aka Charlie Sheen (2025)
Who other than Charlie Sheen could bring Sean Penn, Jon Cryer, Chuck Lorre, Chris Tucker, Denise Richards, and Heidi Fleiss together? They have gathered as a part of the new two-part Netflix documentary that assembles Sheen’s friends, family members, employees, co-workers, partners in crime, and a former boss. Alongside Sheen himself, in intimate detail, they recount his meteoric rise, his many self-imposed troubles and run-ins with the law, his missteps, shocking turns, and finally, hopefully, his sustained move towards redemption.
To his credit, Charlie Sheen (born Estévez) is the main talking head in the series, speaking with what at times is stunning honesty about the good, the bad, the ugly and the uglier episodes in his, what should have been, charmed life. Sheen’s is not the story of an abused child. He was raised in a loving two-parent home with three siblings (including older brother Emilio Estévez, also a famed actor) and movie star father Ramón Gerard Antonio Estévez (stage name Martin Sheen). His friends, childhood and early adulthood, included Sean Penn, Nicolas Cage, and George Clooney. While his paternal grandfather was from Spain, Sheen’s mother, Janet Templeton, is from Ireland. Born Carlos Irwin Estévez in New York City, he emerged without signs of life and an umbilical cord wrapped around his neck. Resuscitated by the doctor for whom he was given the middle name Irvwin, Sheen connects his near brush with death as an infant with his pounding drive to feel alive. But at what cost?
The documentary unfolds with Sheen seated alone at a booth in a diner speaking frankly about his life from birth in 1965 until today. It captures the other contributors in spaces that look like their homes or places of work and intersperses the commentary with an abundant variety of engaging film clips including Charlie and Martin’s film and TV work, as well as excerpts from talk shows, red carpets, and the news, and insightful early images of home movies. Interestingly, the home movies are not ones orchestrated by Janet and Martin to showcase their children’s firsts. Disturbingly, they are mainly excerpts of routinely violent movies created by Emilio and Charlie as children; they were extremely interested in scenes where one or the other was dying. Perhaps this is because they’d caught the acting bug from their father after a visit to the set of one of the most acclaimed films of the twentieth century, Francis Ford Coppola’s Apocalypse Now (1979).
You can say that the acting bug infected both Estévez boys early and they both went on to considerable acclaim and fame in Hollywood productions, Emilio with early breakout successes in films like The Outsiders (1983), The Breakfast Club (1985) and St. Elmo’s Fire (1985), and Charlie whose small, but stand-out performance in Ferris Bueller’s Day Off (1986) quickly led to larger and leading roles in Platoon (1986), Wall Street (1987), and Major League (1989).
As Charlie’s career went from hit to bigger hit, growing his acclaim and fan base, he began a pattern of almost systematic self-sabotage and near fatal collapses; a pattern that even the constancy of an incredibly supportive family and group of friends could not fully interrupt despite several interventions and stints in drug rehab.
If you are of a certain age, there are many scandals and insights that will trigger your memory and spark ruminations about how your perceptions and judgements may have changed over the years and about how the people in his life have experienced (or perhaps the better word is survived) their relationships with him. This is the case with Heidi Fleiss, the once high-flying madam to the stars whose clients included the famous and the infamous. Surrounded by squawking tropical birds in what appeared to be her home, Fleiss speaks honestly about meeting and providing call girls to Sheen, a regular customer, until the fateful mistake of accepting a travel’s cheque instead of cash as payment. It was cheques such as these that became evidence in the criminal case against her and a tool which prosecutors used to turn Sheen into a key witness to secure his own immunity. In what many would call a “dick move,” Sheen sacrificed Fleiss (who of course was not innocent either) to save himself. Fleiss served twenty months of a thirty-seven-month sentence for tax evasion and money laundering and Sheen walked. Perhaps surprisingly, Fleiss comes across as assured and firm instead of completely bitter, which many could argue, she has more than reason to be.
In the surviving Sheen category, perhaps most illuminating are former second wife (of three) Denise Richards and former cast mate Jon Cryer (from Two & a Half Men 2003-2015). When asked why she is participating in the series, Richards states that she in invested in the accuracy of the film. In moving scenes, she is brought to tears recalling the damage Sheen has done to himself, to her, their marriage, and to their children, two daughters. At one point she recalls taking in and caring for his twin boys from his third marriage to Brooke Mueller (also a recovering drug addict) when both Sheen and Mueller were mired in legal and/or personal drama. As Richards quietly admits on camera through tears and as she clearly displayed in her selfless and heroic actions, despite it all, she still loves Sheen.
As for Cryer, his tone is more resentful than both Fleiss and Richards, especially when recalling that despite his abhorrent behaviour, Sheen was ultimately offered a contract of $2 million dollars per episode when Cryer got only 1/3 of that figure. Recounting the early days of Two & a Half Men, Cryer described Sheen pulling him aside to confirm his commitment to and seriousness about the show. However, the documentary explains how Sheen’s by then established pattern of huge successes were routinely followed by reckless actions that eventually led to missed call times, flubbed lines, sickly appearances, and overall unreliable behaviour that threatened to derail what was one of the high-rated and top revenue generating TV shows. For Cryer, whose comments often demonstrated deep thought about the “whys” of Sheen’s behaviour, his conclusion is that “Charlie is…a mass of fears and he goes in and out of heathy and unhealthy ways of dealing with it.” In a similar vein, Richards explains that Sheen sabotaged the success of the show and their marriage. To his credit, Sheen did not shy away from this painful truth either. In his own words, parents frequently counsel their children about how to deal with failure, but no one teaches you how to deal with success.
What becomes clear is a truth shared across the tragic biographies of many a Hollywood star, a truism that is as much about human nature and the way life is for the common person as for the celebrity. That is, the company you keep matters! Throughout the documentary, besides the love of this father, Martin, Sheen speaks openly about the constant support of his lifelong friend Tony Todd. Indeed, the African American Todd was at times the most present and stabilizing force at moments where Sheen would otherwise surround himself with people who were intent on watching him fall, as long as they profited on his way down. Such was clearly the case when Sheen recounts the spiral of the one-man show tour which intersected with wild, drug-fuelled (and testosterone taking) social media rants about ingesting tiger blood, his biological uniqueness, altered states of consciousness, and overall exceptionalism. This is the period in which he likely contracted HIV. But as the documentary reminds us, the outrageous behaviour of this period emerged after Sheen was finally fired from the long-running CBS hit sit-com, Two & a Half Men, after briefly becoming the highest paid TV actor in history. But what Sheen himself and Cryer encapsulate best is that the out-of-control behaviour was linked to the stunning successes and Sheen’s inability to manage them.
Recalling this period, Sheen admits that he feels as if he is watching someone else: “I wish someone would have stepped in,” he says, trailing off. But at that point, who knows who else was around and who else Sheen let get close. Sheen’s story calls to mind celebrities who died before they got that message, people like Kurt Cobain, Whitney Houston, Michael Jackson, Elvis Presley, Prince, Amy Winehouse, and Matthew Perry. It is clear that the documentary itself, may have caused some strain in his family, with dad Martin and brother Emilio opting not to participate. To his credit, Sheen readily admits that the project may hurt or bring up bad memories for people he loves (people who staged interventions, took him to drug rehab, and attended his court hearings).
What’s the bottom line? Sheen is blessed. He is a man who is deeply loved by this family and friends and a person of extraordinary talent. He is also a great comedic and dramatic actor with the film credits to prove it. At this stage in his life, at the age of sixty, he is unafraid to expose his deepest darkest moments. It takes courage to be this vulnerable, and most of us could not or would not do it, even with issues far less scandalous.
But Sheen has also been given way more chances than most people, especially black people, a point which the documentary makes vividly in its juxtaposition of the reactions to Sheen’s questionable illegal activities vs. Tiger Woods’ profoundly immoral behaviours. (Let’s just say, one of them was held to account more than the other!) Sheen is also deeply troubled (or at least he has been in the past). He is now blessedly eight years sober and forging a new path as a father, a path in which he is focused on and mindful of his children’s well-being.
As with Matthew Perry’s recent memoir, Friends, Lovers, and the Big Terrible Thing (2022), written almost a year before his death from a ketamine overdose, we believe that Sheen’s documentary has the potential to reach vulnerable people in the grip of similar addiction, showing them a way forward and another way of being. Here’s hoping! Redemption is real and we’re rooting for Sheen to stay the course.