Charlie Sheen's Long List of Legal Woes

Sheen's treatment of women has taken him to court many times.

March 9, 2011 — -- So far, he's tried to dominate the Internet, radio, and television. Now, Charlie Sheen wants to have his way with the law.

The 45-year-old former "Two and a Half Men" star is expected to sue Warner Bros. after his unceremonious firing from the show on Monday.

"We will sue," Sheen lawyer Marty Singer told The Hollywood Reporter. "It's a matter of when. It could be this week, it could be in a little while. We're in no rush. But we will sue."

It's a departure from the majority of his legal battles, which have tended to be with women. He's engaged in bitter custody disputes with two of his three ex-wives; he's been accused of abusing women multiple times.

So as Sheen prepares to make Warner Bros. pay, he's waging a war on more familiar grounds. With the help of lawyer Mark Gross, Sheen is expected to contest his child custody arrangement with his estranged wife, Brooke Mueller. Last Tuesday, he was forced to give her their twin boys, Bob and Max. According to a restraining order requested by Mueller, Sheen must stay at least 100 feet away from her and their sons pending a March 22 court hearing.

Gross declined to comment on the status of the custody agreement. Mueller's lawyer did not immediately respond to's requests for comment.

As Sheen readies himself for what's likely to be two epic courtroom dramas, it's worth looking at the litany of run-ins he's had with the law. Below, a timeline of Sheen's legal trials and tribulations:

1990: Sheen shot then-fiancee Kelly Preston in the arm. The incident was declared an accident. As the New York Times noted in a recent op-ed, she ended their engagement soon after.

1994: Sheen was sued by a college student who claimed that he struck her in the head after she refused to have sex with him. The Times reported that the case was settled out of court.

1995: Sheen was one of several famous clients named in the trial against "Hollywood Madam" Heidi Fleiss. "I love sex and I can afford it," he said at the time, admitting in videotaped testimony that he ordered Fleiss' call girls at least 27 times and ran up a tab of more than $50,000. (His rationale appears unchanged: he touted the benefits of prostitutes in his recent interview with "20/20.")

1997: A court convicted Sheen of battery with serious injury after his then-girlfriend Brittany Ashland said Sheen attacked her at his home. Ashland's attorney at the time, Gloria Allred, told that he pleaded no contest, paid a fine and was placed on two years' probation.

1998: Sheen violated the terms of his parole when he overdosed on cocaine. A warrant was issued for his arrest. Sheen avoided jail time by going to rehab at the Promises Treatment Center in Malibu, Calif.

2005: Sheen's second wife, Denise Richards, filed for divorce, accusing Sheen of substance abuse and making violent threats. They briefly reconciled.

January 2006: Richards filed a restraining order against Sheen, saying he had shoved and threatened to kill her. She renewed her bid for a divorce, formally filing papers in April. She alleged he was unstable, violent, addicted to gambling and prostitutes, and visited pornographic Web sites featuring young men and girls who appeared to be underage.

April 2006: A judge ordered Sheen to stay at least 300 feet from Richards, her home, her car and their two daughters, except during supervised visits with the kids. The judge extended the order in July.

September 2007: Richards filed documents seeking "the assistance of the court to obtain orders to protect her children" from Sheen. She accused Sheen of "an attraction to underage women," providing numerous printouts of porn websites he allegedly visited during their marriage. Sheen lashed out at Richards in response, saying she "behaves as though she owns our children. She does not. A day of legal reckoning for her is fast approaching."

December 2009: Sheen was arrested Christmas morning after his then-wife Mueller told police he had threatened her with a knife. Three months later, he was charged with two misdemeanors -- felony menacing and assault and criminal mischief. He entered court-ordered rehab.

August 2010: As a part of a plea bargain for his December '09 arrest, Sheen pleaded guilty to misdemeanor assault in exchange for having the rest of the charges against him dismissed. He was sentenced to 30 days in rehab, 30 days of probation, 36 hours of anger management, and barred from possessing guns for the rest of his life.

October 2010: Sheen was hospitalized after reportedly going on a drunken rampage through New York City's Plaza Hotel, causing several thousand dollars' damage to his suite. According to the NYPD, Sheen also admitted to doing cocaine. Capri Anderson, the adult film star who partied with Sheen, claimed she hid in a closet because she was afraid of him. She later filed a criminal complaint saying she had been assaulted and harassed. No arrest was made.

March 2011: Mueller got a restraining order against Sheen after she claimed he threatened to cut her head off, put it in a box and send it to her mother. Police transported Sheen's sons from his Beverly Hills mansion to Mueller, whose whereabouts remain unknown.