The Ink: Jack Black – You Can’t Win

Jack Black author

Jack Black was a late 19th-century writer and self-proclaimed hobo and professional burglar who lived in the final days of the Wild West. He was dishonest, conniving, but also a guy with a lot of heart. It’s funny to say, but he had the best intentions when it came down to it, even when he was stealing from people.

Black ultimately gained fame through his friendship with William S. Burroughs. And though he didn’t write any other novels, Black’s influence echos throughout the beats’ writing and serves as a basis for some of their strongest “live-free” philosophies. If you love the beats, his writing is definitely worth checking out.

9781936239658_p0_v2_s600His only novel, You Can’t Win, is kind of a literary nerd version of a cult favorite reaching the mainstream. It’s a wonderful piece of Americana writing first published in 1926, and tells the woeful but adventurous tale of a criminal’s life. It’s been in and out of print over the years, but was recently given a grand treatment with its latest edition.

The book is sometimes seemingly written strictly for the lover of timestamped narrative, only because it takes a dedicated or seasoned literary dedication to get through it  at times. It can get slightly monotonous and didactic (it was intended to also discourage future criminals), especially toward the end, but it’s never boring or uninteresting. The best sections are the ones that introduce strange new characters and the anecdotes of their relationship with Jack and their subsequent adventures. Salt Chunk Mary and Sanctimonious Kid are some of the standouts, and they appear far too infrequently.

It’s said that Black’s actually an anonymous man. It’s thought that his birth name is Thomas Callaghan, and the name Jack Black is used as the “everyman” version in the story and in life as a way to drive home his anti-criminal teachings. He lived as a burglar, a hobo, and a general criminal throughout his years, and was outspoken against the North American prison system. His firsthand knowledge of their ineffectiveness gave him a tremendous voice on the topic.

Feral House prints the newest version of You Can’t Win, and includes two nonfiction articles by Jack Black written for Harper’s Magazine in the 1920s. Awesome illustrations by Joe Coleman and new biographical findings by Donald Kennison only add to the new edition’s gloss and collectability.

The beats and friends are getting a lot of a cinematic love lately, with the release of On the Road and Big Sur, so it’s no surprise that a full-length feature film of You Can’t Win starring Michael Pitt is has wrapped production and is to be released in Spring 2013.