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Charlie Sheen Legal Timeline

By Charlotte Brittan on

Actor Charlie Sheen (C) arrives for trial at the Pitkin County Court house on June 7, 2010 in Aspen, Colorado. Sheen is expected to plead guilty to a misdemeanor assault charge in exchange for prosecutors dropping felony menacing and criminal mischief charges. (Getty Images)more pics »

Charlie Sheen (Getty Images)Charlie Sheen has seen his fair share of trouble with the law.

The Two and a Half Men star has had the following legal issues:

In 1990, Charlie Sheen shot his then-fiancee, Kelly Preson, in the arm. The shooting was declared in accident.

In 1995, Sheen was one of the several celebrities named as clients of a high-profile brothel run by Heidi Fleiss. When questioned about it, Sheen responded, "I love sex and I can afford it."

Sheen overdosed on cocaine in 1998, violating the terms of his parole, which was reported by his father Martin Sheen. A warrant was issued for his arrest, with Sheen eventually avoiding jail time by attending rehab.

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Sheen was involvedin a lengthy custody battle over his two daughters with ex-wife Denise Richards, although they eventuallys settled the dispute. "We had to do what's best for the girls," said Sheen.

On December 25, 2009, Sheen was arrested on charges of domestic violence, including second-degree assault and menacing against his wife, Brooke Mueller. In a court appearance in February 2010, Sheen was formally charged with felony menacing, and third-degree assault and criminal mischief.

While reports have said that Sheen may serve jail time, as of June 2010, he is not currently incarcerated.