From Goddesses to Tiger Blood -- Charlie Sheen's 10 Craziest Moments

As the actor celebrates his birthday, look back at his not-so-winning times

Charlie Sheen is known for his critically acclaimed performances in movies and on TV shows, but it's his run-ins with the law and sheer crazy outbursts that keeps the Anger Management star in the headlines.

Since 1995, Charlie has gained a not-so-winning reputation for shacking up with "goddesses", partying hard, being accused of assault, entering rehab for drug use and much, much more.

From his outrageous antics to his nationwide catchphrases, see Charlie's top O-M-G moments. 

When Charlie Was "Winning"

Courtesy of YouTube

You would think arrests, drug use, rehab, divorces and meltdowns would get someone down -- but not Charlie! The actor used the word "winning" to prove that he is not troubled or crazy, but that he is just living the dream. When told by ABC that people think Charlie is bipolar due to his erratic behavior, Charlie responded, "I'm bi-winning." Clearly.

When Charlie Was Booed Off Stage

Courtesy of YouTube

He gave the violent truth, but it wasn't funny. Charlie may be entertaining to watch on Two and a Half Men and when he's making bizarre statements during interviews, but not on stage. The actor received boos during his first leg of the My Violent Torpedo of Truth tour when he spent the 70-minute show ranting. Charlie responded to the crowd's displeasure by saying, "I've already got your money." Well played, Charlie. 

When Charlie Got Fired From 'Two and a Half Men'

Courtesy of YouTube

Charlie took his Two and a Half Men firing abnormally well! The actor celebrated the expected boot by toasting with tiger blood, waving a machete and screaming "free." This man knows how to party. 

When Charlie Partied Naked While on a Family Vacation

Courtesy of YouTube

When in New York! In 2010, Charlie took his ex-wife, Denise Richards, and their two children, Sam and Lola, on vacation in New York City. Luckily, they were staying in different hotel rooms when Charlie was found naked and highly intoxicated around 1:30 a.m. Charlie was sent to the hospital for a psychiatric evaluation. But it's not what you think. According to his publicist, Charlie suffered from an allergic reaction to medication. Right...

When the World Met Charlie's Goddesses

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Two is better than one! During a 20/20 interview in 2011, Charlie welcomed the world into his home and his relationship with "goddesses" Natalie Kenley and Bree Olson. That's right, there are two of them. Although Charlie sees it as winning, we see it as really creepy.

When Charlie Cured Himself With His Mind

Courtesy of YouTube

In a 2011 interview with Today Show's Jeff Rossen, Charlie tried to prove his sobriety. Here is a rundown of Charlie's responses. Is he on drugs? "Look at me, duh, drugs tests don't lie." When was the last time he did drugs? "Don't know, don't care, drug tests don't lie." How did he beat the addiction? "I closed my eyes and made it so with the power of my mind." So many questions, so many unconvincing answers.

When Charlie Streamed His Meltdown

Coutesy of YouTube

Charlie Sheen let it all out during episode 3 of his webcast, "Sheen's Korner." During a phone conversation with friend Bob Maron, Charlie insulted Howard Stern, attempted to speak Italian and admitted that he wants to marry a tree. We have no words.

When Charlie Played Himself in 'Being John Malkovich'

Coutesy of YouTube

What do you do when you think you're going crazy? Consult the king of crazy himself, of course! Charlie played himself in the 1999 film, Being John Malkovich. Believe it or not, he was just as crazy in 1999.

When Charlie Was Arrested For Domestic Assult

Courtesy of YouTube

The former Two and a Half Men star was arrested for domestic assault when he allegedly held a knife to his then-wife Brooke Mueller's throat on Christmas day in 2009. Somehow, the couple reconciled. This wasn't his first domestic assault charge. In 1996, he was charged with attacking girlfriend Brittany Ashland.

When Charlie "Shot" Kelly Preston

Courtesy of YouTube

Did he or didn’t he? That was the question everyone wondered when Charlie’s then-fiance, Kelly Preston, was shot in 1990. Charlie finally cleared up the rumor during his My Violent Torpedo of Truth tour in 2011. "I was downstairs early in the morning making coffee and I thought she was still asleep upstairs," he said. "And I heard a f***ing gunshot go off. I thought, 'She did it, she finally f***ing did it. She killed herself and they're going to f***ing blame me.' She explained to me when she lifted my pants off the scale in the bathroom… the tiny revolver I used to carry… it fell out of the back jeans pocket and hit the floor and shot a bullet right between her legs. So she got hit with shrapnel from the toilet bowl." Much to the surprise of many, the relationship ended soon after. 

Teresa Roca is an iVillage contributing writer. Follow her on Google+.

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