- Accidentally shot then fiancée Kelly Preston in the arm. Soon after that incident, she left him and married her formerly platonic friend John Travolta.
- Credited actor Keith David with saving his life during the shooting of Platoon (1986). According to Sheen, while shooting a battle scene in an open-doored Huey helicopter, the pilot banked too hard and Sheen was thrown towards the open door. He would have plunged through the door and fallen to his death, but David grabbed on to him and pulled him back in. The same thing happened to his brother Emilio Estevez during downtime in Apocalypse Now (1979) when Laurence Fishburne rescued him from quicksand.
- Played a stoner in Ferris Bueller's Day Off (1986). Even though his real life drug addiction hadn't started yet, Sheen told a magazine he stayed up for 48 hours to look the role.
- Was born a "blue baby". The doctor who saved him was named Irwin and his parents named him after the doctor.
- Before his Two and a Half Men (2003) termination, he was the highest paid actor on a primetime series in the history of television. During that time, he was making $2 million per episode.
- 8/3/90: His family held an intervention to try to get him to control his drug and alcohol abuse and enter rehab. He entered rehab for 30 days and ended up staying sober for exactly 366 days. His main goal was to make one year, and after making it, he drank the very next day at Nicolas Cage's home.
- Is the only member of his family to legally change his name to Sheen and pass that new name onto his children. Like his father and all his siblings, his birth name was Estevez. His father is still legally Ramon Estevez, and all his siblings still use the name Estevez.
- Drove Ben Affleck to Promises Rehabilitation Center in Malibu, CA, for treatment of alcohol abuse. (August 2001)
- On November 17, 2015, he admitted his HIV positive condition during an interview with Matt Lauer in Today (1952), in which he said that he was diagnosed four years ago. He chose to go public in order to stop people from blackmailing him for money.
- On May 20, 1998, Sheen suffered a stroke after overdosing while using cocaine and was hospitalized. Sheen was found in his seaside home by a friend, after which paramedics had to give emergency life-saving treatment and rushed him to Las Robles hospital. He was described as being in a "serious condition" after his stomach was pumped. Sheen subsequently checked into a rehab clinic days later but told doctors within hours that he did not intend to stay. Sheriffs later forced Sheen back into the clinic after he fled only hours after arriving. On August 11, 1998, Sheen, already on probation in California for a previous drug offense, had his probation extended for an extra year and entered a rehab clinic. In a 2004 interview, Sheen admitted that the overdose was caused by his injecting of cocaine.
- He was interested in the role of Glen Lantz in A Nightmare on Elm Street (1984), but according to producer Robert Shaye, he wanted more money than the production could afford. The role went to Johnny Depp in his film debut.
- He was considered for the role of Maverick in Top Gun (1986), but was deemed too young for the role. He would later star in the parody film Hot Shots! (1991).
- He and brother Emilio Estevez have both played the son of real father Martin Sheen; Emilio in The War at Home (1996), Charlie in Wall Street (1987) No Code of Conduct (1998) and two episodes of Spin City (1996). Martin also played the father of one of Charlie's girlfriends on Two and a Half Men (2003) and his father on Anger Management (2012).
- He was offered a scholarship to play baseball by the University of Kansas.
- He fought constantly with older brother Emilio Estevez.
- Robert Kirkman wanted him to appear in the second season of The Walking Dead (2010).
- The noticeable scar on his chin occurred while filming No Man's Land (1987). A prop explosive detonated accidentally, ripping into his chin and requiring eight stitches.
- Has done both Army boot camp and Navy Seals boot camp for his movies Platoon (1986) and Navy Seals (1990).
- Surrendered custody of his daughters Sami Sheen and Lola Rose Sheen to Denise Richards. Richards sought full custody after Sheen and his wife Brooke Mueller had a domestic dispute over Christmas 2009. (May 2010)
- Attended Santa Monica High School along with Robert Downey Jr..
- 5/20/98: Hospitalized in Thousand Oaks, CA, for a drug overdose. Upon release from the hospital two days later, he checked into a rehab center called Promises, where he stayed for only one day. His car was later pulled over and police arrested him for using medications and drinking. Sheen re-entered Promises on doctor's orders.
- Has a tattoo on his chest that looks like a note pinned to it that reads, "Be Back in 15 Minutes."
- His first film with George Clooney, Grizzly II: Revenge (1983), stayed unreleased because of FX problems.
- 1991: He and a close friend found themselves in possession of Guinea Pig: Devil's Experiment (1985), rumored to contain actual snuff footage. Unable to convincingly explain away the atrocities as special effects work, they called the FBI, which tracked down the makers of the film, who convinced them that the onscreen deaths were indeed special effects.
- Turned down the role of Daniel LaRusso in The Karate Kid (1984), which ultimately went to Ralph Macchio.
- He was considered for Tom Cruise's role in Born on the Fourth of July (1989). He thought he had the role in the bag until Emilio Estevez broke the news that Cruise won the role. Sheen was so angry about losing the role that he didn't speak to Oliver Stone again for years.
- (07/04/2020) Celebrated his one year anniversary of quitting smoking. He previously smoked for 32 years, starting in 1987 while filming Platoon.
- He has admitted smoking 40 cigarettes a day since 1986.
- Announced on The Dr. Oz Show (2009) (on January 11, 2016) that he quit drinking on November 18, 2015, the day after his HIV announcement on Today Australia (1982).
- 4/23/98: A thief stole two dozen rare baseball cards belonging to Sheen in NYC -- the cards, on loan from the star and valued at $170,000, were housed in a display case at the Official All-Star Cafe, a sport-themed restaurant in Times Square.
- Turned down the role of Henry Hill in Goodfellas (1990), which went to Ray Liotta.
- Has starred on three television series in which his character has been named "Charlie". They are Spin City (1996), Two and a Half Men (2003) and Anger Management (2012).
- Children: daughter Cassandra Jade Estevez, with ex-girlfriend Paula Profit, daughters Sami Sheen (born March 9, 2004) and Lola Rose Sheen (born June 1, 2005), with Denise Richards.
- He has appeared in three films that have been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: Badlands (1973), Ferris Bueller's Day Off (1986) and Platoon (1986).
- Is a baseball fanatic and is extremely knowledgeable about the sport as well as past and current players.
- He was considered for the role of Vincent Corleone in The Godfather Part III (1990), which went to Andy Garcia.
- Sheen is staunchly opposed to vaccinations. After separating from Denise Richards he sent a legal notice to his daughters' physician stating his lack of consent to vaccinate them. The dispute over vaccines seems to have played an important role in the failure of the marriage. Richards said in an interview in 2008, "When I vaccinated Sam, he accused me of poisoning her. And I knew when he said that that the marriage wasn't going to work.".
- He and Denise Richards both had very small roles in Loaded Weapon 1 (1993) (they do not share on-screen time), years before they met and fell in love on the set of Good Advice (2001).
- Of the Highest Paid TV Actors, he was ranked no. 1 in 2008, 2009, 2010 and 2011. He was ranked no. 12 in 2013 and 2014.
- He once owned the baseball that was hit by Mookie Wilson in the 1986 World Series that went under Boston Red Sox's first baseman Bill Buckner's legs for the game-winning RBI (He has since sold the ball).
- He was awarded a Star on the Hollywood Walk of Fame at 7021 Hollywood Boulevard in Hollywood, California on September 23, 1994.
- Plead no contest to a misdemeanor charge at a June 7 hearing, and will be sentenced to 30 days in jail instead. Due to this plea deal, the actor will avoid being sentenced to probation once he finished the time in jail. The sentence is a result of the domestic dispute with his wife Brooke Mueller and Sheen's arrest in late 2009. (June 2010)
- Was in attendance at Chris Penn's funeral at Holy Cross Cemetery in Culver City, California.
- A lifelong fan of the Cincinnati Reds, he announced in August 2012 that he would donate $50,000 to the team's community fund, which supports various charities. The donation came after the team raised another $50,000 in an attempt to get broadcaster Marty Brennaman to shave his head on the field after a Reds victory. After Brennaman shaved his head, Sheen offered to match the previous donation total.
- In 2011, Sheen set a Guinness World Record for Twitter as the "Fastest Time to Reach 1 Million Followers" (adding an average of 129,000 new followers per day).
- Former brother-in-law of Paula Abdul.
- His father is of half Spanish and half Irish ancestry, and his mother has English and Scottish ancestry.
- Enjoys deep-sea fishing.
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