Never sleep with someone whose troubles are worse than your own.
Chicago is an October sort of city even in spring.
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.
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.
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.
There is no way of being a creative writer in America without being a loser.
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.
Any writer who knows what he's doing isn't doing very much.
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.
...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.
For the masses who do the city's labor also keep the city's heart.
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.
... 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 avocation of assessing the failures of better men can be turned into a comfortable livelihood, providing you back it up with a Ph.D.
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.
(Chicago is) the only major city in the country where you can easily buy your way out of a murder rap.
Literature is made upon any occasion that a challenge is put to the legal apparatus by conscience in touch with humanity.
Never lie down with a woman who's got more troubles than you.
It is strange how fragile this man-creature is.....in one second he's just garbage. Garbage, that's all.
I don't recommend being a bachelor, but it helps if you want to write.
He was falling between glacial walls, he didn't know how anyone could fall so far away from everyone else in the world. So far to fall, so cold all the way, so steep and dark between those morphine-coloured walls...
The devil lives in a double-shot", Roman explains himself obscurely. "I got a great worm inside. Gnaws and gnaws. Every day I drown him and every day he gnaws. Help me drown the worm, fellas.
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.
The only way I could finish a book and get a plot was just to keep making it longer until something happens.
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