Sheen jumps over to the family friendly sitcom Two and a Half Men, playing the playboy brother to Jon Cryer's fussy, soon-to-be divorced single dad. The show, which also stars child actor Angus T. Jones, becomes a hit for CBS, averaging 14 million viewers per new episode, and eventually makes Sheen the highest-paid actor in primetime, with a reported $2 million per episode paycheck.
Sheen and Richards welcome their first child together, a baby girl named Sam. "I can't imagine my life without her now," says Sheen of his newborn. Richards adds that Sam is "a daddy's girl" and "looks exactly like Charlie wrapped in a little blanket."
Pregnant with baby No. 2, Richards files for divorce from Sheen. Though the pair briefly reconcile after daughter Lola's birth in June, Richards ultimately proceeds with their divorce, claiming in a legal declaration that Sheen gambled, abused prescription drugs and acted in a "very volatile" way during their marriage, which ends in the midst of a vicious custody battle over their daughters.
The 41-year-old actor proposes to his girlfriend, real estate investor Brooke Mueller, 29, with an 11-carat yellow diamond ring during a Costa Rican getaway. The pair, who were introduced by mutual pal Rebecca Gayheart in June 2006, marry in a small ceremony in front of about 60 guests at a private estate in Los Angeles on May 30, 2008.
Sheen and Mueller welcome twin boys Max and Bob. "I see him being a better man now that the boys are here. He’s totally involved," the new mom says of her husband. "I was a little worried I’d be the one doing most of the work, but I was wrong."
Sheen is arrested in Aspen, Colo., after Mueller calls 911, tearfully saying that her actor husband physically threatened her. "My husband had me with a knife," she says in the call. "I was scared for my life." After returning to the set of his show, Sheen pleads guilty to a misdemeanor assault charge and is ordered to 30 days in rehab and probation.
Sheen is hospitalized after he's found intoxicated in a trashed room in New York's Plaza Hotel, where he allegedly taunted adult film actress Capri Anderson. Days later, Sheen and Mueller each file separate divorce petitions. Struggling with her own sobriety, Mueller checks into a sober living facility.
After being rushed to an L.A. hospital for "severe abdominal pains," Sheen enters rehab, putting Two and a Half Men on hiatus while he recovers. "We are profoundly concerned for his health and well-being, and support his decision," CBS, Warner Bros. Television and the show's executive producer Chuck Lorre say in a joint statement.
While going through a personalized rehab treatment at home, Sheen begins sounding off to media outlets about his two live-in "Goddesses", his "b----ing" life and his CBS bosses, who pull the plug on the rest of the eighth season of the series. Days after Sheen loses temporary custody of his twin boys, Two and a Half Men execs fire the actor on March 7, calling him "dangerously self-destructive" and "very ill." Sheen, who is later replaced by Ashton Kutcher, responds with a $100 million lawsuit against Chuck Lorre and Warner Brothers for breach of contract.
Sheen returns to TV with a vengeance on FX's Anger Management. "I'm excited as hell, and I don't get excited about a lot of stuff," he tells PEOPLE. "The dialogue is really smart. I have a prison group on the show that is going to blow your mind." The premiere draws 5.5 million viewers, making it the highest-rated debut in FX history.
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