They don't make unhinged celebs like they used to, but at least we've still got Charlie Sheen. We can all remember the 2011 meltdown when he lost the highest-paying job on TV despite his "tiger blood" and "Adonis DNA". But the trainwreck that is Charlie Sheen went off the rails long before 2011—and to be honest, it continues to this day.
1. He's Not Charlie Sheen
Charlie Sheen isn't really Charlie Sheen. Carlos Estevez was born in New York City, the youngest son of Ramon Estevez and Janet Templeton. Ramon, an actor, eventually took the name "Martin Sheen" to help his career. Years later, Carlos would follow suit—though his older brother Emilio decided to keep the birth name. And that wasn't the only way little Carlos took after his father.
2. He Got Started Early
Charlie Sheen (though still Carlos back then) got his first role before he hit double digits. At age nine, he appeared in his dad's movie The Execution of Private Slovik. He couldn't have realized it, but it was his first step down a dark path. The company he kept didn't exactly help matters either.
Wall Street (1987), Twentieth Century Fox
3. His Friends Got Famous Too
As Martin Sheen's acting career took off, the family moved from New York out to California. There, Sheen eventually attended Santa Monica High School, where he met some very famous friends. Along with his older brother Emilio, Sheen ran around with Robert Downey Jr, Rob Lowe, and Sean Penn.
That's a pretty messy group of buddies—but Sheen still probably takes the crown.
4. He Loved Making Movies
It wasn't all about partying and dope at first. Young Charlie Sheen had a genuine interest in acting, making amateur Super 8 movies with his brother and the other little Brat Packers like Penn and Lowe. Good thing, too: Because the whole "school" thing really wasn't Sheen's strong suit.
Platoon (1986), Orion Pictures
5. He Got Expelled
The teenaged Charlie Sheen was a great baseball player—but an absolutely terrible student. Although he enrolled at Santa Monica High for his senior year, he couldn't quite get himself over the finish line. Mere weeks before he was supposed to graduate, school officials expelled him for his terrible grades and his lack of attendance. But while he didn't get a degree, he did get something out of his high school experience...
Major League (1989), Paramount Pictures
6. He Had A Child Before Getting Famous
Charlie Sheen's love life is a chaotic mess, but it started simply, with a high school sweetheart. Sheen started seeing Paula Profit at Santa Monica High, and they had a child together: Sheen's oldest, Cassandra Estevez. The pair never married, and their relationship didn't last long after Sheen left high school.
Maybe Profit saw what kind of man Sheen was becoming, and got the heck out of there while she still had a chance.
7. He Started At The Bottom
Carlos Estevez's acting career started with more of a fizzle than a bang. He left school, took the name Charlie Sheen, and started looking for roles. When he finally landed one, it didn't go exactly as planned. Producers cast Sheen in the role of Ron in Grizzly II: The Predator—a low-budget sequel to a 1976 horror movie.
It wasn't a glamorous role, but hey, beggars can't be choosers, right? Well, this was even worse than it appeared.
8. It All Fell Apart
Just a single day into making Grizzly II, disaster struck. One of the film's lead producers, Joseph Ford Proctor, simply vanished from the set—and it gets worse: Proctor was the one with the money. Eventually, the truth came out: Proctor was behind bars. The remaining producer managed to drum up enough funds to finish the movie, but the damage was done.
Wall Street (1987), Twentieth Century Fox
9. It Took Decades To See The Light Of Day
Lots of actors get their start with a cheap B-movie—but usually, at the end of it, people actually get to see it. Because of all the shenanigans with Proctor, Grizzly II never actually got released. That's what a baseball player like Charlie Sheen would call "a swing and a miss". But at least Sheen had company: Both George Clooney and Laura Dern had roles in Grizzly II, not that anyone saw them...
But Sheen wasn't going to let the failure stop him. He was tenacious, passionate, and—most importantly—a nepo baby! He wasn't going to take no for an answer.
E/R (1984), Sony Pictures Entertainment
10. His Career Took Off
Sheen didn't have to wait long for his career to start taking off. In 1984, he starred in the teen drama Red Dawn. Not long after that, he got a role in Ferris Bueller's Day Off. Not only were both of those movies, you know, released, but they were also huge hits! Then, in 1986, Sheen got the role that would turn him into a bonafide star.
11. He Starred In The Best Picture Of The Year
A lot can change in three years. One moment, Sheen appeared in a movie that didn't even get released. Next, he had the starring role in a Best Picture-winning film: Oliver Stone's Platoon. He teamed up with Stone again the following year in Wall Street—this time starring across from his own father. Charlie Sheen was officially a movie star, and he had Oliver Stone to thank.
So why didn't they work together again for almost 25 years? Well, as occasionally happens with Charlie Sheen, there was drama behind the scenes.
Platoon (1986), Orion Pictures
12. They Had A Falling Out
Oliver Stone's next movie was Born on the Fourth of July, which stars...not Charlie Sheen. Allegedly, Stone wanted to cast Sheen, but some wires got crossed and Sheen never got the offer. Eventually, Stone cast Tom Cruise in the lead role instead. Sheen had no idea until his brother Emilio told him the news.
Sounds like a simple misunderstanding, right? Well then, you haven't met Charlie Sheen.
Platoon (1986), Orion Pictures
13. He Stopped Working With Oliver Stone
Charlie Sheen was not happy Oliver Stone had offered his next leading role, and he knew how to hold a grudge. He refused to appear in another Stone movie ever again (though he eventually reprised his Wall Street role for a cameo in the 2010 sequel).
Cutting out the man who'd made him a star might seem like a bad idea, but it didn't slow Sheen down at all. He remained an extremely bankable movie star through the 90s—though that's around the time his public scandals started piling up.
14. He Wanted To Marry Kelly Preston
In the late 80s, Sheen started dating Kelly Preston. He must have been head over heels, because he soon popped the question—and she said yes! Unfortunately, Preston didn't yet realize how dangerous being with Charlie Sheen was. She was about to learn that the hard way.
15. He Shot Her
There are lots of reasons to call off an engagement, but "My fiance shot me" might be the best one. In early 1990, Sheen accidentally shot Preston in the arm. Maybe someone could forget something like that, but apparently, Preston is not one of them. She ended their engagement not long after the incident. Probably the smartest decision she ever made.
Sheen hit the open market yet again—and his next partners were a little more scandalous than Kelly Preston.
16. He's Always Been Into Adult Actresses
Charlie Sheen was a huge star in the 90s. He could date anyone he wanted—and he wanted to date adult movie stars. He was tied to several performers after his split from Preston, including Ginger Lynn and Heather Hunter. None of them got Sheen to settle down, though. But in 1995, during a job, Sheen finally found someone else he wanted to marry.
As long as he could keep himself from shooting her...
17. He Finally Tied The Knot
Charlie Sheen met up-and-coming model Donna Peele in 1995 and asked her to marry him almost immediately. He didn't even have time to shoot his new fiancee, because they married within just six weeks of their meet-cute. Maybe Donna Peele thought she'd hit the jackpot. In reality, she hit...whatever the opposite of "jackpot" is...
18. His Name Made Scandalous Headlines
Hollywood saw far bigger headlines in 1995 than Charlie Sheen's marriage. For instance, the infamous Hollywood Madam Heidi Fleiss's prostitution ring was big news. She allegedly serviced some of Hollywood's biggest names...including Charlie Sheen. His indiscretions became public not long after he tied the knot with Peele. Is it any wonder they called it quits after less than a year?
But Sheen's scandals were just beginning.
19. His Addiction Took Its Toll
On May 20, 1998, a friend of Sheen's arrived at his home and made a disturbing discovery: Sheen had had a stroke. Paramedics rushed him to the hospital, where doctors pumped his stomach, though he remained in serious condition. Anyone who had spent any time with Sheen probably guessed the cause of the hospitalization: Sheen had OD-ed.
Was this the wake-up call that Sheen needed to get clean? Well, not really...
20. He Didn't Want To Get Clean
Once he left the hospital, Sheen checked into a rehab clinic, but he wasn't exactly serious about it. He outright told the doctors that he didn't intend to stay. True to his word, he soon left, only for local sheriffs to force him to return almost immediately. Oh, we should mention, Sheen was already on probation from an earlier drug offense at the time of his OD.
He eventually completed rehab and finished his probation—just about the time his career started taking off again.
21. He Hit It Big On TV
Up to this point, Charlie Sheen had mostly been a movie star, but it was time for him to make the jump to the small screen. He replaced Michael J. Fox on Spin City, and people loved it! Sheen eventually won his first Golden Globe for his role on the show. But Spin City was nearing the end of its run. Sheen only appeared in the final two seasons.
Still, the show revitalized his career. After the health scare and rehab stints, things were starting to look up for Charlie Sheen. And his love life was going well too!
22. He Married Denise Richards
Sheen met Denise Richards in 2000, and for once in his life, he decided to play it slow. They bumped into each other again the following year when Richards guest-starred on Spin City. They started dating in October 2001—and, in classic Sheen style, he immediately cranked it up to 11. He popped the question by December 26, and the two of them married on June 15, 2002.
For once, it actually looked like Charlie Sheen was ready to settle down. (Spoiler Alert: He wasn't).
23. He Got The Role Of A Lifetime
The early 2000s were like a dream for Charlie Sheen. He won a Golden Globe, he married Denise Richards, and he had two beautiful daughters. And while Spin City may have ended in 2002, TV producer Chuck Lorre was looking for someone to star in his latest show. Capitalizing on Sheen's "bad boy" image, Lorre cast him in the sitcom Two and a Half Men.
The show would go on to be massively successful. It also broke Charlie Sheen for good.
24. His Marriage Fell Apart
Charlie Sheen had it made in the shade with Two and a Half Men—but behind the scenes, he just couldn't keep his life together. In March 2005, after less than three years of marriage, Denise Richards filed for divorce. She cited Sheen's drinking and substance problems, but that wasn't all the filing contained. It also revealed some disturbing accusations.
25. She Made Some Serious Accusations
Charlie Sheen's affinity for adult performers wasn't news—but it may have been worse than it appeared. While filing for divorce, Richards claimed that Sheen enjoyed gay films with "boys who looked underage", and that he was also attracted to underage girls. Looking at her court filing, it's honestly amazing that Richards lasted three years with Sheen.
But while Sheen was making scandalous headlines yet again, he was also making bank. It turns out, Two and a Half Men was an even bigger hit than anyone had dreamed of.
American Violence (2017), Status Media Entertainment
26. He Got PAID
By the end of his run on Two and a Half Men, Charlie Sheen earned a whopping $1.8 million per episode, making him the highest-paid TV star in history. But remember that whole OD, stroke, and rehab thing? Well, Sheen never really got clean—and now he had more money than he'd ever had before. How do you think that worked out?
27. He Got Married Again
Although I don't think anyone would describe Charlie Sheen as a "marriage guy," it's not for lack of trying. In 2008, he married his third wife, Brooke Mueller. She soon gave birth to twin sons—but if she thought she was going to be the one to finally change him, she was horribly mistaken. It wasn't long before he crossed the line.
28. He Spent Christmas In Handcuffs
Sheen and his wife spent Christmas 2009 in Aspen—he was the highest-paid man on TV, after all. But this was no holiday fairy tale. It was more like a horror story. Before Christmas Day was out, officers detained him for hurting his wife of barely a year. He was sentenced to rehab, probation, and anger management. Did they really think that was going to work?
This was the time when Sheen's life really went off the rails.
29. He Checked Into The Plaza
In October 2010, Sheen checked into New York City's opulent Plaza Hotel. His ex-wife Denise Richards was there as well, along with their two daughters—though Sheen stayed in his own room. His current wife, Brooke Mueller, was nowhere to be found. But if you think Sheen was going to take it easy because his family was across the hall...then you haven't learned anything yet.
30. He Lost It
In the middle of the night, a woman called the front desk from Sheen's room. Security went to investigate, and they found Sheen, barely clothed in a drug-fueled rage, tearing apart the room—he'd allegedly lost his phone and wallet after he'd gone "out partying". Oh, and that woman who called the front desk? Well, let's say she wasn't there for free...
According to reports, security found her unclothed and locked in a closet, fearing for her life. But, as always with Charlie Sheen, it gets worse.
31. He Was Supposed To Be "Clean"
Not only was Charlie Sheen partying with a working girl across the hall from his two young daughters. Not only did he cause $7,000 of damage to his hotel room. He was also just two months out of rehab when he did it. When the dust finally settled, Richards brought him to New York Columbia Presbyterian Hospital, though Sheen allegedly only agreed to go because it was either the hospital or handcuffs.
And this was just the start of Sheen's meltdown.
32. HE Left HER
Despite his team reporting that he'd checked into the hospital after "an allergic reaction to medication", word of Sheen's rant soon got out. Maybe he was looking for someone to blame his problems on, because mere weeks after the Plaza incident, he filed for divorce. Brooke Mueller had stayed with him after he hit her, but it was actually him who divorced her.
And, if you can believe it, the split soon got messy.
33. She Believed He Was Insane
A few months after Sheen filed for divorce, Mueller got a restraining order against him. In the document, she wrote: "I am very concerned that [Sheen] is currently insane". The authorities soon went to Sheen's home and removed the couple's twin sons. Sheen's addiction was well and truly ruining his life. And it was about to ruin his career too.
34. The Show Took A Break
Two and a Half Men was still airing at the time of the Plaza meltdown, but in January 2011, the show went on hiatus so that Sheen could enter rehab. However, the rehab took place in Sheen's home, and it was the third time he'd tried getting clean in a year. His family tried to support him through it—but Sheen wasn't interested in getting help.
35. He Didn't Want Support
With Charlie Sheen gone completely off the deep end, his father had to field constant questions about him. Martin Sheen tried his best, calling addiction a disease like cancer, and trying to offer his son support, concern, and love. Charlie wasn't having it though. His response? "I have a disease? Bull! I cured it...with my mind"!
Well, if he really was cured, he had a funny way of showing it.
36. He Went On Alex Jones
To this point, CBS still planned on having Sheen return to work on Two and a Half Men. It was, after all, one of the most successful shows on TV. Even despite everything he'd done, they still wanted to keep their cash cow. But then Sheen called into Alex Jones' radio show for another one of his deranged interviews.
Except this time, he crossed a new line.
37. He Went After His Boss
No one listening to Charlie Sheen on Alex Jones would have called him "cured". The rambling and erratic interview showed just how unhinged Sheen had become—especially when he started talking about Two and a Half Men creator Chuck Lorre. That turned out to be a terrible mistake. Lorre still thought Sheen needed help. Sheen disagreed—so he called Lorre a clown (and an anti-semitic slur for good measure).
Sheen said he was sorry that he embarrassed Lorre in front of his children by "healing at a pace that [Lorre's] un-evolved mind cannot process". And just like that, Sheen lost the cushiest gig on TV.
38. They Banned Him From Set
After the Alex Jones interview, CBS canceled the remaining episodes from that season and banned Sheen from the production lot. I guess Sheen thought they were just playing a big game, because he responded by asking for a 50% raise, claiming he was underpaid. How do you think that worked out?
39. He Got Fired
Chuck Lorre wasn't playing around. He fired Sheen and unceremoniously killed off his character on Two and a Half Men. This is when the "Charlie Sheen Meltdown" that everyone remembers truly began. Who doesn't remember him going on TV and saying he was a warlock with tiger blood and Adonis DNA? Who doesn't remember "winning"?
But while we all had a laugh at the crazy movie star, the truth behind the scenes was just plain sad.
40. He Moved In With Goddesses
At the time of his dismissal from Two and a Half Men, Sheen was living with an adult actress, Bree Olson, and a model, Natalie Kenly—both 24 and half his age. This is around the time the authorities took his sons from his home. He called Olson and Kenly his "goddesses"—but not even they could put up with his antics anymore. Both of them left him within months of his firing.
41. Another Relationship Fell Apart
For anyone, this would have been rock bottom—but rock bottom is just where Charlie Sheen lives. In 2014, he proposed to his latest girlfriend, adult actress Brett Rossi. They planned a wedding for that fall, but called it off just a month before the big day. Sheen said, "I've decided that my children deserve my focus more than a relationship does right now. I still have a tremendous fondness for [Rossi] and I wish her all the best".
Sounds quite mature, doesn't it? Well, as usual, there was more to this story than it appeared.
42. She Went After Him
Right around the time they were supposed to be wed, Rossi ended up in the hospital from an OD. Soon after, she took Sheen to court. The allegations included assault, emotional distress, false imprisonment, and negligence. It was terrible, but sadly, unsurprising for anyone who'd followed Sheen's troubles.
But this time, there was something new. Just when you thought Sheen couldn't sink any lower...
43. He Hid A Terrible Secret From Her
In 2015, Charlie Sheen made a shocking announcement: He was HIV positive, having been diagnosed four years earlier. He claimed to have the condition under control with an antiviral cocktail, saying it was impossible that he could have infected any of his partners. Well, apparently Rossi disagreed. She claimed that he hid his diagnosis from her when they were together.
I tend to believe her—especially when you hear the lengths Sheen went to in order to keep his condition a secret.
44. He Paid People Off
Sheen claimed that, between 2011 and 2015, he paid extortionists upwards of $10 million in order to keep his HIV status hidden from the public. Little wonder that Rossi decided to sue. But, despite their split, she wasn't free of Sheen yet—not by a long shot.
45. The LAPD Investigated Him
In April 2016, the LAPD announced that their stalking unit was investigating Sheen. This time, he allegedly threatened to kill his ex-fiancee Rossi. As we said: There isn't really rock bottom for Charlie Sheen. It's all rock bottom.
46. His Daughter Joined An Adult Website
Charlie Sheen has done a remarkably good job of staying out of the spotlight in recent years. Is he finally starting to settle down? We can only hope so. But new stories still find their way to him. In June 2022, the Sheen name made headlines, but this time it was his daughter. Sami Sheen started a fan subscription page soon after her 18th birthday, and you know people noticed.
In classic Charlie Sheen fashion, he managed to step in it almost immediately.
47. He Blamed Her Mom
This time, we'll give Sheen a little credit: It's probably quite the shock to find out your little girl is...not really your little girl anymore. Still, his reaction was far from ideal. He claimed it never would have happened if she lived with him, and put the blame on his ex, Denise Richards. Well, Richards didn't like that, and it wasn't long before Sheen changed his tune.
The Real Housewives of Beverly Hills, Evolution Media
48. He Got Over It
Richards must have had some choice words for Sheen, because only a day later, he announced that his daughter had his full support. He claimed that Richards had made some good points, and he wanted to be supportive. He was also supportive when Richards announced her own page on the same site soon after that.
In an odd twist, it seems like this latest scandal helped him finally mature, if only a little bit. Unfortunately, though, the demons from his past are always lurking.
49. An Old Scandal Resurfaced
In the 80s, when he was still getting established, Sheen starred in a movie with another young up-and-coming star: Corey Haim. After Haim's tragic passing in 2010, stories began to circulate regarding what Haim had suffered when he was a young actor. The National Inquirer published a piece that claimed Sheen had violated Haim in 1986 when they were working together and Haim was only 13 years old.
Sheen quickly sued the paper for libel—but the story wouldn't go away.
50. Corey Feldman Says It Was Him
Corey Feldman, another 80s child star who suffered horrible mistreatment, maintains the claim that it was Sheen who had gone after the 13-year-old Corey Haim. However, Haim's mother claimed it couldn't have been Sheen, because she believes it couldn't have happened without her knowing. Sadly, without Haim here to tell his story, the truth may never come out—but it remains perhaps the darkest stain on Charlie Sheen's already troubling legacy.
