15 Photos Of Charlie Sheen’s Hottest Hookups

When California slides into the ocean and the glitz and glamor of Hollywood and those within it becomes nothing but a thing children read about in history books, Charlie Sheen will be remembered as one of the most accomplished actors of all time. With starring roles in movies such as Wall Street, Platoon, and Hot Shots!, as well as his role as Charlie Harper in the sitcom Two and a Half Men, Sheen has experienced unbridled success in both film and television, which he has made stretch across almost four decades.

Of course, when all is said and done, Sheen is also likely to be remembered for his much-publicized personal life and his tempestuous relationships with literally dozens of women. The actor is perhaps the biggest Hollywood womanizer and can count the likes of model Denise Richards, actress Brooke Mueller, and adult film star Bree Olson among his former lovers. Most recently, Sheen has been linked to Julia Stambler, a 26-year-old former bikini model who has served as nanny to his twin sons.

Of course, Sheen’s sexual promiscuity culminated in the actor’s 2011 HIV diagnosis; but for one beautiful moment there, the guy must have felt like the king of the world.

Here are 15 of the hottest photos of Charlie Sheen’s hookups.


15 Georgia Jones

When appearing on an episode of Piers Morgan Tonight in early 2013, Charlie Sheen announced that he had entered into a relationship with Georgia Jones, an adult actress and 2011 Penthouse Pet of the Month.

A lot of people view adult film stars as artificial beauties, unable to attract men unless they are half-naked and covered in various shades of makeup. In this image, however, Georgia Jones disproves that theory and then some. Here, Sheen’s former fiancée appears with her torso fully shielded by a tight white cardigan with minimal cosmetics on her face. Her hair is a mess, but that only serves to enhance her beauty.

Despite Sheen describing Jones as “the love of his life”, the couple parted ways just a couple of weeks before he became engaged to Brett Rossi.

14 Denise Richards


In the summer of 2002, Charlie Sheen married his second wife, Denise Richards, who he met on the set of Good Advice two years earlier (the pair would not begin dating until Richards scored a guest role on Spin City in 2001).

Although Richards differed from the kind of women Sheen usually gravitated towards, in that she was not an adult film star, she had posed for a series of semi-erotic photo shoots during her time as a model. It was one such photo shoot that produced this image, which shows Richards clad in a bikini, her hair perfectly parted and her lips fixed in a smile which is not necessarily seductive but nonetheless alluring.

Sheen and Richards separated in 2005 and divorced in 2006, with the latter accusing her former husband of incessant drug use and threats of violence.

13 Winona Ryder

Winona Ryder, an actress who did not make a name for herself through taking her clothes off, has a natural beauty. There is something about the Minnesota native that makes her absolutely irresistible, even when she is wearing a somewhat modest outfit like the one seen in this image.

Here, we see a simple Ryder clad in black, with shoulder length hair. It is in reserved pictures such as this that the true beauty of Winona Ryder is revealed to viewers.

Charlie Sheen and Winona Ryder go way back, with their relationship beginning when the latter was still known as Winona Horowitz. According to Sheen, he and the Mermaids star were so close at one point in time that she began using the surname Ryder after he suggested it while they were listening to Riders on the Storm by The Doors.

12 Kelly Preston


Kelly Preston has starred in literally dozens of films since making her first movie appearance in 10 to Midnight all the way back in 1983. However, Preston has not been particularly successful in any of her performances and has been nominated only for awards designed to recognize the worst actors, actresses, and movies of a particular year.

When you see pictures such as this one, however, it is no wonder Preston continues to be cast in films despite her abysmal track record. This image shows Preston, the current wife of John Travolta, lying stomach-down on a grey bedspread as a mop of thick blonde hair frames her flawless face. Behind her head, we can see her legs, as smooth as they are long, as they run into a pair of pink high heels.

Just one year prior to marrying John Travolta, Preston became engaged to Charlie Sheen. The relationship was marred by problems from the beginning and came to an end shortly after Sheen accidentally shot his fiancée in the arm.

11 Bree Olson

In 2011, only a couple of months removed from his much-publicized separation from Brooke Mueller, Charlie Sheen suffered an equally, if not more publicized meltdown. During his infamous 2011 personal troubles, Sheen began living with adult film star Bree Olson and a graphic designer by the name of Natalie Kenly. Sheen lived with both women concurrently, but it was Olson who received the most attention from the press owing to her career, which spawned countless titillating films and pictures, including this one.

Here, we see the blonde-haired beauty all dolled up for the 2011 instalment of the AVN Awards Show. Her bejewelled gold dress clings tightly to her body while her earrings dangle all the way down to her shoulders. Her white teeth come in stark contrast to Sheen’s chompers, which are known to be yellow and decaying owing to decades of substance abuse.

Since this picture was taken, Olson has left Charlie Sheen and the adult film industry and is now a vocal critic of both.

10 Brett Rossi


Charlie Sheen may have a reputation as a one-night stand kind of guy, but he has actually been in seemingly committed relationships on a number of occasions. One of Sheen’s most famous relationships began in 2014 when he proposed to Brett Rossi, a former adult film star several decades his junior.

This picture, taken of Rossi prior to her leaving the adult film industry, serves as the perfect example of why Sheen was ready to give up his womanizing ways and enter into what would have been his fourth marriage. In it, the actress is shown clad in pink and black mesh lingerie while her white teeth do battle with her full lips for command of her face.

Sheen and Rossi separated just one month before their planned wedding and the newly single millennial resumed her career in the adult film industry (every cloud, boys, every cloud).

9 Capri Anderson

Charlie Sheen and adult film star Capri Anderson have had an odd relationship. The pair first began appearing in headlines together during Sheen’s very public meltdown, when the actor invited her to his room in the Plaza Hotel in New York City. Fuelled by drugs and alcohol, Sheen would cause almost $10,000 worth of damage to the room before threatening to kill Anderson, who locked herself in the bathroom for her own safety. They found themselves in the spotlight again three years later when Anderson began living with Sheen in his Los Angeles home.

In this image, Capri Anderson appears like a vision from above, clad in a white mesh one-piece which just barely covers her chest. A pair of feathery white wings can be seen protruding from her back, making her look even more like an angel than she already does.


8 Cathy St. George


During the early 1980s, Charlie Sheen wasn’t quite the major Hollywood star he would go on to become. That being said, his good looks and obvious talents allowed the rising star to mix with some particularly beautiful women, including Playboy Playmate Cathy St. George.

A lot of fans of the Playmate believe Cathy St. George to be the quintessential 1980s model, something which is difficult to argue with when you see a picture such as this one. Here, we are shown St. George as she gazes into the camera while wearing a gold dress and a necklace of the same color. George’s hair isn’t too far off the color of her dress and rests perfectly atop her head, creeping downwards to frame her delicate cheeks and piercing eyes.

7 Kacey Jordan

In 2015, when Sheen announced that he had been diagnosed with HIV four years prior, dozens of his past lovers came out to criticize the star, accusing him of knowingly putting them at risk of contracting the devastating disease. Kacey Jordan, however, came to Sheen's defense and insisted that he would never have intentionally avoided disclosing his HIV-positive status.

Jordan also claimed that she had spent a night with Sheen at his California home the same year he contracted HIV. According to the adult film star, she paid $30,000 to spend an evening watching adult entertainment with Sheen which resulted, as you might have guessed, in the two being intimate.

Just why Sheen made Kacey Jordan pay $30,000 to visit his home is unclear, especially when you see a picture such as this one, which shows the gold-haired adult film star clad in a pair of pink stockings, a velvet corset, and a pair of black satin opera gloves.

6 Donna Peele


In September of 1995, after a number of failed serious relationships, Charlie Sheen married for the first time. Unfortunately for Sheen, he was unable to tear himself away from the “professional women” he had come to enjoy during his days as a single man and was named as a frequent client of a Hollywood escort agency just a couple of months after tying the knot with Donna Peele. The revelation destroyed his relationship with his new wife and the couple divorced in 1996.

Although their relationship was short-lived, it saw the two appear in public together on a number of occasions, with Sheen proudly flaunting his beautiful young love. The allure of Donna Peele is on display in this image, taken of her and Sheen during their happier days.

Here, we see Peele wearing a long but figure-hugging dress as she rests her slender fingers, one of which is decorated with an unmissable ring, against the Wall Street star.

5 Stephanie Seymour

Actress and model Stephanie Seymour has had successful men vying for her attention since she was a teenager. At just 16 years of age, she entered into a relationship with John Casablancas of Elite Model Management. She would move on to romantic relationships with Axl Rose, Peter Brant, and, of course, Charlie Sheen.

Seymour’s ability to attract millionaires and billionaires is undoubtedly incredible, but it isn’t all that surprising when you think about it. I mean, just look at this picture. In it, we see Seymour clad in a red one-piece which hugs her body as she wafts through an ocean. The salt water of the sea in which she is engulfed renders the model’s swimsuit almost transparent, reminding Charlie Sheen what he has been missing out on all these years.

4 Charlotte Lewis


London-native Charlotte Lewis began her career as a teenager with a role in Roman Polanski’s 1986 film Pirates. Shortly after production finished, she relocated to Los Angeles, where she would appear in a multitude of films, including Tripwire, Storyville, and Men of War. It was also during this period of her career that the young actress became romantically involved with a series of Hollywood bad boys such as Mickey Rourke And Charlie Sheen.

Charlotte Lewis’ status as a self-proclaimed “wild child” is a little surprising when you see pictures such as this one. In this image, the Excessive Force star doesn’t exactly look like somebody who is in the habit of going out every night and embarking on a variety of drug and alcohol-fuelled escapades. To the contrary, Lewis looks rather refined. With her face void of any blemishes, the elegant star looks directly into the camera with smoky eyes while a single strand of curly hair hangs over her face.

3 Robin Wright

In 1989, Robin Wright became involved in a relationship with actor Sean Penn, shortly after Penn’s much-publicized divorce from “singer” Madonna. That relationship would result in a marriage of 14 years. Before discovering her love for Sean Penn, however, Wright had a brief relationship with Charlie Sheen, who was still a couple of years off discovering the full extent of his love for drugs and alcohol.

Wright is one of those actresses who just seems to be getting better with age, both in her acting ability and in her appearance. In this picture, the House of Cards star can be seen, decades removed from her relationship with the former star of Two and a Half Men, with her hair cut short and her face hidden behind a thick pair of glasses. Those are two features which often serve to render a woman unattractive, especially when combined with the passing of time, but Wright pulls them off perfectly, as I’m sure she would anything.

2 Chloe Jones


Charlie Sheen has faced and overcame dozens of scandals in his life, but in 2006 his career was very nearly derailed when the mother of a deceased Penthouse Pet filed a wrongful death suit against him. According to the mother of Chloe Jones, Sheen drove the model to take her own life through incessant emotional abuse which began after their romantic relationship came to an end.

Prior to her death, Jones seemed to be in a promising place both professionally and personally. While her relationship with Charlie Sheen had left her with a degree of emotional baggage, she was able to use it as a means of obtaining publicity which, when combined with images such as this one, set her on track to becoming the most sought-after model in the world.

This image shows Jones looking the picture of health as she stares seductively into the camera. Her bare body is covered by a black blanket while her hair looks impossibly blonde and her lips an equally unlikely shade of red.

1 Brooke Mueller

Perhaps the most famous of all of Charlie Sheen’s former lovers is Brooke Mueller, whom he married in May of 2008. Sheen and Mueller went on to have two sons together, twins, born one year after they tied the knot. Just prior to Sheen’s very public meltdown, the couple split up under more than acrimonious circumstances.

While Mueller has appeared in a number of films over the years, she has devoted most of her time to building a career in the real estate industry, which is surprising considering she has the combination of incredible talent and even more incredible good looks necessary to become a major star in Hollywood.

In this image, the ex Mrs. Sheen shows off her baffling ability to seamlessly combine the professional and the sexy. The entrepreneur enhances her semi-formal straightened hair and blazer combo with a pair of tight brown leggings and thigh-high leather boots, reminding us all that while she is an independent woman of business, she is also a former Sheen girl.


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