The best wise guy books you’ll love

Who am I?

I’ve worked both in politics and as an investigative reporter in print and broadcasting in Chicago, Miami, Key West, San Francisco, and Honolulu. I’ve had an up-close look at how the system doesn’t work and how the wise guys get their share. I find it easy to use fiction to get to the truth.


I wrote...

Disappearing Act: A Las Vegas Love Story, Sort of...

By Ray Pace,

Book cover of Disappearing Act: A Las Vegas Love Story, Sort of...

What is my book about?

A Las Vegas magician disappears, two million bucks are missing, Chicago wants its money. What does any of this have to do with Area 51? Or Roswell? Can two wise guys, a hooker and a lesbian softball team save the day?

The books I picked & why

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Wise Guy

By Nicholas Pileggi,

Book cover of Wise Guy

Why this book?

This book takes you on Henry Hill’s journey from a streetwise kid to a major mob player. Along the way it hits all the highs and lows without pulling punches. It doesn’t get bogged down in excess rituals found in The Godfather. It lets the reader have it straight, no chaser.


Get Shorty

By Elmore Leonard,

Book cover of Get Shorty

Why this book?

Chilli Palmer, the main man in Get Shorty, is an unforgettable character capable of thinking way outside the box and acting on it. The book keeps the reader off balance as Leonard introduces one far-out character after another. The fast-paced novel takes liberal swipes at characters trying to make it in Hollywood.


The Maltese Falcon

By Dashiell Hammett,

Book cover of The Maltese Falcon

Why this book?

This classic crime story set the pattern for many private eye stories to come. The fast-paced story unfolds as characters try their best to double-cross each other in the space of hours. Noir wasn’t invented in this book, but it sure got a big kick in the right direction by Hammett.


Tourist Season

By Carl Hiaasen,

Book cover of Tourist Season

Why this book?

Everybody has a South Florida story they’ll tell about the wilds of Miami. Carl Hiaasen outdoes most of them. Body parts are washing up on the shores of Dade County Is it a hungry crocodile? Maybe not. Some of the body parts are in a suitcase and a lot of the players may not be playing it straight.


Boss: Richard J. Daley of Chicago

By Mike Royko,

Book cover of Boss: Richard J. Daley of Chicago

Why this book?

Chicago is where I grew up watching the fascinating interplay between the so-called forces of law and order battle the criminal element. It wasn’t much of a battle unless the law-and-order guys and the crooks found themselves reaching for the same loot. Mike Royko’s book describes very well the interplay. On a personal note, I once worked for one of the Illinois governors who ran as a reform candidate. He ended up going to jail on a fraud scheme.


5 book lists we think you will like!

Interested in private investigators, Illinois, and criminals?

5,887 authors have recommended their favorite books and what they love about them. Browse their picks for the best books about private investigators, Illinois, and criminals.

Private Investigators Explore 121 books about private investigators
Illinois Explore 60 books about Illinois
Criminals Explore 35 books about criminals

And, 3 books we think you will enjoy!

We think you will like Deep Blues, Urban Blues, and The Day of the Locust if you like this list.