The 5 Most Egregious Charlie Sheen Roles

Charlie Sheen….well, what more can be said about Charlie that hasn’t already been said a thousand times? I mean, let’s face it: the guy is not connected with the real world.

But that’s not what this article is about. You won’t see jokes about tiger blood or winning here, so if you came for that, you should leave and change as a person because seriously, what’s wrong with you? Now that those unfortunates are banished, we can focus on what this article is really about: pointing and laughing at stupid things Charlie Sheen pulled in the movies.

5. The Three Musketeers

Picture, if you will, the four actors that, in your opinion, would form the worst combination of Musketeers in movie history. Do you have it? Now, Walt Disney has taken your idea of horrible, and laughed at it, before saying, “Get a load of this”:

That is, from left to right, Jack Bauer, Charlie Sheen, Robin, and George Steinbrenner. Now, I can look beyond the fact that it looks as if that’s a high school clique, what with the hair growing everywhere and the adorable fat guy on the far right. I’m even willing to look beyond the fact that Charlie Sheen is Aramis, lover of Truth, Honor, and Jesus, all three of which Charlie is opposed to at all times, and as such, wears a gaudy cross on his uniform that I’m surprised doesn’t burn him.

What I can’t get over, what irks me more than anything, is that a guy manages to shoot Charlie Sheen in this movie, right in the chest, but he didn’t die. The bullet was deflected by the gigantic cross he wore around his neck. Charlie Sheen, one of the world’s truly godless people, was saved by Jesus paraphernalia.

It just figures this guy can’t even kill a man correctly.

4. Red Dawn

Let the record reflect that for the most part, I have no problems with this movie. Any time a group of teenagers kill the crap out of some communists in the mountains and feature Patrick Swayze strutting around being all badass, I’m a happy guy. However, the Johnny Raincloud to Swayze’s buoyant personality is his supposed brother, Charlie.

That’s Charlie’s “serious” face.

First of all look at that picture. Do those two look even remotely related? Most of the time siblings, particularly brothers, tend to look kinda sorta similar to each other. The only way Charlie and Patrick could look more different is if one of them was missing a nose. Now, I’m not saying they aren’t related, I’m just saying they should probably ask Mom if she slipped any milkmen the tongue at some point. As for the rest of the movie, all I have to say is this: if you’re going to kill Charlie Sheen off in a movie, at least give us the satisfaction of showing him die so we can cackle at the guy. I mean, jeez.

3. Young Guns

There was a time in the 1980s when the women of America swooned over a group of young male actors who appeared in a lot of the same movies together, known collectively as The Brat Pack. There was also a time in the 1980s when the women of America swooned over cowboys in movies. The geniuses in Hollywood came to a shocking conclusion: combine them both and create a cash cow of a movie that makes women wet themselves and their boyfriends jealous. The result? Young Guns.

There’s Kiefer, again sporting a regrettable beard. Lou Diamond Phillips appears in this movie because this was an age when Lou Diamond Phillips was a bankable actor, and the whole gang is led by Charlie’s brother Emilio Estevez, notorious leader of the Brat Pack (in real life) and the cowboy gang in the movie. He’s Billy the Kid, of course. And then there’s Charlie. He plays a guy named Dick, naturally, and is the first boss of their posse until someone finally manages to kill Charlie onscreen, violently.

Huh, without context I guess it’s just kind of awesome instead of mind blowingly so. Oh well Charlie, look on the bright side: you could have portrayed the character Dirty Steve.

2. The Rookie

Clint Eastwood has had a lot of partners shot out from under him over the years, it always seems the psychopath that Clint’s chasing proves too much for the number two man on the investigation. Such was the case at the beginning of The Rookie, when Eastwood’s partner was shot to death and he finds himself saddled with a new partner, our friend Charlie.

No one but Charlie can look that bored over police work.

Drug dealers are shot, Clint Eastwood is raped by a woman (but come on, when has that guy ever said no?) and Charlie Sheen ends up working under Lt. Eastwood with a Playboy model as a partner because it always farts rainbows in the world of Charlie Sheen.

1. Himself

Remember when I said I wasn’t going to ramble on about Winning and such? Well, I’m still not, but you have to acknowledge that the biggest acting role Charlie Sheen has ever had is the role of Charlie Sheen. This is a man who dropped out of high school three weeks before graduation to become an actor, who shot Kelly Preston in the arm (accidently of course) whose idea of a hot date is picking up porn stars, often more than one at a time, who has overdosed on cocaine on more than one occasion, and been arrested for, among other things, destroying seven thousand dollars in property in a hotel room he was staying in. But he didn’t show his true potential for nuttiness until this past year.

All of us watched the drama unfold in the press: Charlie was fired from his lucrative job starring on Two and a Half Men after publicly insulting his bosses and just making an ass of himself in front of the entire world. It was like we were all sitting there watching him self destruct before our very eyes. We encouraged it, laughed at his insane antics. When Comedy Central roasted Charlie, six and a half million people tuned in. Think about that: six and a half million people watched a television program featuring a bunch of celebrities making fun of another celebrity, one who we had been using the SAME jokes on for months beforehand.

Yet, somehow, Charlie found a way. Charlie ALWAYS finds a way. When he couldn’t hack high school, he became a millionaire actor. When serious acting roles stopped coming for him, he switched to comedy. When movie studios stopped calling him, he switched to television, and became one of the most highly paid actors in the history of television. When he was fired from that, he moved on to America’s Court Jester, hitting not just the social media scene (he was being followed by 100,000 new people a day for months last year) but also doing live…I want to call them stand up shows, but he mostly sat on a stool and insulted his audience while drinking a lot (which is pretty much what his audience came to see him do.)

When he’s not doing that, he’s endorsing a line of kids clothing (SheenKidz) or freakin’ electronic cigarettes (NicoSheen) and is now employed by a marketing agency specializing in Facebook and Twitter promotions. We spend so much time laughing at him that we don’t realize he’s playing us. Charlie Sheen found a way to make millions off of his nervous breakdown, is probably still getting laid every night in bed made of money and cocaine, and somehow we allowed him to get away with it. I don’t know how he did it, I don’t even want to know how he did it. But I have to acknowledge this about Charlie, no matter how much it pains me to say this…Charlie Sheen…is….


I’m so sorry.

By Ben Adelman

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