'%20x='0'%20y='0'%20height='100%25'%20width='100%25'%20%0A%20%20%20%20%20%20%20%20%20%20xlink%3Ahref='data:image/jpg;base64,/9j/2wBDAAYEBQYFBAYGBQYHBwYIChAKCgkJChQODwwQFxQYGBcUFhYaHSUfGhsjHBYWICwgIyYnKSopGR8tMC0oMCUoKSj/2wBDAQcHBwoIChMKChMoGhYaKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCj/wgARCAAFAAoDASIAAhEBAxEB/8QAFQABAQAAAAAAAAAAAAAAAAAAAAb/xAAVAQEBAAAAAAAAAAAAAAAAAAACA//aAAwDAQACEAMQAAAArKYFf//EAB8QAAEEAQUBAAAAAAAAAAAAAAECAwQRAAUHEhMiYf/aAAgBAQABPwDXjEG6fe7DSuVHMYoeschbSxQNWB6NjHBTih9z/8QAFxEAAwEAAAAAAAAAAAAAAAAAAAECMf/aAAgBAgEBPwCdZ//EABoRAAAHAAAAAAAAAAAAAAAAAAABAgMxccH/2gAIAQMBAT8AchNaY//Z'%3E%3C/image%3E%3C/svg%3E)
Charlie Sheen is one of the most well-known actors in the world, but his rise to fame hasn't always been easy. From growing up in a famous Hollywood family to starring in Two and a Half Men, Sheen has become a household name.
But along the way, he's made headlines for the many beautiful women he's dated and his personal struggles that have pushed him to the brink. Let's dive deeper into the whirlwind romances and the tumultuous life of Charlie Sheen.
A Star is Born
Trending
Charlie Sheen was born Carlos Estévez on September 3rd, 1965, in New York City to actor Martin Sheen (real name Ramon Estévez) and artist Janet Templeton. He has two older brothers, Emilio and Ramon, and a younger sister, Renée, all of whom caught the acting bug as well.
During his early years, the family moved to Malibu, California. At just nine, Charlie Sheen made his first movie appearance. No one could have known just how big of a star the young boy would become.
High School
At Santa Monica High School, Sheen’s growing love for the entertainment industry continued to develop. He and schoolmates Robb Lowe and Sean Penn collaborated on amateur Super 8 movies, honing their budding acting abilities.
But just a few weeks before graduation, Sheen was expelled from school because of his poor grades and low attendance, marking the beginning of his lifelong taste for trouble. He decided to pursue an acting career, modeling his stage name after his father’s, inspired by the Catholic theologian Fulton J. Sheen. He didn't know then that it wouldn’t be long before Charlie Sheen became a household name.
Career Beginnings
Sheen’s movie career kicked off in 1983 when he was cast in the low-budget horror sequel Grizzly II: The Predator. He landed minor roles in movies such as Red Dawn and Ferris Bueller’s Day Off before getting his big break.
In 1986, the young actor was cast in his first major role in the Vietnam war drama Platoon. He received critical acclaim for his performance as US Army volunteer Chris Taylor. This role was about to launch Sheen’s career to heights he could never have imagined.
Becoming a Dad
While his career was just starting to take off, Sheen had a significant life event. He fathered his first child with his high school sweetheart, Paula Profit.
Profit and Sheen’s daughter, Cassandra Estevez, was born on December 12, 1984. The two were only 19 at the time and separated shortly after she was born. Cassandra was mostly raised by her mom, but she maintained a relationship with her dad. However, during her early years, Sheen was distracted by his burgeoning career.
Makings of a Movie Star
It quickly became clear that Sheen had what it took to become a star. Following his success in Platoon, he starred in the celebrated stock market drama Wall Street and the baseball flick Eight Men Out, as well as numerous action movies and comedies.
In 1990, Sheen starred alongside his father in Cadence and Clint Eastwood in the buddy cop movie The Rookie. But acting wasn’t the only thing on the rising star’s mind. He was also on the hunt for romance.
New Leading Lady
By 1990, Sheen was engaged to Hawaiian actress Kelly Preston who had already starred in multiple commercials, teen romcoms, and adventure movies. However, the engagement was shortlived because of an event shrouded in mystery. Rumors at the time suggested that Sheen shot his wife in the arm and she broke off the engagement shortly after.
What exactly happened is still unknown, although both Sheen and Preston have since denied that Sheen was involved in the accident. Preston went on to marry John Travolta, while Sheen returned to the Hollywood dating scene.
Dating Life
Throughout the early 1990s, Sheen engaged in a very active and public romantic life, dating numerous women, famously including adult film stars Ginger Lynn and Heather Hunter.
The Hollywood heartthrob became the subject of intense media scrutiny, with tabloids keen to capitalize on his colorful personal life and reveal the latest subject of his attention. But Sheen was about to meet a woman who would change his bachelor ways and make him want to settle down.
Wedding Bells
Always on the lookout for the most beautiful girl in the room, Sheen met up-and-coming model Donna Peele in July 1995 and the two began dating. Sheen and Peele got married on September 3, 1995, just a short six weeks after their courtship began.
After tying the knot, the whirlwind romance lasted just four months before the couple began having troubles. Sheen appeared to be struggling to leave his partying and womanizing lifestyle behind.
Calling it Quits
Just a few months after their wedding, Sheen and Peele filed for divorce. Married life just wasn’t for Charlie Sheen. “I couldn't breathe. I like breathing too much. I had to come up for air," he shared with Entertainment Tonight.
However, it's rumored that the breakdown of the marriage had something to do with Sheen being named as a client of Heidi Flyss’s escort agency, racking up a bill of over $50,000 for the services of call girls. The divorce was finalized in 1996 and Sheen quickly returned to his wild ways.
Health Scare
It wasn’t long before Sheen’s extravagant lifestyle caught up with him. On May 20th, 1998, the 32-year-old actor was discovered unconscious by a friend in his seaside home.
He was rushed to Los Robles Hospital & Medical Center in Thousand Oaks, California after suffering a stroke, precipitated by his excessive drinking and use of illegal substances, according to CNN. His friends and family hoped this would be the wake-up call that the party animal needed to focus on his health.
Going to Rehab
After recovering in the hospital for a few days, Sheen checked into a rehab clinic, but he didn’t stick around for long. Just hours after checking in, Sheen fled and had to be chased down by the local sheriff's deputies who finally got him to return, as the Daily Record reported.
Following the episode, Sheen worked hard to clean up his act and achieve sobriety. However, as usual, the serial lady's man had other things on his mind.
Bouncing Back
Following his dice with death, Sheen was determined to bounce back and keep on living his life. In 1999, he went back to work, appearing in Being John Malkovich and several installments of Scary Movie.
He also began dating model Summer Altice who was Playboy’s “Playmate of the Month” in August 2000. But like most of Sheen’s relationships, the romance was short-lived. Shortly after the spark fizzled out, he met someone new, someone who was about to change his life forever.
Fresh Start
Sheen met actress Denise Richards on the set of Good Advice in 2000. The two began dating in October 2001, when Richards made a guest appearance in Sheen’s successful sitcom Spin City.
They got engaged in December of that year and married on June 15, 2002. Richards was keen to help Sheen forget his chequered past and start a new life. The couple enjoyed a beautiful star-studded wedding on a country estate. Sheen was over the moon and told People, "Richards has taught me more about myself than anybody I’ve ever been close to. I just feel so supported all the time.”
"Two and a Half Men"
The following year, Sheen had the biggest break of his career. In 2003, he was cast in the leading role of Charlie Harper in the CBS sitcom Two and a Half Men.
Alongside Jon Cryer and Angus T. Jones, Sheen played a hedonistic jingle writer (loosely based on Sheen himself) whose brother and nephew move into his Malibu beach house and disrupt his extravagant lifestyle. Created by Chuck Lorre and Lee Aronsohn, the show aired on the primetime Monday night slot after Everybody Loves Raymond. No one could have known how successful the show would be.
Smash Hit
Two and a Half Men became a smash hit, winning Sheen an ALMA award and earning him multiple Emmy and Golden Globe nominations. Sheen's sharp wit, comedic timing, and effortless charm made him the heart and soul of the series.
Audiences tuned in religiously to witness his hilarious antics and relatable flaws, and the show quickly became one of the most-watched and critically acclaimed sitcoms on television during its run. However, Sheen was about to have another very significant milestone in his life.
Family Man
On March 9th, 2004, Richards gave birth to a daughter, Sami J. Sheen, making Sheen a father for the second time. The following year, Denise Richards and Charlie Sheen welcomed their second daughter, Lola Rose Sheen, into the world.
These precious additions to their family brought plenty of joy to the couple, but Sheen was once again on a downward spiral. He and Richards were about to face challenges that they would struggle to overcome. And now that children were involved, Richards had to make their wellbeing her number one priority.
Splitsville
In May 2005, Richards filed for divorce, accusing her husband of being violent, unstable, and addicted to gambling and substances. She even filed a restraining order against Sheen, citing threats to her life, as E! News reported.
The shocking allegations against the actor made headlines, with both Richards and Sheen the targets of media attention. Things got very ugly as the court case dragged on. The divorce was finalized in November 2006 and preceded a lengthy custody dispute over their two daughters.
Single Again
After wrapping up the divorce and messy custody battle, Charlie was single once more. In 2006, actress and model Rebecca Gayheart introduced him to her friend Brooke Mueller. Mueller was an actress and reality star, known for co-starring on her friend Paris Hilton’s show The World According to Paris.
They hit it off and the couple got engaged in 2007 with a $500,000 diamond ring. In May 2008, they tied the knot in a small 60-person ceremony.
Twin Boys
Soon after the wedding, Brooke Mueller fell pregnant and gave birth to twin boys, Bob and Max, in March 2009. Sheen now had five children with three different women. But like many of Sheen’s relationships, the new family's moment of domestic bliss was short-lived.
Both parents struggled with addiction and emotional instability, and the relationship quickly became turbulent. However, things were about to take a turn for the worse.
Arrested for Assault
On Christmas Day 2009, Sheen was arrested when police were called to the family holiday home in Aspen after reports of violence. BBC News at the time reported that Mueller had accused Sheen of threatening to kill her and holding a knife to her throat.
It's rumored that the fight broke out before Mueller asked Sheen for a divorce. The report said that Sheen told officers he became "very upset with this threat [of divorce] because of prior experiences."
Final Straw
Sheen was released on $8,500 bail, but the incident marked the end of his relationship with Mueller. He filed for divorce in November 2010, citing irreconcilable differences. The divorce petition requested joint physical and legal custody of the twins.
According to CNN, Sheen signed the divorce petition just six days after police reported discovering him "emotionally disturbed" in a New York hotel room. Sheen spent a brief stint in hospital for what his representative said was an allergic reaction to medication. However, speculation abounded that the actor's mental health had once again taken a downward turn.
Feud With Chuck Lorre
It’s not surprising that during this crisis in his personal life, Sheen was also having a difficult time with his career. He started feuding with Chuck Lorre, creator of Two and a Half Men and his job was in danger.
As a result, production of the show was put on hiatus in January 2011 while Sheen was in rehab. The following month, CBS canceled the show’s remaining episodes after Sheen went on an offensive rant about Lorre on radio.
Warner Bros. Dismissal
In the fallout, CBS banned Sheen from entering their production lot, and the Two and a Half Men star retaliated by publicly demanding a 50% pay rise. At the time, he was already the highest-paid actor on television.
On March 7th, 2011, CBS and Warner Bros. terminated Sheen’s contract, and his character, Charlie Harper, was killed off on the show. The gap the character left was filled by Ashton Kutcher.
Public Meltdown
Soon after his dismissal, Sheen had a highly public meltdown, leaving his friends and family deeply concerned for his mental health. He made several profanity-laced livestreams and YouTube videos and gave interviews, attacking his former employers, making wild claims about having tiger blood, and calling himself a “rockstar from Mars”.
During this time, he also coined his catchphrase “winning”. However, many people concluded from Sheen’s manic state that he was far from winning at anything.
Life With the Goddesses
During this period of instability, Sheen was living in his Beverley Hills home with two girlfriends whom he referred to as “his goddesses”. They were 24-year-old adult film actress Bree Olson and 24-year-old model and graphic designer Natalie Kenly.
Sheen didn’t feel the need to keep his unusual living arrangements on the down low, keen to show off about life with the goddesses. But Sheen was about to face a personal catastrophe that would rock his world.
Rock Bottom
In March 2011, Sheen hit rock bottom. His sons were forcibly removed from his home by the police after Mueller won a restraining order against the disgraced actor.
"I am very concerned that [Sheen] is currently insane," Mueller stated in her legal declaration, as reported by People. "I am in great fear that he will find me and attack me, and I am in great fear for the children's safety while in his care," she went on. The 23-month-old boys were taken into the care of Sheen’s ex-wife Denise Richards, and later by Mueller’s parents.
Comedy Central Roast
Despite his popularity plummeting after his dismissal from Two and a Half Men, Sheen was invited to be the subject of a Comedy Central Roast while recovering from this personal tragedy. Sheen took the hot seat in September 2011, and took a beating from the celebrity roasters.
However, his whipsmart comebacks showed that the former comedy star still had his old charm, and the episode was the highest-rated roast to date, with 6.4 million viewers tuning in to watch.
New Love Interest
Things seemed to calm down a little for Sheen, with the actor claiming to have cut back on his excessive behavior. But true to form, he was also on the lookout for a new lady in his life, and sure enough, he was spotted locking lips with adult film star Georgia Jones at a New Year’s Eve party in Mexico in December 2012.
Jones moved into Sheen’s mansion and the couple was very happy together. At this time, Sheen was also starring in Anger Management, a popular series about a baseball pro-turned-anger management therapist.
Another Engagement
The relationship with Jones didn't last and in November 2013, Sheen began a relationship with Scottine Ross, an adult film star known professionally as Brett Rossi. They announced their engagement in February 2014.
"I was not expecting it at all. We had a beautiful Valentine's Day and he proposed to me early this morning after we watched the sunrise," Rossi told E! News. Both Rossi and Sheen were excited to start a new life together, but it wasn’t long before things went south.
Separate Ways
However, Sheen and Rossi broke off their engagement in October of the same year. "Scotty and I had a great year together as we traveled the world and crossed a lot of things off our bucket list. She's a terrific gal, but we've mutually decided to go our separate ways and not spend the rest of our lives together," Sheen said in a public statement reported by CBS News.
A month later, it was reported that Rossi had been hospitalized following an apparent drug overdose and Sheen remained the target of media attention. But the failed engagement wasn't the only reason Sheen was making headlines.
Twitter Feud
That same year, Sheen was in the news again after he lashed out at Ashton Kutcher on Twitter after Kutcher told him to stop criticizing his appearance on Two And A Half Men, which he replaced him on in 2010.
While Sheen took to Twitter to apologize the following day, minutes later he said, "But news flash Dood, you ever tell me to shut the F--- up, EVER again, and I'll put you on a hospital food diet for a year. c #YaFeelMe Jr?" However, during this time, no one knew that the actor had been hiding a dark secret for the last few years.
Public Announcement
In November 2015, Sheen made an announcement that would shake the world. In a live interview with Matt Lauer on TODAY, the notorious playboy revealed that he was HIV positive. Sheen had received the diagnosis four years earlier when he’d sought medical help for headaches and migraines, thinking he had a brain tumor.
“It’s a hard three letters to absorb. It’s a turning point of one’s life,” he told Lauer, his voice shaky. Sheen had previously only revealed his diagnosis to close friends, family, and, partners.
Revealing the Truth
Sheen also revealed that several people had demanded money to keep quiet about the actor’s condition. He confirmed that an escort snapped a photo of his anti-retroviral medication and threatened to sell it to the press if he didn’t pay her off.
“We’re talking about shakedowns,” he said, admitting he’d paid extortionists around $10 million to keep his condition secret. Sheen described the feeling of coming out publicly about his diagnosis as “releasing himself from prison”. He also said it was “impossible” for him to transmit the virus because of the medication he was taking.
The Charlie Sheen Effect
Sheen’s disclosure of his HIV status had an enormous impact on HIV awareness, known as "The Charlie Sheen Effect". Academics at JAMA Internal Medicine reported that his tell-all interview with Lauer "corresponded with the greatest number of HIV-related Google searches ever recorded in the United States."
People were educating themselves about the virus, how to get tested, and how to protect themselves. In fact, journalist Julia Belluz wrote on Vox.com that “Charlie Sheen did more for HIV education than most UN events do.” But not everyone was impressed with Sheen's candidness.
The Lawsuit
Following the revelation, People reported that Sheen’s ex-fiancee Brett Rossi filed a lawsuit against the actor, accusing him of assault and battery, emotional distress, false imprisonment, and negligence. She also claimed that he hid his HIV status.
Sheen vigorously denied all the allegations and his lawyers told People that they were “confident that Mr. Sheen will prevail in this action and will prevail on his claims for affirmative relief against her.”
Retreating From the Spotlight
Despite the messy lawsuits, Sheen’s HIV announcement marked a turning point in his life. He retreated somewhat from the public eye, taking a break from intensive film and television production and focusing on his health.
While he continued to be involved in controversies, including custody and child support battles with Richards and Mueller, as well as other allegations, Hollywood's most controversial playboy seemed to be leading a somewhat quieter life.
Latest Love
Sheen’s latest love is the model and occasional actress Julia Stambler. The two met in 2017 when Stambler was working as a nanny for Sheen and Mueller’s twin boys.
Stambler faced some backlash when she got together with Sheen but she “isn't scared” of her partner having HIV and has claimed those warning her away from him because of his illness are “ignorant", as the Daily Mail reported. The former nanny has encouraged Sheen to focus on a healthy lifestyle, eat a plant-based diet, and take up yoga. What a turnaround for the former party animal!
Celebrating Sobriety
In 2019, Sheen took to Twitter to celebrate a monumental milestone in his life: over a year of sobriety! He posted a picture of his sobriety token with the caption: “So, THIS happened yesterday! a fabulous moment, in my renewed journey.”
Sheen told USA Today that the turning point came when he had drank too much to drive his daughter to an appointment. He realized his addiction was keeping him from being a present father and that was the catalyst he needed to make a change.
New Projects
Since getting clean, the actor has been focusing on new projects. In 2022, Sheen appeared in an episode of Ramble On, a comedy-drama series following celebrities looking to reinvent their careers. He plays himself. He has also made guest appearances on multiple podcasts.
As of April 2023, Sheen is said to be working on a new comedy series How to Be a Bookie. The series stars Sebastian Maniscalco and has been written and created by Chuck Lorre, suggesting that Lorre and Sheen have reconciled since their rift.
Looking to the Future
Charlie Sheen's life has been a rollercoaster ride, marked by fame, addiction struggles, three marriages, the joys of fatherhood with five children, and a colorful array of romantic encounters.
Today, as he commits to a life of sobriety and stability, we're eager to see how this new chapter unfolds. We hope Sheen can focus on being a great dad and grandad, and we’re excited to see him return to acting with his latest project. With all that he has overcome, it's fair to say that the actor really is "winning".
