Charlie Sheen’s escorts: Over and over again

2010 was a big year for Charlie Sheen. Two-months out of rehab, he trashed a NYC Plaza Hotel Suite, causing $7,000 worth of damage and terrifying the woman that had been partying with him. What followed was a roller coaster of prime-time drama: the obnoxious re-branding of the word “winning”, his getting kicked off Two and a Half Men in 2011 (where he had been making $1.8 million dollars an episode), a failed attempt at making something of the sold-out tour of his solo show (it flopped, he got booed, people were pissed) and the whole affair becoming even too pathetic for the masses.

Obviously this didn’t come out of nowhere. Sheen’s rocky past of booze, drugs and sex just caught up with him in the ugliest, most public way possible.

No, you can't be Charlie Sheen

Sheen was born Carlos Irwin Estevez in 1965 to beloved Hollywood actor Martin Sheen. After dropping out of high school a few weeks before graduation due to bad grades and poor attendance, he decided to become an actor, and his first big break was in 1984 with Red Dawn, a teen flick with Patrick Swayze, Lea Thompson and Jennifer Grey.

28 years later, he has 68 projects on his resume.

He’s also had his share of ladies as well. According to him, he’s slept with 5,000 women. Here’s a breakdown of a select few:

Paula Profit: high school girlfriend and mother to their daughter, Cassandra Jade Estevez, born when Sheen was 19 years old.

Kelly Preston: they were engaged in 1990 but she called it off soon after he shot her in the arm. They now both claim it was an accident, and she says “he’s such a good person underneath all of it”.

Ginger Lynn: former porn star Lynn and Sheen dated for two years in the early nineties. Though she speak of him kindly today, she is trying to cash in on the current scandals by selling some of her mementos of their time together, including the 1991 edition of “The Complete Drug Reference” which he inscribed to her, “from one druggie to another”.

Donna Peele: after four weeks of dating, Sheen and model-actor Peele married. Less than a year later, when it was revealed that he was a client of an escort agency run by Heidi Fleiss, they divorced.

Denise Richards: during a period of supposed calm, Richards and Sheen were married in 2002 and had two children, Sam and Lola. Richards filed for divorce in 2005 when she said Sheen was abusing alcohol and drugs.

Brook Mueller: Sheen and Mueller married in 2008 and had twin sons, Max and Bob. Evidently their mutual addictions to sex, drugs and alcohol prompted them both into several forms of rehab. They divorced in 2011.

Currently Sheen lives with two women he’s dubbed his “goddesses”, porn star Rachel Oberlin and designer/model Natalie Kenly.

About 4,992 more women out there can claim to have had a bit of Charlie Sheen, if his boasting is correct. The majority of those women, many who have been seen with him in the public spotlight, are professional escorts, porn stars and prostitutes. A smaller number are Hollywood celebrity with serious credits to their names.

But it’s the porn stars, prostitutes and escorts that seem to take the most of Sheen’s time, and the definition of which woman fit which occupation is a deeply gray area. One such woman, Kacey Jordan, spilled details about her two-and-a-half-minute sexual encounter with Sheen that let her walk out with a check for $30,000 and another $25,000 to come. Heidi Fleiss reported that Sheen would pay her escort agency in $50,000 checks. Yes, he signed checks to her service, which is why he was one of the few clients who got named when her service fell under legal assault. Different sources have listed Capri Anderson, the woman who spent that famous night at the Plaza, as a porn star, prostitute and escort.

All we know is, Sheen likes his women.

And then there’s the violent streak in Sheen that lurks, ready to come out whenever drugs and booze are at the party. After the Kelly Preston incident (which was followed by his first stint in rehab), he settled out of court when a UCLA student claimed he hit her on the back of the head after she refused to have sex with him. Ex-girlfriend Brittnay Ashland also claimed legal victory after Sheen threw her to the ground and split her lip. Mueller reported that her then-husband threatened with a knife to kill her. He also settled out of court with Anderson for that drug-infused, violent night.

In this circumstance, we can only wonder—how much of Sheen’s life is fueled by addiction? With five failed attempts at rehab, three marriages and five children, a pathetic solo-show, a completely unrealistic sense of self, an abundance of court dates and settled lawsuits, and the realization that you are not, in fact, more powerful than your network… well, you can’t blame all of that on Hollywood.

And where is Sheen now? A few months ago we couldn’t get enough of him, and now he’s gone almost completely MIA, not putting his hat in the ring for his 5th Emmy nomination nor taking his planned trip to see Sean Penn in Haiti. But evidently he’s still got projects brewing: a new sitcom from Lionsgate would feature Sheen in an “anger-management” situation inspired by the Adam Sandler / Jack Nickolson movie made years ago.

Maybe living his violent streaks vicariously will help take some of the pressure off his personal life?


  1. Ginger Lynn:
  2. Kelly Preston:
  3. The Rise and Fall of Charlie Sheen Women:
  7. Brooke Mueller:
  8. Charlie Sheen’s Rap Sheet: