Close your eyes and recall the halcyon days of 2011. Yes, there was an economic recession that just wouldn’t let up and the portentous rise of the proto-Trumpian Tea Party and all sorts of terrible natural disasters but … you could be a near-absolute skeeze and very nearly get away with it! (Not that much has changed … I mean Donald Trump is president currently, right now, in 2025.) The absolute skeeze in question isn’t the current leader of the fascist world, though. It’s Charlie Sheen, one man of Two and a Half Men fame, who is out with a new memoir detailing the sordid events that led up to his very public, maybe tiger-blood-induced, flameout of 2011. That year, CBS decided to finally fire the actor from America’s then-most-watched sitcom after turning a blind eye to his well-documented involvement in a sex ring, domestic-abuse charges, substance-use issues, and overall sleazy behavior. Sheen took the boot and swung a machete around on a rooftop to the tune of a million Twitter followers in a day and die-hard fans cheering his meltdown one-man shows. Getting canceled a decade and a half ago sure was different.
Sheen comes across as a bit glib about all the destruction and headaches he wrought in The Book of Sheen. Written in a very bad-boy, sex, drugs, and rock-and-roll tone, the book fills its pages with stories of paid-sex encounters, benders lasting so long that the thought how his house smells makes you mentally gag, and assertions of innocence. Sheen mostly glosses over discussions about his most glaring allegations of wrongdoing throughout the 350-page roller coaster that spends an inordinate amount of time on his twin fictionalized Vietnam-film obsessions, Apocalypse Now (starring his dad, Martin Sheen) and Platoon (starring himself); baseball metaphors; and his anger over losing a childhood ping-pong match with O.J. Simpson. To accompany the book, Sheen also has a documentary out on Netflix on September 10, aka Charlie Sheen. If you’re ready for some name-dropping and dope-taking, then here are the most Charlie Sheen of Charlie Sheen stories for you to read.
Trying “the other side of the menu” (gay sex) during his crack-fueled years:
Maintaining he only slept with consenting adult men, Sheen confirms that he frequently dabbled in “the other side of the menu” that sometimes “was catering the event.”
“In fact lemme take the pressure off and answer a few questions so I don’t get hit with them later on any fancy talk shows.
“Was some of it fun? You betcha.
“Was the “other side” in play without crack? Never.
“Were those the times that led to the extortion you had to pay?
“Those times and others.
“Is there a sense of relief to finally being honest about these experiences? A big one.”
Addressing battery charges against former girlfriend “Jane”
He claims that the “media’s slanted portrayal” of his highly publicized assault case in the ’90s “didn’t fall anywhere close to the truth” because the survivor allegedly slept with him twice after that. Okay. “Bottom line: I didn’t have the luxury to ponder her motives,” he admits, adding that he didn’t want to violate parole if anyone heard he saw her despite the restraining. “I also had a bunch of crack to keep me on my toes.”
Ratting out friend and convicted madam Heidi Fleiss:
Back in the ’90s, Sheen frequently used Fleiss’s services to book paid sex. “I remember my first conversation with her on the phone as though it were yesterday,” he writes. “Heidi was kool and friendly, with a relaxed sexiness that enveloped her voice. It was genuine and had a way of masking or delaying the realization of how razor-sharp she was. Intentional or otherwise, that thing worked like a charming charm. Before I knew it, I had agreed to twelve grand for two women from midnight ’til whenever and was convinced I’d pulled one over on her.”
When the Feds caught of whiff of her activities, Sheen made a deal to snitch in exchange for his freedom: “I never had to appear at the trial for any of it — we cut a deal for immunity and they videotaped my testimony at a neutral office. Heidi and her lawyers were in the room with me, and I felt like such a fukken a-hole as I laid it all out like a two-bit canary.”
September 11 inspiring him to propose to second wife, Denise Richards:
Known 9/11 truther says the tragedy opened up his heart to a second round of nuptials. “My motivation to tie the knot wasn’t connected to the usual emotional suspects — it was galvanized by the life-changing events of 9/11,” he remembers. “All of that shit came knocking on America’s front door, and when we went to answer, it blew up the whole fukken house. On September 10, I was fine; by the morning of the 12th, I didn’t wanna die alone.”
Bill Clinton allegedly eyeing Sheen’s then-girlfriend Dolly Fox while filming Three for the Road in 1986:
The former president gets a shout-out, this time as an allegedly creepy Arkansas governor. After being invited to Clinton’s governor’s mansion with co-stars Alan Ruck and Kerri Green, “Ruck overheard Clinton whisper to one of his aides: ‘Find out what you can about the brunette,’” Sheen claims. “The brunette was Dolly, and to this day Alan swears it was an exact quote.”
Photo: Sonia Recchia/WireImage
Thinking the HIV community “hijacked his vulnerability” and ending up on Dr. Oz:
Sheen publicly revealed that he was HIV positive in 2015, but that doesn’t mean he wanted to be an advocate. “With little effort to conceal the plot, that community did their best to hijack my vulnerability and nominate me for poster-child status,” he complains. “I went along with some of it, and ultimately wound up in the crosshairs of Dr. Oz and his televangelic medical circus.
“I hated being on his show but I did owe that man a solid. When Bob and Max were discharged from the hospital, Oz was in the neighborhood and made a house call to check on their tiny tickers. When it came to all matters of the heart (save for romance), his thumbs-up was a cosign second to none. The yellow-brick-doctor was only with them for ten minutes and I wound up in four episodes of his show. Maybe Turkish even-Steven is a bit different and if so, I guess we both won. (But he for sure got way more Steves.)”
Visiting Slash and Mira Sorvino after violating parole:
Sheen recounts this 1998 tale in a way that makes you wonder how much creative license he took with the dialogue: “‘Dood!’ he chided. ‘I have never seen someone who needs to be in rehab more than you do. And I have seen so many people who needed it in the most desperate ways imaginable.’ That struck me deep, but I was still pondering, fighting the obvious with potent denial. Slash pressed me harder: ‘If you don’t go today my friend, you are going to die.’”
Later, he claims Sorvino promised to sleep with him if he turned himself in: “That woman took it to another level when she grabbed me by the shoulders and shook me to attention: ‘Listen to me, you crazy, beautiful man, I understand why you don’t wanna go, but you are out of options. This isn’t a game anymore, these people are playing for keeps. Look at me Charlie, look at me: I will sleep with you — if you just promise to get yourself to court this morning.’”
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Losing his virginity to a “Vegas escort” courtesy of Martin Sheen’s credit card:
On a trip to Vegas during his sophomore year of high school, he charged a night with an “escort” on his dad’s Mastercard. “We explained our situation to Candy, and she responded with a level of physical generosity neither of us knew existed,” he recounts. “She was Ann-Margret in her prime with a Mastercard swiper. (I didn’t care that the swipe took longer than the sex.)” He did not procure his dad’s autograph like she asked. When dad found out, Sheen got an earful.
“During Dad’s two-hour lecture to me about sex versus love, I kept stressing how gorgeous Candy was and what a great deal Dad and I both got for the price,” he writes. “The look on his face told me we were done.”
Frequenting massage parlors with bestie Chris Penn armed with fake IDs and allowance money:
Telling their parents they were heading for dinner and a movie, Sheen and Penn would use the “moolah” to frequent “illegal” sex parlors in Santa Monica with homemade fakes. “As fabulous and enticing as that world seemed, it was easy enough to lose sight of the fact that we were still in school,” he adds. “The only way to keep it below the radar was to pick our spots and not get greedy.”
Hanging out with his sex doll:
During his ’98 rehab stint, a manager brought him a “traveling hand” courtesy of his second Real Doll. His first melted at his lake house. “As an elaborate joke months earlier, I set her up in the jacuzzi to scare the shit out of a buddy of mine. (I was too high to factor in the basic logic of really hot water and latex.),” Sheen writes. “The prank was a masterpiece, but Real Doll didn’t survive beyond the laughter.”
Buying so much crack the suppliers thought he was a small-time dealer:
That infamous summer of 2011 saw Sheen’s dope consumption hit record levels, according to his plug. “Phil looked me right in the eyes and very evenly explained, ‘My guys are shutting you down because they’re convinced that you’re dealing. They’ve never seen this much dope go to one guy who wasn’t dealing, and they’re giving you a pass — because you’re my guy.”
Combining of coco-puffs and porn:
“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.” It’s magically delicious.
Photo: Michael Buckner/Variety via Getty Images
Thanking Johnny Depp for his smoking habit:
Sheen says he first started smoking cigarettes on the Platoon set with the litigious actor with a still-rabid fandom. “Depp began to offer the cigs more frequently; I began to accept them less cautiously (usually after P.T. or a meal),” he writes. “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 non-smoker on each of his previous three films … (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.)”
Still mad about losing a ping-pong match to O.J. Simpson on The Cassandra Crossing set:
Winning a ping-pong game on the set of Platoon: “I thought back to O.J. and what a classless bully he was, denying the kid-me a moment I’d have cherished forever.”
Watching the O.J. car chase: “Like everyone else, we were speechless and shocked as the final twisted chapter of a sports and media icon was disintegrating before our very eyes. My childhood ping-pong bully had crossed the ultimate line.”
Choosing between wife Denise Richards’s Armani wedding-dress appointment and the last Spin City wrap party: “It will come as no surprise to anyone that I lost the Italian debate like that O.J. ping-pong game.”
Calling his clique with Nicolas Cage “The Jackson Five”:
With “ecstasy as our rocket fuel” the five-man clique descended on Vegas during the last month of shooting The Rookie. “Barely able to count but still in need of a check-in pseudonym at The Mirage, we declared ourselves as The Jackson Five.” Sheen even absconded from rehab to party with the J-5 for a bikini contest, promising the nurse $1 million if he didn’t return by the end of her shift at 9 a.m. sharp. (He made it back, he writes.)
God sending him signs to quit drinking:
One of the signs included two accidental proposals to porn stars. “Up at the lake in the mid-’90s, I took a flawless-D pinkie-ring off my finger while drunk outta my mind in the bathroom and proposed to a porn star I was madly in lust with for three days,” he writes. “When I sobered up, and Steph told me what I’d done, I saddled her with the task of going to the girl’s house with an apology, and strict orders to get the fukken ring back. Like a champ Steph did, but it still left me in a shame-pit and damn near ringless. Years later I proposed to another porn star, whom I met as a high-dollar call girl. I was so embalmed the second time, I invited all of my friends and family to a big engagement party for everyone to celebrate my porny future wife. Again, once just wasn’t enough; I had to get thrown from that carnival ride a second time to confirm it as a rickety hazard. (My security guard had to deal with that one; her baggage was way too heavy for Steph to carry.) God sent me a boat, which I deemed unseaworthy.”
Getting high on testosterone cream made him susceptible to tiger-blood theories:
“[Brian Wilson] was explaining how guys like us were different in that we have ‘tiger blood’ running through our veins — veins held together with ‘Adonis DNA,’ a substrate so unique it was never programmed to ‘lose’ because ‘guys like us’ are always ‘__.’ (I don’t need to write that seven-letter word. You can already hear me saying it, with that specific inflection and rhythm from atop Mount Bedlam.) That’s how it went down. I was so jacked on the Krazy Kreem, those phrases went into my brain and stayed on a loop just below the surface.”
