67 pages 2-hour read

The Book of Sheen: A Memoir

Nonfiction | Autobiography / Memoir | Adult | Published in 2025

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Chapters 23-33Chapter Summaries & Analyses

Content Warning: This section of the guide includes discussion of substance use, addiction, and death.

Chapter 23 Summary

After checking into Saint John’s in Santa Monica, Sheen calls Ginger Lynn and Nicolas Cage, admits he is in treatment, and immediately schemes to honor a prior plan to judge a bikini contest. A night nurse warns him not to leave; he counters by saying that if he is not back by nine o’clock in the morning, he will pay her “one million dollars” (152). At 8:01 pm, he departs Santa Monica Airport with Cage and friends, bound for Palm Springs.


The night becomes a blackout binge; to revive himself, he buys cocaine and spends the hours talking with a woman whose father has just undergone an intervention. Her account reframes his own situation, and she urges him to limit use before detoxing. Near dawn, his stunt double wakes him, and his friends hustle to the return flight. On board, Cage asks if the trip was worth it. Sheen is unsure. A car drops him a block from the hospital so he can walk in casually. He meets the nurse at 8:44 am, wins the bet, and asks to be called Charlie. Lingering hallucinations from the drug use flicker as he reenters to begin a 30-day program.

Chapter 24 Summary

Chapter 24 is presented as an imaginary six-day journal of Sheen’s first week in rehab. On Day 1, he regrets the Palm Springs detour, learns the nurse’s name is Deb, eats and sleeps, meets an elderly patient named Carl, and reflects on rescuing people and keeping things neat, resolving to spend more time with his daughter. Day 2 brings group therapy; he resists sharing, clashes with a woman he labels “Grumpy-girl,” and admits the exchange briefly gratified him before her history sobers him. Ginger stays at his condo.


On Day 3, Nicolas Cage visits, offers a comic anecdote, and says he will not miss hard drugs. Sheen acknowledges that he lied when he said the same, notes fading hallucinations, witnesses a new patient’s crisis, and worries about sober intimacy. Day 4 is his first Alcoholics Anonymous (AA) meeting, which he dislikes for its rote responses, religious language, and storytelling that romanticizes intoxication. On Day 5, he begins a drug history assignment and meets Rick, a dentist who overdosed on nitrous oxide. He wonders who he will be without substances. On Day 6, he vows to quit gambling, questions the program’s reliance on the Bible, notes that Deb protected his privacy, and closes with modest hopes for others and a tighter plan for himself.

Chapter 25 Summary

At noon on a Friday, Sheen leaves rehab during post-lunch yard time with a small duffel bag. Familiar with Santa Monica, he walks briskly toward the street. An orderly chases him. Sheen boards a city bus and rides away while several riders recognize him. He later learns the orderly only wanted an “Against Medical Advice” signature and that he did not need to flee.


He gets off near 4th Street, goes into a pawnshop and buys a saxophone for no reason, then sits at Zucky’s diner on Wilshire. He calls his assistant, Scott G, who arrives and helps him call treatment centers. He insists on outpatient terms. He enrolls in a new program in Calabasas, telling himself he left not to get high but to try treatment on his own terms. After thanking Scott, he checks in and meets the head therapist, who asks why he is “trying to kill [himself]” (165). He has no answer.

Chapter 26 Summary

After rehab, publicly, Sheen seems restored. He headlines the comedy Hot Shots, promotes recent films, poses for a family photo book, shoots Japanese ads, and buys his first home near Malibu, reinforcing the narrative that sobriety has repaired his reputation, as friends like Rob Lowe predicted. Privately, he admits he did not get sober for himself. He feels anxious, performative, and out of place in any “complicated social setting” (167), resentful of AA rhetoric and its pressure to conform. He and his friends try to recreate camaraderie without substances, but the effort feels forced and only heightens their nostalgia.


On August 3, the anniversary of his intervention, he breaks his sobriety at Nicolas Cage’s house by drinking a Foster’s. He resumes drinking covertly, hiding wine in mugs to protect his image, and vows to avoid cocaine. From early 1992 through early 1994, Sheen works continuously, filming sequels to Major League and Hot Shots, The Three Musketeers, The Chase, Terminal Velocity, and Beyond the Law. The pace erodes his control. The chapter closes as his path intersects with Heidi Fleiss, whom the press will call “the Hollywood Madam” (169).

Chapter 27 Summary

In June 1992, at On the Rox, he learns from Steve Bing that the woman presiding over a table of models is Fleiss, a high-end madam. Sheen begins booking expensive encounters, rationalizing the transactions as a convenient and finding the secrecy intoxicating. His “cocaine boycott” ends, and he pays Fleiss with personal checks. Later, in New York, he pays with American Express traveler’s checks after a night at the Parker Méridien.


In June 1993, while filming The Chase in Houston, he hears that Fleiss has been arrested in a sting. Rumors swirl about her “little black book” (173). Sheen panics over the paper trail he left, and prosecutors secure his videotaped testimony in exchange for immunity. In it, he confirms dozens of payments as purchases of sexual services, a cooperation he soon regrets, feeling he was pressured by threats of a pandering charge.


The case centers on tax evasion; Fleiss receives a heavy sentence, and they never speak again. Media attention is intense, peaking with an Oscar joke at his expense in 1994. He says the lesson was not to write checks, and he refuses to expose other clients, holding to a rule that their stories are not his to tell.

Chapter 28 Summary

In the summer of 1994, Sheen films Terminal Velocity in Arizona, calling it poor but noting a career-high $6 million payday. Despite “the Fleiss fallout” (177), he maintains lucrative Japanese endorsements for air conditioners, shoes, and cigarettes. During a Parliament commercial in New York, he meets Donna, a model whose calm manner attracts him. After the shoot, he invites her to Los Angeles.


Two weeks later, he proposes while drunk, and Donna accepts. He sets the wedding date for his 30th birthday to simplify remembering the date. Over the year, they shuttle between Orlando and Malibu, meet families, and he bonds with Donna’s father Jim over heavy drinking. Work takes them to Richmond and Baltimore for Shadow Conspiracy, which he later ranks among his worst films.


On location, their relationship seems to go awry. Donna feels unseen, and he feels unappreciated. Sheen senses warnings but avoids postponing the wedding, assuming she would resist. On September 3, 1995, his 30th birthday, they marry in Malibu before the judge who had handled his first arrest.

Chapter 29 Summary

The wedding quickly becomes a “mess.” Sheen drinks heavily and ends the reception by kicking lawn lights, which he does not remember. The honeymoon opens with an eight-day Bordeaux tour that Sheen chose for wine, rather than the tropical trip Donna preferred. Mid-flight after an argument, Sheen drinks multiple double shots of scotch, accepts a cockpit invitation, dons the captain’s jacket and cap, and briefly flies the Airbus after the copilot disengages the autopilot. He returns to his seat, apologizes, and withholds the story.


The Tahoe leg of the trip is worse. During a limo fight, he throws both wedding rings out the sunroof. A guard later finds them. He and Donna sleep in separate rooms and remain tense. He drinks vodka in his morning juice. He blames himself for many of the conflicts but also notes that they forgot how to be friends. He departs for Mexico City to film The Arrival. Donna joins for two weeks, yet the strain continues. They split before their first anniversary. He praises her “pure class” for never selling their story and closes with regret and conditional maybes.

Chapter 30 Summary

Sheen warns readers against trying crack cocaine. In 1992, he reconnects with Sandy, a former girlfriend, who calls from a dangerous house full of meth users. He arrives armed, pays $2,000 to clear her debt, and takes her to his Malibu townhouse. She is thin and exhausted and has been smoking cocaine rather than snorting it. Although concerned, he agrees to join her when she produces a pipe. The first hit, coupled with sex, produces an overwhelming euphoria that he says “rewired [his] frontal cortex into light-speed oneness times two” (187).


He concludes that only two paths exist: remain with Sandy and the pipe until it destroys him, or quit entirely. He vows to abstain, tells Sandy that she is welcome, but the drug is not, and they drift apart. About a year later, Tommy Howell calls to tell him Sandy has died, which leaves him grief-stricken, replaying their night together while acknowledging the drug’s power. He keeps his vow not to do it again through the end of 1996, noting that even solemn promises can become “negotiable.”

Chapter 31 Summary

In 1997 and early 1998, Sheen completes six films and deems five of them “rancid,” crediting only Money Talks, due to Chris Tucker and a supportive ensemble. He arrives to set drunk or high, forcing first-time director Brett Ratner to improvise schedules and, in a last attempt at control, ask him to halve his intake rather than stop.


Sheen agrees. He improves enough to shoot until a 32-hour cocaine nosebleed halts production, and producers threaten to fire him. Sheen sobers briefly, finishes the film, and moves on without deeper self-examination. He rejects therapy and sober companions, deciding instead that the problem is not cocaine itself but the delivery method. He begins to smoke it, linking that escalation to his introduction to crack.


The work that follows is chaotic: a project in Scotland, time in Montreal with Marlon Brando, and a low-budget shoot for Five Aces that he largely misses, prompting a castmate’s joke that the production is four aces and a stand-in. Sheen concludes that his creative drive gave way to an addiction to crack and pornography and that he is ready to “be done with all of it” (191).

Chapter 32 Summary

Sheen arrives in Arizona for a film exhausted and detached, noting a “bone-dry landscape” that mirrors his condition. He criticizes producers and directors for ignoring his obvious decline and pursuing cheap projects, arguing that his 1997 slate could have been replaced without consequence. The job itself yields nothing, but he leaves with a new dependency: daily injectable Nubain, a synthetic morphine. At a party, he meets Sarah, a registered nurse, who introduces him to Nubain, which she has been stealing from her hospital. He first injects it intramuscularly, then, later, in Los Angeles, intravenously, which he describes as “unlike anything [he had] felt previously” (193). He believes the drug can help him reduce his crack and alcohol intake.


Sarah is also dealing to clients in Phoenix and Tucson. The initial rule to use only when she is present quickly gives way. Through his bodyguard Zip, he arranges FedEx shipments of the drug and uses it when she is away. His usage escalates to about 80 milligrams per day. He accepts that his decisions, not hers, drove the crisis.

Chapter 33 Summary

Charlie begins a relationship with Jane, a striking woman whose “offbeat” charm initially suits him. In quieter moments, he notices a mean streak but dismisses it. The relationship ends abruptly when she makes inappropriate remarks after seeing a photograph of his teenage daughter. He tells her to leave; a brief struggle follows, after which public accounts portray him negatively. He chooses not to contest the narrative, resolves the matter with a payment, and accepts a restraining order.


About a month later, Jane calls, in violation of the order, and pressures him to meet her. He complies and, afterward, reflects on the encounter as an exercise in power and control rather than reconciliation. A second meeting occurs at his Malibu Lake house. The mood is subdued, and he explains he is in the final days of withdrawing from a powerful opioid-type drug. He is using alcohol and prescribed sedatives to cope, hoping to avoid treatment.


Jane stays through the end of the acute period and then leaves. He emphasizes that if sensational media reports about the earlier incident were accurate, these later meetings would not have occurred, and says that legal constraints kept him from revealing “the truth.”

Chapters 23-33 Analysis

The Book of Sheen is presented as an autobiography, a celebrity memoir in which Charlie Sheen tells his story in chronological order from his own perspective, illustrating his emphasis on Self-Narration as a Bid to Reclaim Identity. As the narrative reaches the point where his addictions take hold, the book shifts further from anecdotes to the deeper purpose of Finding the Roots of Addiction. Despite his flippant, joking tone, the book is a reckoning with Sheen’s past, a demonstration of his struggles to engage seriously with the damage caused by his addiction. Key to understanding this tension are the choices that he makes throughout the narrative and the way in which he often breezes past the consequences and ramifications of these choices. These past choices are contextualized with the narrative voice of his present self. However, Sheen also adheres to his past perspective, explaining events and highlighting the way he reacted to them then, using his present perspective to offer subtle commentary. His addictions to alcohol, drugs, and sex are a manifestation of his desire to avoid introspection: He refuses to reckon with his precarious psychological state, drowning his own insecurities and anxieties in a deluge of physical pleasure. His repeated escapes from rehab and insistence on dealing with his addictions in his own manner (a method that almost always leads to relapse) show how, in the past, he attempted to avoid accountability and confronting his addictions directly. Meanwhile, his drug use evolves from marijuana to cocaine to crack cocaine, a shift that illustrates how his addictions are spiraling out of control even as he assures himself that his fame and success show that he must be making good decisions. Charlie’s judgment in the moment is clouded by his addiction; the book itself quietly charts these repeated failures in judgment, with each choice functioning as a retrospective condemnation.


These chapters also highlight another way in which Sheen’s addictions become a problem; although he loves films and filmmaking, he slowly abandons his craft, illustrated by the changes in his choice of movies. After Platoon, Sheen was satisfied with his acting, but the work and vulnerability required for the role were extremely difficult for him. He believed that the praise he received from critics and the public was justified and sincere. In many ways, he agrees, and Platoon remains—at least from his perspective—the pinnacle of his film career. After the release of Wall Street, Sheen begins to doubt himself. He feels much less pleased with his own performance, yet he continues to receive praise. People tell him that he was good in the film, yet he does not value his own performance. Everyone, he decides, is insincere. More damagingly, he comes to realize that he can be paid vast sums for taking on roles in bad films, churning out work which he himself does not respect, without risking vulnerability, as he had on the set of Platoon. The way in which Sheen talks about his post-Wall Street output illustrates the extent to which he does not respect his own performances in these movies. In essence, the movies simply enable the lifestyle to which he has become addicted. They lose their artistic interest in Sheen when he stops viewing acting roles as creative ventures and starts to see them as a financial necessity to pay for his lifestyle.


Sheen’s litany of poor choices, from the choice of drug to the choice of role, is also evident in his choice of friends. Throughout the book, he flits among various friend groups. At various points, he spends time with fellow actors like Chris Penn, Nicholas Cage, and other peers. These people only make fleeting appearances in the book, however, often coinciding with the degree to which they are available to party with Sheen. Similarly, the women in his life are often those who enable his lifestyle, rather than those with whom he makes meaningful connections. More of the book is dedicated to Sheen’s relationship with the “Hollywood Madam,” Heidi Fleiss, than to any of his wives, for example. His association with Fleiss is an example of the extent to which Sheen chooses only to surround himself with those who are most able to indulge his addictions. From fleeting friendships to employees, the only constant in Sheen’s life is the extent to which other people become vehicles for his own indulgence. His choice of associates illustrates the extent to which everything has become tangled up in his addictions, continuing the narrative’s documentation of his escalating dependence.

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