Welcome To The Crazy Life Of Charlie Sheen

Nobody has graced the celebrity world quite like Charlie Sheen. The man who blew our minds on Two And A Half Men has had plenty of action both on and off the screen, as well as a crazy personal life.

Sheen has been successful both on the big screen and through his exploits on television. Movies such as Platoon, Wall Street and Hot Shots have etched his name into Hollywood lore. But how did it all begin for Charlie?

Let’s take it back to the very beginning. Janet Templeton delivered her baby into the world on September 3, 1965 in New York City. But life got off to a rough start as he was born a “blue baby.” Naturally, parents Martin and Janet were alarmed by this news and wanted their newborn son to be healthy. Thankfully, a doctor by the name of Irwin saved his life. So his parents named him in honor of the doctor, calling him Carlos Irwin Estevez.

Sheen comes from a talented family and many of his immediate relatives have also been successful in the acting world. This certainly applies to his father, Martin Sheen, who has starred in classic movies such as Apocalypse Now and Badlands as well as NBC’s hit show The West Wing. Charlie’s brother Emilio Estevez also made a name for himself as a Hollywood star, mainly due to his involvement as a member of The Breakfast Club supergroup, The Brat Pack.

Not only did he come from Hollywood royalty. Sheen also had a star studded list of friends during his formative years. Future film stars such as Sean Penn, Robert Downey Jr. and Rob Lowe all attended Santa Monica High School with Charlie. These actors spent a lot of time together making home movies. Also, Penn’s brother Chris and Lowe’s brother Chad would contribute to the Sheen’s amateur productions. Even Tom Cruise got in on the act!

Another Hollywood star who apparently was close with Sheen at one point was 90s icon, Winona Ryder. According to Charlie, he was responsible for creating the actresses stage name. Believing that working under her birth name Horowitz wouldn’t fly, he advised her to perform under a different moniker. Sheen claimed that while they were listening to “Riders On The Storm” by The Doors, they agreed that having the name Rider with a “y” would be cool.

Despite having friends around him who would also go on to do great things, Charlie’s years in education would come to an abrupt and unceremonious end. Only a few weeks before he was expected to graduate, Sheen was expelled from his high school after poor grades and bad attendance. He had also been arrested for credit card fraud only a few months prior to graduation. And despite having a dream to play baseball as well as going to college, Sheen missed out.

Even before hitting the big time, Sheen had made somewhat of a family of his own. After being romantically involved with his high school sweetheart Paula Profit long after dropping out, the couple had some good news coming their way. Profit gave birth to Cassandra Jade Estevez on December 12, 1984, which delighted Sheen. Both parents were only 19, and Cassandra would be the first of the five children Charlie would end up having with different women. But more on that later.

Like many actors, Sheen’s early career in Hollywood featured a string of low-profile cameos. Despite being uncredited, he made a brief appearance in his father’s movie, Badlands. But one of Sheen’s most memorable early roles came in 1985 when he played an intoxicated teen in the classic Ferris Bueller’s Day Off. In order to get into the right shape for the role, Sheen didn’t sleep for two whole days before shooting his scene. Despite his recent meltdowns, Sheen was completely sober during this period.

Charlie Sheen’s big break came a year later when he starred in Oliver Stone’s Oscar winning war movie, Platoon. But Charlie’s career (and life) could’ve been over before it even started. In a scene involving an open-doored helicopter, Charlie was inside the aircraft with his co-star Keith David. When Sheen tripped and was on his way out of the chopper, David clung onto him and saved his life. Thanks to David, Charlie lived to fight another day.

Platoon wouldn’t be the only occasion that Sheen diced with death. Only a year later, while filming the action movie No Man’s Land, Sheen once again risked his life while on set. After a squib had hardened overnight, it exploded right next to Charlie’s face, scarring his chin and caused a loss of hearing. Sheen couldn’t hear for four weeks and required eight stitches to the chin. But he survived and still has the scar to prove it.

Sheen was engaged to actress and former model, Kelly Preston. But in January 1990, things took a terrible turn for the worst. A serious advocate for the right to bear arms, Sheen usually had many firearms at his disposal. On one fateful day, Sheen accidentally shot Preston in the arm. This was swiftly followed by her decision to cancel the engagement and finish with Sheen completely. Despite feeling terrible about what had transpired, Charlie kept his arsenal.

During the early nineties, Sheen was offered a variety of roles but turned many down. Movies that the actor was offered to star in included White Men Can’t Jump, Indecent Proposal and The Cowboy Way. While the three movies all had mixed receptions both critically and commercially, Woody Harrelson was the man who took the roles that Sheen declined. While both actors have had similar trajectories in terms of their careers, Harrelson pretty much overcame all his major setbacks…

Let’s return to Sheen’s personal life. His first marriage came in 1995 when he tied the knot with Donna Peele. However, the marriage would turn out to be short lived and end under terrible circumstances. After it was revealed that Sheen was a client of an escort agency run by Madam and TV personality Heidi Fleiss, Peele was heartbroken and immediately filed for the divorce. The couple officially separated in 1996. Unfortunately, his commitment issues would come back to haunt him…

One of Sheen’s most high profile relationships came five years later. But admittedly, it wasn’t love at first sight. Charlie met fellow Hollywood star Denise Richards while shooting the comedy Good Advice. But the couple barely spoke off camera. However, they eventually hit it off when Richards featured on the TV show Spin City, which also starred Sheen. After being engaged for a year, the couple tied the knot at the showrunner Gary David Goldberg’s house on June 15, 2002.

Shortly after marrying Richards, Sheen got his biggest role to date, when he was cast as Charlie Harper in CBS’s Two And A Half Men. The sitcom became an instant classic and this was in no small part due to creator Chuck Lorre’s masterstroke to let Sheen essentially play himself. Three Emmy and two Gold Globe nominations later, Sheen became the highest paid TV star in the world and was making $1.8 million per episode during his final season.

With one of the most stunning actresses by his side and his superstar status, Charlie was at the peak of his powers. Then the couple was blessed with two daughters, Sam J and Lola Rose. When Sam was born, Sheen was in the middle of shooting the hit horror spoof, Scary Movie 3. So in honor of this, Charlie and Denise wanted to use the letters “S” and “M” in her name. It seemed like “Sam” was the perfect choice.

But like most things in Sheen’s life, his relationship with Richards wouldn’t last. After accusing Charlie of numerous incidents of substance abuse, Denise felt like this was detrimental to the dynamic of their relationship. She had not signed up for this when they hit it off in 2001. There was also numerous reports of Sheen having threatened Richards. So the Hollywood couple came to an end and were divorced by the end of 2006. A custody dispute over Sam and Lola followed.

It only took one year after his split with Richards for Sheen to move on and find someone else. This time, the actor hit it off with actress and real estate investor Brooke Mueller. Then on May 30, 2008, the couple tied the knot. Would it be third time lucky for Charlie? Only time would tell. And things seemed promising, especially after the newlyweds brought twin sons, Bob and Max into the world. But by November 2010, they had divorced. Why?

On December 25, 2009, Christmas Day of all days, Sheen had been arrested on suspicion of domestic abuse. He was charged with a variety of felonies, including felony menacing, third-degree assault and criminal mischief. Sheen was dismissed of most of the charges but pleaded guilty to misdemeanor assault. In the end, he did not need to spend one day in prison. Instead, Sheen was required to spend 30 days in rehabilitation, 30 days probation and to receive 36 hours worth of anger management.

The event completely turned the relationship on its head and paved the way for their separation. As a result of the allegations, Mueller had a restraining order put in place against Sheen and in March 2011, police took Bob and Max out of Sheen’s residence. But it turns out that both Mueller and Sheen were fighting similar demons during the relationship. It was just a bad match from the start. The divorced was finalized on May 2, 2011.

After his marriage with Mueller completely broke down, due to the shared instabilities, Sheen went into rehab for the third time in 12 months. The production of Two And A Half Men was stalled and would only continue once Charlie was back up to speed. However, CBS decided to cancel the season altogether. This is because Sheen spoke out publicly against show runner Chuck Lorre. As a result, Sheen demanded a 50 percent raise, believing that he was underpaid in relation to the show’s success.

Sheen’s downward spiral into chaos continued when he invited two women to move in with him. In 2011, the actor was sharing an apartment with adult actress Bree Olsen and graphic designer Natalie Kenly. Sheen referred to them as his goddesses. But the “divine” arrangement was short lived, and both women left Charlie, one shortly after the other. But it didn’t take long before he was dating another adult star, Georgia Jones. She was 2011 Penthouse magazine Pet of the Month.

The circus that was Sheen’s love life did not stop there. A few years later, he proposed to former adult star Scottine Ross, better known as Brett Rossi. But something changed in Sheen’s mind, and the couple mutually decided to call off the wedding. “I’ve decided that my children deserve my focus more than a relationship does right now,” he said. “I still have a tremendous fondness for Scotty and I wish her all the best.”

Charlie’s philanderous ways were starting to catch up with him. After ex-wives Brooke and Denise demanded more child support, Sheen furiously reduced the amount he was already paying from $55,000 to $10,000. In the very same month, the actor was reportedly being investigated by the LAPD. This was because he was accused of threatening to kill Brett Rossi, his previous lover. It seemed like whatever direction he turned, Charlie simply couldn’t avoid the drama he had amassed over the years.

Sheen’s decline was in full effect, and this was truly apparent after the actor’s infamous public meltdown, which was broadcasted for the entire world to see. Charlie used numerous bizarre phrases in his interviews. Some of the catchphrases that derived from these meetings such as his claim to having “tiger blood” and that he was “winning” have become world famous. “I’m tired of pretending I’m not special. I’m tired of pretending I’m not a total b****in’ rock star from Mars,” he said.

Despite the drama, the self-declared “warlock” has a lot to brag about in a controversial but illustrious career. Sheen even has his name in the Guinness Book Of World Records, after breaking the record for the “Fastest Time to Reach 1 Million Followers” on Twitter. He had about 129,000 new followers per day, meaning that he reach a million followers in just over a week. He has also broken the record for “Highest Paid TV Actor Per Episode” multiple times.

Since his high school days, Sheen has been a huge baseball fan and is a loyal fan of the Cincinnati Reds. His love for all things nostalgic in baseball runs deep. This was certainly evident when he owned the 1986 playoff ball that Mookie Wilson hit and rolled through Bill Buckner’s legs. Since then, Charlie sold the ball and has loaned out many rare baseball cards to one of his favorite New York sports restaurants. Sadly, they were stolen.

Charlie isn’t shy when it comes to ink. The actor has over a dozen tattoos on his arms and chest. Over the years, some have come and gone, but Sheen has kept the majority of them. Just below his chest, there is a banner reading “death from above” with an apple dropping from it. Other highlights include an image of Charlie Brown with a thought bubble that reads “MOM.” He even has his catchphrase “winning” planted on his wrist.

Even though he has had plenty of debts and child support to pay, Sheen’s net worth, which has significantly dipped in recent times, is still very impressive. While on Two And A Half Men, 22 episodes per season meant that the actor made approximately $48 million every year. Sheen is also extremely fond of classic race cars such as his prized possession, the 1966 NASCAR Ford Mustang. He also owns a Mercedez Benz S600 and even delved into property during his heyday.

Sadly, Sheen revealed on November 17, 2015 that he’s HIV positive. The actor was apparently diagnosed four years prior to the announcement and called the term HIV: “three hard letters to absorb.” It is reported that Sheen has paid extortionists in excess of $10 million to not reveal his condition to the public. Despite the chances, Sheen has repeatedly claimed that it’s impossible any of his partners could have caught the virus from him, has always been open with partners about his condition since being diagnosed.