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01
While engaged to Kelly Preston, Sheen accidentally shot her in the arm, prompting her to leave him and later marry John Travolta.
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02
Sheen credited actor Keith David with saving his life during the filming of Platoon 1986 by pulling him back into a helicopter after the pilot banked too hard.
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03
Before his Two and a Half Men termination, Sheen was the highest paid actor on a primetime series in television history, making $2 million per episode.
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04
In August 1990, Sheen’s family held an intervention for his drug abuse; he entered rehab for 30 days and stayed sober for exactly 366 days before drinking again at Nicolas Cage’s home.
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05
To prepare for his role as a stoner in Ferris Bueller’s Day Off 1986, Sheen stayed awake for 48 hours to look the part, even though his real-life addiction hadn’t begun.
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06
On May 20, 1998, Sheen suffered a stroke after a cocaine overdose and was hospitalized; he subsequently checked into a rehab clinic but fled after a few hours, only to be forced back by sheriffs. He later admitted the overdose was caused by injecting cocaine.
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07
Sheen was born a blue baby and was named after the doctor, Irwin, who saved his life.
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08
Sheen is the only member of his family to legally change his surname to Sheen; his father and siblings still use Estevez.
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09
Sheen drove Ben Affleck to Promises Rehabilitation Center in Malibu for alcohol abuse treatment.
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10
On November 17, 2015, Sheen publicly announced his HIV-positive status on the Today show, saying he was diagnosed four years earlier and chose to go public to stop blackmail.
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11
Sheen was offered a baseball scholarship by the University of Kansas.
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12
He auditioned for the role of Glen Lantz in A Nightmare on Elm Street 1984 but asked for more money than the production could afford; the role went to Johnny Depp.
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13
The noticeable scar on his chin resulted from a prop explosive that detonated accidentally while filming No Man’s Land 1987, requiring eight stitches.
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14
Sheen was considered for the role of Maverick in Top Gun 1986 but deemed too young; he later starred in the parody Hot Shots! 1991.
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15
He underwent both Army and Navy Seals boot camps for his roles in Platoon 1986 and Navy Seals 1990, respectively.
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16
Sheen attended Santa Monica High School alongside Robert Downey Jr..
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17
After a domestic dispute with his wife Brooke Mueller over Christmas 2009, Sheen surrendered custody of his daughters Sami and Lola to ex-wife Denise Richards.
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18
Robert Kirkman wanted Sheen to appear in the second season of The Walking Dead 2010.
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19
Sheen and his brother Emilio Estevez have both played sons of their real father Martin Sheen on screen: Emilio in The War at Home 1996 and Charlie in Wall Street 1987 and No Code of Conduct 1998.
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20
Sheen has a tattoo on his chest that reads Be Back in 15 Minutes.
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21
He fought constantly with older brother Emilio Estevez.
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22
On May 20, 1998, Sheen was hospitalized for a drug overdose; after his release he checked into Promises rehab for only one day, then was arrested for using medications and drinking, and re-entered Promises on doctor’s orders.
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23
Sheen was considered for Tim Robbins’ roles in Bull Durham 1988 and The Shawshank Redemption 1994.
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24
In 1991, Sheen and a friend obtained the film Guinea Pig: Devil’s Experiment 1985, rumored to contain snuff footage; they called the FBI, which tracked down the makers and confirmed the deaths were special effects.
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25
He turned down the role of Henry Hill in GoodFellas 1990, which went to Ray Liotta.
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26
He turned down the role of Daniel LaRusso in The Karate Kid 1984, which went to Ralph Macchio.
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27
On April 23, 1998, a thief stole two dozen rare baseball cards belonging to Sheen from a display case at the Official All-Star Cafe in Times Square, valued at $170,000.
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28
His first film with George Clooney, Grizzly II: Revenge 1983, remained unreleased due to FX problems.
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29
Sheen was considered for Tom Cruise’s role in Born on the Fourth of July 1989; he believed he had the part until his brother Emilio broke the news that Cruise had won it, leading to a years-long rift with Oliver Stone.
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30
Three films featuring Sheen have been selected for the National Film Registry: Badlands 1973, Ferris Bueller’s Day Off 1986, and Platoon 1986.
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31
Sheen has five children: daughter Cassandra Jade Estevez with ex-girlfriend Paula Profit, and daughters Sami Sheen born March 9, 2004 and Lola Rose Sheen born June 1, 2005 with Denise Richards.
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32
On July 4, 2020, Sheen celebrated one year of quitting smoking after having smoked for 32 years since 1987 while filming Platoon.
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33
Sheen announced on The Dr. Oz Show on January 11, 2016 that he quit drinking on November 18, 2015, the day after his HIV announcement on Today.
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34
Sheen has starred on three television series where his character was named Charlie: Spin City, Two and a Half Men, and Anger Management.
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35
Sheen and Denise Richards both had small roles in Loaded Weapon 1 1993 years before they met and fell in love on the set of Good Advice 2001.
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36
Sheen has admitted to smoking 40 cigarettes a day since 1986.
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37
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, which Richards said contributed to the marriage’s failure.
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38
Sheen is a baseball fanatic and knowledgeable about the sport and its players.
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39
He was considered for the role of Vincent Corleone in The Godfather Part III 1990, which went to Andy Garcia.
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40
Sheen is the brother of actors Emilio Estevez, Renée Estevez, and Ramón Estevez.
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41
Sheen received a star on the Hollywood Walk of Fame at 7021 Hollywood Boulevard on September 23, 1994.
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42
In 2011, Sheen set a Guinness World Record for Fastest Time to Reach 1 Million Followers on Twitter, adding an average of 129,000 followers per day.
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43
He was considered for the lead role in The Mighty Ducks 1992, which went to his brother Emilio Estevez.
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44
A lifelong Cincinnati Reds fan, Sheen donated $50,000 to the team’s community fund in August 2012 after the team raised a matching amount to have broadcaster Marty Brennaman shave his head on the field.
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45
Sheen was ranked the highest-paid TV actor in 2008, 2009, 2010, and 2011, and was ranked 12th in 2013 and 2014.
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46
Sheen pleaded no contest to a misdemeanor charge in June 2010 and was sentenced to 30 days in jail for a domestic dispute with his wife Brooke Mueller.
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47
He was considered for the role of Marty McFly in Back to the Future 1985, which went to Michael J. Fox.
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48
His father is of half Spanish and half Irish ancestry, and his mother has English and Scottish ancestry.
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49
Sheen once owned the baseball hit by Mookie Wilson in the 1986 World Series that went under Bill Buckner’s legs, later selling it.
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50
He became the highest-paid comedy star on television, earning $350,000 per episode for the upcoming season of Two and a Half Men at one point.