871 voters

The Craziest Charlie Sheen Screw Ups of All Time

Updated December 5, 2020 3.8k votes 871 voters 383.3k 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. 

  • 1

    He (Allegedly) Pulled A Knife on His Dentist

    In October 2014, Sheen was undergoing treatment for an abscess on his tooth. His dental technician claims that he suddenly became belligerent after being administered nitrous oxide, striking the technical and pulling a knife on the dentist. Then, his bodyguard informed the dentist that Sheen was high on rock cocaine as well.

    Though Sheen's publicist claimed there were no illegal substances or a knife involved at all, as other items on this list indicate, this wouldn't be the first time Sheen reached for a knife.

    Is this crazy?
  • 2

    Charlie Sheen Gambles During Childbirth, Threatens to Kill Wife (Denise Richards)

    Photo: Wikimedia Commons / CC-BY

    Charlie Sheen and Denise Richards's divorce was one of the ugliest battles in Hollywood history.

    In court papers filed in 2006, Denise Richards, Sheen's second wife, made 17 pages worth of allegations against Sheen, including, but not limited to:

    1. "Sheen abused prescription drugs after the 2004 birth of our first daughter, Sam, and told Richards "I 'better not tell anybody about his using these drugs and better keep it to myself.' I understood by these statements that (he) would physically harm me and our baby."

    2. Richards also claimed that on the way to the hospital for the birth of their daughter Lola last year, Sheen placed a gambling bet by phone, and was checking his pager, yes pager, for the results as she was wheeled into surgery for her C-section.

    3. Things turned violent on Dec. 27, 2005, according to the papers, when Sheen allegedly hit Richards's wrist and shoved her in the stomach after she confronted him about p*********y Web sites featuring "very young girls" that he'd been visiting. She claims Sheen told her that "if I revealed anything about his lifestyle, 'You won't lay your head down at night.' I understood this to mean that he would kill me."

    Sheen has pulled this sh*t before; in 1996, he was charged with assaulting his girlfriend at his home in California. He pleaded no contest and got two years probation.
    Is this crazy?
  • 3

    Drunkenly Pulls a Knife on Girlfriend, Gets Arrested

    Photo: flickr / CC0

    After he drunkenly pulled a knife on Brooke Mueller, Sheen was carted away to Pitikin County Jail for an eight hour incarceration... on Christmas Day.

    That's right, he pulled a KNIFE on a significant other. A KNIFE - like a greaser in the 50s. He's a multi-millionaire and he pulls a KNIFE.

    He was released on $8,500 bail (WTF, seriously), and of course, faced a court date and subsequent legal issues, including a restraining order. After the incident, Sheen was charged with felony menacing, third-degree assault and criminal mischief. Sheen copped to misdemeanor assault as part of a plea bargain in which the other charges against him were dismissed.

    According to a story written by Associated Press reporter Solomon Banda, Sheen was "sentenced to 30 days in a rehabilitation center, 30 days of probation, and 36 hours of anger management."

    Sheen is also prohibited from owning a gun for the rest of his life (see item 15 for irony). 

    Oh yeah, this also happened on Christmas day. CHRISTMAS. DAY.
    Is this crazy?
  • 4

    Accidentally Shoots Kelly Preston with a Gun

    Photo: Metaweb / CC-BY

    Clearly not exactly sober at the time, Sheen "accidentally" shot his then-fiance Kelly Preston in the arm; the wound required two stitches - which, as you can imagine, didn't exactly work wonders for their engagement at the time.

    Soon after that, Preston dumped Sheen and ultimately ended up with her current beau, cult-ambassador, possible-LGBT-leader and actor John Travolta.

    Apparently no one filed charges, probably because everyone involved already knew Charlie Sheen and what to expect from the guy, and hey, at least this one wasn't on Christmas.
    Is this crazy?