Griffiths on what makes an outsider:
To be an outsider is to feel disconnected from life, from other people, from oneself, the sight lines of communication always just slightly skewed. Outsiders can be perceptive readers of inmost thoughts, but they slip off surfaces and are awkward on firm ground. It is their unfortunate role to stand against life, in Heidegger's sense of next-to yet in conflict-with. No outsider wants to be one, it is not a lifestyle choice. Whatever its psychological aetiology, it is like an accident of birth: you are either in or you're out.Number One on his list:
Notes from the Underground by DostoyevskyRead about the other nine outsider books.
The first modern novel features the first modern outsider. A monologue of sarcastic rage from a man who has chosen isolation because he knows he doesn't fit in. Irascible, clever, proud, the Underground Man harangues the ordinary world for its naivety, optimism, self-regard; he knows - feels - that man's freedom is in the choice to decide against himself, to spurn benefit and reward, to turn himself inside out and display the fear, misery, meanness of his desperate self. The Underground Man is the outsider as dark mirror. The final pages are some of Dostoyevsky's best, and they are some of his grimmest. Grim Dostoyevsky: it doesn't get better than that.