2003

Charlie Sheen

September

Show Me the Money

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.

2004

Charlie Sheen

March 09

Charlie's Angel

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."

2005

Charlie Sheen

March

Family Feud

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.

2007

Charlie Sheen

Moving On

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.

2009

Charlie Sheen

March 14

A Double Dose

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."

Charlie Sheen

December 25

Holiday Fight

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.

2010

Charlie Sheen

October 26

Charlie Gets Trashed

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.

2011

Charlie Sheen

January 27

On Hiatus

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.

February

Firing Off

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.

2012

Charlie Sheen

June 28

Under New Management

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.

Photo Credits

BIOGRAPHY (top to bottom): E.J. Camp/Getty; Splash News Online; Gregg DeGuire/WireImage; Starzlife; Aspen Police Department/Landov; Frederick M. Brown/Getty; Greg Gayne/FX

Name
Charlie Sheen
Real Name
Carlos Irwin Estevez
Date of Birth
September 03, 1965
Birth Place
New York, N.Y.
Relationships
Brett Rossi, ex-fiancée (2013 to 2014)
Natalie Kenly, ex-girlfriend (2011)
Rachel Oberlin, ex-girlfriend (2011)
Brooke Mueller, ex-wife (2008 to 2011)
Denise Richards, ex-wife (2002 to 2006)
Brittany Ashland, ex-girlfriend (1996)
Donna Peele, ex-wife (1995 to 1996)
Stephanie Seymour (briefly dated in 1992)
Ginger Lynn Allen, ex-girlfriend (1990 to 1995, on and off)
Kelly Preston (1990, engaged)
Dolly Fox, ex-girlfriend (dated in mid-1980s)
Paula Profitt, ex-girlfriend (1983 to 1984)
Children
Cassandra, daughter (12/12/1984)
Sam, daughter (3/9/2004)
Lola, daughter (6/1/2005)
Max, twin son (3/14/2009)
Bob, twin son (3/14/2009)
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Edited by Julia Wang

Charlie Sheen

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