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.”
Scroll through the gallery below to see Charlie through the years!
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.”
2021
Charlie confirmed in September 2021 that daughter Sami was living with him after moving out of Richards’ home. The exes’ eldest daughter claimed in a TikTok video at the time that she was previously “trapped in an abusive household,” seemingly referring to the Bold and the Beautiful star’s residence. A source told Us at the time that Richards “set normal rules” that Sami “didn’t want to follow.”
The actor’s request to stop paying Richards child support was granted the following month. “I think what transpired today is extremely fair,” he told Us at the time. “It speaks to not just today, but it speaks historically to that same fairness.”
