Charlie Sheen Through the Years: From ‘Platoon’ to ‘Two and a Half Men’ and Every Scandal in Between
1984
The Santa Monica High School expellee became a father in December 1984 when his then-girlfriend, Profit, gave birth to Cassandra.
1986
Charlie played U.S. Army volunteer Chris Taylor in the Vietnam War film Platoon, which hit theaters in December 1986.
1987
He starred as stockbroker Bud Fox in Wall Street, which premiered in December 1987.
1989
Charlie had another box office hit on his hands in April 1989, thanks to Major League.
1995
Charlie wed his first wife, Peele, in September 1995, only to divorce the following year.
2000
Charlie made his TV debut in Spin City in October 2000, taking over for Michael J. Fox as the lead of the ABC sitcom. He won a Golden Globe Award for his role as Charlie Crawford. The show ended in April 2002.
2002
Nearly two years after meeting on the set of the movie Good Advice, Charlie married Richards in June 2002.
2003
The Three Musketeers star reintroduced himself as Charlie Harper on Two and a Half Men in September 2003, playing a hedonistic character loosely based on himself. He starred on the sitcom until May 2010 and received three Emmy nominations for his role.
2004 and 2005
Charlie and Richards welcomed daughters Sam and Lola in March 2004 and June 2005, respectively. The Real Housewives of Beverly Hills alum left her husband while pregnant with Lola. They finalized their divorce in November 2006.
2008
Charlie walked down the aisle again in May 2008, this time with Mueller.
2009
The couple welcomed twins Bob and Max in March 2009. The following year, the Hot Shots! star filed for divorce from Mueller. They finalized the case in November 2011.
2011
Charlie lost his $1.8 million-per-episode paycheck in March 2011 when CBS terminated his contract due to his offscreen issues with Lorre. Ashton Kutcher subsequently replaced him on the show, and Charlie’s jingle-writing character was killed off.
2011
One hour after Kutcher’s debut on Two and a Half Men, the Comedy Central Roast of Charlie Sheen aired in September 2011. Mueller was among the celebrities in the audience, while the roasters who skewered Charlie included Jon Lovitz, Jeff Ross, Amy Schumer, William Shatner and Mike Tyson.
2012
When Anger Management debuted in June 2012, it broke the record as the most-watched sitcom premiere in U.S. cable TV history with 5.74 million viewers. It lasted two seasons, ending in December 2014.
2014
After short-lived romances with adult film actress Bree Olson and model Natalie Kenly, whom he called his “goddesses,” Charlie got engaged to another porn star, Brett Rossi, in February 2014. They planned to marry that November but called off their engagement one month before the wedding.
2015
Charlie appeared on the Today show in November 2015 to publicly reveal that he was diagnosed with HIV in 2011, calling the acronym “three hard letters to absorb.” He insisted during the interview that he had informed all of his sexual partners about his condition.
2019
Us exclusively reported in September 2019 that the actor was set to compete on season 28 of Dancing With the Stars with pro partner Cheryl Burke. However, he walked away before the premiere, telling Us, “At the end of the day, I have two left feet and I just can’t dance.
