Here’s A WINNING Ranking Of Charlie Sheen’s Most Charlie Sheen-iest Moments

By: 09.03.14  •  10 Comments
Celebrity Sightings In New York City - March 29, 2012

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I’ve got to get something off my chest. A couple of weeks back, I covered Charlie Sheen doing the ice bucket challenge from the angle “Charlie Sheen Just Ruined the Ice Bucket Challenge For Everyone.” Basically, in case you missed it: Charlie Sheen dumped a bucket of money, not water, on his head — in the most grandiose, Charlie Sheen way possible — which he then said he was donating to the ALS fund as an excuse to antagonize his former Two and a Half Men employer, co-star, and replacement.

It was not well received. Comments to the post, both on UPROXX and by the thousand on Facebook were in the general consensus of “HURRRRRRR how did he ruin anything he donated a lot of money, ur stoopid Charlie Sheen is a #HERO #WINNING.”

Let me address two points, here. Yes, it was certainly an act of generosity for Charlie Sheen to donate to the ALS fund. I’m not denying that. But $10,000 is also not a tremendous amount of money for Charlie Sheen. I’d have to wager that $10,000 is only a fraction of Charlie Sheen’s “hooker and blow” budget when he’s on a bender. Which is probably like every other week.

Secondly, lest we all forget: Charlie Sheen is, at his worst, a disturbed individual with a history of domestic abuse and violence. At his best, he’s a buffoon absolutely subject to our ridicule — and one charitable act does not cancel any of that out. So on this day, which happens to be Charlie Sheen’s 49th birthday — because somehow he’s only forty-nine — here is a ranking of Charlie Sheen’s Charlie Sheen-iest moments from the past four years, so we can all put things in perspective. And, hopefully, heal.

#10) Drunk Charlie Sheen in Paris



Charlie Sheen was stumbling around the Seine River in Paris last April when a gaggle of bros came along and proceeded to engage him in some drunk photography. As one does when encountering Drunk Charlie Sheen! No one knows what he was doing by himself drunk in Paris — but is further reason needed other than that he’s Charlie Sheen?

#9) Trying To Trademark His Own Catchphrases

Following his hugely public meltdown, Charlie Sheen tried to capitalize off of his insanity (because if nothing else, he’s a very shrewd businessman) by attempting to trademark words and phrases such as “Duh, Winning,” “Vatican Assassin,” “Tiger Blood” and “Rock Star From Mars.” Yes. Charlie Sheen tried to trademark “winning,” a word that has been around much longer than Charlie Sheen. I don’t think he was successful in his efforts.

#8) Drunk Charlie Sheen at Taco Bell

As with Charlie Sheen drunk in Paris, Charlie Sheen drunk at Taco Bell involves Charlie Sheen just stumbling around drunk by himself, only this time at Taco Bell instead of Paris — to the delight of bystanders who caught this most special of creatures in the wild. If you’re wondering why it was ranked higher than Charlie Sheen being drunk in Paris, well, it’s because Taco Bell is far sadder than Paris and therefore that much more Charlie Sheenier.

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#7) Discussing Threesomes with Jay Leno

In September of last year, just a scant five months before his next engagement (we’re almost getting to that) Charlie Sheen went on The Tonight Show with Jay Leno and discussed his three girlfriends — two of which were already involved in a sexual relationship prior to getting involved with Sheen. So there’s that cozy little mental imagery to get you through the rest of your day.

#6) Becoming Engaged for the Fifth Time to a Porn Star



Because the fifth time’s the charm? Charlie Sheen has only actually been married three times previously although this will be his fifth engagement. His engagement to Kelly Preston was never made official because he SHOT HER. At any rate, Sheen decided to settle down earlier this year with just one porn star instead of several, Brett Rossi — who has since changed her name to Scottine Sheen, her birth first name and his last. Presumably because they can’t wed yet since she’s technically still married to some other dude. Ah, romance.

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