began a relationship, but it did not last for that long. Even so, Heather has fond memories of the man (for some reason) and doesn’t have too many nasty words to say about him. At age 46, you can now find Heather rapping, painting, or just taking it easy as “Double-H,” as she is known in the rapping world.
11 Brittany Ashland
Yikes, this one was quite scary for Charlie Sheen. He had been accused of battery and was taken to court by Brittany Ashland. The lawsuit was filed back in 1997, with the altercation occurring one year earlier. Brittany said that Charlie had hit her and then threatened that he would do it again if she didn’t keep the whole thing under wraps. Totally believable if you ask us! In the end, Charlie ended up receiving probation and a jail sentence of one year, but that was only the beginning of his crazy problems. The same thing happened with his former wife, Brooke Mueller.
10 Donna Peele
Donna Peele was Charlie Sheen’s first wife, but their marriage only lasted for about a year. From 1996 to, well, 1996, they were husband and wife until Donna realized just how messed up Charlie is. While Charlie got remarried (and re-divorced) Donna sort of stepped away from the public eye and she has pretty much been on the down-low for years. Hey, even a 6-month marriage to wacky man Charlie Sheen would be enough to send us into exile for decades. But we all make mistakes, and Donna shouldn’t feel too bad about it now. We’re glad she got out when she did.
9 Tara Phillips
Tara Phillips was a hot young thing when Charlie Sheen met her and the two had a little bit of fun together. After dating for just a few months back in 1997, Tara called it quits. Apparently she was the one to break off the relationship with Charlie, saying that she was not too keen on his partying and wild lifestyle. Hey, we hear ya, girl. It is a good thing that she ended things when she did, because we all know what happened after that. Charlie Sheen went straight off the deep end and the rest is sad history.
8 Jayme Langford
Earning the nickname as one of Charlie’s “Angels,” Jayme Langford got into some hot water after Charlie seriously went off the deep end. The actor claims that Jayme and other adult stars caused him to lose out on thousands of dollars. In short, they somehow scammed him. He then went on to call them all sorts of terrible names and to say that he wishes them a death via a can of pressed turkey. We can’t make this stuff up. Jayme was in a foursome with other actresses Celeste Star and Jana Jordan. Apparently they all wanted a piece of Charlie Sheen.
7 Kacey Jordan
Another adult star that reportedly got it on with Charlie Sheen, Kacey Jordan has spoken out about Charlie’s erratic behavior as well as his HIV diagnosis, which she said was not a surprise at all. Huh. According to Jordan, she was paid a very large sum ($300,000) to go to Charlie Sheen’s home, watch films with him, and then engage in sexual activities afterwards. This was in 2011, and thanks to that hired rendezvous, Kacey ended up pregnant (she got an abortion). Was she scared about Charlie’s HIV diagnosis? At the time she didn’t know, but she said that she doesn’t think Charlie would endanger his hook-ups.
6 Natalie Kenly
In the ever-developing saga of Charlie Sheen’s past lovers and one-night stands, Natalie Kenly actually rose to defend the actor after Bree Olson accused him of infecting her with HIV. How much can we really trust Natalie though? After all, the girl was a model for a marijuana publication. Um. Anyway, she says that she actually got to know the real Charlie Sheen (scary!) and that he would never put someone else’s life in harm’s way. That is why she thought that Bree Olson was making the whole thing about Charlie giving her HIV. This is so much drama for one guy.
5 Denise Richards
Another woman who actually went ahead and married the crazy Charlie Sheen is Denise Richards. She has worked as a model, actress, and reality television star. She has also been nominated for a Razzie award for “Worst Supporting Actress.” And did we mention that she actually married Charlie Sheen?! Anyway, Charlie was probably drawn to Denise because she is stacked, pretty, and she even posed nude for Playboy just months after having a baby. So she’s got moxie. The couple were married from 2001 to 2006. They also have two daughters together and we hope they didn’t inherit the tiger blood.
4 Georgia Jones
Oh, here we go...another angry adult star ex-girlfriend. This one is Georgia Jones, and although she is beautiful, she should have known better than to get caught up in the likes of Charlie Sheen. After the actor received his HIV diagnosis, a lot of his lovers and one-night stands from the adult circuit were coming under fire to passing on the virus to him. However, many of the stars, including Georgia, said that they were HIV-negative. According to Georgia, she hasn’t been with Charlie since 2013 and she is not responsible for his HIV. Shall it remain a mystery?
3 Bree Olson
The young Bree Olson ended up meeting Charlie Sheen through some mutual friends (some friends they were!) and Bree moved into the actor’s home in 2011. We know that Charlie Sheen was diagnosed with HIV, but he claims that he was not infected with the disease when he met Bree. Even so, Bree contracted the illness and she puts all of the blame on Charlie. Tough break. It turns out that Bree just ended up being yet another sad girlfriend story about why no one should ever get with Charlie Sheen. Ever. Bree also goes by the name Rachel Oberlin, and she’s a girl that naughty film lovers will recognize.
2 Capri Anderson
Back in 2013, Charlie Sheen was in an on-again, off-again relationship with adult actress Capri Anderson. They had already been dating for a couple of years, and then there was a terrible night they had at the Plaza Hotel. Just another Charlie Sheen tiger blood-infused drama. Well, it looks as though Capri didn’t learn her lesson. Three years later, she moved into Charlie’s Los Angeles digs. We have no idea why she would want to get back with a guy who left her naked and locked in a hotel bathroom that he proceeded to totally trash. Oh well, it’s her life.
1 Brett Rossi
Brett Rossi almost became another wife of Charlie Sheen. The couple were engaged, but Brett reportedly called it off after realizing just how drunk with rage Charlie always was. Stating that the romance was toxic and super violent, she walked away from him. Good on ya, girl. She also filed a lawsuit against Charlie for assault and battery. Brett had formerly worked in adult entertainment (no surprise there) and said that Charlie was ready to settle the lawsuit for $1,000,000, but then he backed out. Citing love, then fear, Brett (who is about 3 decades Charlie’s junior) described their scary relationship and said she even feared for her life.