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The Craziest Charlie Sheen Screw Ups of All Time

Updated December 5, 2020 3.8k votes 876 voters 383.5k views19 items

If you put all of the crazy things Charlie Sheen has done in one place, you start to notice a trend. The guy does not give a f*ck. We've seen more of Charlie Sheen's insanity than ever before since he started opening his mouth defending himself, most notably when he's gone literally against the hand that feeds him by starting a "war" with CBS and Two and a Half Men creator Chuck Lorre. Not to mention his trip to the ER with a hernia after doing cocaine for 36 hours with prostitutes, hookers, and porn stars, AND that story where Charlie Sheen shot wife-to-be Kelly Preston on accident.

This may all lead you to ask: What drugs has Charlie Sheen done? Too many to count. The guy is crazy. Through the years, few stars have seen more trainwrecks than Charlie Sheen. So here, in full list-form and in all their headline glory, are the craziest things Charlie Sheen has ever done - high or sober - and that's saying something. From taking a knife to your girlfriend, to flat out shooting her, to threatening your wife's life, to using your status to try to get a hooker, here are his most dumbass, "Charlie Sheen crazy" shenanigans all in one place.

What did Charlie Sheen do? Probably anything you can think of, and his arrest record proves it. He may be a movie star, but he's also technically a criminal. Enjoy these (accidentally funny) totally crazy Charlie Sheen stories and be glad that you (probably) have your life together just a little bit more than this guy. 

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    Did So Much Cocaine That His Dad Called the Cops

    Photo: Metaweb / CC-BY

    In 1998, after a cocaine overdose, Martin Sheen reported Charlie Sheen for violating his parole and issued a public appeal for fans to "pray for him."

    He was arrested and sent to rehab; this one was the first of many for Sheen. A little embarassing to have your parents call the cops though... especially at age 33.
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    YOU MEAN YOU CAN HAVE COKE DELIVERED!?

    Photo: Wikimedia Commons / CC-BY

    That's right folks. A Briefcase filled with cocaine delivered by to none other than the Hollywood bad boy, Charlie Sheen. The night before the "hernia" hospitalization, Sheen's bender included a very "special" delivery, probably handed to him directly by one of the three different escorts of the night. Sheen has snorted coke for years, but so far, this was the first incident of an entire briefcase worth of the stuff.

    That's right, a BRIEFCASE. If this sounds unrealistic, please keep in mind that Charlie Sheen earns nearly $2 Million per episode of Two and a Half Men.

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  • 7

    Charlie Sheen Wins an Argument Over a Song Using a Knife. A KNIFE.

    Video: YouTube

    Here we go again. Sheen held a knife to then wife Brooke Mueller's neck in an altercation that started with the Train song "Drops of Jupiter."

    That's right, they were arguing over a song - which, in turn, caused Charlie to threaten a woman's life.

    According to Mueller's account of events, Sheen said, "You better be in fear. If you tell anybody, I'll kill you, I have ex-police I can hire who know how to get the job done and they won't leave a trace."

    Embedded here is the song which, as far as anyone can tell, would drive most people to murder.
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  • 8

    Kids? Eeeeh, No, I'm Okay: Charlie Sheen Gives Up Custody

    Photo: flickr / CC0

    When Charlie Sheen and Denise Richards originally got divorced in 2005, they shared custody of their two daughters, Sam and Lola.

    However, after many a drug and hooker binge, Sheen gave Denise full custody of the kids.

    He pays $50,000 a month in child support, is happy to remarry, has plenty of time to shamelessly bang escorts, generally s**ts around, and snorts coke religiously, but spending time with the kids? Eeeeeehhh, commitment and family values are for squares.
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