These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Crosses the Line Twice: At least. His character on Two and a Half Men was basically a watered down, family friendly version of himself, a character so popular it made him the highest paid TV actor of all time. Then the mask started to slip, and started less than charitable remarks about his boss on the public forum, the line was well and truly crossed. But then, instead of backing down, Sheen turned the crazy up to eleven. He started talking about his Tiger Blood, and his fire breathing fists and his addiction to winning. He shacked up with a porn star and a model at the same time. Now he's the biggest Memetic Badass of the decade and even the lame stuff he says like "Duh-Winning!" sound cool because he said them.
Crowning Moment of Awesome: His recent explosion of highly eccentric interviews has vaulted him firmly into the pantheon of awesome celebrities. Not only has he not expressed a bit of regret for his drug binges, he keeps raving about how much FUN he and the people around him had and suggests he has transcended "normal" human life.
Hypocritical Fandom: The media seemed to laugh either at or with Charlie Sheen during the Febuary public meltdown. Meanwhile, Britney Spears' and Lindsay Lohan's woes were viciously mocked. The fact that Charlie Sheen is living out a common male fantasy and the fact that his work was, until recently, unaffected may have something to do with this.
Even worse when you compare Sheen's troubles to Chris Brown, who both went through situations involving domestic violence. But despite Sheen being a chronic offender, Brown to this day still gets vilified for beating Rihanna (even though his situation was a one-time event, and he had to do tons of community service, unlike Sheen, who hardly received any legal punishments).