Charlie Sheen—the son of Martin Sheen and brother to Emilio Estevez—was one of the original “men” in Two and a Half Men, playing Charlie Harper in the first eight seasons of the CBS sitcom opposite Jon Cryer as his on-screen brother. The eighth season was cut short in 2011 amid Sheen’s battle with addiction.
He famously clashed with executive producer Chuck Lorre in the press and social media, resulting in his dismissal from the series (and the coinage of the phrases “winning” and “tiger’s blood”). His character was killed off and later played as a ghost by Kathy Bates.
After exiting Two and a Half Men, Sheen booked the TV version of Anger Management, which aired from 2012 to 2014 and produced 100 episodes over two seasons. Since, he popped up on The Goldbergs and on the big screen in Scary Movie 5, Machete Kills and 9/11.
In 2023, the actor—who shared in 2015 he is HIV-positive—made a cameo as himself on Lorre’s Max series Bookies. He released his memoir The Book of Sheen as well as aka Charlie Sheen in 2025.
Sheen, who has now been sober for years, shares sons Bob Sheen and Max Sheen with ex-wife Brooke Mueller, daughters Sami Sheen and Lola Sheen with ex-wife Denise Richards and daughter Cassandra Estevez from a previous relationship.