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  • Gilbert and Sullivan:
    • The Pirates of Penzance are likable chaps who refuse to attack a weaker party or harm an orphan (they're all orphans themselves, you see). Unsurprisingly, they are not very successful pirates.
    • The Mikado of Japan, who isn't a bit angry that three of the main characters killed his son (or claimed to) on accident, but he's going to burn them in melted lead or boiling oil.
    • Wilfred Shadbolt, who is head jailer and assistant tormentor, but wants to be more affable by becoming a jester.
  • Bertolt Brecht's Threepenny Opera seems to have some level of inspiration from the Pirates of Penzance in its Karma Houdini ending, and much like the quote above, a stage direction notes of Macheath's henchman at the wedding feast that rather than the stereotype of criminals as crude and covered in scars, they are all soberly dressed and look like the average person you would see on the street. They are nice chaps and make sure to bring wedding presents, although regrettably, they procured these by killing or maiming several people. Macheath himself is charming and charismatic and wins the affection of numerous women, although the Moritat ("Mack the Knife" in English) which opens the play tells of deeds such as killing an entire family in an act of arson and raping a child bride. The Karma Houdini ending comes from an 18th Century work, The Beggars' Opera, which Brecht adapted to a 20th Century setting. In the original work, the play's narrator says outright that the protagonist deserves to hang but he is being spared to placate all the sentimental fools in the audience.
  • During his dealings with Christine, the eponymous Phantom of the Opera carries this off in spades. Otherwise...
  • Hamlet, speaking of his uncle, laments that "one may smile, and smile, and be a villain".
  • Abby and Martha Brewster in Arsenic and Old Lace are the kindest pair of old maid sisters one could ever meet. Better watch out, though, whenever they pour someone a glass of wine. Arguably, it's more an act of misguided charity than actual evil in their case.
  • The Wizard from Wicked is friendly, kind, and supportive to Elphaba, presenting himself as a kind father figure who only wants to help every citizen of Oz to fly. Unless, of course, you're one of the talking animals, in which case you are to be cowed into submission, brainwashed, and/or exterminated. Elphaba is his mirror image, nasty, insulting, and condescending to others, and flies into classic villain hissy fits (in the book, she mutilates an old woman's corpse because the woman had the audacity to die before Elphaba could kill her; in the play, she responds to her friend's death by having her minions unleash a wave of off screen terror upon Oz), but has good intentions. It's no surprise that the casual observer in Oz mistakes which one is the villain.
  • Smee from Peter Pan. He's not a nice man--after all, he is trying to kill the Lost Boys--but he's so unintentionally pleasant and charming in his dim-witted way that everyone loves him. Captain Hook observes that Smee is happy because he thinks that the boys fear him, even though he lets Michael try on his spectacles.
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