Charlie Sheen's Most Shocking Moments

From accidentally shooting his ex to trashing to Plaza, the actor has had a wild run

01 of 10

KELLY PRESTON SHOOTING

KELLY PRESTON SHOOTING
Globe

When Charlie Sheen was engaged to actress Kelly Preston in 1990, he left a loaded gun in the pocket of his pants on the bathroom floor. When Preston picked up the pants, the gun discharged, and the actress was hit with shrapnel in her wrist and ankle. She married John Travolta a year later.

02 of 10

PROSTITUTION BILL

PROSTITUTION BILL
David Keeler/Liaison

During Hollywood madam Heidi Fleiss's 1995 tax-evasion trial, Sheen testified that he had spent $53,000 on hookers.

03 of 10

ASSAULT ON EX

ASSAULT ON EX
Chris Pizzello/AP

"You will not see me back in this courtroom," Sheen told the judge in 1997 after he pleaded no contest to smashing then-girlfriend Brittany Ashland's face into the marble floor of his Agoura Hills, Calif., home. The actor was fined $2,800, ordered to attend counseling and perform community service.

04 of 10

OVERDOSE

OVERDOSE
David Claborn/Getty

As rumors circulated that Sheen had died, the actor was admitted to the hospital on May 20, 1998. Dad Martin Sheen confirmed that Charlie had suffered a drug overdose, saying "It is my hope that he will accept recovery and become free." It would be the actor's second stint in rehab.

05 of 10

WEB ADDICTION

WEB ADDICTION
Kevin Mazur/WireImage

The custody dispute against ex-wife Denise Richards got particularly nasty in 2007, when the actress asked the judge to protect their children from her ex-husband, citing "his attraction to underage women and his sexual explicitness on the Internet, including revealing his private parts."

06 of 10

THREATING WIFE WITH KNIFE

THREATING WIFE WITH KNIFE
Landov

The actor pleaded guilty to a misdemeanor assault charge following his arrest for a 2009 Christmas Day fight with then-wife Brooke Mueller. During the fight, Sheen allegedly threatened her with a knife, saying "If you tell anybody, I'll kill you."

07 of 10

CAR CRASH

CAR CRASH
X17

Police found Sheen's stolen Mercedes at the bottom of a cliff in the Hollywood Hills last June. "It was nice to have police come to my house and for once I didn't have to leave with them," the actor joked.

08 of 10

TRASHING THE PLAZA

TRASHING THE PLAZA
Steve Mack/Getty

Sheen was taken to the hospital after police found him drunk and naked at New York's Plaza Hotel in late October 2010. Details soon emerged that Sheen's companion, a porn star named Capri Anderson, had locked herself in the bathroom, fearing for her safety.

09 of 10

JANUARY BENDER

JANUARY BENDER
Gabriel Bouys/AFP/Getty

The actor was rushed to Cedars-Sinai Medical Center in January after allegedly partying for two days. The actor entered rehab, but shortly thereafter enrolled in a

10 of 10

TIRADE AGAINST CHUCK LORRE

TIRADE AGAINST CHUCK LORRE
Nick Ut/AP

The actor went on a bizarre rant against Two and a Half Men's creator Chuck Lorre (among other targets) – and bragged about his own "fire breathing fists" – causing CBS to cancel the rest of the sitcom's 2011 season. his father, Martin Sheen said.

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