Book Review: You Can’t Win by Jack Black

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Star Ratings for Nonfiction

Writing: *****  (5 stars)

Narrative: **** (4 stars)

Interesting Subject: ***** (5 stars)

Objectivity and research: **** (4 stars. This is a memoir.)

Overall: ***** (5 stars)

Age range recommendation: 14 and up.

The gents at my favorite coffee shop are on a roll with the book recommendations, lately.  You Can’t Win was described to me as “the memoir of a hobo turned safe-cracker turned house burglar turned highwayman turned librarian.”  You can probably imagine that I nearly dropped my maple spice coffee (yum) in eagerness to get my hands on a copy.  I ordered one the moment I got back to work, and have ordered another since to give as a gift.  It was just that good.  I want to call the book “inspiring,” but it’s probably a bad idea to immortalize one’s admiration for such a practiced criminal as Mr. Black on the internet.  So let’s just call it a riveting story, told with level-headed clarity and enough rollicking anecdotes to turn Jack Black’s life into a series of adventures well worth re-telling.

America in the early 20th century was a wild and crazy place. Saloons and opium dens were everywhere, housing wayward women and desperate men; bad men; or pretty much any other crooked variety of fella. Prisons were uniformly horrifying – even more so than they are today – and reforms had only just started. People still carried gold money on horseback. And security measures for houses and trains weren’t quite up to snuff. The West, especially, was paradise for train-hoppers; hobos; “yeggs”; stick-up men; gamblers… any manner of folk who made their living going against the law.

Jack Black (an alias, I believe) didn’t start out as a criminal. His story begins with a quite loving description of childhood years at a Christian school. Right off the bat, he ruminates on the lack of a mother in his life, though his portrayal of the nuns who took care of him shows that there was no lack of decent adult influence in his upbringing.

“It has often been a question with me just how much the best of it a boy has, who has his mother with him until his feet are well planted under him; who has a home and influences until he gathers some kind of a working philosophy that helps him to face the world… Looking back at it, it seems to me that I was blown here and there like a dead leaf whipped about but the autumn winds till at last it finds lodgment in some cozy fence corner. When I left school at fourteen I was as unsophisticated as a boy could be. I knew no more of the world and its strange way than the gentle, saintly woman who taught me my prayers in the convent.”

Jack’s father, too, is described with respect and care. In fact, I was touched by how Mr. Black’s protective nature towards his father’s reputation and feelings only grew throughout his life of crime, which is why it’s not hard to sympathize with the distance he keeps between them in later, more adventurous, years. Even as a kid, his knack for business and shrewd observational skills get Jack into troublesome learning experiences.

“The books so fired me with the desire for travel, adventure, romance, that I was miserable most of the time.”

Well, it won’t be long before travel and adventure fill Jack’s days, though misery is always snapping at his heels. (As for romance… you won’t find much of it in You Can’t Win. One of many reasons I loved the book.) His first arrest is a classic case of being in the wrong place at the wrong time. Subsequent incarcerations are the unhappy results of more purposeful ventures. Jack Black writes candidly about his resilience in crime, neither apologizing for his misdeeds nor whining openly about the hard life of a roving thief.

I was wrong. I knew I was wrong, and yet I persisted. If that is possible of any explanation it is this: From the day I left my father my lines had been cast, or I cast them myself, among crooked people. I had not spent one hour in the company of an honest person. I had lived in an atmosphere of larceny, theft, crime. I thought in terms of theft. Houses were built to be burglarized, citizens were to be robbed, police to be avoided and hated, stool pigeons to be chastised, and thieves to be cultivated and protected. That was my code; the code of my companions. That was the atmosphere I breathed. ‘If you live with wolves, you will learn to howl.”

Black’s unabashed memoirs are told in a fairly linear fashion, though every now and then he’ll mention the untimely demise of a fellow “yegg,” or write ominously about a future mistake as yet unknown to his younger self during the exploit of the moment. Most cases of foreshadowing lead to reciprocal and gratifying anecdotes later on in the narrative. Jack Black is a good writer: trust that he will reveal the conclusions of any and all story-lines that conclude neatly enough.

Characters – real people, yes, but certainly their colorful personalities deserve the term – filter in and out of his acquaintance as fate (or the judiciary system) lead their paths together and astray. From the first time he witnesses a fellow train-hopper get squashed by the cargo, through partnerships with the likes of “Smiler;” “Foot-and-a-Half George;” and “The Sanctimonious Kid,” Jack is a diligent observer of the attitudes that best suit a man on the road. Charming criminals, hardened ladies who orchestrate connections in crime, and even leaders of bloody prison break-outs take Jack into their confidence quickly and easily. I think that his quiet, unassuming nature serves him well in the field. Reading his recollections has made me want to write careful descriptions of the people I encounter: their mannerisms, their ways of speech, and even the measure of their moral standing. You never know when they might turn up in your life again, fifteen years later, harboring a grudge or willing to spring you from behind bars. Bums and highwaymen tend to have interesting backgrounds of their own accord, but it takes a memory like Mr. Black’s and a simple-but-crystallized handle of the English language to give such individuals real life on the printed page.

His voice never falters into sentimentality or veers towards the arrogance of a man who has succeeded where others have not. Sometimes he needs help, and he is grateful when he gets it. Sometimes he has the chance to assist a fellow disreputable soul, and he does so without expecting congratulations. There were runs of bad luck which made me cringe at the injustice of it all – a real life of crime has no guarantee of satisfaction at the end of several months’ plotting, despite what novels and films would have us believe. But there are still moments of triumph and even unexpected kindness to keep his mind in the game for so many years.

The era of saloon shoot-outs, railroad heists, and sacks of gold has dwindled into our less-thrilling modern age of electronic money and biometrics. I probably wouldn’t like to go through my days in a hail of bullets and a succession of jail cells, but it was awfully fun to read Jack Black’s account of such a life. His subdued good humor and unusually merciful view of human nature have rubbed off on me a little bit. If more “good” people adopted an attitude like this one “bad” man, I think we would all have a better idea of how luck and life all even out in the end.

“A bleak background! Crowded with robberies, burglaries, and thefts too numerous to recall. All manner of crimes against property. Arrests, trials, acquittals, convictions, escapes. Penitentiaries! I see in the background four of them. County jails, workhouses, city prisons, Mounted Police barracks, dungeons, solitary confinement, bread and water, hanging up, brutal floggings, and murderous straitjacket.

“I see hop joints, wine dumps, thieves’ resorts, and beggars’ hangouts.

“Crime followed by swift retribution in one form or another…

“In those twenty-five years I took all these things, and I am going to write about them.

“And I am going to write about them as I took them –with a smile.”

(Here’s another good review of the book, which helped inspire me to buy it sight unseen.)

Four New Books from HarperCollins: The Bookshelf Pirate Has Dinner With Authors

People keep making the mistake of letting me out into public. A pirate on cold medicine in a restaurant full of book people: this situation had the potential to end in broken glass, spoiled endings, and elaborate apologies. But, for reasons which continue to befuddle yet flatter me, my coworkers and other literary grown-ups keep treating me like a real person. I got the wonderful opportunity to have dinner at Erbaluce – in Boston – with some fellow booksellers from the area, the lovely reps from HarperCollins, and four absolutely smashing debut authors. The food was amazing, the books sound fantastic, and as far as I can tell no one was physically injured in the course of the evening! At least, no one was run through with a cutlass or butter knife, and therefore I can call the night a success.

In a strange and delicious combination of musical chairs and literary speed dating, a knife was clanged against a wine glass in between each course to haul the poor authors out of their chairs and to a different end of the big table. This ensured that we got to speak to each of them for a part of the evening, and kept the waiters on their toes. (I should note that the staff at Erbaluce was so patient with us. They’re obviously enthusiastic about the food and the atmosphere where they work, and it was such a pleasant experience.) There was a really interesting mix of people; each of them had such a different writing experience to share and wacky areas of expertise gleaned from research and work and life. The books aren’t necessarily similar to one another in genre or purpose, but all four seem really interesting and I can’t wait to get started on the stack once I finish reading The Accursed.  Here are the books HarperCollins was promoting.

The book which intrigued me most, with its mysterious summary and a sinister atmosphere that practically leaked out of the pages, is called Bird Box by Josh Malerman. I’m certainly going to read this one first. I’m a grim little person and the very little I know about Bird Box makes it sound like just my cup of menacing and brackish tea.

No one will let slip any concrete details about the plot of Bird Box, but it seems to be one of those gripping, horrifying tales which ensnares your attention at the beginning and completely ruins you for any weekend plans. That’s what I hear from everyone who’s read it, anyway… Hugh Howey, author of Wool, says this about Bird Box: “A book that demands to be read in a single sitting, and through the cracks between one’s fingers” One thing I can say for sure is that no one seems to have read only a few chapters of this book. It’s of the dreaded “unputdownable” variety, the sort of tense and mind-blowing read – supposedly – which gets into your brain and shakes you awake at night.

The story follows a woman as she rows down a river with two young children, blindfolded. That image alone is enough to hold my attention hostage. If there’s a combination I love, its desperation and boats! Where are they going? Why aren’t they looking? So many questions, and I’m nervous about the answers. While I’m not always keen on post-apocalyptic settings, I am very keen on atmospheric adventure novels and surreal horror stories. Bird Box brings characters out of a boarded up house into an outdoors so dangerous you can’t look around you without going fatally mad. Damn it, I’m already desperate to find out more, and I haven’t even started the book yet!

An author willing to eat his own book. Photo from Josh’s twitter. (Note the fine photography skills of his portside dining companion.)

Josh Malerman was great fun to sit next to for the first portion of our dinner. He listens to horror movie soundtracks, is part of a band (I really hope we get to hear a sinister soundtrack to go along with Bird Box someday), and knew an awful lot about all things freaky and weird. I’ve got to say that it put me at ease to sit next to someone who would talk about about H. P. Lovecraft at my first-ever professional dinner. (At the last dinner party I attended, my dining companions were confused about my “halloween scarf” and no one had any opinions about haunted houses. This evening was way more fun.) Nice to let the inner demons out in public now and then. Josh and his fiancee were so interesting and full of creative energy; I envy their talent, and wish I could harness some of that artistic vigor. It sounds like the book has already been snatched up by the film world, too, and I’m intrigued to see what they do with a story which relies so much upon what is not seen and what is unknown. I can’t wait to read Bird Box and get stuck in a nightmarish world full of scenes to fuel my own sleep-screaming fests.

Smith Henderson, who used his years as a social worker to inspire Fourth Of July Creek, sat by me next when the wine glass was clanged and the appetizers cleared away. (My starter was a very good fishy broth with chunks of lobster and veggies.) If I recall correctly, it took him something like ten years to write this novel, but I get the feeling it will have been worth all the time and effort. Fourth Of July Creek will probably be the sort of book one person in Concord reads and then starts talking about to all their friends. We do love our stories of isolated weirdos and messed up families. So much fodder for book clubs and heated conversation!

Henderson’s book sounds like it will be a distinctly American and utterly fascinating read. Here’s the summary from HarperCollins:

After trying to help Benjamin Pearl, an undernourished, nearly feral eleven-year-old boy living in the Montana wilderness, social worker Pete Snow comes face to face with the boy’s profoundly disturbed father, Jeremiah. With courage and caution, Pete slowly earns a measure of trust from this paranoid survivalist itching for a final conflict that will signal the coming End Times.

But as Pete’s own family spins out of control, Pearl’s activities spark the full-blown interest of the F.B.I., putting Pete at the center of a massive manhunt from which no one will emerge unscathed.

You may recall from my University years that I am really interested in wild children living in wacky environments. I spent six months dwelling on (and writing about/weeping over) literature portraying kids in volatile environments where adults are either nonexistent or irresponsible. So the premise of Fourth of July Creek really appeals to me. I’ve also been thinking about the wilderness, survival, and the strange world of inland America a lot lately. I have never been to the Midwest; the bookshelf pirate clings to various coastlines, and Montana seems as alien to me as Antarctica or Saturn. But it’s important that we broaden our horizons, and since there’s a really compelling story to sweep my imagination across the country, I think I’ll really enjoy this novel’s setting.

Smith has lived in conservative Montana but also Portland, I believe, and therefore he has a really good grasp on the area’s unique brand of weirdness both as a first-hand observer and a rational outsider. I trust him to portray the situations in his novel with integrity and vivid detail, because when we spoke I was entertained by the details and stories he shared with us about each of the very different places where he’s lived. He might not be good at guessing peoples’ weird fetishes after a few big glasses of wine, but he has an eye for human nature and a talent for turning little oddities into really amusing anecdotes. (Do I look like the cloven-hoof sort? Now I’m re-thinking the scull scarf decision…) I hope that his experience in social work will ensure that this novel’s characters are believable and complex as well as dramatic. I can see myself recommending Fourth of July Creek to people looking for a riveting airplane read or something diverting to bring on a camping trip. It comes out in June, but I want to read my advanced copy before the summer starts as a reminder that the USA can be a stage for all sorts of big bad drama and strange beliefs.

The Bees, by Laline Paull, might give Bird Box a run for its money as the most unusual premise from the evening. I know that there are tons of books with “bees” and “beekeepers” in the title on bookshop shelves these days. There are mysteries, family drama, and plenty of historical fiction. But The Bees is genuinely about bees, and I think that’s awesome. The story follows Flora 717, one lowly bee who climbs the ranks from sanitation worker, as she challenges the natural order of the rigid hive system. Themes of maternity, loyalty, and natural instinct will come up as Flora 717 uncovers the mysteries behind her hive and brings danger upon herself with each question.

While The Bees is Laline’s first novel, she has written several plays which have been performed in the United Kingdom. One of them, Boat Memory, is about the “native hostages” brought back to England on the Beagle, during a voyage with Charles Darwin. I really want to see this play. The intensity of investigation which has to go into writing about such cool bits of history must be similar to that which goes along with a sudden interest in Entomology. She told me about all the research which went into writing The Bees; how she wasn’t always interested in them but got drawn into the fascinating world after the death of a friend, and realized how much there was to learn about nature and ourselves in the study of these creatures. My family actually keeps bees and makes honey, so I bet I’ll be seeing our own white-boxed hives differently this summer in the aftermath of this novel.

They’re advertising The Bees as a sort of Handmaid’s Tale set in the natural world, but I bet it’ll be more unique than that. Laline Paull has written a book exploring a brutal social order, but to do so without including any major human characters is ambitious. Even in The Handmaid’s Tale, we can imagine ourselves into the situations without too much difficulty. It will take careful writing and very precise descriptions to bring most causal readers into a beehive and keep them invested in the characters, when most of us only think of the honey bees who make our tea so tasty when we’re walking through clover patches in bare feet. George Orwell managed to seize us by the hearts and minds in Animal Farm, but even that had a setting which would be familiar enough to most of us. We can cast ourselves in a horrible future, and we can understand the predicaments faced by unhappy allegorical farm animals. I am so excited to see how Laline Paull will bring us into the complex world of beehives and natural politics – with plenty of creative license, I’m sure – and make us follow the adventures of an insect with emotional investment and suspense.

The final author I spoke to on Thursday evening was David McCullough Jr., the only author at the dinner from around these parts. He had given the graduation speech at Wellesley High School in 2012, and made quite an impression on the graduates, the community, and then the country at large. McCullough is the son of David McCullough the famous historian and author, and he teaches English at Wellesley High School. You can read the transcription of his inspiring and refreshing commencement here.

His irreverent words of wisdom made such an impact that he’s now written a whole book elaborating on the ideas he touched on. You Are Not Special…And Other Encouragements is full of the sort of truth-bombs I wish my fellow graduates and I had been hit with upon leaving our (honestly rather snobby and unrealistic) prep school. He’s a preppy guy but he’s got a realistic view of the world, striking the right balance between recognizing teenagers as individuals and reminding them that so many other people are going through the same stuff and want the same things out of life. I do think that we’d all be a lot less depressed about the post-high school and post-college years if we had stepped out of those hideous graduation gowns knowing that our futures didn’t need to be so competitive and self-centered. I barely remember the graduation speech from my own High School experience; I think it was some laughably unhelpful extended juice-metaphor, since the guy owned some big beverage company or something. But if McCullough’s students keep in mind his suggestion that you don’t need success to validate your own worth, but should work hard and keep learning simply because you love what you’re doing, I think they’ll be more prepared for adulthood than many.

Here’s a quote from the speech itself, and the sort of advice I really hope will be in the book:

Climb the mountain not to plant your flag, but to embrace the challenge, enjoy the air and behold the view.  Climb it so you can see the world, not so the world can see you.  Go to Paris to be in Paris, not to cross it off your list and congratulate yourself for being worldly.  Exercise free will and creative, independent thought not for the satisfactions they will bring you, but for the good they will do others, the rest of the 6.8 billion–and those who will follow them.

Now that there’s going to be a book elaborating on his tough-love (but still loving) rally to intelligence and passion, I predict that a great many classes of 2014 will be getting book-shaped graduation gifts explaining how they aren’t special, with other encouragements. The book comes out in April and I intend to press it upon all those doting grandparents and starry-eyed relatives who believe that their special little someone is destined to step out of that crowded gymnasium and into all sorts of gratifying superstardom. If they read the book before they give it to the hapless new adult, I hope they’ll find some fresh perspective within the pages. The adults in these situations are so often the worst offenders at cultivating a desire for adoring recognition at every step of life, and it seems like David McCullough Jr, who has teenagers himself, has found a way to articulate this in a way which might actually shake things up without tearing things down. It was great to hear him swapping stories about favorite vacation spots with other locals at the table and telling us about his own (rather literary) youthful years. If You’re Not Special… and Other Encouragements is as earnest and clearheaded as he is in conversation, then there might be hope for the future go-getters and must-havers of the world.

I left Erbaluce nearly four hours after dinner began with my stomach full of chocolate hazelnut truffles and my mind swimming with anticipation. I have to know what is lurking just out of sight in Bird Box! I want to find out what the characters in Fourth Of July Creek seem to think the End Times entails, and how a rational hero might possibly deal with all that nonsense. I’ve got to see if The Bees convinces me to rise against social expectations I didn’t even know existed, and if nature turns out to be utterly cruel to poor Flora 717. And I’m curious to see if learning how very un-special I am proves to be encouraging after all, as I suspect it will.

Bird Box might actually bump The Brothers Karamazov off my To Be Read Next pecking order. I’m so impatient to get sucked into a story which twists my dreams and makes me nervous – it’s been far too long since I spent a disturbed evening jumping at noises with a book and my own messed-up subconscious. Far too long.

Difficult decisions, but I think the scary book wins.

Difficult decisions, but I think the scary book wins.

I’m very grateful to HarperCollins for treating us to dinner and for introducing us to such creative and hard-working writers. I’ve been inspired to read faster, to get to these books sooner. I’m also feeling the writerly energies building up in myself again after a week of not writing much at all, due to this damned cold, which took all the salt and gunpowder out of my piratical thoughts and replaced them with congestion and a desire for naps. All four of these writers were so encouraging and helpful when I told them that I was currently slogging through a novel myself.

Now that I can picture faces and hear voices behind the names on the spines of these books, I know I’ll be really excited to see the first printing on our shelves in a few months. The bookshelf pirate will be keeping a weather eye out for those readers who need to read them, even if they don’t know it yet, themselves. By then, I hope to have read all four galleys and formed opinions of my own. If we’re lucky, those opinions will be of the “Avast! Read this now!” variety.