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I realized that I think of Jack Nicholson by far foremost for his portrayal of (clinically or comically) insane characters.

What movies has he played such a character, and (roughly) what proportion of his roles do such characters compromise?

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    Just go his IMDB page, read the synopsis and find out for yourself. This is clearly a "LMGTFY" question, because no one has this info off the top of their head. – Johnny Bones Jul 5 '16 at 13:32
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    What do you consider to be "insane/mentally compromised"? Seems like, without some broader explanation from you, it will be sort of opinion-based as to determining which of the characters fit your definition and which do not. – Catija Jul 5 '16 at 19:34
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    @JohnnyBones That doesn't make it a bad question... and, honestly, being something that takes some work means that it's specifically not a LMGTFY question... because those questions require that the answer be extremely simple and immediately available from a Google search. – Catija Jul 5 '16 at 19:35
  • @Catija Is "where the viewer is clearly supposed to infer the individual is insane from the narration" good enough? Not necessarily medically classifiable as insane, but that narrative the character is supposed to be "crazy" or "insane." Alternately if I can borrow the 'reasonable man' from common law, "the reasonable man would consider the character insane." – Ranger Jul 5 '16 at 20:01
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    Perhaps help people out a bit by listing some examples that you think fit the description and some that do not? Preferably including some less-than-obvious ones. Most films don't have narration, so I don't know that you can use that as a defining element – Catija Jul 5 '16 at 20:03
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First, a bit about insanity. Currently insanity is not a term used by the medical profession. It is used by people in general to refer to mental illnesses that are no longer grouped as a single condition by medical professionals. There is also a legal definition of insanity.

On IMDB I count 65 feature films or made for TV movies with Jack Nicholson in them. He did not star in all of those. As far as I can tell, when he did not star, he was never portrayed in as mentally ill.

As far as I can tell, Jack Nicholson has one starring role where his character is clearly intended to be mentally ill. Of course that is:

  • As Good As It Gets

Beyond that, there are two starring roles where his character starts the movie mentally healthy (as far as the viewer can tell) and is driven to what most people might call "criminal insanity" by other forces:

  • Batman (his character falls into a chemical vat)
  • The Shining (he is "driven mad" or possibly possessed by a spirit that inhabits a hotel)

And finally, he masterfully played the role (which might have started the whole "insanity" casting of Jack Nicholson) of a man pretending to be insane (in the legal sense) to get out of serving jail time:

  • One Flew Over the Cuckoo's Nest

The proportion of actually mentally ill characters then is 1/65 or about 1.5%. For characters that exhibit authentic behavior that a reasonable person would describe as "insane", we can say 3/65 or about 4.6%. And if we want to just look at Nicholson's ability to act like an insane person (or even more challenging, act like a person acting like an insane person), we have 4/65 or 6.2%.

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    It's questionable whether the Joker in Batman could be considered legally insane. He knew right from wrong and was deliberately trying to wreak havoc. In The Shining, however, every indication is that Jack becomes convinced that killing Wendy and Danny is the right thing to do. – John Sensebe Jul 6 '16 at 23:20

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