A Timeline of Charlie Sheen's Strange Legal Woes

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As the actor moves ahead with plans to sue CBS and Warner Brothers, a look back on his infamous entanglements with everyone from Kelly Preston to Heidi Fleiss.

Charlie Sheen is suing CBS to get his $1.2 million-per-episode salary the eight Two and a Half Men shows the network canceled. It's not the first time he's faced legal troubles -- but it may be the first time he's tussled with an employer. Below, a timeline of the troubled actor's run-ins with the law.

1990: Then-fiancee Kelly Preston is shot in the arm after she picks up a pair of pants with Sheen's gun in the pocket. It is declared an accident and no charges are filed.

1995: He is one of several-high profile clients named in the trial against madam Heidi Fleiss, where it is revealed he spent more than $35,000 on call girls. "I love sex and I can afford it," he reasoned.

1997: Adult film star Brittany Ashland, Sheen's girlfriend at the time, files a lawsuit accusing Sheen of grabbing her by the hair and slamming her onto the marble floor of his home, knocking her unconscious and busting open her lip, requiring seven stitches. She also says he forced her to strip and throw away her bloody clothes, and threatened to kill her if she told anyone about the assault. Prosecutors filed misdemeanor battery with serious injury criminal charges against Sheen. He initially pleaded not guilty, but then changed his plea to no-contest, and was sentenced to a one-year suspended prison term, two years probation, eight counseling sessions and $2,800 in fines and restitution.

1998: The actor violates the terms of his parole stemming from his suspended prison sentence for injuring Ashland when he overdoses on cocaine in Los Angeles. His father, Martin Sheen, reports him, a warrant is issued for his arrest. Sheen avoids jail time by entering rehab.

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2005: Wife Denise Richards filed for divorce when six months pregnant with their second daughter.

2007: Sheen says ex wife Richards will face "a day of legal reckoning" after she files a motion asking a judge to bar their daughters, Sam and Lola, from spending the night with their father. She cites "his attraction to underage women and his sexual explicitness on the Internet, including revealing his private parts." He counters: "Clearly the mother of my children has no interest in responsible co-parenting when it comes to my relationship with our girls. "

2009: Sheen is arrested Christmas morning after his then-wife Brooke Mueller tells police he threatened her with a knife. Police charge him with second-degree assault and menacing. He enters court-ordered rehab.

2010: In light of his legal issues surrounding Mueller, he surrenders custody of his daughters, Sam and Lola, to his ex wife, Denise Richards, according to  TMZ.com.

2010: He is arrested in New York City after trashing his room at the Plaza Hotel. Adult film star Capri Anderson, who claims she hid in a closet because she was afraid of him, declines to press charges.

2011: Sheen's high-powered attorney Marty Singer writes a letter to CBS and Warner Bros., Two and a Half Men's production company, claiming they are violating Sheens' contact by canceling the season's remaining eight episodes "not because of my client's condition but in retaliation for your show runner [Chuck Lorre] being criticized."

2011: Mueller is granted a restraining order against Sheen after she claims he threatened to cut her head off, put it in a box and send it to her mother. He denied saying that in an interview on the Today show. His twin boys, Max and Bob, are removed from his house.