Not to be confused with the raucous comedian and front-man of the band Tenacious D, Jack Black is one of the few American authors that have ever really written a book as what can only be known as Vagrant Literature. Black even may have been the first to depict the life of a drifter, a vagabond, and safe-cracking thieves in story form. Writers of the Beat movement have even mentioned the large influence Black had with their literature. William Burroughs is the most notable since Burroughs does write the introduction to Black’s only book, You Can’t Win.
Published in 1926, Black’s book You Can’t Win recounts his upbringing from the adolescent obsession with the stories of Jesse James that flooded newspapers, to falling in love with a prostitute, his many trips to prison, and his ascension into the yegg brotherhood. Black describes the vagrant lifestyle almost like a conspiracy theory. He repeatedly notes that the vagrants of the yegg brotherhood routinely met in secret meetings, which they called “conventions,” and they all had secret aliases that they referred to each other as. Sometimes through the book, it becomes unclear if this was true or just an embellishment by Black in order to make his story seem more mysterious and interesting. In fact, it is has been revealed through the California Call that Jack Black may even not be his real name. And if it is not his real name, why hide his identity and what would be the purpose of writing it? The intention of the author is pervasive through the book and propels the reader to continue to bend the bindings, lick their fingers, and turn the page. On top of that, his writing is unlike any writer of his period. He was a story-teller ahead of his time.
Black’s prose is the embodiment of a well-read traveler who has been to exposed to the many dialects of the late 19th and early 20th century United States subculture. He keeps his sentences short and varied, but there always a few hiccups where he will use words that are not entirely accurate or just standout as odd. Yet, it is amazingly consistent how inconsistent his writing can be that it does come off as natural after a while. Few books seem to written to be said aloud like it should be read at a campfire. A lot of modern literature has done away with practical writing, where the writer jots down or states exactly as best they can what they are thinking or witnessing. Writers afterwards, with the likes of Gertrude Stein, wanted to be more abstract and artistic with their narrative. Black’s writing is definitely the last of its kind. Paradoxically enough, Black’s book is the poor man’s version of Victorian literature. It definitely is not the best of Victorian literature, but it might be the truest. You Can’t Win contains elements of Victorian literature such as the story revolves around the impoverished, but it also criticizes it as well. There are moral dilemmas that are lose-lose situations and terrible events may unfold to consciously good people for no reason at all, which is the antithesis to common themes in Victorian literature.
It is a disservice not to read You Can’t Win. It is the most honest a book can get with a man that had to live a dishonest lifestyle. You Can’t Win is a ubiquitous statement about the culture of American homelessness and vagrants. Many of the thoughts and lifestyle is still true today. You Can’t Win is a book that should be archived in the people’s history of the United States.