With his recent admission that he’s HIV positive, Charlie Sheen provided us with another chapter in his always tumultuous personal life. From the time he burst onto movie screens in mid-1980s teen movie such as Lucas and Red Dawn, Charlie Sheen has been making headlines for his high octane personal life that, over the years, has involved drug arrests, stints in rehab, hookers, trashed hotel rooms, shootings, overdoses, family interventions, child services, and legendary feuds with studio executives. He even suffered a stroke in 1998 after a drug overdose. In fact, “Is Charlie Sheen dead?” has been a trending topic on Google on more than one occasion. And while there are occasional periods of calm, it is never long before Charlie Sheen is back on the front pages of newspapers for some new, and usually outrageous, incident. Here then are 10 of Charlie Sheen’s most explosive moments over the years:

9. Being drunk during filming of Wall Street

The 1987 film Wall Street directed by Oliver Stone is considered a modern classic. Actor Michael Douglas won an Oscar for his portrayal of ruthless stock broker Gordon Gekko in the movie. Yet, the entire project was almost derailed by the fact that Charlie Sheen was drunk during shooting of the film. And we mean drunk all the time. In an interview, Sheen stated: “I’d begun drinking all the time. We shot in New York City, so I’d be out to the bars every night till 3 or 4 a.m., then try to show up for a 6 a.m. call to stand toe-to-toe with Michael Douglas and handle 50% of a scene.” It was only an intervention by Charlie’s father, Martin Sheen, who had a supporting part in the movie, that helped stabilize Charlie Sheen’s drinking and got Wall Street completed. Still, director Oliver Stone has stated that he will never work with Charlie Sheen again.

8. Shooting then fiancée Kelly Preston

There are many ways to get a wedding called off. But probably one of the worst, and least advisable ways, is to shoot your fiancée. Yet that is exactly what a drunken Charlie Sheen did back in 1990 when his loaded hand gun accidentally went off and shot actress Kelly Preston in the arm. The two were engaged at the time, but after being treated for a gunshot wound and released from hospital, Kelly Preston promptly called off the engagement and quickly married actor John Travolta a short time later. Fortunately for Charlie Sheen, no charges were filed in the shooting. After some persuading, Kelly Preston went along with the notion that the whole shooting had been an accident and misunderstanding. Yeah, sure. That’s the ticket.

7. Pulling a knife on his dentist

Really, who pulls a knife on their dentist? But that’s exactly what Charlie Sheen did in 2014. While being treated for an abscessed tooth, Charlie Sheen apparently took exception to the pain being inflicted on him, punched out a dental technician and then pulled a knife on the dentist who was performing the procedure. Apparently, all this occurred after Charlie Sheen had been administered nitrous oxide to keep him calm while the abscessed tooth was treated. Fortunately for all involved, one of Charlie Sheen’s bodyguards intervened to tell the dentist that Charlie was allegedly high on rock cocaine at the time and didn’t know where he was or what he was doing. Okay then, that explains it. The problem was that Charlie was smoking rock cocaine before going to the dentist. Well, that seems reasonable… Of course, this isn’t the first time Charlie Sheen has gotten into trouble for pulling a knife on someone. He was famously arrested on Christmas Day 2009 for pulling a knife on his then girlfriend Brooke Mueller. On Christmas Day!

6. The Las Vegas hooker party

In January 2011, Charlie Sheen was hospitalized after partying for 36 hours in Las Vegas with a bevy of hookers and porn stars. Porn star Kacey Jordan claims that Charlie Sheen paid her $30,000 to party with him and a dozen other girls over nearly two days. However, the good times ended when an ambulance was called and Charlie Sheen was rushed to hospital – allegedly suffering from severe abdominal pains. The official medical issue was listed as a hernia, but friends and family were later quoted in the tabloids as saying that Charlie had overdosed on cocaine during the extended party. Bummer, man.

5. Denise Richard divorce allegations

It can be expected that there be some bad blood between people any time they get divorced. After all, the dissolution of a marriage is difficult on everyone involved – and feuding parents can often level unfair charges at each other when battling for custody of the kids. Yet the accusations fired at Charlie Sheen by his then-wife, actress Denise Richards, during their divorce takes things to a new low. In her petition for divorce filed in court back in 2006, Denise Richards claimed that Charlie Sheen is a gambling addict, watches child pornography, frequently buys prostitutes, and once forced her to have an abortion. Yikes! Denise Richards also claimed that Charlie Sheen stopped to place a gambling bet while driving her to the hospital to deliver their second child. Classy! So how did Charlie Sheen respond, you ask? By calling Denise Richards a “sad, jobless pig who is talentless and a bad mom.” Always nice to see people take the high road in these situations.

4. Children are removed from his house

You never like to see kids get caught in the middle of their parents’ problems. But that’s what happened amidst Charlie Sheen’s much publicized 2011 battle against the CBS television network and its producers after they fired him from his popular sitcom Two and a Half Men. As Charlie holed up in his mansion with a crew of porn stars, bodyguards, and various hangers on, and gave one ranting interview after another against his former bosses, his two girls by actress Denise Richards, Sam and Lola, were removed from his home by child protective services and Charlie Sheen subsequently lost joint custody of them. Denise Richards now has sole custody of the kids. Not to worry though, Charlie Sheen still pays a reported $50,000 a month in child support. So that’s good, we suppose.

3. Destroys New York’s Plaza Hotel

A lot of celebrities have busted up hotel rooms over the years. But few took things as far as Charlie Sheen back in 2010. While shacked up in New York’s swanky Plaza Hotel with a hooker, Charlie apparently flew into a rage and completely destroyed the suite he was in – breaking everything from a chandelier to the tables in the room. Police were called and Charlie Sheen was taken to New York Columbia Presbyterian Hospital for a psychotic episode. Estimates at the room damage ranged from $7,000 to $10,000, and several hotel staff who witnessed the room destruction had to take stress leave. Better yet, Charlie Sheen’s daughters were reportedly staying in the adjacent room during the incident. Charlie’s quick thinking publicist blamed the problems on a bad reaction to medication. Sad but true.

2. Testifying at the Heidi Fleiss prostitution trial

Who can forget the trial of famed Hollywood madam Heidi Fleiss? Or that Charlie Sheen was the star witness at the infamous trial? Back in 1996, Hollywood stars and executives were gripped by fear over reports that Heidi Fleiss planned to “name names” at her trial and reveal who some of the high powered men were that used her prostitution services. But, in the end, it was only Heidi’s biggest client, Charlie Sheen, who was outed and called to take the stand at the trial. While in the witness chair, Charlie Sheen admitted under oath that he had spent hundreds of thousands of dollars on prostitutes and used them on a weekly basis. Ironically, Charlie Sheen scored a lot of points by taking the stand and not naming names of the other people he knew that used Fleiss’ services. Many people claim that Charlie Sheen’s career has managed to continue despite his personal problems because many Hollywood executives are indebted to him for keeping quiet during the Heidi Fleiss trial.

1. The messy exit from Two and a Half Men

The television show Two and a Half Men was a major hit for the CBS television network, and, for a while, Charlie Sheen, the show’s star, was the highest paid actor on TV. He earned $1.8 million per episode at the show’s peak. However, all that success and money didn’t prevent Charlie Sheen from imploding and leaving the series in one of the most public and bizarre meltdowns in Hollywood history. Tiring of his antics, tardiness and bad behaviour, Chuck Lorre, the executive producer of Two and a Half Men, fired Charlie Sheen from the show. What followed was literally a two month public meltdown by Charlie Sheen, who, at his most manic, went on television to belittle his former boss and the CBS Network. Along the way, Charlie Sheen coined a number of now legendary phrases for himself, including ‘Winning!’ and “I’m a rock star from Mars.” He also amassed a Twitter following of more than one million people during the public implosion. So popular did the meltdown become, that Charlie Sheen turned it into a one man show that he took on tour to cities across America in the spring of 2011. And, with his popularity soaring, Charlie Sheen was even given a new sitcom – the aptly named Anger Management, where he plays a psychiatrist helping patients with anger issues. Only Charlie Sheen could pull all this off and still come out on top. Well played, sir.