You don't write a novel out of sheer pity any more than you blow a safe out of a vague longing to be rich. A certain ruthlessness and a sense of alienation from society is as essential to creative writing as it is to armed robbery.

Loving Chicago is like loving a woman with a broken nose.

Thinking of Poe, thinking of Mark Twain and Vachel Lindsay, thinking of Jack London and Tom Wolfe, one begins to feel there is almost no way of becoming a creative writer in America without being a loser.

(Chicago is) the only major city in the country where you can easily buy your way out of a murder rap.

The avocation of assessing the failures of better men can be turned into a comfortable livelihood, providing you back it up with a Ph.D.

I don't recommend being a bachelor, but it helps if you want to write.

Never lie down with a woman who's got more troubles than you.