Top 10 Crazy Charlie Sheen Moments

Kicking off our list is the film scene in which Charlie “plays” a guy with three smoking blondes as bedmates! However, as may also be the case in real life, Charlie emerges from the party so depressed he inadvertently downs a bottle of Viagra, which prompts a very large problem! Outrageous? Yes. But frankly, not all that implausible…

A bewildered John Malkovich gets some unhelpful advice from Charlie in this oddly honest film appearance. Aside from the Rubik’s cube, Charlie is basically portraying himself as a stoned, carefree womanizer who is way too into hot lesbian witches and the belief that the truth is for suckers. It’s amazing to think this was shot over a decade before his public meltdown…

Fans of ‘80s flicks will never forget this classic cameo, mainly because Sheen’s role as a leather-clad stoner foreshadowed the Charlie we know and love today. While stuck at the police station, he goes from staring down Ferris’ sister, to offering her advice – in this case, how to not look like a whore and live a better life. Despite him being a jerk, she falls head over heels. Now that’s what we call winning!

Do you ever get the feeling this might be Charlie’s actual retirement plan? This action movie spoof sees Sheen in Thailand, fighting for sport. Of course, in true Sheen style he makes this an unconventional fight scene by showcasing his ability with a lasso, dipping his gloves in condiments, tickling his opponent and finally unleashing the fury below the belt. If you think that’s silly, wait till you see this…

Here we see Charlie, ever the concerned father, checking in on his daughter. As it turns out, this parody of “The Others” develops into an outrageous confrontation with the King of Pop. Ultimately, Sheen discovers he was fighting an alien impersonator all along. This is definitely a memorable moment, if not only because it puts two controversial icons together in the same room, sort of…

In this parody, Sheen and his hot date decide to combine food and sex. At first, it starts off all naughty; however, before long Charlie pushes the boundaries to see how far he can go, and how hot his lady-friend really is. This is your brain; this is your brain on Charlie Sheen…

Now that we’ve taken a trip into film, it’s time to explore the memorable moments from Charlie’s real life. First among these is his long shot victory at the Golden Globes after replacing Michael J. Fox on “Spin City.” His was one of the most unforgettable awards speeches in recent memory, since he was incredibly sweet to his fiancée at the time Denise Richards, and let slip a hilarious line about what victory actually feels like…

Charlie became fodder for countless gags based around his life, exploits and firing from “Two and a Half Men” in this no-holds-barred celebrity free-for-all, hosted by Seth MacFarlane. And, as can be expected, Sheen was a great sport about the entire thing, taking his punches like a champ. An hour later, he got to thank them for the intervention with his own hilarious jabs!

Okay, so it’s not a movie or television show per se, but we have to include Sheen’s live webcasts! Why? 1) Chain smoking, 2) frantic ramblings, 3) the show was tagged “you’re either in Sheen’s corner or with the trolls.” This was kind of an unexpected outlet for this mainstream star, but it allowed him to go ballistic and off-the-rails, while personally addressing a handheld camera in order to “enlighten” his fans.

Taking the top spot on our list is the infamous interview that kicked off Charlie-mania. Not only did Sheen make headlines with this Q&A, he also gave pop culture some much-needed phrases by revealing himself as a winner with Tiger Blood, Adonis DNA, an evolved brain and the power to heal himself. Somehow, he even made time to spill about his shocking drug use, his goddesses and his spat with “Two and a Half Men” creator Chuck Lorre.

Do you agree with our list? What’s your favorite Charlie Sheen moment? For more entertaining top 10s, be sure to subscribe to WatchMojo.com.