The Book Of Sheen - by Charlie Sheen

Read: 2026-02-01

Recommend: 8/10

To some extent, Charlie Sheen already had a bad reputation, and I suspect he doesn’t care what people think of him. I expected his memoir to be brutally honest—and it is. He openly discusses losing his virginity to a sex worker, his drug use, paying for sex, his struggles with relationships, and the fact that he never graduated from high school.

A compelling memoir typically revolves around two themes: personal life (sex) and professional life (work). The personal side covers relationships and identity struggles, while the professional side addresses what made the author famous.

Notes

Here are some text that I highlighted in the book:

  1. “Courage is grace under pressure.” —ERNEST HEMINGWAY

  2. Years later he’d describe her reaction that night as truly mesmerized, hypnotized even. Mom’s retelling, perhaps not quite as fantastical. (Downplay it all you want, Mom, here we all are sixty-four years later.) In a matter of a few months, they were playfully carving up the streets of Manhattan together, Mom already pregnant with my eldest sibling, Emilio. The relationship wasn’t without its challenges. Mom had to hit pause on her dream of becoming a legitimate artist, while selflessly going all in so Dad could remain one. Many sacrifices on both sides, money scarce, jobs infrequent.

  3. The only “home” I had known to that point was a walk-up on 86th and Columbus—the scattered details that begin to shape the idea of home, long before a child has all the puzzle pieces to define it: shared bedrooms, borrowed furniture, tough but fair love.

  4. Change for me was a toe-dip into the unknown. Gators, eels, strangers. This was gonna take some time and patience, the two areas my parents had to be running low on (or out of).

  5. Once inside, parting the beaded curtain that separated waiting area from private massage rooms was like crossing into a section of the abyss you never hear much about: the fun part. Our pilgrimage of bliss was the groovy side of dangerous—dirty, edgy, and sexy.

  6. It’s been overstated that “What happens in Vegas, stays in Vegas.” I’m here to call bullshit on that one. Vegas followed me home, and changed its name to Santa Monica.

  7. The magic juice would hit bottom, warm away the clench and shackles, and give that fucker the night off. The fantasies I built as a kid watching Leo and Eileen Penn dispense their woes with that same magic liquid were now my reality. They’d given me “the fix” a decade in advance. But it’s no secret—every surefire solution comes with its own set of variables. I couldn’t access that fix in the arena where I needed it the most: a film set. That was the one place where I drew the line, with no plans to cross it for a very long time. At some point, everything’s negotiable.

  8. My parents were extremely helpful as well during those early years, and not just with their time. Their resources filled the gaps I couldn’t manage financially. Whoever penned the phrase “It takes a village” would’ve been kick-ass proud of our lineup. We kept the I out of team and set an example to be emulated gracefully.

  9. To get a feel for the rhythm of the scene, we did a cold read that was stumbly at best. Before I had a chance to ask him about a few beats I’d highlighted, he gave me the palm-forward, eye-level, Dad-hand of shut-it: “Don’t change a thing. What you just did is exactly how it needs to be played.” When I explained that I’d really done nothing at all with the words, he cut me off again: “It took me thirty years to learn how to do that.” I threw a look to Mom, and her eyes urged me to follow his advice. It was settled; I had my marching orders. I spent the remainder of the ride back to Point Dume hoping the director was also gonna be on board with Dad’s thirty-year nothing.

  10. I kept it very simple—trying like hell to not try like hell.

  11. Citing everything he’d been following in the news, Dad told me that the film wasn’t worth risking my life for, strongly urging that I decline the offer. Had it not been the third frikkin’ time his advice was asking me to trade an amazing opportunity for the fear of the unknown, I might have tuned in more responsibly. I told him if I didn’t throw caution this time, I might never get to experience the consequences of autonomy and the freedom of risk. We shared a long hug. Pretty safe to say I picked the right time to declare, “I got this.” We broke from the hug, and I couldn’t help myself when I added, “Don’t forget; I’m the guy who hit the game-winner over Jordan. The Philippines should be worried about me.”

  12. The fifteen-hour flight turned into a soggy airborne frat party, hosted by Johnny Depp and myself. (He had the role of Lerner, the platoon’s interpreter.) As thrilled as I was to embrace a solid new friend, I made the mistake of trying to match Johnny booze-wise. That handsome fucker drank me under the tray table. (My Red Dawn pals Darren and Tommy would be glad to hear that I’d finally met my pirate.) I abandoned my first-class seat to spend hours in coach with Depp, so he could chain-smoke at the back of the plane. I remember watching him slaying cig after cig, and while he did look James Dean–kool doing it, I stayed proud of myself for never picking up the hateful habit. (Those fifteen hours in the air would be the last time I flew anywhere as a nonsmoker.)

  13. One thing our camp never suffered a shortage of was cigarettes. One person who relied on their steadfast availability was Johnny Depp. Anytime there was a breeze, my dirt-hole was downwind from his human Marlboro chimney. Ramon smoked when we were teenagers, and I’d grab the occasional puff of his imported Davidoffs. Didn’t grab me back then, so I assumed I’d be able to take it and then leave it—again. Depp began to offer the cigs more frequently; I began to accept them less cautiously (usually after P.T. or a meal). This went on for about a week, with Johnny’s strange glee around it growing by the day. He finally clued me in—he had successfully converted one nonsmoker on each of his previous three films. Oliver wanted me to smoke for the character. A perfect storm was forming just off my nonsmoking shores, which only added to my dilemma. Depp had his man, Oliver had his character detail, I had the nicotine curse. (When I finally quit smoking on the Fourth of July in 2019, I did the math and figured out that I had smoked twenty-five miles of cigarettes when lined up tip-to-butt. Thanks, Johnny; should I ever need one, I’ll send you the bill for my new lung.)

  14. Platoon was filmed in perfect chronological order. My first day of shooting was the first scene in the movie; the final day of production, my last. It remains my only film experience in forty-three years to incorporate that approach. It was a brilliant decision by Oliver. It gifted the actors an opportunity to build a performance in such a way that we never had to remember what had led up to that day’s work or decode how we were supposed to feel about a moment that hadn’t yet happened. As the characters in the story grew weary and emotionally shattered, the actors did as well. Oliver had us marching inside of a timeline that didn’t need to be explained to us; we were living it from one day to the next.

  15. His farewell—being airlifted away in a chopper, screaming, “Adios, motherfuckers!”—remains one of the greatest film exits in cinema history. Watching him leave the jungle that day had everyone torn between the sadness of seeing him go and the jealousy that it wasn’t us.

  16. The main issue with the drug for me was how cunning it was. I’d be going about my day handling a bunch of not cocaine things, and in the next second be launched into a hair-on-fire obsession to get that drug into my bloodstream.

  17. I wasn’t snorting it as much as I was putting it in the end of my cigarettes for a move known as the coco-puff. Decent head rush that lasted about a minute until the next cig-tip had to be filled and lit. Looking back, as my brain became more curious about the connection between fire and cocaine, there’s no doubt that combo served as the precursor to freebasing. I upped the ante further by adding porn to the mix, and presto—my holy trinity was complete.

  18. I never believed for one second those girls would ever walk off the page into my arms, and do so on the same night I bonded with a childhood hero. It was amazing and unforgettable, and like so many days and nights during my chrysalis phase, the events kept topping each other on the mind-blow scale. Knowing that night had established a much loftier bar

  19. Honoring the amazing job in front of me while curtailing my appetites for the endless perks at my disposal stood the same chance in hell as an ice cube. I didn’t want to let Oliver down in a pivotal moment for both of us. The whims of my imagination sat a phone book or a cab ride away, and I’d spend the next three months trying to make sure the movie stayed dry in my hailstorm of unfettered access.

  20. Knowing someone for a few hours and then giving advice for things that took that person years to create is entitled and invasive.

  21. Who are we really without the booze and drugs we relied on for so long? And what happens if we get off everything and meet that new person and absolutely hate him or her?

  22. I loved to drink and take drugs, hang with beauties, howl with laughter and solve everything that crossed my path. I never dodged the truth or broke shit I couldn’t afford to pay for.

  23. Trying to navigate any complicated social setting, I could feel my body and mind literally “creaking” like some unoiled wannabe tin man. I was constantly told by all the sobers how AA was the only answer if I wanted to stay sane and free. So, a lifetime membership to their medieval gibberish club, and I could keep feeling the exact opposite of what they promised? Heck yeah; sign me up. (Just gotta swap out my brain with a clump of ham first.) When I’d ask about alternative modalities to decode and lick this thing, my queries were perceived as threats until I was ultimately branded a denialist. It was basically, “shut the fuck up and eat your mango.”

  24. The feeling I’d get from the gate-buzz or doorbell when the girls arrived was like a hundred Christmas mornings all at once in my favorite age from childhood. It was the mystery of the unknown, wrapped in the giddy mischief of secrets that had to be kept in the shadows. I’m still not sure which aspect of it was more intoxicating: the women themselves or the decision to make the call. The sensation of the stomach vertigo was identical to placing a large bet with a shady bookie. Climbing inside that rush with the outside chance of opening the door to handcuffs instead of girls was a risk I was willing to take anytime I picked up that phone to deck my halls. The women were never misdescribed or falsely represented with their age or personalities. Heidi knew the value of customer trust, and she built on that with her consistency. What most people don’t understand is if you took the financial component out of the equation, the women were just as classy as the terrific gals I’d meet at clubs, bars, and parties. It never felt dastardly or corrupt. I justified the encounters as paying a convenience-tax for a guaranteed outcome the other dating scenarios couldn’t offer. Maybe I blurred the lines, maybe the lines blurred me. I was having way too much fukken fun to carve out any time for soppy reflection.

  25. It would mark the first time the rat’s nest had been off my head in five months, and I wasn’t gonna celebrate those nine hours of freedom by myself. The lovely lady who showed up that night enhanced that freedom ’til sunup. She and I stayed in touch and saw each other for several years after that night anytime I was in the city. Heidi could tell when certain clients had taken a shine to a particular girl, and she didn’t meddle or try to shake anybody down when those two had worked out their own deal moving forward. She was smart that way by never coming off as desperate or possessive. It’s one of the reasons when Fleiss got arrested in June of ’93, I was pretty sure it had nothing to do with matchmaking greed.

  26. When I climbed in beside her, she had a freshly loaded crack pipe in one hand and a lighter in the other. She handed me the paraphernalia and told me not to overthink it. My brain heard that, and think and over tapped out. I threw caution and accepted her invite to the extraordinary combo she was offering. As I took that massive first hit, Sandy disappeared under the covers and I disappeared from planet earth.

  27. when Jane saw a photo of my thirteen-year-old daughter Cassandra next to my closet. She stopped in front of it, studied the picture for a few seconds, and without warning launched into a barrage of inappropriate comments that stunned me. I’d never heard anything like it. The sweet, sexy, fun person I’d gotten to know was suddenly gone, eerily replaced with a weird darkness I did not recognize. Her twisted comments led me to a stern and swift verdict: Jane had to leave my house at once.

  28. The reason I bring all of this to light is to offer a peek behind the curtain of the nonexistent epilogue. Stories don’t end because you’ve reached the bottom of the page; there’s always a secondary viewpoint worth listening to. The media’s slanted portrayal of the situation didn’t fall anywhere close to the truth, and left inquiring minds blinded by three-dollar bills ’til the cows came home and left again.

  29. As we all know, MJ hit “the shot.” It was a real moment for me. I needed to hang onto that moment, get inside of it, and stay there. I’d been tossin’ up air balls for far too long. I decided that same day, June 14, 1998, it was time for me to start making a few big shots of my own.

  30. Once I’d regained everyone’s trust from the counselors to the judge, that leash began to loosen, both figuratively and literally. One month after Jordan hit the shot, they finally agreed to pardon my ankle and remove that fukken LoJack. It was complete overkill, but I guess every show trial has to have one or two special effects. I was grateful for the extra slack and used most of my “day passes” to pass the time with America’s favorite pastime.

  31. The light that had once blinded me evolved into the sunlight of each new day as it broke through the shame-clouds of crack, chaos, sex, and booze. The searing truths I embraced during my stay reunited me with a hope and confidence I no longer sought at the end of a pipe or the bottom of a bottle. To finally realize those virtues had been inside of me all along, I just needed the gift of silence.

  32. Drinks were spilled, things got bumped into, migraines awaited me at the end of those days. I didn’t care—pain is temporary; film remains forever.

  33. It wasn’t until the final night in Toronto that I decided my celibacy streak needed the closure I’d find in the matchmaking Yellow Pages of Bell Canada. In less than an hour, a gorgeous brunette rolled in to DND our night into the awe some would frown upon. She was wonderful, but that level of intimacy still housed a frustrating awkwardness that I knew could be cured with substances. I also knew those insane thoughts were a form of sabotage from an alcove in my mind where truth didn’t get a vote. The rehab folks did warn me that it would take time for my brain to adjust, but come on man, it had already been a year. My ongoing debate to appraise the value of booze and dope between the sheets was useless—multiple choices were down to two: sober sex, or no sex at all.

  34. It’s pretty common for a lot of folks to gain a buncha weight after getting sober, especially when stimulants were their drug of choice. I’d always defend it by telling people I’d rather be a bit soft and alive than crack-skinny and fukken dead.

  35. To clarify, a trouble spot is a fear-word I’d gotten stuck on in the past. My specific type of stuttering wasn’t (isn’t) the classic style we’ve all witnessed at some point, where the same letter is buh, buh, buh like an engine that won’t turn over. The card I drew is a lot more subtle—halting that fear-word into a locked silence before any sound makes it to the ignition. When that happens in a film setting, it’s a thousand times worse. Everyone on set knows what the word is because they’re reading it—waiting, for what feels like forever.

  36. We made eye contact a couple times in the gym, and other than being flattered by her glances, I didn’t give it too much thought. I got back to my room, showered, fired up my first-generation (seventeen-pound) Sony VAIO PC, and proceeded to give Nancy way too much thought. Time caved in on itself, and when I finally looked up, I’d been lost in space perusing her website for several hours. It was an empty quest and I knew it; I was chasing the false freedom those cyber halls could no longer provide. Unless there was dope in the mix, recapturing that glory was an Alice burger with a side of white rabbit.

  37. I’ve been married a total of three times (you’ll meet the third wife here shortly), and I need to clarify that I never cheated on any of them. Others may claim different, but I don’t care about those muck-vendors or the fiction they spew; I know the number and it’s zero. (That said, the “addendum” to that zero are the times when I was legally separated. That number was not zero. It was numbers with zeroes.)

  38. By the middle of the audience show, I’d be in full withdrawal, sweating like a Bonnie Brae junkie. My last dose was usually around 11 p.m. the night before, creating a jonze-gap of more than twenty hours before I’d feel whole again. If I could just grind through that final scene, Dylan would soon be driving me home while I devoured the four or five ovals I had stashed in my pocket. Chomp, crunch, soda chug. In under five minutes they’d bum rush the blood barrier with a swan dive into my dope-starved brain. As Brad’s jacuzzi factory churned the ripples of relief, my opiate straitjacket was snugly fastened.

  39. Watching my summons deliveryman disappear into the dark was a check my brain couldn’t cash. In my experience, the main feeling in that situation, between sadness and rage, is something I can only describe as discarded. When a stranger hands over a piece of paper that states you no longer matter, it’s like being a single-use item tossed into a landfill. All the therapy in the world is gonna have a hard time reattaching the hero label to that empty plastic bottle.

  40. As the show wore on (and the pills came back), it was more like two and a half personalities I had to embody. Sober-guy for Chuck, friendly-guy for my costars and crew, half-a-whatever-guy left over for me.

  41. The one question I get asked a lot is why was I in such a hurry to get married again. I’ve had a long time to come up with an answer, and I’m still not sure if I’m satisfied with where I’ve landed. I think half of it had to do with B, and the other half was more about loneliness and fear. I was feeling so overwhelmed, beat down, and outnumbered in my life; I didn’t want to keep fighting those battles alone.

  42. It came on the heels of an impossible situation that needed to be scrubbed from my soul, and I chose the most reliable cleansers I had at my disposal to activate that purge: women and dope.

  43. The price I paid for my riots of self-will was Muh-Manda. She told me I had a choice: her or the bottle. Terrific gal but she lost in a landslide. I hope she found whatever happiness she was looking for and a Humpty who needed a little less glue.

  44. I appreciated all the attempts from everyone who tried to help, but it was time for me to build my own boat. Water rises a lot faster than it does in the movies.

  45. There was only one thing that felt worse than betraying myself, and that was failing my children. In that car, on that day, with my best friend and a child I adore, I joined Sam in those mirrors and saw a guy who was desperate to finally come home for real. The details of that home were no longer scattered, and at long last I did have all the puzzle pieces to define it. I’m the one who left home, and yet somehow; it never left me. I knew exactly what had to be done. Like I’ve always said, life comes down to doers and talkers, and there was really nothing left for me to say—it was time to shut the fuck up and get busy doing.