Winning! See Charlie Sheen Through the Years

Although Charlie Sheen grew up in a family of celebrated actors, he wasn’t always “winning!”

The New York City native (real name Carlos Estévez) started acting as a child, making an uncredited appearance in his father Martin Sheen’s 1974 made-for-TV movie The Execution of Private Slovik. Charlie did not make his own foray onto the big screen, however, until 10 years later when he had a small role in Red Dawn opposite Hollywood heavyweights such as Patrick Swayze and Lea Thompson. His first major part followed in 1986 with the war film Platoon.

Charlie continued to star in box office hits including Wall Street (with dad Martin) and Major League through the ‘80s and ‘90s and received a star on the Hollywood Walk of Fame in 1994. His biggest break, though, came in 2003 when he was cast as Charlie Harper in Two and a Half Men. He starred in the CBS sitcom alongside Jon Cryer for eight seasons before being fired in 2011 for making derogatory comments about the show’s creator, Chuck Lorre. At the time, Charlie had been struggling with drug and alcohol abuse and gave a series of infamous interviews in which he ranted about “tiger blood” and boasted about “winning” in life.

After being roasted on Comedy Central later in 2011, Charlie made his return to the small screen. He starred in the TV adaptation of Jack Nicholson’s movie Anger Management, which aired on FX from 2012 to 2014.

While Charlie’s career has slowed down in recent years, his personal life and relationships continue to make headlines. He was married to Donna Peele from 1995 to 1996, Denise Richards from 2002 to 2006 and Brooke Mueller from 2008 to 2011. He has five children: Cassandra with high school sweetheart Paula Profit, Sam and Lola with Richards and twins Bob and Max with Mueller. He is also a grandfather to Cassandra’s daughter, Luna.

In 2015, Charlie announced that he was HIV positive and had been diagnosed approximately four years prior. While focusing on his health, he also gave up one of his past vices, alcohol, in 2017.

“I made some changes to give myself a shot to do some cool things professionally,” he exclusively told Us Weekly in 2019. “And I’m proud of finally being consistent. And reliable. And noble.”

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Scroll through the gallery below to see Charlie through the years!