And never, ever, no matter what else you do in your whole life, never sleep with anyone whose troubles are worse than your own.
When we get more houses than we can live in, more cars than we can ride in, more food than we can eat ourselves, the only way of getting richer is by cutting off those who don't have enough.
Never play cards with a man called Doc. Never eat at a place called Mom's. Never sleep with a woman whose troubles are worse than your own.
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.
And money can't buy everything. For example: poverty.
Chicago is an October sort of city even in spring.
Yet once you've come to be part of this particular patch, you'll never love another. Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.
A book, a true book, is the writer's confessional. For, whether he would have it so or not, he is betrayed, directly or indirectly, by his characters, into presenting publicly his innermost feelings.
Any writer who knows what he's doing isn't doing very much.
...he said, with sort of a little derisive smile, "How can you walk down the street with all this stuff going on inside you?" I said, "I don't know how you can walk down the street with nothing going on inside you.
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.
For the masses who do the city's labor also keep the city's heart.
I'm not against sentimentality. I think you need it. I mean, I don't think you get a true picture of people without it in writing... It's a kind of poetry, it's an emotional poetry, and, to bring it back to the literary scene, I don't think anything is true that doesn't have it, that doesn't have poetry in it.
Watch for a wild boy of no particular clan, ready for anything, always armed. Prefers fighting to toil, drink to fighting, chasing women to booze or battle: may attempt all three concurrently.
Literature is made upon any occasion that a challenge is put to the legal apparatus by conscience in touch with humanity.
Our myths are so many, our vision so dim, our self-deception so deep and our smugness so gross that scarcely any way now remains of reporting the American Century except from behind the billboards.
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.
It is strange how fragile this man-creature is.....in one second he's just garbage. Garbage, that's all.
... Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you.
To literary critics a book is assumed to be guilty until it proves itself innocent.
The great trains howling from track to track all night. The taut and telegraphic murmur of ten thousand city wires, drawn most cruelly against a city sky. The rush of city waters, beneath the city streets. The passionate passing of the night's last El.
The only way I could finish a book and get a plot was just to keep making it longer until something happens.
Never lie down with a woman who's got more troubles than you.
The hard necessity of bringing the judge on the bench down into the dock has been the peculiar responsibility of the writer in all ages of man.
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