Charlie Sheen is planning his television comeback and mending fences along the way.
The actor was famously fired from his hit sitcom “Two and a Half Men” and instigated a feud with the show’s creator, Chuck Lorre, in the aftermath as he struggled with addiction issues.
Now, Sheen and Lorre are working on a new series, the second added to actor’s roster as he continues a slow and steady return to the public eye.
Here’s a breakdown of the star’s journey from the highs, the lows, and his life in between.
Charlie Sheen has had a turbulent life and career, but appears to be set for a comeback, partnering again with “Two and a Half Men” creator Chuck Lorre following their 2011 feud. (Phillip Faraone/Getty Images for Film Independent)
Early career
Sheen is the youngest son and third child of Martin Sheen’s four children. Born Carlos Irwin Estévez, he changed his name to Charlie Sheen before beginning his career, not unlike his father, who was born Ramón Antonio Gerardo Estévez.
After a couple small parts in 1980s film classics like “Red Dawn” and “Ferris Bueller’s Day Off,” Sheen earned his breakout role in Oliver Stone’s Vietnam War movie “Platoon.”
The next year he appeared in Stone’s drama “Wall Street,” alongside his dad. He also later starred with his brother, Emilio Estévez, in “Young Guns.”
Sheen demonstrated his comedy skills in the “Major League” and “Hot Shots!” films, before landing a role on the sitcom “Spin City,” in 2000. He replaced Michael J. Fox’s character for the final two seasons.
It was his first major TV role, for which he earned a Golden Globe for best performance by an actor in a television series – comedy or musical.
Sheen starred in Oliver Stone’s Vietnam War drama “Platoon.” (Aaron Rapoport/Corbis/Getty Images)
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Personal and legal troubles
Throughout his life, Sheen has been viewed as a bit of a Hollywood “bad boy” due to various legal and addiction issues, as well as a string of girlfriends, some of whom were adult film actresses.
In 1990, he allegedly shot his then-fiancée, Kelly Preston, in the arm. In 2016, Sheen claimed she had done it herself. The exact situation remains unclear, but their engagement ended shortly thereafter.
Sheen married his first wife, Donna Peele, in 1995. But that same year, the “Due Date” star was named as a client of Hollywood madam Heidi Fleiss and testified at her tax evasion trial. A year later, Peele and Sheen divorced.
In 1998, Sheen suffered a stroke after overdosing on cocaine, which he admitted — in a 2004 interview with The Telegraph — that he had been injecting.
After he was discharged from the hospital, his father reported him for violating parole for a previous offense, which forced Sheen to check into rehab at the time.
Martin Sheen has publicly supported his son Charlie throughout his sobriety struggles. (Brian To/FilmMagic)
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‘Two and a Half Men’ success and public meltdown
In 2003, Sheen was cast alongside fellow ’80s star Jon Cryer on the CBS sitcom “Two and a Half Men.”
The sitcom had Sheen playing a slight riff on himself, a semi-reformed “bad boy” living with his recently divorced brother and nephew.
The show was a hit, earning millions of viewers week to week, and collecting nine Primetime Emmy Awards during its run. Sheen was nominated four times for his work on the show.
He was also the highest paid actor on television at the time, earning $1.8 million per episode by the show’s eighth season.
“Two and a Half Men” starred Sheen, Angus T. Jones and Jon Cryer. (E.J. Camp/CBS via Getty Images)
However, during that season, the actor’s personal troubles began to affect his work on the series.
At the beginning of 2011, Sheen voluntarily entered rehab, his third time in a year, and the production went on hiatus.
In February, the remainder of the season was canceled after Sheen called series creator Lorre a “turd” and “a clown.”
By March, the actor was fired from “Two and a Half Men” after continued erratic behavior and interviews, including the now-infamous “20/20” appearance where he claimed to have “tiger blood” and “Adonis DNA.”
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Sheen speaks on stage during his “Violent Torpedo of Truth/Defeat is Not an Option” tour at Radio City Music Hall in New York on April 10, 2011. (Kevin Mazur/WireImage)
He also went on Twitter rants, repeatedly using the catchphrase “Winning!” and even livestreamed his thoughts on a Ustream.tv livestream show called “Sheen’s Korner,” recorded at his home, which he dubbed “Sober Valley Lodge.”
After his firing, Sheen continued his feud with Lorre, suing him and Warner Bros., the studio behind “Two and a Half Men,” for wrongful termination, after demanding a 50% raise before his dismissal from the show.
“Two and a Half Men” continued without Sheen. Ashton Kutcher came aboard as a new character, and Sheen’s character was supposedly killed off between seasons eight and nine. In the series finale, Sheen’s character returned briefly, played by a stand-in and not interacting with the main cast, only to be killed off for real when a helicopter dropped a grand piano on him.
Sheen’s character was supposedly killed off between seasons eight and nine, but came back in the form of a stand-in during the series finale before being killed off for good. (Greg Gayne/CBS via Getty Images)
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‘Anger Management’ and HIV diagnosis
After a turbulent year, Sheen returned to television in 2012 on the FX series “Anger Management.”
For that series, he earned $2 million an episode. “Anger Management” ran for 100 episodes between 2012 and 2014 before being canceled.
In 2015, Sheen announced he was HIV positive and had been since 2011.
In an interview on “Today,” the actor explained he decided to come forward after people in his inner circle threatened to expose his status unless they were paid to stay silent.
“I release myself from this prison today,” Sheen said. He also confirmed a story of a sex worker who took cellphone pictures of his anti-retroviral medications and threatened to sell it to tabloids.
Sheen’s doctor, Dr. Robert Huizenga, also appeared on the show and said the drugs were keeping the virus at an “undetectable level” and confirmed Sheen “does not have AIDS.”
The “Wall Street” star said he wasn’t sure how he contracted HIV, but both his ex-wives, Denise Richards and Brooke Mueller, had known about his diagnosis for some time.
Sheen appeared on “Today” to discuss his HIV diagnosis in 2015. (Peter Kramer/NBCU Photo Bank/NBCUniversal via Getty Images)
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Family focus
Sheen has five children with three different women. The eldest, Cassandra Estévez, was born in 1984 to Sheen’s former high school girlfriend Paula Speert. In 2013, he became a grandpa when Cassandra gave birth to her first child.
In 2000, Sheen met his second wife, Denise Richards. The couple married in 2002 and share two daughters, Sami, 19, and Lola, 17. They later divorced in 2006.
Sheen and Denise Richards married in 2002 and have two children together, Sami and Lola. They divorced in 2006. (Jim Spellman/WireImage)
Shortly after that, Sheen met and married Brooke Mueller and had twins with her, Max and Bob, 14. Their divorce was finalized in 2011 after the boys were removed from Sheen’s home and Mueller obtained a restraining order against the actor.
Sheen had previously been arrested in 2009 after Mueller called the police saying he had physically threatened her; he later pleaded guilty to a misdemeanor assault charge.
In 2022, after a lengthy battle, Sheen and Mueller settled their child support case, agreeing to an undisclosed financial agreement. The “Spin City” star had previously requested his child support payments be reduced due to the change in his income.
Sheen and Brooke Mueller finalized their divorce in 2011, after Sheen previously pleaded guilty to a misdemeanor assault charge. (Jon Kopaloff/FilmMagic)
Sheen and Richards have also had their share of custody and financial disagreements over their daughters.
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In 2020, Sami claimed she was “trapped” in an “abusive” household, potentially with Richards, though her social media post didn’t specify which home she was living in at the time.
In 2021, Sami posted she was “full of self love” after moving out of the “abusive” household. She also mentioned she dropped out of high school.
Sheen seemed to confirm Sami was living with him in a statement to Fox News Digital at the time.
“Sam’s amazing,” Sheen said through his rep, Jeff Ballard. “I love her and all my children unconditionally. We’re having a ball. GED here we come!”
After she turned 18, Sami joined OnlyFans, a platform that allows creators to share and monetize content, which can be explicit.
Sami Sheen, left, is Richards’ oldest daughter. (Instagram)
The “Three Musketeers” star did not initially approve of the action.
“She is 18 years now and living with her mother,” Sheen told Fox News Digital via his publicist Ballard in June 2022. “This did not occur under my roof. I do not condone this, but since I’m unable to prevent it, I urged her to keep it classy, creative and not sacrifice her integrity.”
Later, after Richards defended Sami on her social media, Sheen changed his perspective.
“Denise has illuminated a variety of salient points, that in my haste, i overlooked and dismissed,” he said in a statement obtained by Fox News Digital. “Now more than ever, it’s essential that Sami have a united parental front to rely upon, as she embarks on this new adventure. From this moment forward, she’ll have it abundantly.”
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TV comeback plans
This year, Sheen has two different television projects in the works.
The first one announced was the series “Ramble On,” a new dramedy from the creator of “Entourage.”
According to Variety, the series will star Sheen and some “Entourage” alumni, including Kevin Connolly and Kevin Dillon, as themselves in a show about “established stars looking for career reinvention, alongside aspiring performers looking to make their own name.”
Sheen is also reportedly set to appear in Lorre’s new series for Max, 12 years after their feud over “Two and a Half Men.”
Deadline reports the series, titled “How to Be a Bookie,” will follow a bookie (comedian Sebastian Maniscalo) who is struggling to survive as sports gambling becomes legalized.
Chuck Lorre and Sheen attend the panel discussion for “Two and a Half Men” during the CBS 2005 Television Critics Association’s Summer Press Tour. (Frederick M. Brown)
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In 2021, the now 57-year-old reflected on his actions during and after the “Two and a Half Men” saga, calling them “desperately juvenile.”
“There was 55 different ways for me to handle that situation, and I chose number 56. And so, you know, I think the growth for me post-meltdown or melt forward or melt somewhere — however you want to label it — it has to start with absolute ownership of my role in all of it,” he told Yahoo Entertainment at the time. “And it was desperately juvenile.”
“I think it was drugs or the residual effects of drugs,” he added. “And it was also an ocean of stress and a volcano of disdain.”
Charlie Sheen called his actions during his exit from “Two and a Half Men” “desperately juvenile.” (Bobby Bank)
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Sheen appears to have remained sober since 2017 after previous relapses and struggles in the wake of his HIV diagnosis.
He also noted that his complicated family relationships and divorces added to his stress, saying at the time, “I had four children and went through two divorces in and around trying to navigate the landscape of being on the most popular show in the known universe, so it was a lot.”