Maybe it's the fact Jack Black hails from my hometown or possibly the strong connection I feel to the overall arch this mans life takes but even more likely it is the universal human condition of the traveling man that Jack puts forth on paper flawlessly that makes this my all time favorite book. This is a book that has inspired many great travel writers and adventurers; from the Beatniks to Chris McCandless this book presents a moral compass for those who may have lost themselves down a long road. The story revolves around Jack Blacks own life as a hobo and a thief in the late 1800s. He lays his life down on paper from beginning to unknowingly close to the end, and shares his own trials and tribulations with the reader in a simple but well thought out language. Someone who lives an unconventional life as a traveler may find many mirrors within the pages of his book. From a lost love as a boy, something so simple as a person could alter the entire course of a life, to the people, friends, criminals, and situations he encounters along the way. Jack Black does a wonderful job telling us his reasons for wanderlust and justifies for us his life of crime, detailing the code of conduct he holds himself to as a thief and in turn despairs over the futility of the justice system that punishes him. The book was written as a means to straighten out criminals but also reflect the failure of the justice system.In the end, the traveling bandit is finally taken under the wing of a wealthy man and finds a love for books and writing during his time in prison and after as a librarian. After writing the book he found himself working in for a newspaper and even wrote a play based on a character in his book, but life was "too grim" and he found himself "ready for the river" where it is said he ended his own life.It seems however, to me, this book is more a reflection of an adventurous spirit that longs for stability in his life and the balance between adventure and a straight life seems a fine line to difficult to balance on; hence the title You Can't Win.In the end, this book is a very well crafted and heartfelt story; a piece of history, a personal journey, and simply a good read.http://adventeurs.com/you-cant-win-book-review/