Charlie Sheen has maintained a career in film and television for nearly four decades, and when he’s not appearing on screen, he’s appearing in headlines for his much-storied and controversial lifestyle. So, warts and all, here are 42 facts that help explain Charlie Sheen’s outrageous reputation.
42. All in the Family
Charlie Sheen’s real name is Carlos Irwin Estevez. His parents, Martin Sheen and Janet Templeton, are both actors. Sheen followed his parents into the business, as did his siblings, who all went into the film business using their original names: Emilio Estevez, Ramon Estevez, and Renee Estevez.
41. Named After His Rescuer
Sheen was a ‘blue baby’ when he was born—basically, a baby suffering from cyanosis. The doctor who saved his life was named Irwin, so his parents made “Irwin” Sheen’s middle name in their gratitude.
40. What Can I Say? It’s A Great Name!
As of 2018, Sheen has starred in three separate television series in which his character is also named Charlie: Spin City, Two and a Half Men, and Anger Management. To be fair, the latter two were hardly deep departures from Sheen’s public persona.
Twice in his career, Sheen was considered to play roles that eventually went to Keanu Reeves. They were Jonathan Harker in Bram Stoker’s Dracula and Johnny Utah in Point Break. We could debate forever on whether that was a dodged bullet or a missed opportunity, but we’re still wrapping our heads around the coincidence of the first names being so similar.
38. That’s What I Call Winning!
Sheen held the record for being the highest paid actor on television. He was earning nearly $2 million per episode of Two and a Half Men just before his departure from the show.
37. What a Coincidence!
While Sheen and his older brother, Emilio Estevez, were growing up, they both went to Santa Monica High School. Their love for films was already evident, and they made friends with other like-minded guys. Among these friends were Sean Penn, Chris Penn, Rob Lowe, and Robert Downey Jr. They would collaborate on amateur films together, and all of them ended up making it big in Hollywood. Given their shared connections to the film industry right out of the starting gate, we’re wondering if Santa Monica High School caters specifically to movie royalty—that said, considering the personal problems that many of them went on to, I wouldn’t send my kids there.
36. Ink Aficionado
Sheen has a total 12 tattoos on his body. Sadly, none of them are in the form of a tiger or the expression “Winning!”
35. It was a Very Good Year
For a time, baseball enthusiast Sheen owned the historic baseball which Mookie Wilson sent shooting between Bill Buckner’s legs during the 1986 playoffs. In an interesting coincidence, 1986 was the year his career really kicked off, with films like Ferris Bueller’s Day Off and Platoon giving him worldwide exposure.
34. And Thus I Baptize Thee
According to Sheen, he is the one who came up with Winona Ryder’s stage name. In 2012, he explained that he and Ryder—then known as Winona Horowitz—were hanging out together, listening to music by the Doors. While “Riders on the Storm” played, Sheen allegedly suggested Ryder as a good surname to replace Horowitz. Ryder has yet to confirm this, however, though it’s not like Sheen claimed he introduced her to Tim Burton or something. If anything, Jim Morrison would be just as responsible for Ryder’s name as Sheen!
33. Take That, Shakespeare!
In between his wild antics and film acting, Sheen managed to find the time to publish a book of poetry. It was released in 1988 under the title Peace of My Mind, which we can safely say is one of the most ironic titles ever conceived.
32. “Rocky Relationships” is an Understatement
One tragic side effect of Sheen’s history of substance abuse is the toxic fallout they had on his marriages. During his marriage to Brooke Mueller, Sheen was once arrested on suspicion of domestic abuse, while another ex-wife, Denise Richards, took on sole custody of her children with Sheen during the same time period. Both women also filed restraining orders against Sheen at different points in time. Miraculously, Sheen has since managed to mend his relationships with Mueller and Richards.
31. Near Miss
Being on a movie set with Sheen in the ’80s was a dangerous experience. While Sheen was filming No Man’s Land, A squib went off at the wrong time, knocking Sheen out cold. By the time he was out of the hospital, he was deaf in one ear for a month and needed 9 stitches on his face. He still carries a scar from the incident on his chin. As for No Man’s Land, while it made less than $3 million at the box office, it would go on to inspire—or be plagiarized by—the first Fast and Furious movie. So at least it was worth it, right Mr. Sheen?
30. A Lasting Partnership
One of Sheen’s early hit films was the spoof movie Hot Shots!, which also co-starred Ryan Stiles and Jon Cryer. These three actors would later reunite for Two and a Half Men.
29. If You’re Gonna Mock, Do it Right
Speaking of Hot Shots!, when it came to making its sequel, Hot Shots! Part Deux, they made it a big spoof of action movies, most famously the Rambo series. Sheen decided that if he was going to wear a singlet in a Rambo spoof, he would look as good as possible. He worked out 8 hours a day to prepare for the role, and he must have done something right, because a couple years after the movie came out, in 1995, Sylvester Stallone was asked if he was considering a fourth Rambo movie. His response was to jokingly suggest that they ask Sheen to star in it.
28. No Way! Those Movies Will Suck!
Believe it or not, there was a time when Sheen was much more famous for his films than his personal life. Naturally, he was offered a number of projects, some of which he refused to do. Amongst the films he turned down were Goodfellas, Carlito’s Way, Memento, The Karate Kid, and A Beautiful Mind. Interestingly, two of the films he passed on (White Men Can’t Jump and Indecent Proposal) became back-to-back starring vehicles for Woody Harrelson.
27. You’re Out… Never Mind, You’re In
According to Sheen, he first auditioned for the lead role in Platoon when he was 18 years old. However, his audition tape was rejected. Much to Sheen’s benefit, the project shut down, only to be resurrected a couple of years later. When Sheen met director Oliver Stone at an informal meeting, he was offered the role a few days later.
26. First Time Out West, I See
While filming the Western Young Guns, Sheen was allegedly terrible when it came to riding horseback. On at least one instance, he was unable to control his horse from taking off unexpectedly. Of course, given what he’d already endured on film sets, this issue was relatively minor in comparison.
25. Couldn’t Find a Glove to Slap Him with First?
During his post-Two and a Half Man public meltdown, Sheen heard that the Celebrity Rehab star known as Dr. Drew expressed his concern for Sheen’s well-being. Sheen responded by challenging Drew to a boxing match, offering to show “how unstable” he really was. The fight didn’t go forward, but that’s fine; Sheen’s response more than proved his point.
24. Early Days
Sheen’s first credited film role was in the Cold War-themed Red Dawn. Interestingly, he and co-star Jennifer Grey would go on to appear together in Ferris Bueller’s Day Off.
23. Charles for Fifteen Minutes
For a brief period in the late 1990s, Sheen tried to depart from his comedic background and go back to more the serious films which had made him famous in the first place. To make sure people took him more seriously, he changed his stage name to ‘Charles’ instead of ‘Charlie.’ The phase ended when Sheen plunged back into comedies soon afterward.
22. I Could Have Been a Contender!
Before he had his heart set on acting, Sheen had the potential go into professional baseball. In high school, his talent as a pitcher was such that he was offered a baseball scholarship to the University of Kansas. Unfortunately, the scholarship didn’t work out, on account of Sheen’s budding tendency towards self-sabotage. Bad grades and bad attendance meant that Sheen was expelled from high school. To add insult to injury, he was expelled just a few weeks before he was set to graduate.
21. Definitely a Relationship Deal-Breaker
Sheen is famously—or infamously—opposed to vaccinations. According to his ex-wife, Denise Richards, Sheen accused her of “poisoning” one of their children when Richards had her vaccinated. Richards claimed that was the moment where she knew their marriage was going to fall apart.
20. The Clown Drops a Truth Bomb
During that period of time when the Internet embraced the ALS Ice Bucket Challenge, Sheen was called out to participate. Sheen obliged, but instead of ice, he added a twist by dumping ten thousand dollars cash over his head, declaring that he was donating it to the ALS Foundation. He promptly challenged his former boss Chuck Lorre to donate the same amount of money to ALS research.
19. Toxic Work Relationship
During the filming of Oliver Stone’s Wall Street, co-star Sean Young managed to alienate many of the cast and crew. She and Sheen managed to clash harder than the rest, however. Sheen allegedly stuck a piece of paper on her back, calling her something unprintable. Surprisingly, nobody bothered to tell Young what Sheen had done.
18. Fond Memories?
According to Sheen, he thinks of his breakout film Platoon whenever he smokes. Given the grueling nature of the production—not to mention one of the big scenes in the film which involves the soldiers getting high together—we can certainly imagine why that might be.
17. Wake Up, Charlie, Time for Take Two!
One of his earliest roles was a brief appearance in Ferris Bueller’s Day Off as the juvenile delinquent who catches the eye of Jeanie Bueller in the police station. This was long before Sheen’s first-hand experience with substances, so his plan to prepare for the role was to stay awake for 48 hours to achieve the same look. This makes us wonder if his years of addiction might have been method acting for a sequel that never came.
16. Desperate Times
Shooting the Vietnam War film, Platoon, along with the two weeks of infantry training which counted as ‘rehearsal,’ led to brutal conditions for the cast. Sheen once said that with the lack of access to showers, the bug bites, and the grime of filming in the jungle, he resorted to scratching blood from his body. His co-star, Johnny Depp, had to physically stop Sheen from feeding this destructive habit. Sadly, Depp wasn’t around later on in the 1990s when Sheen’s other habits got out of control.
15. This isn’t Malibu, this is War!
Aside from all the physical troubles around the production, Sheen also clashed with Platoon director Oliver Stone. In one infamous incident, Stone was filming a scene where Sheen’s character helps unload supplies from a helicopter. Prior to filming, Sheen complained that the dirt and rocks being picked up by the whirling helicopter blades would hurt him while he was filming his part. Allegedly, Stone responded by ruthlessly mocking Sheen’s squeamishness with expletives and the suggestion that Malibu boy Sheen couldn’t handle “some pebbles.” Sheen ended up going bare-chested for the scene.
14. Returning Veteran
After shooting Platoon was finally over, and Sheen landed in LAX Airport, he reportedly kissed the ground upon his return to the States. As rough as Sheen seems to have had it, though, this was after he’d already signed the contract to appear in Stone’s next film, Wall Street.
13. Big Spender
In 1995, Hollywood madam Heidi Fleiss was on trial for pandering. At her trial, Charlie Sheen was made to testify under oath that he had hired women who were part of Fleiss’s prostitution ring. In fact, he had spent $50,000 on women who normally charged $2,500 per night.
12. Take-Your-Dad-To-Work Day
While they prepared to make the film Wall Street, Oliver Stone offered Sheen the chance to pick the actor to play his father in the movie. It came down to Jack Lemmon and Martin Sheen, Charlie’s real-life father. Sheen chose his father, though we wonder if this was because Martin was in the room at the time of the discussion.
11. Oh That Wacky Scoundrel
While Sheen and his brother, Emilio Estevez, were making the comedy film Men at Work, Sheen came up with an epic prank at Estevez’s expense. First, Sheen approached Estevez and claimed that he’d punched a member of the paparazzi in the face the night before. Then, while Sheen was filming a scene, he arranged for a police officer working as security to “arrest” him for the incident. Estevez was none the wiser until Sheen returned, laughing his head off. Punk’d!
10. Just to Make it Extra Real
For Sheen, shooting the hit sports film Major League wasn’t new territory, given his background in baseball during high school. However, Sheen did admit that he took steroids during the production to boost his baseball pitches up to 85 mph. And to think, he could have just injected some tiger blood instead!
In the TV series Spin City, Sheen’s character is named Charlie Crawford. This is the same name of a character that is shot by Billy the Kid (Emilio Estevez) in the film Young Guns, which also co-starred Sheen.
8. Clever Trick
Although Sheen’s latest TV show, Anger Management, only lasted two seasons, the makers of the show found a way to allow for the series to be released in syndication, and thus providing a stream of income to the people involved long after the show had officially ended. They did this by making the second season 90 episodes long, which brought the show’s episode number to 100, the minimum number of episodes required for syndication.
7. I Lost Out to Mr. Top Gun?!
After their successful collaborations on Platoon and Wall Street, Sheen and Oliver Stone looked to have a beautiful thing going. According to Sheen, Stone promised him the lead role in Born on the Fourth of July. However, Tom Cruise was cast in the lead role instead, a fact that Sheen didn’t learn until he got a phone call from his brother, Emilio Estevez. Sheen didn’t speak to Stone for years, but they managed to make up just in time for Sheen to make a cameo appearance in Wall Street: Money Never Sleeps.
6. Smells Like a Cookout in Here
In 2011, Sheen took part in The Roast of Charlie Sheen on Comedy Central. The event was watched nearly 6.5 million people, which made it the most popular roast in the history of Comedy Central at the time.
5. This is Becoming Too Meta
At one point in the film Wall Street, Sheen’s character visits his father in the hospital after he is nearly killed by a heart attack. Luckily for Sheen, he had the perfect inspiration to properly convey the emotions required for the scene. His father had suffered a heart attack on the film Apocalypse Now, and so he tapped into the emotions he’d felt during that very real emergency in his early life. In both cases, however, he did not end up receiving an Oscar nomination.
4. The Real Story
Long before she married John Travolta, Kelly Preston was engaged to Charlie Sheen—until one night, when he accidentally shot her in the arm. Well, as the story goes, she was accidentally shot somehow, and shortly after, they broke off their engagement. For decades, there’s been wild speculation about that night, and Sheen has finally addressed the rumors and revealed what really happened that night. He claims that while he was downstairs making coffee one morning, she picked up a pair of his pants and his revolver fell out of the pocket, going off. She was apparently clipped by shrapnel, and he helped her wrap her arm and called 911. We hope at least he got a gun safety lecture from the first responders out of it. Of course, that’s all according to Sheen—we’d love to hear Preston’s side of the story.
3. Strange Tribute
While Sheen was working on Scary Movie 3, he and Denise Richards celebrated the birth of their daughter. They named her Sam, as they wanted to have the letters S and M in her name as an homage to the Scary Movie franchise. Really, Scary Movie 3? Of all the movies you’ve been in?
2. It’s Super Effective!
In 2015, Sheen publicly admitted that he was HIV positive, and had been for four years. While this did cause a flurry of questions into whether Sheen had been responsible with his sex life, a more positive side to this news was the fact that Sheen’s public statement encouraged nearly 3 million Google searches into the subject of HIV. Not only that, a study concluded that there was a 95% increase in over-the-counter at-home HIV testing kits being sold. This was dubbed the “Charlie Sheen Effect,” with people declaring that “Charlie Sheen did more for HIV education than most UN events do.” That seems a little harsh, but I guess every little bit helps.
1. Almost a Casualty of War
While filming Oliver Stone’s Vietnam War film, Platoon, Sheen and fellow actor Keith David were inside a helicopter with its door still open. At one point, the helicopter turned too sharply, and Sheen fell right towards the open door. According to Sheen himself, David grabbed him and pulled him back just in time, saving his life.