5. The Joker Dresses As A Nurse – The Dark Knight
Heath Ledger’s brilliantly unhinged portrayal of Batman’s most feared and famous enemy has gone down in the history of cinema as one of the all-time great villainous pop-culture portrayals, and as an aside to all his savagery, we do get a brief glimpse at his sick sense of humor. After The Joker threatens to blow up a hospital, Gotham General is (mostly) evacuated, with The Joker staying behind in disguise, kitted out as a nurse, complete with a dress and orange wig.
He then goes to say hello to a burned Harvey Dent – who is still in the building – and sits down to deliver the immortal and hilariously awkward line, “Hi”. This is an instance of weird that totally works; it adds to the demented, anarchic portrayal of the character, and makes it clear that he’s neither too playful nor too serious.