A Walk Through The Maze of Charlie Sheen’s Exes, Children and How Much He Is Worth Now

Hollywood is renowned for its love of biopics and one guy whose life will certainly get the biopic treatment one day in the nearest future is none other than one of its biggest, albeit controversial stars, Charlie Sheen.

A scion of a respected acting dynasty, Sheen started acting as a child and eventually became a breakout star of the 2000s hit sitcom, Two and a Half Men. His portrayal of the fun-loving Charlie Harper endeared him to millions of people around the world. It also fetched him numerous accolades. His career would, however, later nosedive thanks to his real-life vices.

From drug and alcohol abuse to patronizing prostitutes and multiple criminal charges, Sheen built up quite the rap sheet and this affected his earning power and consequently his net worth drastically. The New York native, however, refuses to give up and continues to live life to the fullest.

From Porn Stars to Actresses: A Look at Charlie Sheen’s Colourful Love Life

Robin Wright (1981-1982)

Charlie Sheen

Charlie Sheen’s illustrious and controversial dating history goes back to 1981 when he met and started a relationship with fellow upcoming starlet, Robin Wright. He was 16 at that time while Wright was just 15. The whole thing made for a puppy love situation which lasted up until 1982 when the two young people went their separate ways. There is no word on whether the two remain friends but at least, they both eventually achieved stardom on the TV screens.

Winona Ryder (1986)

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Another rising starlet that Sheen dated in the 80s was Winona Ryder. He and the actress met on the set of the 1986 movie, Lucas, and apparently became smitten with each other. They commenced a relationship and dated for several months during which Charlie reportedly helped Winona to formulate her famous last name (her original surname is Horowitz). As the story goes, they were both chilling out and listening to a song titled “Riders on the Storm” when he got the idea that Winona Ryder would sound cool. The actress agreed and so her identity came to be.

Charlotte Lewis (1986-1988)

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Upon breaking up with Ryder, the next person that Charlie Sheen dated was British actress and model, Charlotte Lewis. According to Lewis, she and Charlie first bumped into each other during a party in Hollywood. They had an interesting conversation and subsequently started dating.

In the model’s own words, Sheen’s lovemaking was lovely, sweet, and sensitive, and she thought she had found a good one. Things later went awry when he started drinking excessively. The last straw that broke the camel’s back was when she phoned him at his apartment and another lady picked.

Kelly Preston (1987-1990)

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By 1987, Sheen was dating actress Kelly Preston. The two of them even got engaged three years later but their marriage never became reality as they broke up after Sheen allegedly and accidentally shot his girl in the arm. The actor would later come out to clarify that he never shot Preston. According to him, she was hit after his gun fell out of one of his clothes, hit the floor, and accidentally discharged. The bullet struck the toilet bowl and it was shrapnel from the bowl that cut Preston’s arm. The actress backed up Sheen and maintained that he was a good, beautiful and great person.

Tracy Richman (Early 90s)

Charlie Sheen dated L.A. socialite, actress, and writer, Tracy Richman in the early 90s. Details are scarce about this particular relationship but Richman has been quoted as describing her ex as someone who has an addictive personality and has been on a roller-coaster. She has also described the award-winning actor as having a lot of demons in him.

Donna Peele (1995-1996)

Katie Holmes
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By 1993, Sheen was exposed as one of the frequent customers of one of Hollywood’s notorious madams, Heidi Fleiss. He was even forced to testify at her trial, where he admitted spending tens of thousands of dollars each year to hire prostitutes. His reputation subsequently took a heavy beating.

In a bid to do damage control, the actor got the bright idea to marry a wife and settle down. He then started dating model Donna Peele, and the two got married in 1995. The hastily-put-together union unsurprisingly ended in divorce six months later.

Brittany Ashland (1996-1997)

Charlie Sheen
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Another Charlie Sheen romance that ended with bodily harm is his relationship with actress Brittany Ashland. The duo dated between 1996 and 1997, a time during which the actress accused Sheen of slamming her head into the marble floor of the kitchen during an argument. Sheen was charged with committing battery and serious injuries which he did not contest. This resulted in a one-year suspended prison term as well as two years probation.

Denise Richards (2001-2006)

Charlie Sheen
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Charlie Sheen’s second marriage was to popular actress Denise Richards. He and Richards first met on the set of the movie, Good Advice, in 2000 but only started dating in October 2001. They got engaged that same year and tied the knot in June 2002. The couple would stay married for about four years, a time during which Denise discovered certain things she didn’t like about the actor such as his alcohol and drug abuse as well as other violent tendencies. She also didn’t like the fact that he opposed vaccinations for children. She filed for divorce in March 2005 and it was finalized in 2006.

Brooke Mueller (2008-2011)

Charlie Sheen
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Sheen’s third marriage is to former real estate agent, Brooke Mueller. He and Mueller tied the knot in May 2008 and welcomed twin boys in March 2009. Sadly, eight months later, the actor was arrested for assaulting his wife. He was charged with third-degree assault as well as criminal mischief. He reached a plea deal that saw him avoid jail time in exchange for stints in drug rehab and anger management centers. This sad incident naturally marked the demise of the couple’s union and their divorce was finalized in May 2011.

Rachael Oberlin and Natalie Kenly (2011)

Charlie Sheen
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Hard as it is to believe, by 2011, Charlie Sheen was openly living with two women at the same time whom he described as goddesses. Their names are Rachael Oberlin and Natalie Kenly.

Rachael is a porn star while Kenly is a model who also doubled as a nanny for the actor’s kids. According to Kenly, the relationship may have seemed crazy but they love and respect each other as well as each other’s boundaries. Oberlin would also state that she and Kenly each have their special relationship with Charlie as well as with each other. Oberlin later left Charlie in April 2011 while Kenly followed suit two months later.

Brett Rossi (2014)

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In November 2013, Sheen began dating glamour model and porn star, Brett Rossi. They got engaged in February 2014 and were set to tie the knot in November 2014 before they broke up in October. Rossi has since come out to accuse her ex of physical and emotional abuse. She also sued him for exposing her to HIV. He, however, denied all her allegations and called her an extortionist.

Julia Stambler (2017- )

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Charlie is now going steady with a model named Julia Stambler. As the story goes, Stambler used to be a nanny for his wife, Brooke, and it was she who introduced them. The two started dating in 2017 and are still going strong. Julia has revealed that many of her friends told her not to date Sheen because of his HIV status but she refused to budge as it is a terrible message to send out about the virus.

Charlie Sheen Has a Total of Five Children

Cassandra Estevez

Charlie Sheen
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Charlie Sheen’s very first child is his daughter Cassandra who was born in 1984 when he was about 19 years of age. Her mother was his high school sweetheart whose name has both been given as Paula Profit and Paula Speert.

Cassandra is now in her 30s and has largely stayed out of the spotlight. Things between her and her father haven’t always been smooth but they have managed to mend fences and he attended some of her shows while she was studying at Loyola Marymount College. He also walked her down the aisle when she got married to her high school sweetheart, Casey Huffman.

Sam Sheen

Charlie Sheen’s second child is daughter Sam who was born by Denise Richards in the year 2004. Sam is in her teens and primarily resides with her mother while her father pays about $10,000 (previously $55,000) in child support. Sam has made a few on-screen appearances, including in her father’s show, Two and a Half Men, as well as her mother’s reality TV series, Real Housewives of Beverly Hills.

Denise is reported to be quite strict with her daughter and has installed security cameras in order to forestall her meeting boys.

Lola Sheen

Also born by Denise Richards, Lola is Sheen’s third child. She was actually born while her parents were in the midst of a divorce in 2005 but sadly, it was not enough to stop the split. Just like her elder sister, Lola lives with her mom while her dad supports them financially. She can be seen on her mother’s reality TV series and in May 2020, she graduated from middle school. This means that she will now be heading off to high school by late 2020.

Twins – Max and Bob Sheen

Charlie Sheen has two sons courtesy of his third wife Brooke. The twins were born in March 2009 and are about 11 now. They have unfortunately been caught up in their parent’s drama. Their mom petitioned the police to have them removed from their father’s home in 2011. By 2013, their mom was struggling with alcohol addiction, and custody was given to their maternal uncle, Scott.

Max and Bob later returned to their mother but in 2019, they had to go stay with their maternal grandparents as mom had to seek help in a trauma center. Their father meanwhile makes efforts to see them and in 2018, he shared a picture of them both, asking fans to follow bobby on Instagram.

How Charlie Sheen Became the Highest-Paid TV Star in Hollywood in 2010

Charlie Sheen commenced his career in the mid-70s and has since featured in several movies, including Platoon, Wall Street, Young Guns, Eight Men Out, Major League, and The Three Musketeers. His biggest payday has, however, come on the small screen through the CBS sitcom, Two and a Half Men, where he portrayed the lead role of Charlie Harper, a fun-loving and carefree jingle writer who has to accommodate his uptight brother and nephew in his home.

The Charlie Harper role was modeled on Sheen’s real-life antics and he portrayed it to perfection. This made the sitcom a big hit amongst TV viewers and it rose to be one of the most popular shows at that time. This positively impacted Sheen’s paychecks. The New York native made $350,000 per episode (each season had 22 episodes) for the 4th season of the show in 2006 and by 2008, his pay rose to $825,000 per episode. By the time of his final year on the show came, Sheen made as much as $1.8 million per episode. Overall, it is estimated that he earned about $70 million in total for the show.

Another TV series that paid Sheen quite well is Anger Management. In the FX series, he played the lead role of Charlie, an athlete turned anger management therapist. The show ran for two seasons and a total of 100 episodes during which Sheen earned considerably less than what he made per episode of Two and a Half Men. He was, however, given a 40% share of the profits which saw him make between $75 million to $200 million from the show.

Charlie Sheen
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  • 2006 (4th season of Two and a Half Men) – $350,000 per episode
  • 2008 (6th season of Two and a Half Men) – $825,000 per episode
  • 2010 (8th season of Two and a Half Men) – $1.8 million per episode

He Reportedly Earns About $1 Million Per Annum from Endorsing Products on Twitter

It is often said that any publicity is good publicity and Charlie Sheen is a living example of this. Following his controversial exit from Two and a Half Men in 2011 as well as issues with porn stars and drug abuse, he monopolized the attention of Hollywood fans for a week. This monopoly was so much so that when he decided to join Twitter in early 2011, he reached one million followers in just days, setting a Guinness world record in the process.

Such astonishing stats made the actor sign up with Ad.ly, a company that specializes in social media promotions, in order to be able to monetize his fame. As far back as 2011, Sheen charged about $9500 per sponsored post on Twitter. He represented products such as internships.com and according to his agent, made a total of $1 million per annum from Twitter advertising.

Away from social media, Charlie Sheen has also endorsed several products for different companies and makes about $1 million for each campaign. One of the actor’s most recent sponsorships came in June 2015 when he was appointed as a brand ambassador for a Swedish sex toy company known as LELO. He touted their hexagonal-shaped HEX condom and featured in video ads as well as public events for it.

Shen Once Floated a Clothing Line For Kids

Back in 2006, Charlie Sheen launched a line of children’s clothing known as Sheen Kidz. The brand was a collaborative venture with his pal and business partner, Michael Berens, and featured delicate hidden details as well as intricate sewing patterns. It was carried by several trendy L.A. boutiques and prices ranged from $20 to $80. Sheen was motivated to start the brand as a result of his two daughters and the line carried pieces for only girls. There are no details about the amount of revenue generated by the line but it sold like hotcakes.

Another merchandise of Sheen’s that sold like hot cakes is the t-shirts with his infamous tiger blood remarks. The shirt went for about $20 and the actor put in an initial order for 50,000 pieces.

His Nationwide Tour May Have Been Controversial But It Still Netted Him About $7 million

Charlie Sheen
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Following the termination of his Two and a Half Men contract as well as the consequent fallout, Charlie Sheen decided to head out on the road in the shape of a nationwide tour titled My Violent Torpedo of Truth/Defeat Is Not an Option. The tour spanned about twenty cities in both America and Canada and largely received mixed and negative reviews.

Critics panned it for promising a deep insight into the most secretive aspects of the actor’s life but only providing a hazard act filled with an egomaniac rant, video mashups, as well as rap tributes that can easily be found on the internet. Despite the scathing reviews, Sheen still took it an estimated $7 million from the show thanks to people’s overwhelming curiosity about him.

Charlie Sheen’s Net Worth Has Since Nosedived From $150 Million to About $20 Million

Thanks to all the sources of income enumerated above, Sheen now has a net worth of $20 million. While this is nothing to scoff at, it is a far cry from what it used to be back in the day. At the height of his TV career in the 2000s, the actor had a whopping net worth of $150 million. That amount has sadly dwindled thanks to several factors, including the revelation of his HIV positive status. Sheen was diagnosed with HIV as far back as 2011 but only revealed his status in 2015.

Throughout the intervening years, nobody knew his status and this was because of the fact that he had to shell out about $10 million in order to buy the silence of the few who knew. The trouble did not stop at this juncture. When Sheen revealed his HIV status in 2015, several of his former sexual partners sued him for intentional infliction of emotional distress, fraud, and sexual battery. He maintained though that he disclosed his status to former partners and would never willingly infect anybody. It is not known how these suits were settled but it is possible that the actor paid them off.

Another thing that took a heavy toll on Charlie Sheen’s fortune was his divorces as well as the subsequent settlements he had to pay. For instance, when the Golden Globe winner underwent his third divorce in 2011, he was ordered to pay a total of $1.9 million cash to his ex. He was also required to pay her $55,000 monthly as child support for his two children. This $55,000 was the exact same amount that the actor was already paying second wife, Richard Denise, in child support for their two daughters, following their 2006 divorce.

This made for a total of $110,000 each month and after several years of paying, the burden became too much for the actor and he went to court for a reduction in 2016. He told the court that his income had reduced; his monthly health care cost was quite high; and that his legal fees/credit card debts were about $1 million and $600,000 respectively. The court bought his argument and reduced his payment to $10,000 a month; something his two exes were not happy with.

Chizitere O
Chizitere O
I have several years of experience in editing but I enjoy writing and see it as therapeutic. In my spare time, I like to catch up with my favorite sports teams.


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