The best books written in the 1920s tinged with healthy skepticism of American values and mores

The decade after World War One was the beginning of today's America. We had saved the world from future wars and were basking in a roaring economy. Yet, much like the 1950s (another post-war boom decade) something simmered.

Main Street was Lewis' second published novel, the first in which he used his pen to poke at the edges of his uncertainty of the value we gave to the things we had, and the things to which we aspired. Lewis does this, powerfully, with the story of an educated, big-city, left-of-center woman who moves to her husband's small, conservative town after their marriage. 

I could easily have all five of my picks be novels by Sinclair Lewis. I'll stop at two.

In George Babbitt, Lewis's titular lead, we have a character whose very name became synonymous with conformity. What I absolutely love about this book has a lot to do with the bold plot choices Lewis takes with Babbitt. I write this knowing that many critics did not like the book because, they complained, there really wasn't a plot! (Cripes, what book were they reading?)

These plot turns include his dalliances with socialism (which runs counter to his position as the city of Zenith's most successful realtor) and a socialist woman.

I love this book for its multiple themes of unrequited love, racism, gender, class, even environment.

Fitzgerald's description of the view from a train moving through the ash fields of today's Flushing Meadows is, in my humble opinion, one of the most haunting in literature. I also love this book because it was a commercial failure. (Fitzgerald died never believing he was a success.)

Yet The Great Gatsby became one of those books we can't stop talking about. It's so rich and complex filmmakers have tried four times (and failed) to bring it to the screen. As if to underscore the timelessness of its themes, I recently discovered TGG was also made into a video game. A video game! 

This is not a novel, but a collection of Lardner's newspapers columns and short stories, many of which revolve around a bush league pitcher named Jack Keefe who tells stories to his friend.

I love baseball and am fascinated by the early days of the game, and Lardner's Jack makes me feel as if I am experiencing life in baseball's “bushes” back in the 1920s. Oh, yea, that's the other draw of this book for me a view, from his columns and other stories, of the daily grind of American life in an era that was much more than flappers and bathtub gin. (Although there is a bit of both therein). 

It would be obscene to read this on a Kindle. This early Dashiell Hammett novel has to be read in paperback, the older a copy you can find, the better.

It has everything a great pulp novel should have; murder, crooked cops, gangs, and a rumpled too-honest-for-his-own-good hero. What I love about this book is how Hammett uses his own experience working for the Pinkerton Detective Agency (who were basically hired thugs) and a real historical event (a labor dispute in Montana that resulted in several deaths) to weave a solid crime novel.