You Cant Win is an autobiography, Jack Black the author was a hobo in the dying era of the American wild west. Jack Had grown up idolizing Jesse James and other famous cowboys of that era and soon enough ends up a legend becoming quite a notorious criminal him self, having comitting crimes that ending up in prison 5 times and twice busting out. The book provides an interesting first hand account of a gambling hop addicit criminal and a look into the world of the hobo/criminal underground such as madame houses, opium dens, and illegal casinos. The book ends on a postive note on prision reform which I thought was actually still a good and fresh prespective. Jack Black was flogged in addition to two years time as punishment in Canada. While reading the book I wondered if Jack Black would see American prisions today as better or worse. After Jacks final stint in prision in which he was giving the improbale doubt of a kind judge to turn his 25 year sentence into a 2 year sentence, Jack is inspired by this so much he decides to live a more honest life and believes the justice system should show more mercy in general. Overall I found the book to be an interesting read of a not so historically covered but important era of the death of the cowboy and the turning of the tables for law enforcement, and crime in the country.

Themes: hobo culture, freight hopping, criminal underground, various crimes, autibiography, american history, prision reform, gambling, addiction, honest thief, anti-hero.