When it comes to the golden sombrero of personal strikeouts, Charlie Sheen is really swinging (and missing) for the fences. The film and television star has become more infamous for his revolving door trips to rehab and the county jail than his successful acting career. But, to his credit, his behavior would have you think that he's determined to overshadow all his professional accomplishments with epic feats of stupidity, in which case, we'll label him a wild success.

 

Whether it's his well-documented penchant for class A drugs and prostitutes, or attacking his wife on Christmas, Sheen got a fast start as a delinquent. One of his earliest missteps came in 1990 when he accidentally shot his then-fiancee Kelly Preston. According to his side of the story, he had forgotten about a revolver he put in his pants pocket and it went off while Preston was moving clothes in the bathroom. The bullet struck the toilet and Preston's arm was grazed by shrapnel. Not surprisingly, they called off the engagement soon after.

 

Hey Charlie, is that a revolver in your pocket or are you just...oh, nevermind.

 

He still managed to keep it together through the early 90s even though his reputation as a drug addict and womanizer was becoming common knowledge. He had a short-lived marriage to model Donna Peele in 1995, the same year he was called to testify in Hollywood madam Heidi Fleiss's trial where he admitted that he was a regular customer. When the judge asked him why he would pay for sex, Sheen reportedly responded, "I don't pay them for sex. I pay them to leave." Priceless.

 

In 1997, Sheen was involved in his second domestic violence incident when his girlfriend Brittany Ashland accused him of attacking her when she refused to have sex. He pleaded no contest and was sentenced to probation and a $2,800 fine. But his most serious ordeal happened the following year when he was rushed to the hospital with a drug and alcohol overdose. He checked into rehab soon after he was released. It was his second stint since he entered a facility in 1990 for exhaustion.

 

His life seemed to take a positive turn when he married Denise Richards in 2002. The couple had two daughters together, but their relationship went sour four years later when Richards filed for divorce while she was pregnant with their second child. The break-up got even more bitter when she got a restraining order against him. By the time the dust had settled, she had accused him of everything from relapsing into drug abuse to cheating to threatening to kill her to being addicted to gay and kiddie porn--she probably also blamed him for global warming and the national debt at some point there too.

 

However, accusations of kiddie porn addiction don't have any effect on a celebrity's romantic mojo. He met real estate investor Brooke Mueller shortly after through mutual friends Eric Dane and Rebecca Gayheart, and she became blushing bride number three in 2008. With a starring role on the hit sitcom Two and a Half Men and the birth of their twin sons Max and Bob in the spring of 2009, we were once again lulled into the false hope that Sheen had put his reckless ways behind him for good. But that image was promptly shattered when news broke that he had been arrested for attacking Mueller and threatening her with a knife...on Christmas Day, no less. The incident landed him in rehab for the third time as a "preventative measure." Too bad someone forgot to tell him that "preventative" implies doing something before the fact, not after.

 

He was charged with felony menacing and misdemeanor assault and criminal mischief, but he reportedly copped a plea that dropped the felony charge and landed him 30 days in jail. On top of that, a judge granted him permission to serve the time in a rehab facility instead.

 

But clearly rehab didn’t do him much good. In October 2010, he was carted off to a hospital after police found him drunk, belligerent and wearing nothing but his birthday suit in his Plaza Hotel room, which was as trashed as he was. The star had reportedly flown into a rage when he thought his paid escort—who was also naked and, not to mention, terrified—stole his very expensive watch. He was reportedly treated for an adverse allergic reaction to medication…medication that probably resembled a fine white powder dusting his nostrils.

 

But if fellow actors Robert Downey Jr. and Mickey Rourke can teach us anything, there is hope for embattled stars to make comebacks in the face of adversity, and as much as Sheen's mistakes have offered an enduring source for tabloid fodder, we're rooting for him to turn things around.