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Charlie Sheen

Aspen Police Department

Goodwill toward men? Charlie Sheen's got it. Goodwill toward women? As his unscheduled solo holiday plans have suggested, that's up for a little more debate.

And while we're all for innocent until proven guilty—or, as Sheen's rep would and has implored, "do not be mislead by appearance"—it certainly appears as though the highest-paid sitcom star around is less than adept at managing his personal life, particularly when it comes to his real-life leading ladies.

But don't take our word for it, take his well-worn rap sheet's:

1990: Sheen accidentally shoots then-fiancée Kelly Preston in the arm. As flesh wounds have a funny way of killing the mood, the engagement is called off shortly thereafter.

1995: Two words: Heidi Fleiss. Sheen admits to being a client of the so-called Hollywood Madam, copping to having spent $50,000 for the, um, services of her call girls.

1995: Two months after marrying model Donna Peele, Sheen was sued by a UCLA student who claimed he struck her in the head back in 1994 after she refused him sex. The case was settled out of court.

1997: Sheen pleads no contest to battery charges brought by former girlfriend, model-actress Brittany Ashland, who claims Sheen threw her onto his kitchen floor and split her lip. He earned a year's suspended sentence, two years' probation and a $2,800 fine.

1998: Sheen enters lock-down rehab after being hospitalized for a drug overdose. The get-clean action was necessary after his father, Martin Sheen, turned him in for violating his parole.

2005: Denise Richards files for divorce while pregnant, publicly accusing Sheen of "inappropriate behavior," including dalliances with prostitutes, gambling problems and drug and alcohol problems, that could negatively impact his daughters' upbringing. Sheen denies everything, calling the claims "laughable and inane."

2009: Sheen is arrested on felony menacing charges and spends Christmas in a Colorado jail after wife Brooke Mueller tells cops the actor threatened her with a knife. He's due to return to court to face the charges on Feb. 8.

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It hasn't all been bad times. Check out our gallery of Charlie Sheen & Brooke Mueller: Better Days.