He starred in a slew of successful films such as Red Dawn (1984), Platoon (1986), Wall Street (1987), Eight Men Out (1988), Young Guns (1988), The Rookie (1990), The Three Musketeers (1993), and The Arrival (1996).

Fox as the star of ABC's Spin City, his portrayal of Charlie Crawford earned him a Golden Globe Award for Best Actor.

[5][6] Post-Two and a Half Men, he starred in the films Machete Kills (2013) and 9/11 (2017), and had a recurring role on Lorre's Max series Bookie (2023–24).

In 1984, he had a role in the Cold War teen drama Red Dawn with Patrick Swayze, C. Thomas Howell, Lea Thompson, and Jennifer Grey.

In 1989, Sheen, John Fusco, Christopher Cain, Lou Diamond Phillips, Emilio Estévez and Kiefer Sutherland were honored with a Bronze Wrangler for their work on the film Young Guns.

[16] In 1990, he starred alongside his father in Cadence as a rebellious inmate in a military stockade and with Clint Eastwood in the buddy cop film The Rookie.

[17] Sheen appeared in several comedy roles, including the Major League films, Money Talks, and the spoof Hot Shots!

For his work on Spin City, Sheen was nominated for two ALMA Awards and won his first Golden Globe for Best Performance by an Actor in a Television Series – Musical or Comedy.

In 2003, Sheen was cast as Charlie Harper in the CBS sitcom Two and a Half Men, which followed the popular Monday night time slot of Everybody Loves Raymond.

[2] Production of Two and a Half Men went on hiatus in January 2011 while Sheen underwent a substance rehabilitation program in his home, his third attempt at rehab in 12 months.

[25] Sheen, already the highest-paid actor on television,[2] responded by publicly demanding a 50-percent raise,[26] claiming that in comparison to the amount that the series was making, he was "underpaid".

[40] Also that year, he played a role in the hip hop music video "Steak & Mash Potatoes" by Chain Swangaz featuring Brother Marquis.

[41] In 2012, Sheen was cast to star alongside Jason Schwartzman and Bill Murray in Roman Coppola's surreal comedy film A Glimpse Inside the Mind of Charles Swan III.

[17] For the 2013 film Machete Kills, in which Sheen played the President of the United States, he was credited under his birth name Carlos Estévez.

The film also featured Whoopi Goldberg, Gina Gershon, Luis Guzmán, Wood Harris, Jacqueline Bisset, and Bruce Davison.

[45] During this time, he filmed an advert for car servicing company Ultra Tune, which was the next installment in their controversial "Unexpected Situations" series alongside Parnia Porsche, Laura Lydall, Tyana Hansen, and Imogen Lovell.

[48][49] In 2011, Sheen set a Guinness World Record as the "Fastest Time to Reach 1 Million Followers" on Twitter, adding an average of 129,000 new followers daily,[50] as well as a Guinness record for "Highest Paid TV Actor Per Episode – Current" at $1.25 million while he was a part of the cast of Two and a Half Men sitcom.

[55] However, on April 1, 2011, the Detroit Free Press featured an article that stated as of March 30 that there were over 1000 tickets available from a third-party reseller, some at 15% less than the cheapest seats sold at the Fox Theater.

He received a mixed reaction from the audience,[61] but has expressed appreciation for the culture by describing himself as a Juggalo[62] and wearing a baseball cap featuring the Psychopathic Records logo in public and during production meetings for Anger Management.

[1][91][92] On March 1, 2011, Sheen was concurrently living with 24-year-old pornographic actress Bree Olson and 24-year-old[93] model and graphic designer Natalie Kenly, whom he collectively nicknamed his "goddesses".

[98][99] In a January 2013 interview on Piers Morgan Tonight, Sheen stated that he was in a relationship with adult film actress and 2011 Penthouse magazine Pet of the Month Georgia Jones.

[105] In 2015, Rossi sued Sheen after his announcement of being HIV-positive and for various other allegations such as "assault and battery, emotional distress, false imprisonment and negligence".

Sheen was found in his seaside home by a friend, after which paramedics rushed him to Los Robles Hospital & Medical Center in Thousand Oaks, California, where he was described as being in "serious condition" after his stomach was pumped.

[124] On August 2, 2010, Sheen, represented by Yale Galanter,[125] pleaded guilty to misdemeanor assault as part of a plea bargain that included dismissal of the other charges against him.

[134] Sheen's disclosure of his HIV-positive diagnosis corresponded with the greatest number of HIV-related Google searches ever recorded in the United States.

"[citation needed] Sheen was the 2004 spokesperson for the Lee National Denim Day breast cancer fundraiser that raised millions of dollars for research and education regarding the disease.

[145][146] On March 27, 2008, Sheen and Jenna Elfman co-hosted the Scientology-affiliated New York Rescue Workers Detoxification Project charity event.

[147] Sheen donated one dollar from each ticket sold from his "My Violent Torpedo of Truth/Defeat is Not An Option Show" 2011 tour to the Red Cross Japanese earthquake Relief Fund.

Presenting his views as a transcript of a fictional encounter with Obama, he was characterized by the press as believing the 9/11 Commission was a whitewash and that the former George W. administration may have been responsible for the attacks.

"[157] Sheen has received numerous accolades including a Golden Globe Award for Best Actor – Television Series Musical or Comedy for Spin City in 2002.