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From ‘winning’ to HIV, the epic life of Charlie Sheen

In this April 11, 2013 file photo, Charlie Sheen, a cast member in "Scary Movie V," poses at the Los Angeles premiere of the film. Sheen was sued in Los Angeles Friday, Oct. 3, 2014, by a dental technician who claims the actor punched her in the chest and was abusive during an office visit in late September.
In this April 11, 2013 file photo, Charlie Sheen, a cast member in "Scary Movie V," poses at the Los Angeles premiere of the film. Sheen was sued in Los Angeles Friday, Oct. 3, 2014, by a dental technician who claims the actor punched her in the chest and was abusive during an office visit in late September. Associated Press

Charlie Sheen, who told the world on Tuesday that he is HIV positive, had kept a low profile almost all year.

His only TV appearance since his last series, “Anger Management,” ended in 2014 was a guest spot on the ABC comedy, “The Goldbergs” in February.

The news capped a controversial and rocky few years for the former “Two and a Half Men” star. His personal and work lives have been the stuff of memes. His spectacular fall from the heights of being the highest-paid actor on TV has kept the tabloid industry and entertainment gossip mill well fed.

His manic antics and meltdowns in interviews and all over Twitter in recent years, particularly during 2011, have birthed popular slang phrases like “Winning!”

At this stage of his life Sheen is a grandfather, a title he told David Letterman two years ago he wasn’t ready for.

The 50-year-old son of acting legend Martin Sheen has been married and divorced three times, has five children and one grandchild. He had his oldest child, Cassandra, 21, with his high school sweetheart when he was 19.

Over the years he’s been sexually linked to paid escorts, porn stars and women living in his home he referred to as “goddesses.”

On Monday, the National Enquirer reported that Sheen has already settled one potential lawsuit with a woman he exposed to HIV, one of multiple partners he reportedly had sex with after learning his HIV status.

On Monday an ex-girlfriend and one of Sheen’s “goddesses,” Bree Olson, issued a statement saying she didn’t know anything about the “rumors” of Sheen being HIV positive.

“I, myself have been to my gynecologist at least once a year since we split up and have always been tested across the board for everything and have came back clean across the board every time,” she said.

Here’s a quick look at the lives and loves of this son of Hollywood royalty.

1995

With hit movies like “Platoon,” “Wall Street,” “Young Guns,” “Major League” and “Hot Shots!” under his belt, Sheen was a Hollywood hot commodity who began developing a bad-boy reputation as a drug user and womanizer.

At the trial of infamous Hollywood madam Heidi Fleiss, Sheen testified that he spent nearly $50,000 on 27 of Fleiss' $2,500-a-night prostitutes.

After meeting Donna Peele on the set of a cigarette commercial the two married after six weeks of dating. He moved out of their house after about a month of marriage; they were divorced after nearly five months.

1996

Sheen is charged with assaulting former girlfriend Brittany Ashland. A year later he pleads no contest and receives a suspended sentence and two years probation.

2002

In June he marries actress Denise Richards, who guest-starred on his ABC comedy, “Spin City.” They divorce in 2006 while she is pregnant with their second child.

In a sworn declaration during their bitter divorce proceedings, Richards says Sheen is unstable, violent, addicted to gambling and frequented pornographic websites. She also claims that he assaulted her and threatened her life during one incident in which she claimed he shoved her to the ground and screamed, “I hope you (freaking) die, (expletive.)

In the ensuing custody dispute, a judge issues a restraining order against Sheen.

2008

In May, Sheen marries his third wife, Brooke Mueller. They have twin sons, Bob and Max, born in 2009.

2009

Sheen and Mueller are involved in a domestic violence incident in Aspen, Colo. Mueller, who some tabloids report was legally drunk at the time, accuses him of choking her.

Sheen spends Christmas Day in jail. Three months later he pleads not guilty to charges of menacing, criminal mischief and second-degree assault.

2010

February

Sheen checks himself into rehab as a “preventative measure,” according to his agent.

August

Sheen pleads guilty to a misdemeanor assault charge in the Christmas Day case and is ordered to spend 30 days in rehab as part of a plea deal. The judge also sentences him to three months’ probation and orders him to complete 36 hours of domestic violence counseling.

October

Found naked and apparently drunk in a hotel room, Sheen is hospitalized for medical reasons, his publicist announces.

“What we are able to determine is that Charlie had an adverse allergic reaction to some medication and was taken to the hospital, where (he) is expected to be released tomorrow,” the publicist says.

2011

January

Tabloids report that Sheen had a “briefcase full of cocaine” delivered to his home and was using copious amounts during a 36-hour bender that landed him in the hospital for “severe abdominal pain.”

He’s taken out of his LA home on a stretcher. His agent says in a statement that Sheen has “voluntarily entered an undisclosed rehabilitation center.”

February

The week before he’s scheduled to go back to work on “Two and a Half Men,” Sheen goes on an aggressive, addled rant on the radio in which he refers to his army of “Vatican assassins” and hurls ethnic slurs at Lorre.

“I'm sorry, man, but I've got magic. I've got poetry in my fingertips. Most of the time — and this includes naps — I'm an F-18, bro. And I will destroy you in the air. I will deploy my ordinance to the ground,” he rambles.

March

In an interview with ABC’s “20/20,” that will live in TV infamy, Sheen continues the wackiness, admitting that “I am on a drug. It’s called Charlie Sheen. It’s not available because if you try it once you die. Your face will melt off and your children will weep over your exploded body.”

He says that “the last time I took drugs it was more than anyone could survive,” adding that he’s lucky to have “tiger blood.”

Soon after an L.A. hot dog stand began selling “Charlie Dogs with tiger blood.”

Also in March, the police remove the twins from Sheen’s home after Mueller files a restraining order against him. In the document, Mueller states that she thinks Sheen is insane.

(Two years later, in an interview with David Letterman, the talk show host asks Sheen if crack cocaine caused his headline-making meltdown in 2011. Sheen suggests that something deeper was troubling him at the time.

“Here's the confusing part. I wish it was crack cocaine. It wish it was an ocean of vodka, a bathtub full of pills,” he said. “It was just my brain was kind of separated into itself.”)

In an 11-page letter, the producers of “Two and a Half Men” fire Sheen from the show, describing him as a self-destructive addict deteriorating mentally and physically who has spurned everyone who has tried to help him.

A lawyer for Warner Bros. writes to Sheen’s lawyer that people close to the actor should focus their “energies on what no one so far has been able to do: get your client the sustained, rigorous and effective treatment he so urgently needs.”

Sheen sues Warner Bros. and producer Lorre for $100 million for wrongful termination. They strike a confidential deal in September.

2012

Sheen is hired to star in FX’s comedy series, “Anger Management.” Two years into the show’s run Sheen’s absence at work forces the studio, Lionsgate, to push back production deadlines and use stand-ins for him. His cast mates are angry; some even threaten to leave the show because of Sheen.

2014

February

Sheen gets engaged to Brett Rossi, known as Scottine Ross, a former porn star. They plan to marry in November in a big, elaborate wedding.

The National Enquirer reported on Monday that Sheen waited four months into their relationship to tell Rossi that he was HIV positive.

October

Sheen and Rossi call off their engagement.

November

FX announces “Anger Management” will end after its 100th episode the following month. Sheen hasn’t been seen or heard from much since then.

This story was originally published November 17, 2015 at 7:02 AM with the headline "From ‘winning’ to HIV, the epic life of Charlie Sheen."

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