September 1990: Sheen completes drug rehab a month after checking himself in.
July 1995: Sheen testifies in the tax evasion trial of Hollywood madam Heidi Fleiss, admitting he spent almost $53,000 on her prostitutes.
December 1996: Sheen is arrested for allegedly beating porn star girlfriend Brittany Ashland, who claimed he slammed her into the marble floor of his home and threatened to kill her if she told anyone.
June 1997: Sheen pleads no-contest to the Ashland charges and is sentenced to a one-year suspended prison term and two years of probation.
May 1998: Sheen is hospitalized after a cocaine overdose. Father Martin Sheen turns him over to authorities for violating his probation. Sheen later checks himself into Promises rehab center.
March 2005: Denise Richards, Sheen's second wife, files for divorce while pregnant with the couple's second daughter. She says Sheen had been abusing drugs and alcohol.
April 2006: In order to obtain a restraining order, Richards signs a declaration stating that in the middle of an argument on Dec. 30, 2005, Charlie pushed and shoved her while she was holding their daughter Lola. According to the declaration, Charlie pointed his finger at her and screamed, "I hope you f---ing die, b----."
March 2008: Jason Itzler claims he sent Ashley Dupre (the same Dupre who later had a relationship with Eliot Spitzer) and another girl to have a threesome with Sheen for $20,000. Sheen's reps deny the report.
February 2010: Sheen's Mercedes is stolen and found upside-down at the bottom of a cliff near Mulholland Drive. Police say they do not believe Sheen was in the car because he would have been injured in the accident.
February 2010: Sheen is charged with felony menacing and misdemeanor third-degree assault and criminal mischief in connection with the Aspen arrest. He pleads not guilty in March.
February 2010: Sheen announces he's voluntarily checking into rehab and takes time off from Two and a Half Men. In May, he signs a two-year deal that will pay him $1.8 million per episode.
August 2010: Sheen pleads guilty to the Aspen charges and is sentenced to 30 days in rehab, 30 days of probation and 36 hours of anger management.
October 2010: Sheen is reportedly removed from The Plaza Hotel in New York City after causing a disturbance, and allegedly doing $7,000 worth of damage to the room. Richards, who was also staying at the hotel, separately from Sheen, accompanies him to the hospital. His rep says Sheen had an "allergic reaction" to medicine.
November 2010: Capri Anderson, an adult film star who was with Sheen at The Plaza, sues him, claiming he choked her. Sheen countersues Anderson, claiming she tried to extort him. Sheen is not prosecuted for the incident at The Plaza Hotel.
January 2011: Sheen goes on a reported bender in Las Vegas — where he allegedly parties with a group of women that includes porn stars, strippers, and Michelle "Bombshell" McGee — but returns in time for work on Two and a Half Men.
January 2011: Sheen is rushed to the hospital for severe abdominal pains that a friend of Sheen says came from the actor laughing too hard at the TV. Shortly after, Sheen begins a rehabilitation program in his home. Two and a Half Men goes on production hiatus.
February 2011: Sheen begins a rant about Two and a Half Men creator and executive producer Chuck Lorre on The Dan Patrick Show, where he blames the producers for delaying the return of the show. Lorre responds with a vanity card reading, "If Charlie Sheen outlives me, I'm gonna be really pissed." Sheen's ensuing rants (challenging Lorre to a fight, and saying he owns him) and behavior force CBS and Warner Bros. TV to shut down production for the rest of the season. Sheen responds by saying he would return to the series for Season 9 if Lorre is not involved.
March 2011: Estranged wife Mueller has an emergency restraining order granted against him. Sheen isn't allowed within 100 yards of her or their 23-month-old twins, Max and Bob, who are removed from his home in the middle of the night.