I hope I go to Heaven, and when I do, I’m going to do what every San Franciscan does when he gets there. He looks around and says, ‘It ain’t bad, but it ain’t San Francisco.’ – Herb Caen
The trouble with born-again Christians is that they are an even bigger pain the second time around. – Herb Caen
A good column is one that sells paper. It doesn’t matter how beautifully it is written and how much you admire the author… if it doesn’t sell any papers, it’s not a good column. It’s a terrible yardstick to use, but in the newspaper business, that’s the whole thing. – Herb Caen
A city is a crazy concrete jungle whose people at the end of each day somehow make a small step ahead against terrible odds. – Herb Caen
A city is where you can sign a petition, boo the chief justice, fish off a pier, gaze at a hippopotamus, buy a flower at the corner, or get a good hamburger or a bad girl at 4 A.M. A city is where sirens make white streaks of sound in the sky and foghorns speak in dark grays. San Francisco is such a city. – Herb Caen
The world of Manhattan is small and tightly knit, and the man on top retains a certain humility. He knows how far and fast he can fall by looking at the guy across the street. The view from the $250,000 apartment covers a lot of ground, most of it condemned. – Herb Caen
A city is a state – of mind, of taste, of opportunity. A city is a marketplace – where ideas are traded, opinions clash and eternal conflict may produce eternal truths. – Herb Caen
Satire of satire tends to be self-canceling, and deliberate shock tactics soon lose their ability to shock, especially when they’re too deliberate. – Herb Caen
Cockroaches and socialites are the only things that can stay up all night and eat anything. – Herb Caen
Old San Francisco – the one so many nostalgics yearn for – had buildings that related well to each other. – Herb Caen
A city is not gauged by its length and width, but by the broadness of its vision and the height of its dreams. – Herb Caen
Just two days in Manhattan and you find yourself looking for a place to wash your handkerchief after you wipe your forehead and it comes away black. Is there a dirtier or more fascinating city anywhere in the land? The answer to both parts of the question has to be positively negative. – Herb Caen
