KELLY PRESTON

Dated in: 1990
The short-lived romance between Preston and Sheen, which saw the couple get engaged, was marked by a bizarre incident in which Preston was accidentally shot by a loaded gun Sheen left in the pocket of his pants on a bathroom floor. Shortly after their split in March, Preston went on to wed John Travolta.

GINGER LYNN ALLEN

Dated from: 1990 – 1995
After splitting with Preston, Sheen moved on with adult film actress Allen, whom he dated on-and-off for five years. "When Charlie's sober, he's sweet, kind, loving, generous," she told PEOPLE. "When he's drinking and using, he's out of control."

STEPHANIE SEYMOUR

Dated in: 1992
The stunning supermodel was romanced by Sheen in the midst of her two-year relationship with Guns N' Roses frontman Axl Rose. "We're madly in love and very happy together," Sheen gushed in June 1992, a year before Seymour and Rose officially called it quits.

HEIDI FLEISS'S GIRLS

Dated from: 1991 – 1993
When Hollywood's madam to the stars was brought down for tax evasion in 1995, Sheen served as the star witness in her trial, admitting he had spent $53,000 on 11 of Fleiss's prostitutes. For her part, Fleiss praised Sheen to Vanity Fair, saying, "Charlie was a gentleman. [At his parties,] he'd pay for all his friends."

BRITTANY ASHLAND

Dated in: 1996
The tumultuous relationship between Sheen and Ashland ended in a June 1997 courtroom when Sheen pleaded no contest to charges of battery, with Ashland accusing her ex of throwing her onto the kitchen floor of his San Fernando Valley home and splitting her lip during a December 1996 argument. "I hope that for his good and everybody else's, he decides to change his behavior," Ashland told the court through attorney Gloria Allred.

DENISE & CHARLIE

Reports of Sheen relapsing and making chilling death threats led to wife Richards, who was pregnant with Sheen's child, filing for divorce in 2005.

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