67 pages • 2-hour read
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Content Warning: This section of the guide includes discussion of substance use, addiction, sexual assault, and illness.
The Book of Sheen is written from Charlie Sheen’s first-person perspective, but he often elides the details of various scandals in his life, which stretch back to the 1990s. In December 1996, then-girlfriend Brittany Ashland accused him of assault, and prosecutors filed a misdemeanor battery charge in early 1997. Sheen pleaded no contest and received a suspended jail term, probation, fines, community service, and a stay-away order. In May 1998, he had a serious drug overdose at his Los Angeles-area home and was hospitalized. His father, Martin Sheen, spoke publicly at the time as the family pushed him toward treatment. Earlier still, a tabloid-reported incident involving his then-fiancée Kelly Preston (an accidental discharge of a handgun at Sheen’s home in 1990) lingered for decades in pop culture lore. In 2025, Sheen again characterized it as a ricochet accident that injured Preston with shrapnel.
On Christmas Day 2009, Sheen was arrested in Aspen after an altercation with then-wife Brooke Mueller. He pleaded guilty to misdemeanor assault, avoiding a felony and receiving rehabilitation, probation, and anger-management requirements. Months later, in October 2010, New York police removed him from a Plaza Hotel suite after reported damage and substance use. Adult performer Capri Anderson publicly accused him of assault connected to that night, while Sheen denied her account and sued her for alleged extortion. No criminal charges were filed over the hotel incident. In early 2011, the Aspen case spilled into family court and tabloid spectacle. Mueller obtained a restraining order, authorities removed the twins from Sheen’s home, and a custody fight played out. This was followed by his infamous 2011 blitz of interviews and social-media outbursts aimed at Two and a Half Men creator-producer Chuck Lorre and the studio. Production halted on the successful show. Sheen was fired and filed a $100 million suit before reaching a confidential settlement widely reported to be around $25 million. Afterward, he launched a live tour that debuted disastrously in Detroit, a public failure that Sheen touches upon in his book.
In November 2015, Sheen went on NBC’s Today to disclose he is HIV-positive but on effective antiretroviral therapy. The revelation produced a measurable surge in HIV information-seeking and testing, documented in peer-reviewed studies of news. The disclosure also set off litigation: Ex-fiancée Scottine Ross (Brett Rossi) sued him for nondisclosure and abuse; Sheen denied her claims and pushed for arbitration. The Los Angeles Police Department (LAPD) later examined a separate allegation that he had threatened Ross, reporting that Sheen disputed. Additional civil actions by partners followed in subsequent years. Another controversy surfaced in 2017, when National Enquirer published an allegation that Sheen sexually assaulted Corey Haim in the 1980s. Sheen vehemently denied it and sued the tabloid for defamation. When the claim resurfaced in a 2020 Corey Feldman documentary, Sheen again denied it. In 2021, a Los Angeles judge reduced Sheen’s child support obligation to Denise Richards to zero, a ruling widely described as blindsiding Richards. This followed years of motions in which Sheen sought reductions tied to fluctuating income.
The filming of Apocalypse Now is presented in The Book of Sheen as a pivotal moment in Charlie Sheen’s childhood, in which he discovered a love of filmmaking and his own budding aspirations as an actor. This connection is further contextualized by the film’s longevity and critical success, as well as its turbulent filming process. The film was plagued by difficulties, and within the larger crisis, Martin Sheen’s casting and health became central stress points that shaped the film’s production rhythms, creative solutions, and eventual mythology.
Director Francis Ford Coppola began principal photography in the Philippines in March 1976 after replacing his original lead, Harvey Keitel, with Martin Sheen, whose arrival on April 24 signaled a new approach to Captain Willard as a watchful, inward-looking observer. The recasting forced reshoots and further compressed a schedule already threatened by weather and logistics. On May 26, 1976, Typhoon Olga destroyed between 40 to 80% of the sets and shut the production down, pushing the film deeper into delay and debt. Coppola mortgaged assets and pursued insurance claims to keep cameras rolling, even as he continued rewriting key sections and postponing the film’s release.
One scene in particular, the Saigon hotel prologue, is iconic, both for Martin Sheen’s performance and for the story behind it. Shot on his 36th birthday in early August 1976, the sequence—with Willard drinking, dancing, and punching a mirror—drew on Martin Sheen’s real intoxication and produced a genuine hand injury, which Coppola filmed while worrying about the actor’s safety. The scene’s rawness set the tone for Willard’s interior narration and the film’s hallucinatory texture. It also underscored the production’s tendency to convert off-screen crisis into on-screen affect.
When Coppola resumed filming in early 1977, Martin Sheen’s ordeal deepened. On March 5, 1977, while filming in a remote jungle, he suffered a near-fatal heart attack. Fearing that investors would cut funding if the emergency became public, the production initially attributed his collapse to heat stroke. The shoot paused while Martin Sheen recovered. To maintain momentum, Coppola used Martin Sheen’s younger brother, Joe Estevez, as a stand-in for certain set-ups and as an uncredited sound-alike for Willard’s voiceover.
Martin Sheen’s medical emergency did not unfold in isolation. The Philippine military helicopters rented for the movie were subject to sudden recall because of real insurgent operations, which repeatedly scrambled the planning of the Wagner-scored cavalry assault and other set-pieces. Weather remained unpredictable, effects misfired, and large-scale sets had to be rebuilt after storm damage. Meanwhile, Marlon Brando’s late arrival and improvisatory working methods forced Coppola to reconceive Kurtz and to fashion an ending more mythic and less literal than originally scripted. The cumulative effect was a production that oscillated between paralysis and feverish invention, with Martin Sheen’s recovery and return (on April 19, 1977) marking one more pivot point in a process that ultimately consumed 238 shooting days and years of editorial work.
Contemporary and retrospective accounts make clear that Martin Sheen’s crisis was not merely a biographical footnote but a structural factor in how Apocalypse Now was made. Charlie Sheen, as a child, was often on the periphery of the set and, as he writes in The Book of Sheen, appears as an extra in the background of certain scenes. In the book, Charlie Sheen’s experience of watching his father’s suffering lays the groundwork for the similar struggles he would have on the set of his own Vietnam movie, Platoon.
Throughout The Book of Sheen, Charlie Sheen speaks openly about hiring sex workers, preferring the transactional nature of the relationship. At the height of his fame, a scandal exploded in Hollywood involving an escort service run by Heidi Fleiss, branded by the media as the “Hollywood Madam.” In 1993, after months of multi-agency surveillance, Los Angeles and Beverly Hills police executed a sting that led to Fleiss’s arrest at her Benedict Canyon home on felony pimping, pandering, and narcotics charges. Coverage quickly fixated on a supposed “black book” of elite clients and Fleiss’s links to predecessors and rivals, especially Elizabeth “Madam Alex” Adams and the filmmaker Ivan Nagy. The result was an unusually public criminal proceeding that blurred tabloid fascination with an ordinary set of vice charges, one that Sheen touches on in The Book of Sheen.
Fleiss was tried in Los Angeles Superior Court and, on December 2, 1994, convicted on three pandering counts. In May 1995, a judge imposed a three-year prison sentence consistent with California’s mandatory minimums for pandering. However, the integrity of the verdict soon unraveled. In May 1996, the California Court of Appeals vacated the conviction and ordered a new trial, concluding that jurors had improperly traded votes to avoid a hung jury and minimize punishment. The reversal did not end Fleiss’s legal exposure, but it decisively undermined the state’s case.
Running alongside the state prosecution was a federal financial case that proved more durable. A July 28, 1994, federal indictment targeted bank deposits, real-estate transactions, and unreported income associated with the escort business. In US District Court, prosecutors framed the matter as tax evasion, conspiracy, and money laundering, and Fleiss was convicted and sentenced to 37 months in federal prison. The judge noted that although the sentence was well below guidelines, she deemed it fitting for a prostitution-adjacent case rather than organized crime. The court also noted the asymmetry in the fact that none of the male clients faced prosecution, a point that echoed broader debates about demand-side enforcement in vice policy. Fleiss ultimately served roughly 20 months in prison before transferring to a reentry center in late 1998.
Sheen’s participation entered the court records primarily through his videotaped testimony in the 1995 federal trial. Under a grant of immunity, he identified at least seven checks as his and acknowledged using Fleiss-associated escorts at least 27 times between December 1991 and February 1993, paying more than $50,000 in total. Sheen’s statement, played for jurors in July 1995, was probative not because client identities were criminally charged but because the paper trail supported the federal theory about income flows and laundering. Publicly, Sheen released an apologetic statement, while prosecutors emphasized that celebrity names, insofar as they existed on canceled checks, were ancillary to the central tax-evasion narrative. In practice, however, Sheen became the only widely confirmed entertainment-industry client.



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