Charlie Sheen's Top 8 Screw-Ups

Charlie Sheen
Warner Bros.

“I think enough time has gone by that people have forgotten the second one, and that third abortion that came out has been forgotten as well.”

The "Two and a Half Men" star has a history of troubles, from being outed as a Heidi Fleiss client to making an anti-Semitic attack on boss Chuck Lorre.

Charlie Sheen’s attack on Two and a Half Men co-creator Chuck Lorre on Thursday -- which spurred CBS and Warner Bros. TV to shut down production on the show for the remainder of the season -- is only the latest in a long line of troubles for the actor. Here are eight of his biggest screw-ups (in chronological order).

-- Forgets about loaded gun in pants. In 1990, Sheen became engaged to up-and-coming young actress Kelly Preston, whose credits at the time included HBO's Tales From the Crypt, with a 2.5-karat pink diamond ring. One day, Sheen thought he heard intruders at their Malibu townhouse and picked up his gun to go take a look. "I put my .22 in the pocket of my pants when I went to check it out," he has said of the incident, according to the Orange Country Register. "I forgot about the gun, left my pants in the bathroom, and the next evening Kelly was moving my clothes when the pistol went off." Preston had injuries to her wrist and ankle, broke off the engagement soon after the shooting and married John Travolta one year later.

-- Outed as Heidi Fleiss client. In 1994, famous madam Heidi Fleiss was indicted by a federal grand jury on 14 counts of conspiracy, income tax evasion and money laundering. During her trial, Charlie Sheen was one of only two famous clients who came to the forefront publicly and admitted using her service. He testified during her trial and admitted to using Fleiss' service at least 27 times, running up a total of more than $50,000, according to the Associated Press. Fleiss was convicted of eight counts of conspiracy, tax evasion and money laundering.

-- Overdoses after injecting cocaine. In May 1998, Sheen tried injecting cocaine and accidentally overdosed. He was admitted to a Los Angeles hospital, saying he was having difficulty walking and was experiencing tingling in his hands. To quash reports that his son had had a stroke, Martin Sheen the following day made a statement at the hospital. "We are in the stages, right now, of recovery," Sheen said, as reported by CBS News. "It is my hope that he will accept recovery and become free. I am asking all of his friends and fans to pray for him."

-- Accused of threatening then-wife Denise Richards with violence. Sheen married Richards in June 2002 and had two daughters with the actress. In March 2005, while still pregnant with their second daughter, Richards filed for divorce. In legal documents, Richards accused Sheen of abusing drugs and alcohol and threatening Richards with violence along with an "attraction to underage women and his sexual explicitness on the Internet, including revealing his private parts," according to People. The two became engaged in an acrimonious custody dispute over their two daughters but have since become friendly with each other. "We had to do what's best for the girls," Sheen has said.

-- Arrested on charges of domestic violence against then-wife Brooke Mueller. Sheen married the real estate investor in 2008, and the two had twin boys a year later. In December 2009, the couple were spending the holidays in Aspen, Colo., but the actor spent Christmas Day in jail. In February, he was charged with felony menacing, third-degree assault and criminal mischief and in August plead guilty to misdemeanor assault and avoided jail time. The couple finalized their divorce this month.

-- Hospitalized after trashing hotel room. In October, police were called to Manhattan's Plaza Hotel Tuesday morning around 2 a.m. after a reportedly drunk and naked Sheen had trashed his suite. Sheen was taken to a hospital and released. Later, adult film actress Capri Anderson came forward to say she had been with Sheen at the time. Things grew violent, according to Anderson: "When I became really uncomfortable is when he put his hands around my neck," she told Good Morning America. "He started throwing things. He threw a lamp. That was the first thing he picked up. And he threw it across the room at me. When he started throwing things at me I became shocked, scared."

-- Enters hospital for "severe abdominal pains" after alleged weekend of partying. On Jan. 27, 2011, Sheen was admitted to the hospital because of abdominal pain -- after an alleged weekend of partying -- and entered rehab the next day. His CBS comedy, Two and a Half Men, went on hiatus and was scheduled to go back into production Feb. 28. During the hiatus, Sheen reportedly offered to cover one-third of the salaries of the Two and a Half Men crew during the shutdown if CBS and Warner Bros. TV would pay the rest. Late last month, CBS ordered ordered two additional episodes of Monday sitcoms Mike and Molly and Rules of Engagement to help cope with scheduling issues arising from Sheen's absence.

-- Makes anti-Semitic attack on boss, spurring series shutdown for rest of season. On Thursday, the Two and a Half Men star lashed out at the show's co-creator Lorre during an interview on the syndicated Alex Jones Show. Saying he was told that if he went on "attack" execs would cancel the show, Sheen repeatedly referred to the showrunner as "Chaim Levine." (Lorre's birth name is Charles Levine.) Sheen later went on to attack Lorre on TMZ, saying he "violently hated" Lorre, whom he called "a stupid, stupid little man." Sheen challenged Lorre to a fight, saying "If he wins, then he can leave my show." Hours later, CBS and Warner Bros. TV shut down production on the comedy for the remainder of the season. In May, Sheen signed a new contract worth a reported $1.8 million-$1.9 million per episode, making him the highest-paid actor on TV.