HAL from 2001 by Arthur C Clarke
While it is debatable if an artificial intelligence can truly go insane, the actions of HAL, if performed by a human, would certainly qualify. Also, the reasoning behind these murderous actions, conflicting objectives, would be very much a source of insanity in a human. There is something haunting about the cold calculating computer murdering but then a feeling of sorrow when he asks, "Will I Dream?"
Jack Merridew from Lord of the Flies by William Golding
It has been a very long time since I last read Lord of the Flies but I will always remember the premise. The insanity that can come when people are put into dire situations and the humanity that can be lost when you hide behind a mask. And Jack being the primary antagonist and the one who separates the group into two tribes due to his obsession with continuing the hunt puts him at the top of the list from this particular story.
Jack Torrance from The Shining by Stephen King
While both Jack's (the novel version and the film version) are driven to insanity, the novel version is far more tragic. His relatively quick descent into insanity at the hotel lead him to nearly murder his family. However; in the end he is given the chance to redeem himself by saving them before they are killed in a boiler explosion.
Alex from A Clockwork Orange by Anthony Burgess
Dexter Morgan from Darkly Dreaming Dexter by Jeff Lindsay
Felix from Armor by John Steakley
I think it is easy to argue the fact of Felix's insanity in Armor. The "Engine" could simply be a coping device, however; the desire to die being overridden by the "Engine" leads me to believe that it is almost a second personality inside of Felix's mind. This ambiguity and the duality of Felix's mind is what makes the story of Armor more interesting to me than most space war novels.
Shaun Mason from Deadline by Mira Grant
In this sequel to Feed by Mira Grant, Shaun has a bit of insanity creep into his mind. It gives a great deal of humor that is often seen in more slapstick ways in other zombie novels and movies. His insanity also, oddly enough, serves as a moral compass and voice of reason which can be fascinating at times.
Richard Talbott (a.k.a. Chef Assassin) from Haunted by Chuck Palahniuk
It would have been easy to select the narrator from Fight Club for this list, however; I've always found the Chef even more fascinating. His murderous nature driven by a lack of belief in his abilities and his blackmailing of a knife company make him not only crazy but rather well set with forethought.
Patrick Bateman from American Psycho by Bret Easton Ellis
The Narrator from The Tell-Tale Heart by Edgar Allen Poe
The Tell-Tale Heart may not be a book on it's own but as a story it is one of my favorites by Edgar Allen Poe. The lack of clarity in many aspects of the story (such as the gender of the narrator) and the fact that the details of the narrator's story are unreliable make the story fascinating. Also it hints at the various insanities that the narrator may be suffering from.
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