A Charlie Sheen Timeline

  • 1986 1 of 18
    Charlie appears in his first major role in the movie Platoon playing a young American soldier serving in Vietnam. His future looks bright.
    Read more on Charlie’s career… and crimes
  • 1990 2 of 18
    After starring in two more major films, Wall Street and Major League, Sheen accidentally shoots his then-fiancée Kelly Preston in the arm. They never get married.
    Read the latest on Charlie Sheen
  • 1990-1992 3 of 18
    Charlie ‘broadens his horizons’ and dates porn stars Ginger Lynn and Heather Hunter while starring in less-popular films.
    Read about Charlie’s latest girlfriends
  • 1995 4 of 18
    The same year Sheen marries model Donna Peele, he admits, in court, to spending around $50,000 on the services of about 27 of Madam Heidi Fleiss’ girls. He and Donna divorce the following year.
    Check out photos of Charlie’s new “goddesses”
  • February 1997 5 of 18
    February 1997
    His ex-girlfriend Brittany Ashland files charges claiming that he physically abused her. He was officially charged with misdemeanor battery and pleaded no contest.
    Read what Brittany’s lawyer, Gloria Allred, would say to Charlie now
  • 1998 6 of 18
    Sheen is admitted to the hospital on a drug overdose. That same year, his father, Martin Sheen, turned him in for violating his parole.
    See if you think Charlie is back on drugs in his recent interview on the Today Show
  • September 22, 2003 7 of 18
    September 22, 2003
    With a few more movies under his belt and a star role in the TV series Spin City (2000-2002), Charlie debuts in the soon-to-be hit TV series Two and A Half Men. Drama ensues.
    Read our ideas for a Two and A Half Men spin off
  • 2005 8 of 18
    While six-months pregnant, his then-wife Denise Richards files for divorce, citing Sheen for drug and alcohol abuse and threats of physical violence.
    Read Richards’ most recent comments on Charlie
  • 2009 9 of 18
    Charlie Sheen is arrested for domestic violence and spends Christmas in a Colorado jail after threatening his wife of one year, Brooke Mueller, with a knife. He was charged with felony menacing and was later released on bail.
    Read about the signs of trouble leading up to their divorce
  • October 26, 2010 10 of 18
    October 26, 2010
    Charlie is taken to the hospital after cops were called to the Plaza Hotel where he was staying during a visit with ex-Denise Richards and their two daughters, Sam, 6, and Lola, 5. Sheen was reportedly drunk and hanging out with porn star Capri Anderson while yelling and throwing furniture in the hotel.
    Read more about Charlie’s Plaza Hotel incident
  • November 2010 11 of 18
    November 2010
    Sheen files for divorce from his wife Brooke Mueller and mother of his one-year-old twin boys, Max and Bob. Sheen will now have three divorces to add to his IMDB profile.
    Read about Charlie’s divorce from Brooke Mueller
  • Feb 22, 2011 12 of 18
    Feb 22, 2011
    Charlie starts dating Natalie Kenly, a graphic designer who was formerly a nanny and a model. Sheen refers to both his live-in girlfriends Kenly and porn star Rachel Oberlin (they started dating in January 2011), as "goddesses" during an interview with Good Morning America.
    Read more about Charlie’s women
  • February 24, 2011 13 of 18
    February 24, 2011
    On the Alex Jones’ radio show, Charlie Sheen said, "I violently hate Chaim Levine,” the producer of Two and a Half Men, whose real name is Chuck Lorre. The show is canceled shortly afterward.
    Read more of Charlie’s radio rant
  • February 28, 2011 14 of 18
    February 28, 2011
    Charlie Sheen’s sanity once again comes under question when he rants on the Today Show, “People can’t figure me out; they can’t process me. I don’t expect them to. You can’t process me with a normal brain.” He also claims to have “tiger blood” and “Adonis DNA.”
    Read more infamous Charlie Sheen quotes
  • March 1, 2011 15 of 18
    March 1, 2011
    Charlie Sheen joints Twitter on March 1st and sets a new Guiness World Record by getting one million followers in the shortest time ever: 25 hours and 17 minutes. Currently he has over 2 million followers.
    Read more about Charlie’s Twitter account
  • March 1, 2011 16 of 18
    March 1, 2011
    Charlie smokes on camera, talks about “bangin’ 7-gram rocks” and shares info on his live-in girlfriends, or “goddesses” as he calls them, during a bizarre interview with 20/20.
    Watch the 20/20 interview
  • March 1, 2011 17 of 18
    March 1, 2011
    Charlie loses custody of his sons after ex-wife Brooke Mueller issues a restraining order against him. We wonder, who is really “winning” in Charlie’s life?
    Read more about the restraining order
  • March 7, 2011 18 of 18
    March 7, 2011
    Charlie Sheen is fired from Two and a Half Men. "Winning," no? Where's that tiger blood when you need it?!
    Read more about Sheen's termination here

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