Top 10 Crazy Charlie Sheen Moments

This actor is well known for his wildly outrageous and hilarious antics on and off the screen. Not just wildly entertaining in real life with his 'winning' attitude and 'torpedoes of truth', he has starred in comedies such as 'Hot Shots!', 'Scary Movie', 'Spin City' and 'Two and A Half Men'. Join WatchMojo.com as we count down our top 10 favorite crazy Charlie Sheen moments from film and television.
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Top 10 Hilarious Charlie Sheen Moments


This guy makes winning look easy! Welcome to WatchMojo.com, and today we’ll be counting down our top 10 favorite crazy Charlie Sheen moments from film and television.

#10 – Viagra Overdose: “Scary Movie 4” (2006)


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…

#9 – Friendly Advice: “Being John Malkovich” (1999)


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…

#8 – Uncanny Foreshadowing: “Ferris Bueller’s Day off” (1986)


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!

#7 – Delicious Slapstick: “Hot Shots! Part Deux” (1993)


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…

#6 – The Concerned Father: “Scary Movie 3” (2003)


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…

#5 – Nine ½ Weeks Parody: “Hot Shots!” (1991)


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…

#4 – Sober Acid Trip: “The Golden Globes” (2002)


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…

#3 – Getting Roasted: “The Comedy Central Roast of Charlie Sheen” (2011)


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!

#2 – Torpedoes of Truth: “Sheen’s Korner” (2011)


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.

#1 – The Meltdown: “20/20 Andrea Canning Interview” (2011)


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.
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