Bree Olson
The Penthouse Pet and relative newcomer to the adult-film industry is one of Sheen's current live-in loves. Her real name is Rachel Oberlin, she has a cat named Mr. Sniffles, loves Christmas and was just named a "green goddess" by PETA thanks to her sexy vegan diet. Other likes, according to Bree's website bio, include "older men, c--k in general, porn, knowing guys want to f--k me," etc. Well, you can't say the gal isn't suited for her work then. And she probably wouldn't have briefly left Sheen's side if she didn't have an OWI charge in Indiana to take care of.
Natalie Kenly
Affectionately known as "Natty Baby," the Cali Chronic X cover girl has been dating Sheen since November, and is the other piece of raisin-nut bread in the Charlie-goddess sandwich. Though she's not the one promoting Naked juice, she also hasn't left his side, even accompanying him to important machete-utilizing business meetings!
Kacey Jordan
With porn-star pals like this, who needs enemies? The $30,000 she said Sheen paid her following a 36-hour party marathon apparently wasn't hush money. Jordan didn't hold anything back when she revealed the deets of her day and night with Sheen that included three-minute sex and a tutorial on gold vs. porcelain teeth.
Capri Anderson
This particular porn actress was privy to Sheen's meltdown, er, allergic reaction at NYC's Plaza hotel in October 2010. She claimed Sheen scared the hell out of her and put his hands around her throat at one point, although no charges were ever filed against him. Anderson filed a police report and threatened to sue, but it was Sheen who ended up suing her for supposedly stealing his watch and attempting to shake him down for more cash.
Brooke Mueller
Lucky Mrs. Sheen No. 3! The former real estate investor swapped vows with Sheen in 2008 and is the mother of his twin sons. They didn't technically split up after the once extremely well-paid sitcom star was busted in Aspen for allegedly attacking her, but things were apparently never quite what they were afterward. Mueller ultimately filed for divorce in November and their custody battle is just getting warmed up.
Denise Richards
The Wild Things star was Mrs. Sheen from 2002 to 2006, first filing for divorce in March 2005. Then they reconciled. Then it all blew up in their faces, with Richards accusing the father of her two young daughters of being really into Internet porn and other not-very-family-friendly activities. Now the exes seem to be cordial, with Richards rushing to the hospital with him after his Plaza freakout and later being seen coming and going from Sheen's property a couple of times after he started rehabbing at home. "It is what it is," she said of Charlie's lifestyle in February. "Denise is lovely," he told E! News on March 8.
Heidi Fleiss
When the notorious Hollywood Madam went on trial for tax evasion, Sheen admitted to spending upward of $50,000 on prostitutes from Fleiss' flock. So he wasn't just the President of the Skeevy Club for Men. He was also a client.
Brittany Ashland
One of Sheen's girlfriends in the 1990s, the model-actress accused him of assaulting her in 1996. Their dust-up was the fight Sheen hinted at recently on Piers Morgan Tonight, when he denied ever hitting a woman but claimed self-defense. Sheen pleaded no contest and received a suspended jail sentence, probation and a fine.
Ginger Lynn
They met when he was still engaged to Kelly Preston and the porn star dated Sheen between 1990 and 1992, sticking with him through a stay in rehab. As well, he wrote letters to the court in her favor when she was on trial for tax evasion. She went to prison for four and a half men, er, months. Now a mother and a cancer survivor, Lynn told the Los Angeles Times that she's going to start selling her own Charlie memorabilia on her website. "I have the soft, the considerate, the sensitive, the warm, the scared, the encouraging sides—I have all these sides of Charlie that no one's talking about," she said. Lynn also said that, when it came to drug and alcohol abuse in those days, "I was right there with him."
Kelly Preston
We could say that the future Mrs. John Travolta dodged a bullet by not marrying Sheen...but she didn't. He accidentally shot his then-fiancée in the arm in 1990, the very same year he first entered rehab for alcohol addiction. Hmm, maybe Preston wasn't totally devastated when Ms. Ginger Lynn came along then.