Inside Charlie Sheen’s Worrying Trail of Unsuccessful Marriages

Charlie Sheen has been married three times but none of his marriage ever survived beyond four years. His first marriage was to Donna Peele (1995 to 1996), his second to Denise Richards (2002 to 2006), and his third to (2008 to 2011). 

Professionally known as Charlie Sheen, Carlos Irwin Estévez is a Hollywood actor famous for his outstanding roles in several blockbuster films and TV shows like Wall Street, Young Guns, The Three Musketeers, Platoon, Two and a Half Men, and many others. The multiple-award-winning actor is also distinguished as one of the highest-paid television stars.

Aside from his strides on TV, Sheen has had issues with drug, alcohol abuse, and womanizing. In November 2015, he revealed that he has been living with HIV for four years. With three unsuccessful marriages behind him, one would begin to wonder if the actor will ever give marriage a chance again. Follow us as we explore interesting facts about Charlie Sheen’s love life below.

The Many Faces of Charlie Sheen’s Marital Challenges and Struggles with Substance Abuse

Charlie Sheen has had what could be best described as a turbulent life. As such, he is no stranger to intense media speculation and scrutiny of his wild private life. From his long history of abuse towards women to his unsuccessful marriages to his HIV revelation, the TV star has seen it all. Not to talk of his struggles with drugs and alcohol, notoriety with womanizing, and his gay accusations, the actor has one too many demons as detailed below.

Is Charlie Sheen Gay?

For a man with the reputation of being a chronic womanizer, you would be shocked if you learned he is gay, not so? No one can predict human presumptuousness, remember.

Charlie Sheen’s sexual orientation began to be questioned first when in the divorce papers filed by his ex-wife, Denise Richards, she raised concern over his use of gay porn, which appeared to her to involve young male stars who looked underage.

Denise also alleged that her ex signed up to disturbing porn sites which promoted young girls, who looked underage with pigtails, braces, and no pubic hair performing oral sex with each other, as well as using gay pornography, also involving very young boys.

Additionally, in the wake of the multiple allegations of rape and serious sexual assault against Hollywood figures after the Harvey Weinstein scandal first broke out in October 2017, Charlie was accused by actor and director Dominick Brascia of sodomizing late Corey Haim of The Lost Boys fame.

According to Dominick, Corey, who died in 2010, had opened up to him that he had sex with the then 19-year old Sheen at the time they filmed Lucas back in 1986. Well, Sheen has denied the claims and even sued over it.

Also, Lenny Dykstra wrote in an open letter posted to Facebook that Charlie Sheen’s troubles are a result of his bisexuality and that his failure to accept this has resulted in his alleged drug use and irresponsible behavior.

Charlie Sheen Has Had One Too Many Divorces to Last Him a Lifetime

Charlie Sheen Wiki, Gay, Wife, KIds, Brother, Dad, Height, Girlfriends
Sheen with his former girlfriend Julia Stambler

Sheen has been married thrice, all of which were unsuccessful. His first marriage was in 1995 to Donna Peele, the same year he testifies to his womanizing ways. His testament may have led to the couple’s divorce as Peele called the shot on their marriage a year later.

After he met Denise Richards on the set of Good Advice in 2000, he tied the knots with her two years later, and they had two daughters together. Richards, however, filed for divorce in 2005, citing alcohol and drug abuse, and allegations of domestic violence. The divorce was finalized in 2006.

Sheen’s third marriage was to Brooke Mueller, in 2008. Unfortunately, it went the same path as the ones before it. Their twin sons, Bob and Max were not enough to sustain their marriage as it ended in divorce three years later.

Meanwhile, the Guinness world record-holder has five children in total, including one from his high school sweetheart, Paula Profit. He also has a granddaughter, Luna Estevez, born on July 17, 2013, from his oldest daughter.

Sheen may have recorded a lot of infamies to last him a lifetime but he sure has also heralded some good that cannot be denied, such as his charity causes and the creative roles he took on.

He has committed to staying sober and is now more focused on his health and children. Moreover, he seems to have hung up his boots on marriage. According to the famed actor, “when you’re really bad at something, there’s no reason to keep pursuing it.”

The Renowned Actor Has Become Known As A Chronic Womanizer

The Two and a Half Men actor is also notorious for his womanizing and hard-partying ways. In 1995, Sheen testified to this fact under oath at the trial of Hollywood madam Heidi Fleiss, where he confessed to spending over $US50,000 on prostitutes.

Charlie Sheen also built a reputation for dating adult film actresses, including Ginger Lynn, Heather Hunter, Bree Olson, Georgia Jones, and most recently, Scottine (Brett) Rossi, who he was engaged to in 2014.

Some of his other known girlfriends are Paula Profit with whom he had a daughter named Cassandra. Others include model and graphic designer Natalie Kenly, as well as Brittany Ashland. He was also once engaged to Kelly Preston, who later got married to John Travolta.

He’s Living With HIV

For someone who has had more than 200 sexual partners, contracting a sexually transmitted disease was bound to happen. However, Sheen’s case became an exception when in November 2015 he revealed he had been living with the dreaded virus, HIV, which he referred to as “three hard letters to absorb,” for four years.

In an interview with Today, Charlie Sheen, who seemed unready to come out with the revelation then said he was compelled to speak out about his HIV status after being subjected to ‘blackmail and extortion and a circle of deceit.’

As shocking as his revelation was, one good thing that came out of it was what was referred to as “The Charlie Sheen Effect.” Although his diagnosis initially made him descend into substance abuse and fathomless drinking, he took up the responsibility to better himself and help a lot of people; hence his revelation.

According to a study, Sheen’s disclosure did more for HIV education than most UN events do.

His Struggles With Substance Abuse

Charlie Sheen had a highly publicized history of substance abuse and has already been to drug rehab at least once before he hit the rock bottom in May 1998. He suffered a stroke after a near-fatal drug overdose, which he later revealed in 2004 was as a result of injecting cocaine.

Sheen was hospitalized in Thousand Oaks, CA, and was also ordered back to rehab, though he tried to flee a few days later. In October 2010, he was found intoxicated in a hotel room in New York, and according to the police, Sheen admitted to drinking and using cocaine. More so, the actor has been smoking 40 cigarettes a day since 1986.

A Brief Background of Charlie Sheen

Carlos Irwin Estévez was born into a family well-grounded in entertainment. He is the son of Martin Sheen and his artist wife, Janet Sheen (nee Templeton). The third of four children, he first came into this world on 3rd September 1965 and was born in the city of New York. His siblings are all actors and they include brothers, Emilio and Ramon, and sister, Renée.

He attended Santa Monica High School in Santa Monica, California. While in school, he had a keen interest in acting and baseball. He joined the school’s baseball team and became a star pitcher and shortstop.

Charlie Sheen wasn’t bright academically, he was expelled from school a few days before graduation due to poor grades. Nevertheless, what he lacked by books, he overachieved in front of the camera.

How He Began His Acting Career

He made his acting debut at the age of 9 in his father’s film, The Execution of Private Slovik (1974). For his flair for acting, Sheen, alongside his two friends, Rob Lowe and Sean Penn, produced and starred in several amateur Super-8 films.

After High school, he fully pursued a career in acting and his first major role was in the 1984 teen war flick Red Dawn as a high school student. Charlie Sheen has since compiled a slew of other impressive roles both on TV and in films.

His acting credits include his breakthrough role as a young soldier in Oliver Stone’s Oscar-winning epic Platoon, Wall Street, Hot Shots, Young Guns, Major League, remaining on top of his game throughout the ’80s and ’90s. Sheen joined the league of actors with a star on the Hollywood Walk of Fame in 1994. In 2013, he portrayed the US President in Machete Kills.

His first TV role was in Spin City from 2000 to 2002. Sheen was nominated for two ALMA Awards and also won his first Golden Globe award. In 2003, he joined the cast of the CBS sitcom, Two and a Half Men as Charlie Harper. His role on the show, which is based on his bad-boy image, earned him 6 award nominations, including 3 Emmy and 2 Golden Globe nominations.

Charlie Sheen also became the highest-paid actor on television in 2010 when he commanded $1.8 million per episode in his final season on the show and holds the Guinness world record for “Highest Paid TV Actor Per Episode – Current.”

Nevertheless, on the heels of his TV fame and glory, was his looming shame and downfall. Sheen was fired from the show after a downward spiral in his personal life that played out in public.

Who is Charlie Sheen’s Latest Ex-wife?

Charlie has been married and divorced three times. His most recent ex-wife is Brooke Mueller, who he married in 2008 and divorced in 2011.

How Many Are Charlie Sheen’s Spouses?

Charlie has had 3 spouses. His first marriage was to Donna Peele and it lasted from 1995 to 1996. He got married for the second time to Denise Richards but their union only lasted for four year, from 2002 to 2006. Charlie gave marriage a third shot in 2008 when he tied the knot with Brooke Mueller. Unfortunately, they only stayed together for 3 years.

List of Charlie Sheen’s girlfriends

  • Kelly Preston – An actress and model who died on July 12, 2020
  • Robin Wright – An award-winning actress and director from Dallas, Texas, United States.
  • Brittany Ashland – A 51-year-old adult film star
  • Winona Ryder – A multiple award-winning actress who rose to prominence for her roles in HeathersMermaidsEdward Scissorhands, and Bram Stoker’s Dracula.
  • Heather Hunter (nicknamed Double H) – A rapper, painter, author, and adult film actress from Bronx, New York, United States.
  • Bree Olson – An actress, model, and former pornographic star known for performing in more than 600 pornographic films from 2006 to 2011.
  • Natalie Kenly – A model and pornographic actress
  • Ginger Lynn – A porn actress and model who was a leading X-rated entertainment star of the 1980s.
  • Georgia Jones – An adult film actress and model from Fort Smith, Arkansas.
  • Scottine (Brett) Rossi – A pornographic film actress, glamour model, entertainer, and dancer.
  • Paula Profit – A businesswoman known for being the mother of Charlie Sheen’s first child.

Is Charlie Sheen married now?

Charlie she is currently not married but he is in a relationship with a woman named Julia Stambler, who is said to be the best friend of his ex-wife Brooke Mueller.

Stephen Angbulu
Stephen Angbulu
Stephen’s essays have been published by the Embassy of Ireland, Nigeria. He has also been featured on interviews with BBC News Africa and Daily Trust Newspaper. Stephen has over 6 years experience writing on a wide range of topics from biographies to lifestyle and entertainment. He has authored several articles, journal entries, book reviews, short stories, flash fiction and essays on both local and international media


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